Search our Database of Scientific Publications and Authors

I’m looking for a

    5447 results match your criteria Bioconjugate Chemistry [Journal]

    1 OF 109

    Thiodigalactoside-BSA-Conjugates as High-Potency Inhibitors of Ga-lectin-3: An Outstanding Example of Multivalent Presentation of Small Molecule Inhibitors.
    Bioconjug Chem 2018 Feb 23. Epub 2018 Feb 23.
    Galectin inhibitors are urgently needed to understand the mode of action and druggability of different galectins, but potent and selective agents still eludes researchers to date. Small-sized inhibitors based on thiodigalactoside (TDG) have shown their potential while modifications at their C3 position indicated a strategy to improve selectivity and potency. Considering the role of galectins as a glycoprotein traffic police, involved in multivalent bridging interac-tions, we aimed to create multivalent versions of the potent TDG inhibitors. Read More

    Synthesis of High Relaxivity Gadolinium AAZTA Tetramers as Building Blocks for Bioconjugation.
    Bioconjug Chem 2018 Feb 22. Epub 2018 Feb 22.
    Molecular imaging requires the specific accumulation of contrast agents at the target. To exploit the superb resolution of MRI for applications in molecular imaging, gadolinium chelates, as the MRI contrast agents (CA), have to be conjugated to a specific vector able to recognize the epitope of interest. Several Gd(III)-chelates can be chemically linked to the same binding vector in order to deliver multiple copies of the CA (multimers) in a single targeting event thus increasing the sensitivity of the molecular probe. Read More

    Release of Terminal Alkynes via Tandem Photodeprotection-Decarboxylation of o-Nitrobenzyl Arylpropiolates in a flow microchannel reactor.
    Bioconjug Chem 2018 Feb 21. Epub 2018 Feb 21.
    Photocleavable protecting groups (PPGs) offer a complementary protection paradigm compared to traditional protection groups. Herein, o-nitrobenzyl (NB) PPG was employed to protect a variety of arylpropiolic acids. Upon a cascade of light-triggered photodeprotection in a microchannel reactor (residence time 100-500 s), followed by Cu-catalyzed decarboxylation at 60 °C, the NB-protected arylpropiolic acid afforded a terminal alkyne. Read More

    Enhanced Cellular Ablation by Attenuating Hypoxia Status and Reprogramming Tumor-Associated Macrophages via NIR Light-Responsive Upconversion Nanocrystals.
    Bioconjug Chem 2018 Feb 21. Epub 2018 Feb 21.
    Near-infrared (NIR) light-mediated photodynamic therapy (PDT) especially based on lanthanide-doped upconversion nanocrystals (UCNs), have been extensively investigated as a promising strategy for effective cellular ablation owing to their unique optical properties to convert NIR light excitation into multiple short-wavelength emissions. Despite the deep tissue penetration of NIR light in living systems, the therapeutic efficiency is greatly restricted by insufficient oxygen supply in hypoxic tumor microenvironment. Moreover, the coexistent tumor-associated macrophages (TAMs) play critical roles in tumor recurrence during post-PDT period. Read More

    Nano-assembly of Pamitoyl-bioconjugated Co-Enzyme-A for Combinatorial Chemo-Biologics in Transcriptional Therapy.
    Bioconjug Chem 2018 Feb 21. Epub 2018 Feb 21.
    Pathogenesis of many cancer is driven by the Myc oncoprotein, its dimerization with Max, and the binding of this heterodimer to E-Boxes of target genes. The systemic effectiveness of potent small molecule inhibitors of Myc-Max dimerization has been lim-ited by poor bioavailability, rapid metabolism, and inadequate target site penetration. The potential of gene therapy for target-ing Myc can be fully realized by successful synthesis of a smart cargo. Read More

    Synthesis and evaluation of a novelCu/Ga-labeled neurokinin 1 receptor antagonist for in vivo targeting of NK1R-positive tumor xenografts.
    Bioconjug Chem 2018 Feb 21. Epub 2018 Feb 21.
    Neurokinin 1 receptor (NK1R) is expressed in gliomas and neuroendocrine malignancies, and represents a promising target for molecular imaging and targeted radionuclide therapy. The goal of this study was to synthesize and evaluate a novel NK1R ligand (NK1R-NOTA) for targeting NK1R-expressing tumors. Using carboxymethyl moiety linked to L-733060 as starting reagent, NK1R-NOTA was synthesized in a 3-step reaction, and then labeled withCu (orGa for in vitro studies) in the presence of CHCOONHbuffer. Read More

