Publications by authors named "Santanu Bhattacharya"

212 Publications

Physical-Chemical Characterization of Bilayer Membranes Derived from (±) α-Tocopherol-Based Gemini Lipids and Their Interaction with Phosphatidylcholine Bilayers and Lipoplex Formation with Plasmid DNA.

Langmuir 2022 Jan 25;38(1):36-49. Epub 2021 Dec 25.

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.

Membrane formation and aggregation properties of two series of (±) α-tocopherol-based cationic gemini lipids without and with hydroxyl functionalities at the headgroup region (TnS = 3, 4, 5, 6, 8, and 12; THnS = 4, 5, 6, 8, and 12) with varying polymethylene spacer lengths were investigated extensively while comparing with the corresponding properties of the monomeric counterparts (TM and THM). Liposomal suspensions of each cationic lipid were characterized by dynamic light scattering (DLS), transmission electron microscopy (TEM), zeta potential measurements, and small-angle X-ray diffraction studies. The length of the spacer and the presence of hydroxyl functionalities at the headgroup region strongly contribute to the aggregation behavior of these gemini lipids in water. The interaction of each tocopherol lipid with a model phospholipid, 1,2-dipalmitoyl--glycero-3-phosphatidylcholine (DPPC)-derived vesicles, was thoroughly examined by differential scanning calorimetry (DSC) and 1,6-diphenyl-1,3,5-hexatriene (DPH)-doped fluorescence anisotropy measurements. The binding efficiency of the cationic tocopherol liposomes with plasmid DNA (pDNA) was followed by an ethidium bromide (EB) exclusion assay and zeta potential measurements, whereas negatively charged micellar sodium dodecyl sulfate (SDS)-mediated release of the pDNA from various preformed pDNA-liposomal complexes (lipoplex) was studied by an ethidium bromide (EB) reintercalation assay. The structural transformation of pDNA upon complexation with liposome was characterized using circular dichroism (CD) spectroscopic measurements. Gemini lipid-pDNA interactions depend on both the presence of hydroxyl functionalities at the headgroups and the length of the spacer chain between the headgroups. Succinctly, we performed a detailed physical-chemical characterization of the membranes formed from cationic monomeric and gemini lipids bearing tocopherol as their hydrophobic backbone and describe the role of inserting the -OH group at the headgroup of such lipids.
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http://dx.doi.org/10.1021/acs.langmuir.1c01039DOI Listing
January 2022

Ocular manifestation and visual outcomes in herpes zoster ophthalmicus: a prospective study from a tertiary hospital of Eastern India.

Int J Ophthalmol 2021 18;14(12):1950-1956. Epub 2021 Dec 18.

Department of Ophthalmology, R G Kar Medical College and Hospital, Kolkata, West Bengal 700122, India.

Aim: To estimate the magnitude of different ocular manifestation in clinically established herpes zoster ophthalmicus (HZO) patients and assessment of the visual outcome after two months of initial examination.

Methods: An observational prospective study was conducted on 42 clinically diagnosed Tzanck smear positive cases HZO to observe the occurrence and frequency of different ocular manifestation and their visual outcome in 10-month period with 2mo follow up. Full ophthalmological examination using slit lamp, non-contact tonometry, applanation tonometry, direct and indirect ophthalmoscope were performed.

Results: Out of 42 patients of HZO, 33 had one or more type of ocular manifestation staring from lid skin involvement to conjunctivitis, keratitis, uveitis, increased intraocular pressure (IOP) and optic neuritis but no retinal manifestation. More number of HZO cases and ocular manifestation were found with advancement of ages. Young HZO patients were more associated with human immunodeficiency virus (HIV) infection and HIV infected people with HZO infection had more ocular manifestation. Male to female ratio was 2:1 among HZO cases but ocular manifestation occurred more among males. Female with advanced age were involved more. Lid involvement (73.81%), conjunctivitis (69.05%), and keratitis (59.52%) were most common ocular manifestation followed by anterior uveitis (30.95%) and episcleritis (11.90%). Ocular hypertension (42.86%) was associated with almost every ocular manifestation. Among the cases of more than 45 years of age, 9.52% patients acquired 6/6 vision compared to 7.14% patients at and below 45 years of age after 8wk of follow up.

Conclusion: The visual outcomes are poor in HZO with advanced age group. Visual outcome of the affected eyes is poor than unaffected eyes. The loss of vision is mainly due to keratitis, anterior uveitis, posterior uveitis, and optic neuritis.
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http://dx.doi.org/10.18240/ijo.2021.12.21DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8640756PMC
December 2021

Nanomechanical Insight of Pancreatic Cancer Cell Membrane during Receptor Mediated Endocytosis of Targeted Gold Nanoparticles.

ACS Appl Bio Mater 2021 Jan 30;4(1):984-994. Epub 2020 Dec 30.

Department of Biochemistry and Molecular Biology and Department of Physiology and Biomedical Engineering, Mayo College of Medicine and Science, Jacksonville, Florida 32224, United States.

Nanoscale alterations in the cellular membrane transpire during cellular interactions with the extracellular environment through the endocytosis processes. Although the biological innuendos as well as alterations in cellular morphology during endocytosis are well-known, nanomechanical amendments in the cellular membrane are poorly understood. In this manuscript, atomic force microscope is employed to demonstrate the nanomechanical alterations in membrane dynamics during receptor mediated endocytosis of gold nanoparticles conjugated with either plectin-1 targeted peptide (PTP-GNP) or scrambled peptide (sPEP-GNP). Plectin-1 is aberrantly overexpressed at cell membrane of pancreatic cancer cells and is known to provide and maintain cellular mechanical integrity. During receptor mediated endocytosis of nanoparticles, we demonstrate temporal nanomechanical changes of cell membrane in both immortal pancreatic cancer Panc1 cells and patient derived primary pancreatic cancer cell, 4911. We further confirm the alterations of plectin-1 expression in Panc1 cell membrane during the receptor mediated endocytosis using classical streptavidin-biotin reaction and establish its association with nanomechanical alteration in membrane dynamics. Withdrawal of PTP-GNPs from the cell culture restores the plectin-1 expression at the membrane and reverses the mechanical properties of Panc1. We also show a distinctly opposite trend in nanomechanical behavior in cancer and endothelial cells when treated with sPEP-GNP and PTP-GNP, respectively, signifying receptor independent endocytosis process. This study illustrates the nanomechanical perspective of cell membrane in receptor mediated endocytosis of nanoparticles designed for organ specific drug delivery.
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http://dx.doi.org/10.1021/acsabm.0c01443DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8670601PMC
January 2021

Liposomal nanoparticles based on steroids and isoprenoids for nonviral gene delivery.

