3,287 results match your criteria moiety bind

Identification of peroxiredoxin 6 as a direct target of withangulatin A by quantitative chemical proteomics in non-small cell lung cancer.

Redox Biol 2021 Sep 9;46:102130. Epub 2021 Sep 9.

Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 210009, China. Electronic address:

Peroxiredoxin 6 (PRDX6), as a bifunctional enzyme with glutathione peroxidase activity (GPx) and Ca2-independent phospholipase A2 (iPLA2) activity, has a higher expression in various cancer cells, which leads to the increase of antioxidant properties and promotes tumorigenesis. However, only a few inhibitors of PRDX6 have been discovered to date, especially the covalent inhibitors of PRDX6. Here, we firstly identified Withangulatin A (WA), a natural small molecule, as a novel covalent inhibitor of PRDX6. Read More

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September 2021

Supramolecular Reorientation During Deposition Onto Metal Surfaces of Quasi-Two-Dimensional Langmuir Monolayers Composed of Bifunctional Amphiphilic, Twisted Perylenes.

Langmuir 2021 Sep 10. Epub 2021 Sep 10.

Leibniz Institute of Photonic Technology (Leibniz-IPHT), Albert-Einstein-Str. 9, 07745 Jena, Germany.

Supramolecular dye structures, which are often ruled by π-π interactions between planar chromophores, crucially determine the optoelectronic properties of layers and interfaces. Here, we present the interfacial assembly of perylene monoanhydride and monoimide that do not feature a planar chromophore but contain chlorine substituents in the bay positions to yield twisted chromophores and hence modified π-stacking. The assembly of the twisted perylene monoanhydride and monoimide is driven by their amphiphilicity that ensures proper Langmuir layer formation. Read More

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September 2021

An Activity-Based Probe for Cathepsin K Imaging with Excellent Potency and Selectivity.

J Med Chem 2021 Sep 2. Epub 2021 Sep 2.

Pharmaceutical Institute, Pharmaceutical & Medicinal Chemistry, University of Bonn, An der Immenburg 4, Bonn 53121, Germany.

The cysteine protease cathepsin K is a target for the treatment of diseases associated with high bone turnover. Cathepsin K is mainly expressed in osteoclasts and responsible for the destruction of the proteinaceous components of the bone matrix. We designed various fluorescent activity-based probes (ABPs) and their precursors that bind to and inactivate cathepsin K. Read More

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September 2021

Structural and functional characterization of ubiquitin variant inhibitors for the JAMM-family deubiquitinases STAMBP and STAMBPL1.

J Biol Chem 2021 Aug 20:101107. Epub 2021 Aug 20.

Department of Molecular and Cellular Biology, College of Biological Science, University of Guelph, Guelph, N1G 2W1, Canada; CIFAR Azrieli Global Scholars program, Canadian Institute for Advanced Research, Toronto, M5G 1M1, Canada. Electronic address:

Ubiquitination is a crucial post-translational protein modification involved in a myriad of biological pathways. This modification is reversed by deubiquitinases (DUBs) that deconjugate the single ubiquitin (Ub) moiety or poly-Ub chains from substrates. In the past decade, tremendous efforts have been focused on targeting DUBs for drug discovery. Read More

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Conoidecyclics A-C from marine macroalga Turbinaria conoides: Newly described natural macrolides with prospective bioactive properties.

Phytochemistry 2021 Nov 19;191:112909. Epub 2021 Aug 19.

Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P.B. No. 1603, Cochin, Kerala State, India; Department of Chemistry, Mangalore University, Mangalagangothri, 574199, Karnataka State, India.

Intertidal marine brown alga Turbinaria conoides (J.Agardh) Kützing (family Sargassaceae) is considered as one of the largely abundant species, available in the coastal zones of the Indian subcontinent. Bioactivity-guided chromatographic fractionation of the organic extract of T. Read More

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November 2021

Cannabinoid receptor interacting protein 1a interacts with myristoylated Gα N terminus via a unique gapped β-barrel structure.

J Biol Chem 2021 Aug 19;297(3):101099. Epub 2021 Aug 19.