    Light-Switchable Ion Channels and Receptors for Optogenetic Interrogation of Neuronal Signaling.
    Bioconjug Chem 2018 Feb 21. Epub 2018 Feb 21.
    Department of Molecular and Cell Biology, University of California, Berkeley , 121 Life Sciences Addition, Berkeley, California 94720, United States.
    Optogenetics is an emerging technique that enables precise and specific control of biological activities in defined space and time. This technique employs naturally occurring or engineered light-responsive proteins to manipulate the physiological processes of the target cells. To better elucidate the molecular bases of neural functions, substantial efforts have been made to confer light sensitivity onto ion channels and neurotransmitter receptors that mediate signaling events within and between neurons. Read More

    Structure-property relationships of amphiphilic nanoparticles that penetrate or fuse lipid membranes.
    Bioconjug Chem 2018 Feb 21. Epub 2018 Feb 21.
    The development of synthetic nanomaterials that could embed within, penetrate, or induce fusion between membranes without permanent disruption would have great significance for biomedical applications. Here we describe structure-function relationships of highly water-soluble gold nanoparticles comprised of a ~1.5-5 nm diameter metal core coated by an amphiphilic organic ligand shell, which exhibit membrane embedding and fusion activity mediated by the surface ligands. Read More

    18F-AlF Labeled Peptide and Protein Conjugates as Positron Emission Tomography (PET) Imaging Pharmaceuticals.
    Bioconjug Chem 2018 Feb 21. Epub 2018 Feb 21.
    The clinical applications of PET imaging pharmaceuticals have increased tremendously over the last several years since the approval of 18F-FDG (18fluorine-fluorodeoxyglucose) by the Food and Drug Administration (FDA). Numerous 18F-labeled target-specific potential imaging pharmaceuticals, based on small and large molecules, have been evaluated in preclinical and clinical settings. 18F-labeling of organic moieties involves the introduction of the radioisotope by C-18F bond formation via a nucleophilic or an electrophilic substitution reaction. Read More

    Protein-Mediated Shape-Control of Silver Nanoparticles.
    Bioconjug Chem 2018 Feb 20. Epub 2018 Feb 20.
    Silver nanoparticles were grown in aqueous solution, without the presence of typical surfactant molecules, but under the presence of different proteins. The shape of the resulting silver nanoparticles could be tuned by the selection of the types of proteins. The amount of accessible lysine groups was found to be mainly responsible for the anisotropy in nanoparticle formation. Read More

    Autofluorescence-free Live-cell Imaging Using Terbium Nanoparticles.
    Bioconjug Chem 2018 Feb 20. Epub 2018 Feb 20.
    Fluorescent nanoparticles (NPs) have become irreplaceable tools for advanced cellular and sub-cellular imaging. While very bright NPs require excitation with UV or visible light, which can create strong autofluorescence of biological components, NIR-excitable NPs without autofluorescence issues exhibit much lower brightness. Here, we show the application of a new type of surface-photosensitized terbium NPs (Tb-NPs) for autofluorescence-free intracellular imaging in live HeLa cells. Read More

    Filomicelles deliver a chemo-differentiation combination of Paclitaxel and Retinoic Acid that durably represses carcinomas in liver to prolong survival.
    Bioconjug Chem 2018 Feb 16. Epub 2018 Feb 16.
    Drug resistance and relapse is common in cancer treatments with chemotherapeutics, and while drug combinations with naturally occurring, differentiation-inducing retinoic acid (RA) are highly successful against one type of liquid tumor, solid tumors present major problems for delivery. Here, inspired by filoviruses that can be microns in length, flexible filomicelles that self-assemble from an amphiphilic block copolymer (PEG-PCL) are shown to effectively deliver RA and paclitaxel (TAX) to several solid tumor models, particularly in liver. These hydrophobic compounds synergistically load into the cores of the elongated micelles, and the co-loaded micelles prove most effective at causing cell death, ploidy, and durable regression of tumors compared to free drugs or to separately loaded drugs. Read More

    Fluorescence Imaging of Huntingtin mRNA Knockdown.
    Bioconjug Chem 2018 Feb 16. Epub 2018 Feb 16.
    Huntington's disease (HD) is an autosomal-dominant neurodegenerative genetic disorder caused by CAG repeat expansion in exon 1 of the HTT gene. Expression of the mutant gene results in the production of a neurotoxic polyglutamine (polyQ)-expanded huntingtin (Htt) protein. Clinical trials of knockdown therapy of mutant polyglutamine-encoding HTT mRNA in Huntington's disease (HD) have begun. Read More

    A rapid, stoichiometric, site-specific modification of aldehyde-containing proteins using a tandem Knoevenagel-intra Michael addition reaction.
    Bioconjug Chem 2018 Feb 15. Epub 2018 Feb 15.
    A site-specific modification of aldehyde-containing proteins using a tandem Knoevenagel-intra Michael addition reaction was developed. The reaction featured fast kinetics (50 M-1s-1) and favorable stoichiometry. Various functionalities could be introduced into the protein with little impact on its function and conformation. Read More