Wiley Interdiscip Rev Nanomed Nanobiotechnol 2022 01 2;14(1):e1759. Epub 2021 Nov 2.

Technical Research Centre, Indian Association for the Cultivation of Science, Kolkata, India.

Natural lipid molecules are an essential part of life as they constitute the membrane of cells and organelle. In most of these cases, the hydrophobicity of natural lipids is contributed by alkyl chains. Although natural lipids with a nonfatty acid hydrophobic backbone are quite rare, steroids and isoprenoids have been strong candidates as part of a lipid. Over the years, these natural molecules (steroid and isoprenoids) have been used to make either lipid-based nanoparticle or functionalize in such a way that it could form nano assembly alone for therapeutic delivery. Here we mainly focus on the synthetic functionalized version of these natural molecules which forms cationic liposomal nanoparticles (LipoNPs). These cationic LipoNPs were further used to deliver various negatively charged genetic materials in the form of pDNA, siRNA, mRNA (nucleic acids), and so on. This article is categorized under: Biology-Inspired Nanomaterials > Lipid-Based Structures.
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http://dx.doi.org/10.1002/wnan.1759DOI Listing
January 2022

Novel α-tocopherol-ferrocene conjugates for the specific delivery of transgenes in liver cancer cells under high serum conditions.

Biomater Sci 2021 Nov 9;9(22):7636-7647. Epub 2021 Nov 9.

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.

The delivery of therapeutic genes to a specific organ has drawn significant research attention. Among the pool of various delivery vectors, cationic liposomes (non-viral) are potential candidates for delivering therapeutic genes due to their low immunogenic response. Here, we have developed novel ferrocene-conjugated cationic tocopheryl aggregates as non-viral vectors. These formulations can transfer a reporter gene (pGL3; encoded for luciferase protein) specifically to liver cancer cells (HepG2 and Huh7) instead of non-hepatic cancer cells, such as Caco-2 (human colon carcinoma) and HeLa (cervical cancer) cells. The transfection efficiency (TE) of the optimum liposomal formulation is more significant than commercially available Lipofectamine 2000 (L2K). Notably, it retains its TE under high serum conditions (up to 50% FBS). A coupled effect from conjugated ferrocene and tocopherol in the cationic liposomal formulation might be responsible for the cell-specific delivery and higher serum compatibility. Therefore, the present proposed delivery system may provide a platform for further progress in terms of developing hepatotropic gene delivery systems.
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http://dx.doi.org/10.1039/d1bm00607jDOI Listing
November 2021

Imidazole-Functionalized Y-Shaped Push-Pull Dye for Nerve Agent Sensing as well as a Catalyst for Their Detoxification.

J Org Chem 2021 11 14;86(21):14663-14671. Epub 2021 Oct 14.

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.

A Y-shaped push-pull dye () with ,-dimethylanilino donors and a benzonitrile acceptor connected via an imidazole-based π-conjugated spacer was designed. It showed a dark yellow color in solution due to facile intramolecular charge-transfer interaction, but no fluorescence was detected, presumably due to the photo-induced electron transfer effect of the imidazole moiety. However, addition of nerve agents such as diethyl chlorophosphate (DCP, sarin mimic) and diethyl cyanophosphate (DCNP, Tabun mimic) resulted in a blue-colored fluorescence with fading of the native dark yellow color. Mechanistic studies indicated nucleophilic attack of imidazole at the phosphorus of DCP or DCNP, leading to the formation of a phosphorylated intermediate, which undergoes time-dependent hydrolysis (∼24 h) in aqueous medium. This process recovers the free probe (enzyme-like behavior) and releases a less-toxic organophosphate compound as the byproduct. The phosphorylated derivative of , formed during such interaction, shows a different electronic behavior, which reduces the extent of charge-transfer interaction as well as nonradiative decay and supports emissive properties. Considering the high sensitivity of towards DCP and DCNP with LOD 35 and 42 ppb, we prepared easy test strips for on-site vapor-phase detection of nerve agents.
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http://dx.doi.org/10.1021/acs.joc.1c01488DOI Listing
November 2021

Micro-structural investigations on oppositely charged mixed surfactant gels with potential dermal applications.

Sci Rep 2021 07 30;11(1):15527. Epub 2021 Jul 30.

Department of Chemistry, Vidyasagar University, Midnapore, 721102, West Bengal, India.

Dicarboxylic amino acid-based surfactants (N-dodecyl derivatives of -aminomalonate, -aspartate, and -glutamate) in combination with hexadecyltrimethylammonium bromide (HTAB) form a variety of aggregates. Composition and concentration-dependent mixtures exhibit liquid crystal, gel, precipitate, and clear isotropic phases. Liquid crystalline patterns, formed by surfactant mixtures, were identified by polarizing optical microscopy. FE-SEM studies reveal the existence of surface morphologies of different mixed aggregates. Phase transition and associated weight loss were found to depend on the composition where thermotropic behaviours were revealed through combined differential scanning calorimetry and thermogravimetric studies. Systems comprising more than 60 mol% HTAB demonstrate shear-thinning behaviour. Gels cause insignificant toxicity to human peripheral lymphocytes and irritation to bare mouse skin; they do not display the symptoms of cutaneous irritation, neutrophilic invasion, and inflammation (erythema, edema, and skin thinning) as evidenced by cumulative irritancy index score. Gels also exhibit substantial antibacterial effects on Staphylococcus aureus, a potent causative agent of skin and soft tissue infections, suggesting its possible application as a vehicle for topical dermatological drug delivery.
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http://dx.doi.org/10.1038/s41598-021-94777-2DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8324821PMC
July 2021

Theoretical Insight into the Library Screening Approach for Binding of Intermolecular G-Quadruplex RNA and Small Molecules through Docking and Molecular Dynamics Simulation Studies.

