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Bioconjugate Chemistry

Xiang Li, Zheng Ma, Haoran Wang, Li Ren, Dianwen Zhang, Weiguo Liang, Guangji Zhang, Jinrui Zhang, Dahai Yu, Xuexun Fang
Membrane type-1 matrix metalloproteinase (MT1-MMP) plays a crucial role in many physiological and pathological processes, especially in tumor invasion and metastasis. Bioimaging of this key molecule may find wide usage in various applications. MT-loop is a unique sequence of MT1-MMP and locates in the surface of the protein. In our previous studies, AF7p, an affinity peptide that targeting the MT-loop domain of MT1-MMP was identified by screening a phage display (Ph.D.) peptide library. However, the target of AF7p is a synthetic sequence which lacked native conformation of MT-loop region, thus the binding affinity and specificity in reality may not be optimal...
April 15, 2019: Bioconjugate Chemistry
Ying Xiong, Xiaodong Tian, Hui-Wang Ai
Reactive oxygen species (ROS) not only are by-products of aerobic respiration, but also play vital roles in metabolism regulation and signal transductions. It is important to understand the functions of ROS in biological systems. In addition, scientists have made use of ROS to kill bacteria and tumors through a process known as photodynamic therapy (PDT). This paper provides a concise review of current molecular tools that can generate ROS in biological systems via either non-genetic or genetically-encoded way...
April 15, 2019: Bioconjugate Chemistry
Sarthak Mandal, Xu Zhou, Su Lin, Hao Yan, Neal W Woodbury
Strongly coupled molecular dye aggregates have unique optoelectronic properties that often resemble those of light harvesting complexes found in nature. The exciton dynamics in coupled dye aggregates could enhance the long-range transfer of optical excitation energy with high efficiency. In principle, dye aggregates could serve as important components in molecular-scale photonic devices, however, rational design of these coupled dye aggregates with precise control over their organization, interactions and dynamics remains a challenge...
April 15, 2019: Bioconjugate Chemistry
Tewoderos Ayele, Steve D Knutson, Satheesh Ellipilli, Hyun Hwang, Jennifer M Heemstra
Genetically encoded fluorescent proteins or small-molecule probes that recognize specific protein binding partners can be used to label proteins to study their localization and function with fluorescence microscopy. However, these approaches are limited in signal-to-background resolution and the ability to temporally control labeling. Herein, we describe a covalent protein labeling technique using a fluorogenic malachite green probe functionalized with a photoreactive crosslinker. This enables a controlled covalent attachment to a genetically encodable fluorogen activating protein (FAP) with low background signal...
April 12, 2019: Bioconjugate Chemistry
Adam Shuhendler, Lina Cui, Zixin Chen, Bin Shen, Michelle L James, Timothy Witney, Sanjiv S Gambhir, Frederick T Chin, Magdalena Bazalova-Carter, Edward Graves, Jianghong Rao, Min Chen
Poly (ADP ribose) polymerase (PARP) enzymes generate poly (ADP ribose) post-translational modifications on target proteins for an array of functions centering on DNA and cell stress. PARP isoforms 1 and 2 are critically charged with the surveillance of DNA integrity, and are the first line guardians of the genome against DNA breaks. Here we present a novel probe ([18F]-SuPAR) for non-invasive imaging of PARP-1/2 activity using positron emission tomography (PET). [18F]-SuPAR is a radiofluorinated nicotinamide adenine dinucleotide (NAD) analog that can be recognized by PARP-1/2 and incorporated into the long branched polymers of poly(ADP ribose) (PAR)...
April 11, 2019: Bioconjugate Chemistry
Emily B Ehlerding, Hye Jin Lee, Todd E Barnhart, Dawei Jiang, Lei Kang, Douglas G McNeel, Jonathan W Engle, Weibo Cai
Immune checkpoint expression is highly dynamic, and combination treatments including radiotherapy can particularly modulate this expression. PET imaging using 89 Zr-Df-atezolizumab can provide insight into the levels of PD-L1 variation following radiotherapy treatments. In vitro screening was used to monitor PD-L1 expression by lung cancer cells following radiotherapy. Mice bearing PD-L1+ (H460) or PD-L1- (A549) tumors were subjected to various external beam radiotherapy regimens and then imaged using 89 Zr-Df-atezolizumab PET...