    New mechanism for release of endosomal contents: osmotic lysis via nigericin-mediated K/Hexchange.
    Bioconjug Chem 2018 Feb 15. Epub 2018 Feb 15.
    Although peptides, antibodies/antibody fragments, siRNAs, antisense DNAs, enzymes and aptamers are all under development as possible therapeutic agents, the breadth of their applications has been severely compromised by their inability to reach intracellular targets. Thus, while macromolecules can often enter cells by receptor-mediated endocytosis, their missions frequently fail due to an inability to escape their entrapping endosomes. In this paper, we describe a general method for promoting release of any biologic material from any entrapping endosome. Read More

    Vinylboronic Acids as Efficient Bioorthogonal Reactants for Tetrazine Labeling in Living Cells.
    Bioconjug Chem 2018 Feb 19. Epub 2018 Feb 19.
    Department of Biomolecular Chemistry, Institute for Molecules and Materials, Radboud University , Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
    Bioorthogonal chemistry can be used for the selective modification of biomolecules without interfering with any other functionality present in the cell. The tetrazine ligation is very suitable as a bioorthogonal reaction because of its selectivity and high reaction rates with several alkenes and alkynes. Recently, we described vinylboronic acids (VBAs) as novel hydrophilic bioorthogonal moieties that react efficiently with dipyridyl-s-tetrazines and used them for protein modification in cell lysate. Read More

    Glycoconjugate Oxime Formation Catalyzed at Neutral pH: Mechanistic Insights and Applications of 1,4-Diaminobenzene as Superior Catalyst for Complex Carbohydrates.
    Bioconjug Chem 2018 Feb 13. Epub 2018 Feb 13.
    The reaction of unprotected carbohydrates with aminooxy reagents to provide oximes is a key method for the construction of glycoconjugates. Aniline and derivatives serve as organocatalysts for the formation of oximes from simple aldehydes, and we have previously reported that aniline also catalyzes the formation of oximes from the more complex aldehydes, carbohydrates. Here we present a comprehensive study of the effect of aniline analogs on formation of carbohydrate oximes and related glycoconjugates, depending on organocatalyst structure, pH, nucleophile, and carbohydrate, covering more than 150 different reaction conditions. Read More

    Cross-Linked Peptide Nanoclusters for Delivery of Oncofetal Antigen as a Cancer Vaccine.
    Bioconjug Chem 2018 Feb 13. Epub 2018 Feb 13.
    School of Chemical & Biomolecular Engineering and Petit Institute for Bioengineering and Bioscience, Georgia Institute of Technology , Atlanta, Georgia 30332, United States.
    Peptide subunit vaccines are desirable because they increase control over the immune response and safety of the vaccine by reducing the risk of off-target responses to molecules other than the target antigen. The immunogenicity of most peptides, however, is low. Peptide nanoclusters (PNC) are proposed as a subunit peptide vaccine delivery system made completely of cross-linked peptide antigen that could improve the immunogenicity of a peptide vaccine. Read More

    Bioconjugation through Mesitylene Thiol Alkylation.
    Bioconjug Chem 2018 Feb 13. Epub 2018 Feb 13.
    The design and generation of complex multifunctional macromolecular structures by bioconjugation is a hot topic due to increasing interest conjugates with therapeutic applications. In this regard, the development of efficient, selective, and safe conjugation methods is a major objective. In this report, we describe the use of the bis(bromomethyl)benzene scaffold as a linker for bioconjugation with special emphasis in antibody conjugation. Read More

    Human Telomeric G-Quadruplex Selective Fluoro-Isoquinolines Induce Apoptosis in Cancer Cells.
    Bioconjug Chem 2018 Feb 23. Epub 2018 Feb 23.
    Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
    Small molecules that stabilize G-quadruplex structures in telomeres can prevent telomerase enzyme mediated telomere lengthening and subsequently lead to cell death. We herein report two fluoro-isoquinoline derivatives IQ1 and IQ2 as selective ligands for human telomeric G-quadruplex DNA. IQ1 and IQ2 containing different triazolyl side chains have been synthesized by Cu (I) catalyzed azide-alkyne cycloaddition. Read More

    NLS-cholic acid conjugation to IL-5Rα-specific antibody improves cellular accumulation and in vivo tumor-targeting properties in a bladder cancer model.
    Bioconjug Chem 2018 Feb 13. Epub 2018 Feb 13.
    Receptor-mediated internalization followed by trafficking and degradation of antibody-conjugates (ACs) via the endosomal-lysosomal pathway is the major mechanism for delivering molecular payloads inside target tumor cells. Although, a mainstay for delivering payloads with clinically approved ACs in cancer treatment and imaging, tumor cells are often able to decrease intracellular payload concentrations and thereby reduce the effectiveness of the desired application. Thus, increasing payload intracellular accumulation has become a focus of attention for designing next-generation ACs. Read More