Department of Biochemistry and Center for Structural Biology, Wake Forest School of Medicine, Winston-Salem, North Carolina, USA; Center for Molecular Signaling, Wake Forest University, Winston-Salem, North Carolina, USA. Electronic address:

Cannabinoid receptor interacting protein 1a (CRIP1a) modulates CB cannabinoid receptor G-protein coupling in part by altering the selectivity for Gα subtype activation, but the molecular basis for this function of CRIP1a is not known. We report herein the first structure of CRIP1a at a resolution of 1.55 Å. Read More

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Discovery of novel thiophene derivatives as potent neuraminidase inhibitors.

Eur J Med Chem 2021 Aug 13;225:113762. Epub 2021 Aug 13.

Wuhan Yangene Biological Technology Co, LTD, Yuechuang Center of Huazhong Agricultural University, Wuhan, 430070, Hubei, China.

Neuraminidase (NA) is an important target for the treatment of influenza. In this study, a new lead NA inhibitor, 4 (ZINC01121127), was discovered by pharmacophore-based virtual screening and molecular dynamic (MD) simulation. Some novel NA inhibitors containing thiophene ring were synthesized by optimizing the skeleton of the lead compound 4. Read More

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A Density Functional Theory Study on Comparing the Reactivity of [Mn(13-TMC)(OOH)] and [Mn(13-TMC)(O)] for the Sulfoxidation of Thioanisole: Elucidation of Substrate and Non-Redox Metal Ion Effects.

Inorg Chem 2021 Sep 19;60(17):13615-13625. Epub 2021 Aug 19.

Department of Chemistry, Central University of Tamil Nadu, Neelakudi, Thiruvarur 610 005, India.

The reactivities of [Mn(13-TMC)(OOH)] () and [Mn(13-TMC)(O)] () in the sulfoxidation of thioanisole have been compared using density functional theory methods. The orientation of the 13-TMC ligand and substrate and non-redox metal ion effects have been considered to improve the oxidation efficiency of and . In , the - and orientation of the 13-TMC ligand do not change the coordination of the Mn ion. Read More

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September 2021

Number of galloyl moiety and intramolecular bonds in galloyl-based polyphenols affect their interaction with alpha-glucosidase.

Food Chem 2022 Jan 20;367:129846. Epub 2021 Apr 20.

College of Food Science and Engineering, Northwest A & F University, Yangling, Shaanxi 712100, PR China. Electronic address:

The inhibition of α-glucosidase by nine galloyl-based polyphenols with free and unfree galloyl moieties (GMs) was studied. The results show that the inhibitory activity increased with the free GM number increasing. For the compounds with unfree GMs, ellagic acid and hexahydroxydiphenoyl group contributed to the enzyme inhibition. Read More

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January 2022

Engineering Endogenous Tumor-Associated Macrophage-Targeted Biomimetic Nano-RBC to Reprogram Tumor Immunosuppressive Microenvironment for Enhanced Chemo-Immunotherapy.

Adv Mater 2021 Aug 13:e2103497. Epub 2021 Aug 13.

School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, P. R. China.

Immunotherapy has shown encouraging results in various cancers, but the response rates are relatively low due to the complex tumor immunosuppressive microenvironment (TIME). The presence of tumor-associated macrophages (TAMs) and tumor hypoxia correlates significantly with potent immunosuppressive activity. Here, a hemoglobin-poly(ε-caprolactone) (Hb-PCL) conjugate self-assembled biomimetic nano red blood cell (nano-RBC) system (V(Hb)) is engineered to deliver chemotherapeutic doxorubicin (DOX) and oxygen for reprogramming TIME. Read More

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Substrate specificity and conformational flexibility properties of the Mycobacterium tuberculosis β-oxidation trifunctional enzyme.

J Struct Biol 2021 09 8;213(3):107776. Epub 2021 Aug 8.