J Phys Chem B 2021 06 24;125(21):5489-5501. Epub 2021 May 24.

Department of Organic Chemistry, Indian Institute of Science, Bangalore, Karnataka 560012, India.

The interactions of intermolecular G-quadruplex RNA and small molecules have been investigated by computational studies. Various anthraquinone, bisbenzimidazole, and carbazole-benzimidazole based ligands have shown a distinct preference to G-quadruplex structures as opposed to the corresponding duplex forms of DNA that were docked with telomeric G-quadruplex RNA. The comparative binding study of such ligands with G-quadruplex (G4) RNA showed higher binding affinities toward carbazole-benzimidazole ligands than those of the anthraquinone and bisbenzimidazole based ligands. A molecular dynamics simulation study was used to examine quadruplex-ligand interactions. Analysis of the binding free energy indicated the formation of the thermodynamically favorable RNA-ligand complex. The formation of several H-bonding interactions and the change of the solvent accessible surface area (SASA) also support the effective binding of the carbazole-benzimidazole ligands with G4 RNA structures. Thus, the library screening approach has assisted in getting a structure-activity relationship for the selected small molecules toward the G-quadruplex RNA binding, which can be applied in the targeting of G-quadruplex RNA medicated anticancer therapeutics.
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http://dx.doi.org/10.1021/acs.jpcb.0c10991DOI Listing
June 2021

Inkjet-Printed Graphene Sensors for the Bedside Detection of Tear Film pH.

Transl Vis Sci Technol 2021 03;10(3):10

Department of Ophthalmology, Mayo Clinic, Rochester, MN, USA.

Purpose: To determine whether an inexpensive, graphene thin-film electronic pH sensor could be used to measure tear film pH.

Methods: The pH-sensitive electrolyte-gated graphene field-effect transistors (EG-GFETs) were fabricated by patterning graphene ink and ultraviolet-cured dielectric onto 125 µm-thick polyimide substrate using a nanomaterials inkjet printer. A flow-cell was used to exchange test solutions and record current flow through the EG-GFET. Laboratory reference pH test solutions were used to calibrate the sensor. Contrived tears with lipids were pH buffered using HCL (1 M) or NAOH (1 M) to produce tear solutions ranging in pH from 2.0 to 9.5. A laboratory-reference pH meter was used to verify the pH of each solution. Dirac curves that demonstrate pH-dependent changes in current flow through the EG-GFET were measured for each test solution, using dual sourcemeters.

Results: Graphene EG-GFET devices were highly sensitive to changes in artificial tear-film pH. The Dirac voltage was defined as the gate voltage at which minimum source drain current was measured. The relationship between Dirac voltage and tear film pH was highly linear with a slope of 17.2 mV per pH unit over the range of solutions tested, from pH 2.0 to pH 9.5 (r2 = 0.977).

Conclusions: Graphene field-effect transistors accurately measure tear film pH and may be useful in the emergency management of ocular adnexal exposure to acids or bases.

Translational Relevance: Thin-film graphene sensors are low cost and can rapidly map tear-film pH at multiple sites on the ocular surface and within the conjunctival fornices, avoiding subjective, colorimetric test-paper methods.
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http://dx.doi.org/10.1167/tvst.10.3.10DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7961110PMC
March 2021

Cancer Stem Cell-Targeted Gene Delivery Mediated by Aptamer-Decorated pH-Sensitive Nanoliposomes.

ACS Biomater Sci Eng 2021 06 19;7(6):2508-2519. Epub 2021 Apr 19.

Technical Research Centre, Indian Association for the Cultivation of Science, Kolkata 700032, India.

A new pH-responsive cationic co-liposomal formulation was prepared in this study using the twin version of the amphiphile palmitoyl homocysteine, TPHC; natural zwitterionic lipid, DOPE; and cholesterol-based twin cationic lipid, C5C, at specified molar ratios. This co-liposome was further decorated with a newly designed fluorescently tagged, cholesterol-tethered EpCAM-targeting RNA aptamer for targeted gene delivery. This aptamer-guided nanoliposomal formulation, C5C/DOPE/TPHC at 8:24:1 molar ratio, could efficiently transport the genes in response to low pH of cellular endosomes selectively to the EpCAM overexpressing cancer stem cells. This particular observation was extended using RNA against GFP to validate their transfection capabilities in response to EpCAM expression. Overall, the aptamer-guided nanoliposomal formulation was found to be an excellent transfectant for RNA gene delivery.
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http://dx.doi.org/10.1021/acsbiomaterials.1c00110DOI Listing
June 2021

Enriched pharmacokinetic behavior and antitumor efficacy of thymoquinone by liposomal delivery.

Nanomedicine (Lond) 2021 04 26;16(8):641-656. Epub 2021 Mar 26.

Applied Biology Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad, Telangana 500007, India.

Thymoquinone (TQ) has potential anti-inflammatory, immunomodulatory and anticancer effects but its clinical use is limited by its low solubility, poor bioavailability and rapid clearance. To enhance systemic bioavailability and tumor-specific toxicity of TQ. Cationic liposomal formulation of TQ (D1T) was prepared via ethanol injection method and their physicochemical properties, anticancer effects in orthotopic xenograft pancreatic tumor model and pharmacokinetic behavior of D1T relative to TQ were evaluated. D1T showed prominent inhibition of pancreatic tumor progression, significantly greater absorption, approximately 1.5-fold higher plasma concentration, higher bioavailability, reduced volume of distribution and improved clearance relative to TQ. Encapsulation of TQ in cationic liposomal formulation enhanced its bioavailability and anticancer efficacy against xenograft pancreatic tumor.
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http://dx.doi.org/10.2217/nnm-2020-0470DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8173500PMC
April 2021

Recent Update on Targeting G-Quadruplexes by Small Molecules for Anticancer Therapeutics.