    Complement Activation by PEGylated Gold Nanoparticles.
    Bioconjug Chem 2018 Feb 16. Epub 2018 Feb 16.
    Department of Biomedical Engineering and ‡NUS Graduate School for Integrative Sciences and Engineering, National University of Singapore , 115783 Singapore.
    Gold nanoparticles (AuNPs) are widely used in biomedical applications, but much less is known about their immunological properties, particularly their interaction with the complement system, a key component of innate immunity serving as an indicator of their biocompatibility. Using a library of different-sized AuNPs (10, 20, 40, and 80 nm) passivated with polyethylene glycol (PEG) of different molecular weight (M= 1, 2, 5, and 10 kDa), we demonstrated that citrate-capped AuNPs activated the whole complement system in a size-dependent manner, characterized by the formation of the end-point activation product, SC5b-9, in human serum. Although PEGylation of AuNPs mitigated, but did not abolish, the activation level, complement activation by PEGylated AuNPs was independent of both the core size of AuNPs and the molecular weight of PEG. Read More

    Bioorthogonally Applicable Fluorogenic Cyanine-Tetrazines for No-Wash Super-Resolution Imaging.
    Bioconjug Chem 2018 Feb 20. Epub 2018 Feb 20.
    "Lendület" Chemical Biology Research Group, Institute of Organic Chemistry and ‡Institute of Enzymology, Research Centre for Natural Sciences, Hungarian Academy of Sciences , Magyar tudósok krt. 2, H-1117, Budapest, Hungary.
    The synthesis, fluorogenic characterization, and labeling application of four tetrazine-quenched cyanine probes with emission maxima in the red-far red range is reported. Fluorescence of the cyanine-cores is quenched via through-bond-energy-transfer (TBET) exerted by a bioorthogonal tetrazine unit. Upon bioorthogonal labeling reaction with cyclooctyne tagged proteins, the quenching effect ceases, and thus the fluorescence reinstates, resulting in an increase in fluorescence intensity. Read More

    Ferritin Nanocages with Biologically Orthogonal Conjugation for Vascular Targeting and Imaging.
    Bioconjug Chem 2018 Feb 19. Epub 2018 Feb 19.
    Department of Pharmacology, The Perelman School of Medicine, §Department of Chemistry, The School of Arts and Sciences, ∥Department of Bioengineering, The School of Engineering and Applied Sciences, and ¶Center for Targeted Therapeutics and Translational Nanomedicine (CT3N), University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.
    Genetic incorporation of biologically orthogonal functional groups into macromolecules has the potential to yield efficient, controlled, reproducible, site-specific conjugation of affinity ligands, contrast agents, or therapeutic cargoes. Here, we applied this approach to ferritin, a ubiquitous iron-storage protein that self-assembles into multimeric nanocages with remarkable stability, size uniformity (12 nm), and endogenous capacity for loading and transport of a variety of inorganic and organic cargoes. The unnatural amino acid, 4-azidophenylalanine (4-AzF), was incorporated at different sites in the human ferritin light chain (hFTL) to allow site-specific conjugation of alkyne-containing small molecules or affinity ligands to the exterior surface of the nanocage. Read More

    Shape of Nanoparticles as a Design Parameter to Improve Docetaxel Antitumor Efficacy.
    Bioconjug Chem 2018 Feb 19. Epub 2018 Feb 19.
    Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College , No. 151, Malianwa North Road, Haidian District, Beijing 100193, China.
    It was reported that the shape of nanocarriers played an important role in achieving a better therapeutic effect. To optimize the morphology and enhance the antitumor efficacy, in this study based on the amphiphilic PAMAM-b-OEG codendrimer (POD), docetaxel-loaded spherical and flake-like nanoparticles (DTX nanospheres and nanosheets) were prepared via an antisolvent precipitation method with similar particle size, surface charge, stability, and release profiles. The feed weight ratio of DTX/POD and the branched structure of OEG dendron were suggested to influence the shapes of the self-assembled nanostructures. Read More

    High-Throughput Cysteine Scanning To Identify Stable Antibody Conjugation Sites for Maleimide- and Disulfide-Based Linkers.
    Bioconjug Chem 2018 Feb 9;29(2):473-485. Epub 2018 Feb 9.
    Genentech Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
    THIOMAB antibody technology utilizes cysteine residues engineered onto an antibody to allow for site-specific conjugation. The technology has enabled the exploration of different attachment sites on the antibody in combination with small molecules, peptides, or proteins to yield antibody conjugates with unique properties. As reported previously ( Shen , B. Read More