Faculty of Biochemistry and Molecular Medicine, University of Oulu, Oulu, Finland. Electronic address:

The Mycobacterium tuberculosis trifunctional enzyme (MtTFE) is an αβ tetrameric enzyme. The α-chain harbors the 2E-enoyl-CoA hydratase (ECH) and 3S-hydroxyacyl-CoA dehydrogenase (HAD) activities and the β-chain provides the 3-ketoacyl-CoA thiolase (KAT) activity. Enzyme kinetic data reported here show that medium and long chain enoyl-CoA molecules are preferred substrates for MtTFE. Read More

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September 2021

Binding of Tetracyclines to TetR Involves Two Arginines as Specificity Determinants.

Front Microbiol 2021 19;12:711158. Epub 2021 Jul 19.

Institute of Biochemistry, Goethe-University Frankfurt, Frankfurt, Germany.

is an important nosocomial pathogen that requires thoughtful consideration in the antibiotic prescription strategy due to its multidrug resistant phenotype. Tetracycline antibiotics have recently been re-administered as part of the combination antimicrobial regimens to treat infections caused by . We show that the TetA(G) efflux pump of AYE confers resistance to a variety of tetracyclines including the clinically important antibiotics doxycycline and minocycline, but not to tigecycline. Read More

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Selective MOR activity of DAPEA and Endomorphin-2 analogues containing a (R)-γ-Freidinger lactam in position two.

Bioorg Chem 2021 Jul 28;115:105219. Epub 2021 Jul 28.

Department of Pharmacy, University G. d'Annunzio Chieti, Via dei Vestini 31, 66100 Chieti, Italy.

The use of α-amino-γ lactam of Freidinger (Agl) may serve as an impressive method to increase the biological stability of peptides and an appropriate tool to elucidate their structure-activity relationships. The endomorphin-2 (EM-2) and [D-Ala, des-Leu] enkephalin amide (DAPEA) are two linear opioid tetrapeptides agonists of MOR and MOR/DOR respectively. Herein, we investigated the influence of the incorporation of (R/S)-Agl in position 2 and 3 on the biological profile of the aforementioned products in vitro and in vivo. Read More

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Galectin-3 promotes noncanonical inflammasome activation through intracellular binding to lipopolysaccharide glycans.

Proc Natl Acad Sci U S A 2021 Jul;118(30)

Taiwan International Graduate Program in Molecular Medicine, National Yang-Ming University, Taipei 11221, Taiwan;

Cytosolic lipopolysaccharides (LPSs) bind directly to caspase-4/5/11 through their lipid A moiety, inducing inflammatory caspase oligomerization and activation, which is identified as the noncanonical inflammasome pathway. Galectins, β-galactoside-binding proteins, bind to various gram-negative bacterial LPS, which display β-galactoside-containing polysaccharide chains. Galectins are mainly present intracellularly, but their interactions with cytosolic microbial glycans have not been investigated. Read More

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Case Study 9: Probe-Dependent Binding Explains Lack of CYP2C9 Inactivation by 1-Aminobenzotriazole (ABT).

Methods Mol Biol 2021 ;2342:765-779

Nonclinical Development, Plexxikon Inc., Berkeley, CA, USA.

The potential for new chemical entities to inhibit the major cytochrome P450 (CYP) isoforms is routinely evaluated to minimize the risk of developing drugs with drug-drug interaction liabilities. CYP inhibition assays are routinely performed in a high-throughput format to efficiently screen large numbers of compounds. In evaluating a time-saving assay using diclofenac as the CYP2C9 probe substrate, a discrepancy was observed in which minimal inhibition was detected using diclofenac whereas using (S)-warfarin resulted in potent inhibition, supporting the presence of dual-binding sites in the relatively large CYP2C9 active site cavity. Read More

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Argentivorous Molecules with Oxyethylene Chains in Side-Arms: Silver Ion-Induced Selectivity Changes toward Alkali Metal Ions.

Inorg Chem 2021 Aug 13;60(15):11320-11327. Epub 2021 Jul 13.

Department of Chemistry, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.