J Med Chem 2021 01 23;64(1):42-70. Epub 2020 Dec 23.

School of Applied & Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata 700032, India.

Guanine-rich DNA sequences have the propensity to adopt four-stranded tetrahelical G-quadruplex (G4) structures that are overrepresented in gene promoters. The structural polymorphism and physicochemical properties of these non-Watson-Crick G4 structures make them important targets for drug development. The guanine-rich nuclease hypersensitivity element III present in the upstream of P1 promoter of oncogene has the ability to form an intramolecular parallel G4 structure. The G4 structure that forms transiently in the promoter functions as a transcriptional repressor element. The oncogene is overexpressed in a wide variety of cancers and plays a key role in cancer progression. Till now, a large number of compounds that are capable of interacting and stabilizing the G4 have been reported. In this review, we summarize various G4 specific molecules and discuss their effects on gene expression and .
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http://dx.doi.org/10.1021/acs.jmedchem.0c01145DOI Listing
January 2021

Antibody-Conjugated Vitamin E-Derived Liposomes for Targeted Gene Transfer.

ACS Appl Bio Mater 2020 Dec 29;3(12):8375-8385. Epub 2020 Nov 29.

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.

Construction of a vitamin E-based liposomal biomaterial and its ability to deliver therapeutic genes selectively across liver cancer cells are demonstrated herein. In humans, liver regulates the levels of α-tocopherol, i.e., vitamin E, and hepatic cells carry the machinery for its transport. To exploit the presence of tocopherol transport protein, we have selected an efficient gene transfecting α-tocopherol-based twin lipid bearing a hydroxyethylated headgroup and octamethylene spacer (TH8S) for liposome formation. Also, based on the abundancy of the low-density lipoprotein receptor (LDLr) on the cellular surface in the case of hepatocellular carcinoma, anti-LDLr monoclonal antibody is used to confer the targeting ability to liposomes. A facile thiol-maleimide click chemistry is used for antibody decoration on the liposomal surface. Selective delivery of reporter and therapeutic genes (GFP and p53) to cells of hepatic origin was observed using anti-LDLr-tagged TH8S liposomes. Cellular internalization by receptor-mediated endocytosis renders the bioconjugate highly specific as well as highly efficient. Compatibility of the designed material with human blood points to its safety of use in systemic circulation thereby highlighting its potential. Thus, we report here a versatile biomaterial derived from an essential vitamin that promises potential for targeted suicidal gene therapy.
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http://dx.doi.org/10.1021/acsabm.0c00656DOI Listing
December 2020

Myosin 10 Regulates Invasion, Mitosis, and Metabolic Signaling in Glioblastoma.

iScience 2020 Dec 13;23(12):101802. Epub 2020 Nov 13.

Department of Cancer Biology, Mayo Clinic, 4500 San Pablo Road, Jacksonville, FL 32224, USA.

Invasion and proliferation are defining phenotypes of cancer, and in glioblastoma blocking one stimulates the other, implying that effective therapy must inhibit both, ideally through a single target that is also dispensable for normal tissue function. The molecular motor myosin 10 meets these criteria. Myosin 10 knockout mice can survive to adulthood, implying that normal cells can compensate for its loss; its deletion impairs invasion, slows proliferation, and prolongs survival in murine models of glioblastoma. Myosin 10 deletion also enhances tumor dependency on the DNA damage and the metabolic stress responses and induces synthetic lethality when combined with inhibitors of these processes. Our results thus demonstrate that targeting myosin 10 is active against glioblastoma by itself, synergizes with other clinically available therapeutics, may have acceptable side effects in normal tissues, and has potential as a heretofore unexplored therapeutic approach for this disease.
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http://dx.doi.org/10.1016/j.isci.2020.101802DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7702012PMC
December 2020

First example of engineered β-cyclodextrinylated MEMS devices for volatile pheromone sensing of olive fruit pests.

Biosens Bioelectron 2020 Oct 18;173:112728. Epub 2020 Oct 18.

Technical Research Center, Indian Association for the Cultivation of Science, Kolkata, 700032, India; Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560012, India; School of Applied and Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata, 700032, India. Electronic address:

Olive oil is more preferred than other vegetable oils because of the increasing health concern among people throughout the world. The major hindrance in large-scale production of olive oil is olive fruit pests which cause serious economic damage to the olive orchards. This requires careful monitoring and timely application of suitable remedies before pest infestation. Herein we demonstrate efficacious utilization of covalently functionalized β-cyclodextrinylated MEMS devices for selective and sensitive detection of female sex pheromone of olive fruit pest, Bactocera oleae. Two of the MEMS devices, silicon dioxide surface-micromachined cantilever arrays and zinc oxide surface-microfabricated interdigitated circuits, have been used to selectively capture the major pheromone component, 1,7-dioxaspiro[5,5]undecane. The non-covalent capture of olive pheromones inside the β-cyclodextrin cavity leads to the reduction of resonant frequency of the cantilevers, whereas an increase in resistance has been found in case of zinc oxide derived MEMS devices. Sensitivity of the MEMS devices towards the olive pheromone was found to be directly correlated with the increasing availability of β-cyclodextrin moieties over the surface of the devices and thus the detection limit of the devices has been achieved to a value as low as 0.297 ppq of the olive pheromone when the devices were functionalized with one of the standardized protocols. Overall, the reversible usability and potential capability of the suitably functionalized MEMS devices to selectively detect the presence of female sex pheromone of olive fruit fly before the onset of pest infestation in an orchard makes the technology quite attractive for viable commercial application.
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http://dx.doi.org/10.1016/j.bios.2020.112728DOI Listing
October 2020

Breaking the Barrier of Polynucleotide Size, Type, and Topology in Smad2 Antisense Therapy Using a Cationic Cholesterol Dimer with Flexible Spacer.