    A Microfluidic Chip Integrated with Hyaluronic Acid-Functionalized Electrospun Chitosan Nanofibers for Specific Capture and Nondestructive Release of CD44-Overexpressing Circulating Tumor Cells.
    Bioconjug Chem 2018 Feb 20. Epub 2018 Feb 20.
    Department of Ultrasound, Shanghai General Hospital, Shanghai Jiaotong University School of Medicine , Shanghai 200080, People's Republic of China.
    Detection of circulating tumor cells (CTCs) in peripheral blood is of paramount significance for early-stage cancer diagnosis, estimation of cancer development, and individualized cancer therapy. Herein, we report the development of hyaluronic acid (HA)-functionalized electrospun chitosan nanofiber (CNF)-integrated microfludic platform for highly specific capture and nondestructive release of CTCs. First, electrospun CNFs were formed and modified with zwitterion of carboxyl betaine acrylamide (CBAA) via Michael addition reaction and then targeting ligand HA through a disulfide bond. Read More

    SN-38 Conjugated Gold Nanoparticles Activated by Ewing Sarcoma Specific mRNAs Exhibit In Vitro and In Vivo Efficacy.
    Bioconjug Chem 2018 Feb 19. Epub 2018 Feb 19.
    University of Minnesota Masonic Cancer Center , Minneapolis, Minnesota 55455, United States.
    The limited delivery of chemotherapy agents to cancer cells and the nonspecific action of these agents are significant challenges in oncology. We have previously developed a customizable drug delivery and activation system in which a nucleic acid functionalized gold nanoparticle (Au-NP) delivers a drug that is selectively activated within a cancer cell by the presence of an mRNA unique to the cancer cell. The amount of drug released from sequestration to the Au-NP is determined by both the presence and the abundance of the cancer cell specific mRNA in a cell. Read More

    ReducedF-Folate Conjugates as a New Class of PET Tracers for Folate Receptor Imaging.
    Bioconjug Chem 2018 Feb 19. Epub 2018 Feb 19.
    Department of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, ETH Zurich , 8093 Zurich, Switzerland.
    5-Methyltetrahydrofolate (5-MTHF), a reduced folate form, is the biologically active folate involved in many different metabolic processes. To date, there are no studies available in the literature onF-labeled 6S- and 6R-5-MTHF radiotracers for imaging folate receptor (FR)-α-positive tissues. Therefore, the goal of this study was to synthesize fourF-labeled 5-MTHF derivatives conjugated at either the α- or γ-carboxylic functionality of glutamate and to assess their suitability for FR-targeting. Read More

    Multifunctional Serine Protease Inhibitor-Coated Water-Soluble Gold Nanoparticles as a Novel Targeted Approach for the Treatment of Inflammatory Skin Diseases.
    Bioconjug Chem 2018 Feb 23. Epub 2018 Feb 23.
    Departament de Farmacologia, Toxicologia i Química Terapèutica, ‡Institut de Nanociència i Nanotecnologia (IN2UB), §Secció de Bioquímica i Biologia Molecular, Departament de Bioquímica i Fisiologia, Facultat de Farmàcia i Ciències de l'Alimentació, ∥Institut de Biomedicina de la Universitat de Barcelona (IBUB), #Institut de Recerca Sant Joan de Déu (IR-SJD), and ⊥Departament de Farmàcia, Tecnologia Farmacèutica i Fisicoquímica, Universitat de Barcelona , Av. Joan XXIII, 27-31, 08028 Barcelona, Spain.
    The overexpression and increased activity of the serine protease Kallikrein 5 (KLK5) is characteristic of inflammatory skin diseases such as Rosacea. The use of inhibitors of this enzyme-such as 4-(2-aminoethyl)benzenesulfonyl fluoride hydrochloride (AEBSF·HCl) or the anti-human recombinant Kallikrein 5 (anti-KLK5) antibody-in the treatment of the disease has been limited due to their low bioavailability, for which their immobilization in drug delivery agents can contribute to making serine protease inhibitors clinically useful. In this work, we synthesized gold nanoparticles (GNP) coated with a mixture of hydroxyl- and carboxyl-terminated thiolates (GNP. Read More

    Modular, Bioorthogonal Strategy for the Controlled Loading of Cargo into a Protein Nanocage.
    Bioconjug Chem 2018 Feb 16. Epub 2018 Feb 16.
    Laboratory of Bio-Organic Chemistry, Eindhoven University of Technology , PO Box 513 (STO 3.31), 5600 MB Eindhoven, The Netherlands.
    Virus capsids, i.e., viruses devoid of their genetic material, are suitable nanocarriers for biomedical applications such as drug delivery and diagnostic imaging. Read More