Argentivorous molecules with mono, di, tri, tetra, and penta-oxyethylene chains in aromatic side-arms were prepared (-). Titration experiments using proton nuclear magnetic resonance and cold electrospray ionization (cold-spray ionization, CSI) mass spectrometry showed that silver ions were trapped in the cyclen moiety and the arranged oxyethylene chains of the side-arms when two equivalents of silver ions were added. The silver complexes formed by adding one equivalent of silver ion to - bind alkali metal ions using the oxyethylene chains; alkali metal ion-induced CSI mass spectral changes of - were measured in the absence and presence of silver ions to compare the binding properties of the ligand for Li, Na, and K ions. Read More

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Bioinspired Luminescent Europium-Based Probe Capable of Discrimination between Ag and Cu.

Inorg Chem 2021 Jul 8;60(14):10791-10798. Epub 2021 Jul 8.

Université Grenoble Alpes, CNRS, CEA, IRIG, LCBM (UMR 5249), 38000 Grenoble, France.

Due to their similar coordination properties, discrimination of Cu and Ag by water-soluble luminescent probes is challenging. We have synthesized LCC4, an 18 amino acid cyclic peptide bearing a europium complex, which is able to bind one Cu or Ag ion by the side chains of two methionines, a histidine and a 3-(1-naphthyl)-l-alanine. In this system, the naphthyl moiety establishes a cation-π interaction with these cations. Read More

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Cellular binding and uptake of fluorescent glucose analogs 2-NBDG and 6-NBDG occurs independent of membrane glucose transporters.

Biochimie 2021 Jul 2;190:1-11. Epub 2021 Jul 2.

Calvin University, Department of Chemistry & Biochemistry, 1726 Knollcrest Circle SE, Grand Rapids, MI 49546, USA. Electronic address:

The classical methods for determining glucose uptake rates in living cells involve the use of isotopically labeled 2-deoxy-d-glucose or 3-O-methyl-d-glucose, which enter cells via well-characterized membrane transporters of the SLC2A and SLC5A families, respectively. These classical methods, however, are increasingly being displaced by high-throughput assays that utilize fluorescent analogs of glucose. Among the most commonly used of these analogs are 2-NBDG and 6-NBDG, which contain a bulky 7-nitro-2,1,3-benzoxadiazol-4-yl-amino moiety in place of a hydroxy group on d-glucose. Read More

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Amphiphilic Distyrylbenzene Derivatives as Potential Therapeutic and Imaging Agents for Soluble and Insoluble Amyloid β Aggregates in Alzheimer's Disease.

J Am Chem Soc 2021 Jul 2;143(27):10462-10476. Epub 2021 Jul 2.

Department of Chemistry, Beckman Institute for Advanced Science and Technology, The Neuroscience Program, University of Illinois at Urbana-Champaign, 600 S. Mathews Avenue, Urbana, Illinois 61801, United States.

Alzheimer's Disease (AD) is the most common neurodegenerative disease, and efficient therapeutic and early diagnostic agents for AD are still lacking. Herein, we report the development of a novel amphiphilic compound, LS-4, generated by linking a hydrophobic amyloid-binding distyrylbenzene fragment with a hydrophilic triazamacrocycle, which dramatically increases the binding affinity toward various amyloid β (Aβ) peptide aggregates, especially for soluble Aβ oligomers. Moreover, upon the administration of LS-4 to 5xFAD mice, fluorescence imaging of LS-4-treated brain sections reveals that LS-4 can penetrate the blood-brain barrier and bind to the Aβ oligomers . Read More

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Structural Insights into the Interactions of Digoxin and Na/K-ATPase and Other Targets for the Inhibition of Cancer Cell Proliferation.

Molecules 2021 Jun 16;26(12). Epub 2021 Jun 16.

Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.

Digoxin is a cardiac glycoside long used to treat congestive heart failure and found recently to show antitumor potential. The hydroxy groups connected at the C-12, C-14, and C-3'a positions; the C-17 unsaturated lactone unit; the conformation of the steroid core; and the C-3 saccharide moiety have been demonstrated as being important for digoxin's cytotoxicity and interactions with Na/K-ATPase. The docking profiles for digoxin and several derivatives and Na/K-ATPase were investigated; an additional small Asn130 side pocket was revealed, which could be useful in the design of novel digoxin-like antitumor agents. Read More

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Crystal structure of human brain-type fatty acid-binding protein FABP7 complexed with palmitic acid.