ACS Appl Bio Mater 2020 Nov 19;3(11):7712-7721. Epub 2020 Oct 19.

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.

A liposomal formulation comprising a dicationic cholesterol based lipid, Chol-(CH)-Chol, and a helper zwitterionic lipid, DOPE (1:4), was prepared to deliver polynucleotides of different topologies, molecular weights, and backbones. This formulation was used to transfect HeLa cells with circular and linearized plasmid pEGFP-C3. The transfection efficiency of the dicationic cholesterol based coliposomal formulation Chol-(CH)-Chol/DOPE (1:4) was observed to be better when compared against different commercial delivery agents, Lipofectamine2000, Effectene, and a known oligonucleotide delivery agent, Oligofectamine. The efficacy was also compared with the respective monocationic cholesterol based liposomal formulations. Western blot analysis for Smad2 protein detection showed almost 100% downregulation of the Smad2 protein by polynucleotides delivered by Chol-(CH)-Chol/DOPE (1:4), which was better than that with Oligofectamine and Effectene. Similarly, semiquantitative RT-PCR showed the downregulation of Smad2 RNA along with that of a downstream target of Smad2, Id2. The higher efficiency of different types of nucleic acid delivery was also evident with Chol-(CH)-Chol/DOPE (1:4) in A549 cells. As an added benefit, the formulation Chol-(CH)-Chol/DOPE (1:4) was found to be highly biocompatible at all the compositions investigated herein.
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http://dx.doi.org/10.1021/acsabm.0c00924DOI Listing
November 2020

A two-component charge transfer hydrogel with excellent sensitivity towards the microenvironment: a responsive platform for biogenic thiols.

Soft Matter 2020 Nov 5;16(43):9882-9889. Epub 2020 Oct 5.

Department of Organic Chemistry, Indian Institute of Science, Bangalore, Karnataka 560012, India.

A two-component charge transfer (CT) hydrogel has been derived from a supramolecular heteroassembly of a pyrene amino acid conjugate (PyHisOH, donor) with a 4-chloro-7-nitrobenzofurazan (NBD-Ox, acceptor) derivative in aqueous medium. The mechanical stiffness, as well as the thermal stability of the CT hydrogels largely depend on the relative ratios of donor and acceptor units as well as on their overall concentration. Moreover, the gel-to-sol transition is found to be susceptible to various external stimuli such as heat, pH, metal ions, etc. Circular dichroism and morphological investigation reveal the formation of left-handed helical fibers in the CT gel network. XRD studies show the lamellar packing of the interactive units in the 3D network of the CT hydrogel. The determination of different rheological parameters confirms the viscoelastic as well as the thixotropic nature of the CT gel. Furthermore, the CT gel is employed for turn-on sensing of biogenic thiols, cyan fluorescence was observed with cysteine/homocysteine, while blue fluorescence with glutathione. Nucleophilic attack at the NBD moiety leads to the formation of thermodynamically stable amino-linked derivatives for cysteine or homocysteine and kinetically controlled thiol-linked adduct for glutathione. Thus, the current system presents a unique opportunity, where a CT hydrogel sample is involved for discriminating biogenic thiols via specific chemodosimetric interactions.
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http://dx.doi.org/10.1039/d0sm00502aDOI Listing
November 2020

A thermo-responsive supramolecular hydrogel that senses cholera toxin via color-changing response.

Chem Commun (Camb) 2020 Jul;56(56):7789-7792

A Department of Organic Chemistry, Indian Institute of Science, Bangalore, Karnataka 560012, India. and School of Applied & Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata 700032, India.

A Pyrene-based amphiphile with C4-alkanoyl spacer and lactose (PyLac) self-assembles in the aqueous media to form an injectable hydrogel. It shows preferential binding with Cholera Toxin (CT) via its terminal galactose residue, and hence can be employed for the selective detection of CT via color-changing response.
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http://dx.doi.org/10.1039/d0cc00839gDOI Listing
July 2020

Transparent, flexible MAPbI perovskite microwire arrays passivated with ultra-hydrophobic supramolecular self-assembly for stable and high-performance photodetectors.

Nanoscale 2020 Jun 27;12(22):11986-11996. Epub 2020 May 27.

School of Applied & Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.

The emergence of organic-inorganic hybrid perovskites (OHPs) has revolutionised the potential performance of optoelectronic devices; most perovskites are opaque and hence incompatible with transparent optoelectronics and sensitive to environmental degradation. Here, we have reported a single-step fabrication of ultra-long MAPbI perovskite microwire arrays over a large area using stencil lithography based on sequential vacuum sublimation. The environmental stability of MAPbI is empowered with a newly designed and synthesized transparent supramolecular self-assembly based on a mixture of two tripodal l-Phe-CH/CF molecules, which showed a contact angle of 105° and served as ultra-hydrophobic passivation layers for more than 45 days in an ambient atmosphere. The MAPbI microwire arrays passivated with the supramolecular self-assembly demonstrated for the first time both excellent transparency of ∼89% at 550 nm and a remarkable photoresponse with a photo-switching ratio of ∼10, responsivity of 789 A W, detectivity of 10 Jones, linear dynamic range of ∼122 dB, and rise time of 432 μs. Furthermore, the photodetector fabricated on a flexible PET substrate demonstrated robust mechanical flexibility even beyond 1200 bending cycles. Therefore, the scalable stencil lithography and supramolecular passivation approaches have the potential to deliver next-generation transparent, flexible, and stable optoelectronic devices.
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http://dx.doi.org/10.1039/d0nr01394cDOI Listing
June 2020

Specific stabilization of promoter G-Quadruplex DNA by 2,6-disubstituted amidoanthracene-9,10-dione based dimeric distamycin analogues and their selective cancer cell cytotoxicity.