    Reversible Control of Network Properties in Azobenzene-Containing Hyaluronic Acid-Based Hydrogels.
    Bioconjug Chem 2018 Feb 19. Epub 2018 Feb 19.
    Department of Bioengineering, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.
    Biomimetic hydrogels fabricated from biologically derived polymers, such as hyaluronic acid (HA), are useful for numerous biomedical applications. Due to the dynamic nature of biological processes, it is of great interest to synthesize hydrogels with dynamically tunable network properties where various functions (e.g. Read More

    Multifunctional Porous Iron Oxide Nanoagents for MRI and Photothermal/Chemo Synergistic Therapy.
    Bioconjug Chem 2018 Feb 19. Epub 2018 Feb 19.
    State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University , Suzhou, Jiangsu Province 215123, China.
    Nanoagents of integrating multiple imaging and therapeutic modalities have attracted tremendous attention for biomedical applications. Herein, we synthesize porous hollow FeOas a theranostic agent for MRI and combined photothermal/chemo cancer therapy. The as-prepared porous iron oxide nanoagents allow for T-weighted MR imaging. Read More

    Synthesis of DNA Modified with Boronic Acid: Compatibility to Copper(I)-Catalyzed Azide-Alkyne Cycloaddition.
    Bioconjug Chem 2018 Feb 9;29(2):431-436. Epub 2018 Feb 9.
    Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT) , Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
    The postsynthetic and sequence-specific ligation chemistry of a phenylboronic acid to oligonucleotides using the amide bond formation was worked out. In the first coupling experiments with 4-carboxyphenylboronic acid, a 5'-hexylamino-modified oligonucleotide was used to evaluate and optimize the reaction conditions. This postsynthetic modification works best in the presence of TBTU and triethanolamine and in a degassed DMF/carbonate buffer solvent mixture. Read More

    Tuning the Hydrolytic Stability of Next Generation Maleimide Cross-Linkers Enables Access to Albumin-Antibody Fragment Conjugates and tri-scFvs.
    Bioconjug Chem 2018 Feb 31;29(2):486-492. Epub 2018 Jan 31.
    Department of Chemistry, University College London , 20 Gordon Street, London, WC1H OAJ, United Kingdom.
    We describe investigations to expand the scope of next generation maleimide cross-linkers for the construction of homogeneous protein-protein conjugates. Diiodomaleimides are shown to offer the ideal properties of rapid bioconjugation with reduced hydrolysis, allowing the cross-linking of even sterically hindered systems. The optimized linkers are exploited to link human serum albumin to antibody fragments (Fab or scFv) as a prospective half-life extension platform, with retention of antigen binding and robust serum stability. Read More

    Sulfinate Based Selective Labeling of 5-Hydroxymethylcytosine: Application to Biotin Pull Down Assay.
    Bioconjug Chem 2018 Feb 2;29(2):245-249. Epub 2018 Feb 2.
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 21 Nanyang Link, Singapore , 637371.
    We developed an enzyme-free, chemical method to selectively label the epigenetic base, 5-hydroxymethylcytosine (hmC) with versatile sulfinate reagents in aqueous solvent under mild reaction conditions. This method allows efficient single step conjugation of biotin to hmC site in DNA for enrichment and pull down assays. Read More

    Vx3-Functionalized Alumina Nanoparticles Assisted Enrichment of Ubiquitinated Proteins from Cancer Cells for Enhanced Cancer Immunotherapy.
    Bioconjug Chem 2018 Feb 9. Epub 2018 Feb 9.
    Department of Microbiology and Immunology, Medicine School of Southeast University , Nanjing, Jiangsu 210009, P.R. China.
    A simple and effective strategy was developed to enrich ubiquitinated proteins (UPs) from cancer cell lysate using the α-AlOnanoparticles covalently linked with ubiquitin binding protein (Vx3) (denoted as α-AlO-Vx3) via a chemical linker. The functionalized α-AlO-Vx3 showed long-term stability and high efficiency for the enrichment of UPs from cancer cell lysates. Flow cytometry analysis results indicated dendritic cells (DCs) could more effectively phagocytize the covalently linked α-AlO-Vx3-UPs than the physical mixture of α-AlOand Vx3-UPs (α-AlO/Vx3-UPs). Read More

    Immobilization by Surface Conjugation of Cyclic Peptides for Effective Mimicry of the HCV-Envelope E2 Protein as a Strategy toward Synthetic Vaccines.
    Bioconjug Chem 2018 Feb 19. Epub 2018 Feb 19.
    School of Chemistry, University of Glasgow , Joseph Black Building, University Avenue, Glasgow G12 8QQ, United Kingdom.
    Mimicry of the binding interface of antibody-antigen interactions using peptide-based modulators (i.e., epitope mimics) has promising applications for vaccine design. Read More