Ki Hyun Nam

Acta Crystallogr D Struct Biol 2021 Jul 29;77(Pt 7):954-965. Epub 2021 Jun 29.

Department of Life Science, Pohang University of Science and Technology, Pohang, Republic of Korea.

The brain-type fatty acid-binding protein FABP7, which is expressed in astrocytes and neural progenitors, is a member of the intracellular lipid-binding protein family. This protein is not only involved in various cellular functions such as metabolism, inflammation and energy homeostasis, but also in diseases such as cognitive disorders and tumors. Structures of unsaturated fatty acids, such as oleic acid (OA) and docosahexaenoic acid (DHA), bound to FABP7 have been elucidated; however, structures of saturated fatty acids bound to FABP7 remain unknown. Read More

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Mucin Binding to Moraxella catarrhalis During Airway Inflammation is Dependent on Sialic Acid.

Am J Respir Cell Mol Biol 2021 Jun 30. Epub 2021 Jun 30.

University of Gothenburg Sahlgrenska Academy, 70712, Biomedicine, Goteborg, Sweden;

Chronic obstructive pulmonary disease (COPD) is associated with colonization by bacterial pathogens and repeated airway infections, leading to exacerbations and impaired lung function. The highly glycosylated mucins in the mucus lining the airways are an important part of the host defense against pathogens. However, mucus accumulation can contribute to COPD pathology. Read More

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Structure-Activity Relationship Analysis of Cocrystallized Gliptin-like Pyrrolidine, Trifluorophenyl, and Pyrimidine-2,4-Dione Dipeptidyl Peptidase-4 Inhibitors.

J Med Chem 2021 Jul 30;64(14):9639-9648. Epub 2021 Jun 30.

Department of Chemistry, Faculty of Medicine, University of Nis, Bulevar Dr Zorana Djindjica 81, 18000 Nis, Serbia.

Approved and potent reported dipeptidyl peptidase-4 (DPP-4) inhibitors with gliptin-like structures are classified here according to their structures and mechanisms of the inhibition in three groups: (i) those with pyrrolidine or analogs as P1 fragment with α-aminoacyl linker, (ii) structures with trifluorophenyl moiety or analogs as P1 fragment with β-aminobutanoyl linker, and (iii) DPP-4 inhibitors with pyrimidine-2,4-dione or analogs as P1' fragment. The structure-activity relationship analysis was performed for those whose cocrystallized structures with the enzyme were published. While inhibitors with pyrrolidine and trifluorophenyl moiety or analogs as P1 fragment bind in a similar way in S1, S2 and S2 extensive domains of the enzyme, the binding mode of pyrimidine-2,4-dione derivatives/analogs differs with additional interactions in S1' and S2' pockets. Read More

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Analysis of ligand binding and resulting conformational changes in pyrophosphatase NUDT9.

FEBS J 2021 Jun 30. Epub 2021 Jun 30.

The Hamburg Advanced Research Center for Bioorganic Chemistry (HARBOR) & Department of Chemistry, Institute for Biochemistry and Molecular Biology, University of Hamburg, Germany.

Nudix hydrolase 9 (NUDT9) is a member of the nucleoside linked to another moiety X (NUDIX) protein superfamily, which hydrolyses a broad spectrum of organic pyrophosphates from metabolic processes. ADP-ribose (ADPR) has been the only known endogenous substrate accepted by NUDT9 so far. The Ca -permeable transient receptor potential melastatin subfamily 2 (TRPM2) channel contains a homologous NUDT9-homology (NUDT9H) domain and is activated by ADPR. Read More

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Synthesis and immunological effects of C14-linked 4,5-epoxymorphinan analogues as novel heroin vaccine haptens.

RSC Chem Biol 2021 Apr 19;2(3):835-842. Epub 2021 Apr 19.