Eur J Med Chem 2020 Jun 16;195:112202. Epub 2020 Mar 16.

Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560012, India; School of Applied & Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Kolkata, 700032, India. Electronic address:

We have designed and synthesized anthraquinone containing compounds which have oligopyrrole side chains of varying lengths. These compounds stabilized the G-quadruplex DNA formed in the promoter regions of c-MYC oncogenes selectively over the duplex DNA. These observations were recorded using UV-vis spectroscopic titrations, fluorescence measurements and circular dichroism (CD) spectral titrations. The potency of the compounds to stabilize the G4 DNA has been shown from the thermal denaturation experiments. The compound interacts with c-MYC G-quadruplex DNA through stacking mode as obtained from ethidium bromide displacement assay, cyclic voltammetric titration, and docking experiments. Molecular modeling studies suggested that the stacking of the anthraquinone moiety over the G-tetrad of the G4 structures are responsible for the stability of such quadruplex secondary structure. Furthermore, polymerase stop assay also supported the formation of stable G4 structures in the presence of the above-mentioned compounds. The compounds have shown selective cancer cell (HeLa and HEK293T) cytotoxicity over normal cells (NIH3T3 and HDFa) under in vitro conditions as determined from MTT based cell viability assay. Apoptosis was found to be the mechanistic pathway underlying the cancer cell cytotoxicity as obtained from Annexin V-FITC and PI dual staining assay which was further substantiated by nuclear morphological changes as observed by AO/EB dual staining assay. Cellular morphological changes, as well as nuclear condensation and fragmentation upon treatment with these compounds, were observed under bright field and confocal microscopy.
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http://dx.doi.org/10.1016/j.ejmech.2020.112202DOI Listing
June 2020

Controlled drug release from polyelectrolyte-drug conjugate nanoparticles.

J Mater Chem B 2020 04;8(14):2887-2894

NanoScience Technology Center, University of Central Florida, Orlando, Florida 32826, USA. and Department of Chemistry, University of Central Florida, Orlando, Florida 32816, USA and Department of Material Science and Engineering, University of Central Florida, Orlando, Florida 32816, USA.

Encapsulating drugs in functional nanoparticles provides controlled and targeted release of drugs. In this study, a general approach for encapsulating hydrophobic drugs in polyelectrolyte nanoparticles was developed for a controlled drug release. Gemcitabine (GEM), an anticancer drug for pancreatic ductal adenocarcinoma (PDAC), was used as a model drug to produce poly(acrylic acid) (PAA)-GEM conjugate nanoparticles to achieve a controlled release of GEM in cells. The PAA-GEM conjugate nanoparticles were fabricated by coupling GEM onto PAA through the formation of amide bonds. The hydrophobic interactions of GEM molecules induced the formation of the nanoparticles with the GEM core and PAA shell. Fabrication conditions such as the PAA/GEM ratio and pH were optimized to achieve high structure stability and drug loading efficiency. The size and surface charge of the nanoparticles were characterized by transmission electron microscopy (TEM), dynamic light scattering (DLS) and zeta potential measurement. The optimized PAA-GEM nanoparticles had a size around 12 nm, 30 nm and 60 nm in dry state, water, and phosphate buffered saline (PBS), respectively. The encapsulation efficiency was 29.29 ± 1.7%, and the loading capacity was 9.44 ± 0.46%. Less than 7% GEM was released from the PAA-GEM nanoparticles after 96 hour incubation in phosphate buffered saline. The cytotoxic efficacy of the PAA-GEM nanoparticles in cancer cells was investigated through viability studies of PANC-1, a human pancreatic cancer cell line. It was found that the PAA-GEM nanoparticles had more than a 48 hour delay of releasing GEM and had the same cytotoxic efficacy in PANC-1 cells as free GEM. The uptake of the PAA-GEM nanoparticles by PANC-1 cells was investigated using PAA-GEM labeled by rhodamine G6. Fluorescence and bright field overlay images indicated that the PAA-GEM nanoparticles were taken up by PANC-1 cells within 2 hours. It is believed that the PAA-GEM nanoparticles were decomposed in PANC-1 cells and GEM was released from the nanoparticles.
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http://dx.doi.org/10.1039/d0tb00012dDOI Listing
April 2020

Switchable Optical Probes for Simultaneous Targeting of Multiple Anions.

Chem Asian J 2020 Jun 28;15(12):1759-1779. Epub 2020 May 28.

Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560012.

Traditional optical probes primarily work on the concept of one-to-one recognition strategy. Therefore, simultaneous detection of multiple anions is difficult using this kind of sensory systems. Similarly, designing of multi-responsive array-based materials is synthetically challenging as well as difficult to optimize. Thus, researchers across the globe became interested in developing single molecular probes, capable of detecting multiple anions (or anionic biomolecules) by simultaneously activating optically distinguishable output channels. Here, the modes of interaction largely depend on the structural features of the binding sites (cleft size, number of available coordination sites etc.), characteristics of the anions (ionic radius, hydration enthalpy, basicity, coordination number, pk of corresponding acids etc.) and the microenvironment around the probe molecules (micropolarity, viscosity, dielectric constant etc.) in the host matrix. In this review, we are mostly focusing on the structure-activity relationships of such multiple anions sensing optical probes and their stimuli-responsive properties.
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http://dx.doi.org/10.1002/asia.201901811DOI Listing
June 2020

Natural tripeptide capped pH-sensitive gold nanoparticles for efficacious doxorubicin delivery both in vitro and in vivo.

Nanoscale 2020 Jan;12(2):1067-1074

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.