    Bioorthogonal Masking of Circulating Antibody-TCO Groups Using Tetrazine-Functionalized Dextran Polymers.
    Bioconjug Chem 2018 Feb 9;29(2):538-545. Epub 2018 Feb 9.
    Department of Radiology and ∥Program in Molecular Pharmacology, Memorial Sloan Kettering Cancer Center , 1275 York Avenue, New York, New York 10065, United States.
    Pretargeting strategies have gained popularity for the in vivo imaging and therapy of cancer by combining antibodies with small molecule radioligands. In vivo recombination of both moieties can be achieved using the bioorthogonal inverse electron demand Diels-Alder (IEDDA) chemistry between tetrazine (Tz) and trans-cyclooctene (TCO). An issue that arises with pretargeting strategies is that while part of the antibody dose accumulates at antigen-expressing tumor tissue, there is a significant portion of the injected antibody that remains in circulation, causing a reduction in target-to-background ratios. Read More

    Toll-like Receptor Agonist Conjugation: A Chemical Perspective.
    Bioconjug Chem 2018 Feb 16. Epub 2018 Feb 16.
    Department of Tumor Immunology, Radboud Institute for Molecular Life Sciences, Radboud University Medical Center , 6525 GA Nijmegen, The Netherlands.
    Toll-like receptors (TLRs) are vital elements of the mammalian immune system that function by recognizing pathogen-associated molecular patterns (PAMPs), bridging innate and adaptive immunity. They have become a prominent therapeutic target for the treatment of infectious diseases, cancer, and allergies, with many TLR agonists currently in clinical trials or approved as immunostimulants. Numerous studies have shown that conjugation of TLR agonists to other molecules can beneficially influence their potency, toxicity, pharmacokinetics, or function. Read More

    Polyethylene Glycol-Engrafted Graphene Oxide as Biocompatible Materials for Peptide Nucleic Acid Delivery into Cells.
    Bioconjug Chem 2018 Feb 7;29(2):528-537. Epub 2018 Feb 7.
    Department of Bioscience and Biotechnology, Konkuk University Neundong-ro 120, Gwangjin-gu, Seoul 05029, Republic of Korea.
    Graphene oxide (GO) is known to strongly bind single-stranded nucleic acids with fluorescence quenching near the GO surface. However, GO exhibits weak biocompatibility characteristics, such as low dispersibility in cell culture media and significant cytotoxicity. To improve dispersibility in cell culture media and cell viability of GO, we prepared nanosized GO (nGO) constructs and modified the nGO surface using polyethylene glycol (PEG-nGO). Read More

    Highly Efficient and Stable Strain-Release Radioiodination for Thiol Chemoselective Bioconjugation.
    Bioconjug Chem 2018 Feb 8;29(2):467-472. Epub 2018 Feb 8.
    Center for Molecular Imaging and Translational Medicine, State Key Laboratory of Molecular Vaccinology and Molecular Diagnostics, School of Public Health, Xiamen University , Xiamen 361102, China.
    We report a novel thiol selective radioiodination method based on strain-release reaction. A new heterobifunctional radioiodination agent which has very good thiol selectivity and excellent stability with high radiolabeling yield was synthesized, characterized, and applied successfully for thiol-contained peptide labeling. Read More

    Multifunctional Nanoflowers for Simultaneous Multimodal Imaging and High-Sensitivity Chemo-Photothermal Treatment.
    Bioconjug Chem 2018 Feb 9;29(2):559-570. Epub 2018 Feb 9.
    Instrumental Analysis Center of Xi'an Jiaotong University , Xi'an 710049, P. R. China.
    Liver cancer is currently among the most challenging cancers to diagnose and treat. It is of prime importance to minimize the side effects on healthy tissues and reduce drug resistance for precise diagnoses and effective treatment of liver cancer. Herein, we report a facile but high-yield approach to fabricate a multifunctional nanomaterial through the loading of chitosan and metformin on Mn-doped FeO@MoSnanoflowers. Read More

    Immolation of p-Aminobenzyl Ether Linker and Payload Potency and Stability Determine the Cell-Killing Activity of Antibody-Drug Conjugates with Phenol-Containing Payloads.
    Bioconjug Chem 2018 Feb 7;29(2):267-274. Epub 2018 Feb 7.
    Drug Metabolism & Pharmacokinetics, ‡Biochemical and Cellular Pharmacology, §Molecular Oncology, ⊥Discovery Chemistry, and ∥Protein Chemistry, Genentech , South San Francisco, California 94080, United States.
    The valine-citrulline (Val-Cit) dipeptide and p-aminobenzyl (PAB) spacer have been commonly used as a cleavable self-immolating linker in ADC design including in the clinically approved ADC, brentuximab vedotin (Adcetris). When the same linker was used to connect to the phenol of the cyclopropabenzindolone (CBI) (P1), the resulting ADC1 showed loss of potency in CD22 target-expressing cancer cell lines (e.g. Read More