Drug Design and Synthesis Section, Molecular Targets and Medications Discovery Branch, Intramural Research Program, National Institute on Drug Abuse and The National Institute on Alcohol Abuse and Alcoholism, National Institutes of Health, Department of Health and Human Services 9800 Medical Center Drive Bethesda MD 20892-3373 USA +1 301-451-4799 +1 301-451-5028.

Active immunization is being explored as a potential therapeutic to combat accidental overdose and to mitigate the abuse potential of opioids. Hapten design is one of the crucial factors that determines the efficacy of a candidate vaccine to substance abuse and remains one of the most active areas of research in vaccine development. Herein we report for the first time the synthesis of three novel opiate surrogates with the linker attachment site at C14, (6,14-AmidoHap), (14-AmidoMorHap), and (14-AmidoHerHap) as novel heroin haptens. Read More

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A Novel Strategy for Caries Management: Constructing an Antibiofouling and Mineralizing Dual-Bioactive Tooth Surface.

ACS Appl Mater Interfaces 2021 Jul 22;13(26):31140-31152. Epub 2021 Jun 22.

Paediatric Dentistry and Orthodontics, Faculty of Dentistry, The University of Hong Kong, 34 Hospital Road, Hong Kong SAR 999077, China.

Existing single-functional agents against dental caries are inadequate in antibacterial performance or mineralization balance. This problem can be resolved through a novel strategy, namely, the construction of an antibiofouling and mineralizing dual-bioactive tooth surface by grafting a dentotropic moiety to an antimicrobial peptide. The constructed bioactive peptide can strongly adsorb onto the tooth surface and has beneficial functions in a myriad of ways. Read More

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Unravelling the microhydration frameworks of prototype PAH by infrared spectroscopy: naphthalene-(water).

Phys Chem Chem Phys 2021 Jun;23(25):14016-14026

Lehrstuhl für Physikalische Chemie II, Ruhr-Universität Bochum, 44801, Bochum, Germany.

Hydration of aromatic molecules is a fundamental chemical process. Herein, microhydration framework of the prototypical neutral polycyclic aromatic hydrocarbon (PAH), naphthalene (naphthalene-(water)n≤3), is investigated by infrared spectroscopy inside helium nanodroplets. The measured data are analyzed by quantum chemical calculations at the MP2/6-311++G(d,p) level. Read More

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The structure of isolated thalidomide as reference for its chirality-dependent biological activity: a laser-ablation rotational study.

Phys Chem Chem Phys 2021 Jun;23(24):13705-13713

Departamento de Química Física y Química Inorgánica, Facultad de Ciencias, IU CINQUIMA, Universidad de Valladolid, 47011 Valladolid, Spain.

Thalidomide is a drug that presents two enantiomers with markedly different pharmacological and toxicological activities. It is sadly famous due to its teratogenic effects mostly caused by the preferential docking of the (S)-enantiomer to the target protein cereblon (CRBN). To compare the structure of the bound CRBN thalidomide enantiomers with that of the isolated molecule, the rotational spectrum of laser-ablated thalidomide has been studied by chirp-pulsed Fourier transform microwave spectroscopy in supersonic jets complemented by theoretical computations. Read More

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Nanogold Functionalized With Lipoamide-DGR: A Simple, Robust and Versatile Nanosystem for αvβ3-Integrin Targeting.

Front Chem 2021 28;9:690357. Epub 2021 May 28.

Tumor Biology and Vascular Targeting Unit, Division of Experimental Oncology, IRCCS San Raffaele Scientific Institute, Milan, Italy.

Gold nanoparticles functionalized with DGR, a tripeptide motif that recognizes αvβ3 integrin overexpressed in tumor vessels, have been used as nano-vectors for the delivery of cytokines to tumors. Functionalization of nanogold with this peptide has been achieved by coating nanoparticles with a peptide-albumin conjugate consisting of heterogeneous molecules with a variable number of linkers and peptides. To reduce nanodrug heterogeneity we have designed, produced and preclinically evaluated a homogeneous and well-defined reagent for nanogold functionalization, consisting of a head-to-tail cyclized CGDGRG peptide () coupled its thiol group to maleimide-PEG-lipoamide (LPA). Read More

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