Nanobiotechnology has been gaining ever-increasing interest for the successful implementation of chemotherapy based treatment of cancer. Gold nanoparticles (AuNPs) capped with a natural pH-responsive short tripeptide (Lys-Phe-Gly or KFG) sequence are presented herein for significant intracellular delivery of an anti-cancer drug, doxorubicin (DOX). A particularly increased apoptotic response has been observed for DOX treatments mediated by KFG-AuNPs when compared with drug alone treatments in various cell lines (BT-474, HeLa, HEK 293 T and U251). Furthermore, KFG-AuNP mediated DOX treatment significantly decreases cell proliferation and tumor growth in a BT-474 cell xenograft model in nude mice. In addition, KFG-AuNPs demonstrate efficacious drug delivery in DOX-resistant HeLa cells (HeLa-DOXR).
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http://dx.doi.org/10.1039/c9nr08475dDOI Listing
January 2020

Gemini-Based Lipoplexes Complement the Mitochondrial Phenotype in MFN1-Knockout Mouse Embryonic Fibroblasts.

Mol Pharm 2019 12 5;16(12):4787-4796. Epub 2019 Nov 5.

Instituto de Investigación Hospital Doce de Octubre (i+12), Avenida de Córdoba s/n, 28041 Madrid, Spain.

Mitochondria form a dynamic network of constantly dividing and fusing organelles. The balance between these antagonistic processes is crucial for normal cellular function and requires the action of specialized proteins. The mitochondrial membrane proteins mitofusin 1 (Mfn1) and mitofusin 2 (Mfn2) are responsible for the fusion of the outer membrane of adjacent mitochondria. Mutations within Mfn1 or Mfn2 impair mitochondrial fusion and lead to some severe mitochondrial dysfunctions and mitochondrial diseases (MDs). A characteristic phenotype of cells carrying defective Mfn1 or Mfn2 is the presence of a highly fragmented mitochondrial network. Here, we use a biocompatible mixture of lipids, consisting on synthetic gemini cationic lipids (GCLs) and the zwitterionic phospholipid (DOPE), to complex, transport, and deliver intact copies of gene into -Knockout mouse embryonic fibroblasts (MFN1-KO MEFs). We demonstrate that the GCL/DOPE-DNA lipoplexes are able to introduce the intact gene into the cells and ectopically produce functional Mfn1. A four-fold increase of the Mfn1 levels is necessary to revert the -KO phenotype and to partially restore a mitochondrial network. This phenotype complementation was correlated with the transfection of GCL/DOPE-MFN1 lipoplexes that exhibited a high proportion of highly packaged hexagonal phase. GCL/DOPE-DNA lipoplexes are formulated as efficient therapeutic agents against MDs.
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http://dx.doi.org/10.1021/acs.molpharmaceut.9b00449DOI Listing
December 2019

Palladium-induced transformation of nematic liquid crystals to robust metallogel comprising self-assembled nanowires.

Chem Commun (Camb) 2019 Oct;55(84):12651-12654

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. and School of Applied & Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India.

The formation of a nematic liquid-crystalline phase in the bulk along with gelation of a novel asymmetric bolaamphiphilic NDI scaffold has been demonstrated. Further, a discrete metal NDI complex that is capable of forming a robust metallogel through wrapping of the NDI core with the oxyethylene chains of the neighboring molecules has been synthesized.
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http://dx.doi.org/10.1039/c9cc05517gDOI Listing
October 2019

Nanomechanical insights: Amyloid beta oligomer-induced senescent brain endothelial cells.

Biochim Biophys Acta Biomembr 2019 12 9;1861(12):183061. Epub 2019 Sep 9.

Department of Biochemistry and Molecular Biology, Mayo Clinic College of Medicine and Science, Jacksonville, FL, USA; Department of Physiology and Biomedical Engineering, Mayo Clinic College of Medicine and Science, Jacksonville, FL, USA. Electronic address:

Senescent cells accumulate in various peripheral tissues during aging and have been shown to exacerbate age-related inflammatory responses. We recently showed that exposure to neurotoxic amyloid β (Aβ1-42) oligomers can readily induce a senescence phenotype in human brain microvascular endothelial cells (HBMECs). In the present work, we used atomic force microscopy (AFM) to further characterize the morphological properties such as cell membrane roughness and cell height and nanomechanical properties such as Young's modulus of the membrane (membrane stiffness) and adhesion resulting from the interaction between AFM tip and cell membrane in Aβ1-42 oligomer-induced senescent human brain microvascular endothelial cells. Morphological imaging studies showed a flatter and spread-out nucleus in the senescent HBMECs, both characteristic features of a senescent phenotype. Furthermore, the mean cell body roughness and mean cell height were lower in senescent HBMECs compared to untreated normal HBMECs. We also observed increased stiffness and alterations in the adhesion properties in Aβ1-42 oligomer-induced senescent endothelial cells compared to the untreated normal HBMECs suggesting dynamic reorganization of cell membrane. We then show that vascular endothelial growth factor receptor 1 (VEGFR-1) knockdown or overexpression of Rho GTPase Rac 1 in the endothelial cells inhibited senescence and reversed these nanomechanical alterations, confirming a direct role of these pathways in the senescent brain endothelial cells. These results illustrate that nanoindentation and topographic analysis of live senescent brain endothelial cells can provide insights into cerebrovascular dysfunction in neurodegenerative diseases such as Alzheimer's disease.
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http://dx.doi.org/10.1016/j.bbamem.2019.183061DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6791778PMC
December 2019

New Water-Soluble Oxyamino Chitosans as Biocompatible Vectors for Efficacious Anticancer Therapy via Co-Delivery of Gene and Drug.

ACS Appl Mater Interfaces 2019 Oct 7;11(41):37442-37460. Epub 2019 Oct 7.