    Exosomes-Small Players, Big Sound.
    Bioconjug Chem 2018 Feb 9. Epub 2018 Feb 9.
    MEDFUTURE-Research Center for Advanced Medicine, "Iuliu-Hatieganu" University of Medicine and Pharmacy , Marinescu 23 Street, 400337 Cluj-Napoca, Romania.
    Incipiently named extracellular vesicles, exosomes are forming now a separate class of cellular mediators with important functions in physiological and pathological states. Their ability to transfer information between cells through encapsulation of proteins, nucleic acids and lipids for the preservation of the homeostatic equilibrium is translated also in pathological conditions. The recipient cells react to the reception of foreign molecules adjusting their molecular state according to the enclosed message. Read More

    Porphyrin-Loaded Pluronic Nanobubbles: A New US-Activated Agent for Future Theranostic Applications.
    Bioconjug Chem 2018 Feb 31;29(2):234-240. Epub 2018 Jan 31.
    Department of Drug Science and Technology, University of Turin , Via Giuria 9, 10125 Turin, Italy.
    Sonodynamic therapy (SDT) has become a promising noninvasive approach for cancer therapy. The treatment exploits the ability of particular molecules (i.e. Read More

    Kinetic and Conformational Insights into Islet Amyloid Polypeptide Self-Assembly Using a Biarsenical Fluorogenic Probe.
    Bioconjug Chem 2018 Feb 12;29(2):517-527. Epub 2018 Feb 12.
    Department of Chemistry, Quebec Network for Research on Protein Function, Engineering and Applications, PROTEO, University of Québec in Montreal , C.P. 8888, Succursale Centre-Ville, Montreal, Québec H3C 3P8, Canada.
    Amyloid fibril formation and tissue deposition are associated with many diseases. Studies have shown that prefibrillar intermediates, such as oligomers, are the most toxic proteospecies of the amyloidogenic cascade. Thus, understanding the mechanisms of formation and the conformational ensemble of prefibrillar species is critical. Read More

    Labeling of Hyaluronic Acids with a Rhenium-tricarbonyl Tag and Percutaneous Penetration Studied by Multimodal Imaging.
    Bioconjug Chem 2018 Feb 22. Epub 2018 Feb 22.
    Laboratoire des biomolécules, LBM, Département de chimie, École normale supérieure, PSL University, Sorbonne Université, CNRS , 75005 Paris, France.
    Hyaluronic acids were labeled with a rhenium-tricarbonyl used as single core multimodal probe for imaging and their penetration into human skin biopsies was studied using IR microscopy and fluorescence imaging (labeled SCoMPI). The penetration was shown to be dependent on the molecular weight of the molecule and limited to the upper layer of the skin. Read More

    Mobility of Water and Polymer Species and Rheological Properties of Supramolecular Polypseudorotaxane Gels Suitable for Bone Regeneration.
    Bioconjug Chem 2018 Feb 7;29(2):503-516. Epub 2018 Feb 7.
    Department of Chemical Engineering and Pharmaceutical Technology, Institute of Biomedical Technologies (ITB), Center for Biomedical Research of the Canary Islands (CIBICAN), Universidad de La Laguna , 30200 La Laguna, Spain.
    The aim of this work was to prepare polypseudorotaxane-based supramolecular gels combining αCD with two temperature-responsive copolymers of different architecture (i.e., linear poloxamer P and X-shaped poloxamine T), at the lowest concentration as possible to form syringeable depots, and to shed light on the self-diffusion and spatial closeness of all components (including water) which in turn may determine the cooperative self-assembly phenomena and the performance of the gels at the macroscopic level. Read More

    Biomimetic Nanosponges for Treating Antibody-Mediated Autoimmune Diseases.
    Bioconjug Chem 2018 Feb 8. Epub 2018 Feb 8.
    Department of NanoEngineering and Moores Cancer Center, University of California San Diego , La Jolla, California 92093, United States.
    Autoimmune diseases are characterized by overactive immunity, where the body's defense system launches an attack against itself. If left unchecked, this can result in the destruction of healthy tissue and significantly affect patient well-being. In the case of type II autoimmune hypersensitivities, autoreactive antibodies attack the host's own cells or extracellular matrix. Read More

    1 OF 109