Among the many nonviral gene delivery vectors, chitosan, being a polysaccharide of natural origin, has gained special importance. In this report, chitosan (CS) has been solubilized in water by preparing its carboxymethyl derivative, CS(CHCOOH), with an optimum degree of carboxymethylation. This has been further derivatized to get the pyridine-substituted product (py)CS(CHCOOH), where the degree of pyridine substitution (47%) was optimized based on zeta potential measurements. The optimized formulation showed a high gene binding ability, forming nanosized positively charged polyelectrolyte complexes with DNA. These polyplexes were stable to DNase and physiological polyanions such as heparin. They also exhibited minimal toxicity in vitro and showed transfection levels comparable to the commercial standard Lipofectamine 2000 and much higher than polyethylenimine (MW, 25 kDa). Additionally, in this study, a hitherto unknown oxyamine derivative of chitosan has been prepared by phthaloyl protection, tosylation, and Gabriel's phthalimide synthesis. Nearly 40% of the primary alcohols were successfully converted to oxyamino functionality, which was used for forming oxime with the anticancer drug doxorubicin. The pH sensitivity of the oxime ether linkage and stability under biologically relevant conditions were then used to establish the compound as a versatile drug delivery vector. Co-delivery of functional gene (p53) and drug (doxorubicin) was accomplished in vitro and in vivo with the chitosan-pyridine imine vector (py)CS(CHCOOH) and the newly synthesized doxorubicin oxime ether CS(Dox). Complete tumor regression with no tumor recurrence and appreciable survivability point to the in vivo effectiveness and biocompatibility of the designed composite formulation. Overall, the pH sensitivity of the oxime linkage aiding slow and steady drug release, together with the sustained gene expression by pyridine-tethered carboxymethyl chitosan, allows us to generate a nanobiocomposite with significantly high anticancer therapeutic potential.
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http://dx.doi.org/10.1021/acsami.9b09485DOI Listing
October 2019

DNA-SWCNT Biosensors Allow Real-Time Monitoring of Therapeutic Responses in Pancreatic Ductal Adenocarcinoma.

Cancer Res 2019 09 10;79(17):4515-4523. Epub 2019 Jul 10.

Department of Biochemistry and Molecular Biology, Mayo Clinic College of Medicine and Science, Jacksonville, Florida.

Pancreatic ductal adenocarcinoma (PDAC) is a highly desmoplastic cancer with limited treatment options. There is an urgent need for tools that monitor therapeutic responses in real time. Drugs such as gemcitabine and irinotecan elicit their therapeutic effect in cancer cells by producing hydrogen peroxide (HO). In this study, specific DNA-wrapped single-walled carbon nanotubes (SWCNT), which precisely monitor HO, were used to determine the therapeutic response of PDAC cells and tumors . Drug therapeutic efficacy was evaluated by monitoring HO differences using reversible alteration of Raman G-bands from the nanotubes. Implantation of the DNA-SWCNT probe inside the PDAC tumor resulted in approximately 50% reduction of Raman G-band intensity when treated with gemcitabine versus the pretreated tumor; the Raman G-band intensity reversed to its pretreatment level upon treatment withdrawal. In summary, using highly specific and sensitive DNA-SWCNT nanosensors, which can determine dynamic alteration of hydrogen peroxide in tumor, can evaluate the effectiveness of chemotherapeutics. SIGNIFICANCE: A novel biosensor is used to detect intratumoral hydrogen peroxide, allowing real-time monitoring of responses to chemotherapeutic drugs.
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http://dx.doi.org/10.1158/0008-5472.CAN-18-3337DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6726513PMC
September 2019

Engaging Dynamic Surfactant Assemblies in Improving Metal Ion Sensitivity of a 1,4,7-Triazacyclononane-Based Receptor: Differential Optical Response for Cysteine and Histidine.

ACS Appl Bio Mater 2019 Jun 23;2(6):2365-2373. Epub 2019 May 23.

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.

Self-assembly as well as metal ion binding property of an amphiphilic, dansylated 1,4,7-triazacyclononane (TACN) probe have been investigated in the presence of various surfactant assemblies in aqueous media. As expected, the receptor molecule shows highly sensitive, but rather nonspecific, interaction with metal ions in the bulk water medium. Thus, to achieve the good specificity without dampening the sensitivity of the probe, we embedded the sensor in different surfactant assemblies, such as micelles and vesicles, and explored their metal ion sensing ability. Change in microenvironment by restricting conformational mobility and increasing local hydrophobicity renders a drastic improvement in selectivity and also sensitivity toward Cu. Further, the preformed Cu complex of the probe was utilized for exclusive "turn-on" detection of both cysteine (green fluorescence) and histidine (blue fluorescence). The diverse complexation mode of interactions with these amino acids caused a distinct change in the monomer to aggregate ratio, which was reflected in different spectral response. Furthermore, the dansylated probe was involved in developing reusable paper strips for rapid on-site detection of both Cu and cysteine.
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http://dx.doi.org/10.1021/acsabm.9b00083DOI Listing
June 2019

Tumor Chemosensitization through Oncogene Knockdown Mediated by Unique α-Tocopherylated Cationic Geminis.

Biomacromolecules 2019 04 25;20(4):1555-1566. Epub 2019 Mar 25.

Department of Organic Chemistry , Indian Institute of Science , Bangalore 560012 , India.

Herein, siRNA transfection efficiency of a unique set of α-tocopherylated gemini lipids has been established in vitro and in vivo. High efficacy of oncogene silencing achieved using the biomacromolecular assembly, formed from siRNA complexes of co-liposomes containing an α-tocopherylated gemini lipid, has been utilized for tumor regression via chemosensitization. Delivery studies with the gemini bearing hydroxyethyl headgroup with octamethylene spacer (TH8S) pointed to a higher siRNA transfection efficacy than its analog without hydroxyethyl group (T8S). Owing to p53 upregulation, transfected cells showed enhanced sensitivity to the chemotherapeutic agent, doxorubicin. Studies in murine model revealed significantly low levels of survivin mRNA in xenograft tumors injected with siRNA lipoplexes, leading to effective inhibition of tumor growth and an increase in sensitivity of the tumors toward doxorubicin. These findings enable us to propose the anti-survivin siRNA carrying TH8S co-liposomes as a potent member of cancer management strategies using suicide gene therapy.
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http://dx.doi.org/10.1021/acs.biomac.8b01751DOI Listing
April 2019
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