April 11, 2019: Bioconjugate Chemistry
Maxwell M Sakyiamah, Wataru Nomura, Takuya Kobayakawa, Hirokazu Tamamura
A critical part of the development of CXCR4 modulators is to have a simple and sensitive assay system to complement the search by screening and evaluating the binding affinity. Herein, a NanoBRET assay system was developed, and its feasibility as a high-throughput screening tool for potent CXCR4 ligands was ascertained. TAMRA-Ac-TZ14011, a fluorescent-labeled CXCR4 antagonist, was adopted as a fluorescent acceptor of bioluminescent energy from N-terminally fused NanoLuc-CXCR4 stably expressed in CHO cells. The ratio of fluorescence at 620 nm to the luminescence at 460 nm represents the interaction between test compounds and CXCR4...
April 11, 2019: Bioconjugate Chemistry
Hao Sun, Lu Yang, Matthew Peter Thompson, Steve Schara, Wei Cao, Wonmin Choi, Ziying Hu, Nanzhi Zang, Weihong Tan, Nathan C Gianneschi
Over the past decade, the field of polymer-oligonucleotide nanomaterials has flourished because of the development of synthetic techniques, particularly living polymerization technologies, which provide access to polymers with well-defined architectures, precise molecular weights, and terminal or side-chain functionalities. Various "living" polymerization methods have empowered chemists with the ability to prepare functional polymer-oligonucleotide conjugates yielding a library of architectures, including linear diblock, comb, star, hyperbranched-star, and gel morphologies...
April 10, 2019: Bioconjugate Chemistry
Hallie M Hintz, Aidan Cowan, Mariya Shapovalova, Aaron LeBeau
Here we document the discovery of a monoclonal antibody that selectively binds to both human and murine fibroblast activation protein alpha (FAP), a serine protease that is over-expressed on cancer-associated fibroblasts (CAFs) making it an attractive therapeutic target for the aiding and abetting tumor microenvironment. The lead antibody, B12, was identified from a naïve murine single-chain variable fragment (scFv) antibody phage display library screened against human FAP on magnetic beads. The heavy and light chains of B12 were cloned into full-length human immunoglobulin 1 (IgG) vectors and expressed as a chimeric monoclonal antibody (B12 IgG)...
April 10, 2019: Bioconjugate Chemistry
Dian Su, Jinhua Chen, Ely Cosino, Josefa Dela Cruz-Chuh, Helen Davis, Geoffrey Del Rosario, Isabel Figueroa, Leanne Goon, Jintang He, Amrita Kamath, Surinder Kaur, Katherine Kozak, Jeffrey Lau, Donna Lee, M Violet Lee, Doug Leipold, Luna Liu, Peter Liu, Guo-Liang Lu, Chris Nelson, Carl Ng, Thomas Pillow, Paul Polakis, Andrew Gorham Polson, Rebecca K Rowntree, Ola M Saad, Brian Safina, Nicola Stagg, Moana Tercel, Richard Vandlen, Breanna S Vollmar, John Wai, Tao Wang, Keyang Xu, Juanjuan Xue, Zijin Xu, Yan Gang, Hui Yao, Shang-Fan Yu, Donglu Zhang, Fiona Zhong, Peter S Dragovich, Binqing Wei
This work discloses the first examples of antibody-drug conjugates (ADCs) that are constructed from linker-drugs bearing dimeric seco-CBI payloads (duocarmycin analogs). Several homogeneous, CD22-targeting THIOMABTM antibody-drug conjugates (TDCs) containing the dimeric seco-CBI entities are shown to be highly efficacious in the WSU-DLCL2 and BJAB mouse xenograft models. Surprisingly, the seco-CBI-containing conjugates are also observed to undergo significant biotransformation in vivo in mice, rats, and monkeys and thereby form 1:1 adducts with the A1M plasma protein from these species...
April 10, 2019: Bioconjugate Chemistry
Huang-Chi Du, Madison C Bangs, Nicholas Simmons, Martin M Matzuk
A multistep protocol for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles on DNA-chemical conjugates has been developed. A set of six DNA-connected aryl nitriles were converted to corresponding amidoximes with hydroxylamine followed by the O-acylation with a series of aryl and aliphatic carboxylic acids. After cyclodehydration of the O-acyl amidoximes by heating at 90 °C in pH 9.5 borate buffer for 2 h, the desired oxadiazole products were observed in 51-92% conversion with the cleavage of O-acylamidoximes as the major side-product...
April 10, 2019: Bioconjugate Chemistry
Haijiao Dong, Yaoyao Fan, Wei Zhang, Ning Gu, Yu Zhang
The research on nanozymes has increased dramatically in recent years and a new interdiscipline, nanozymology, has emerged. A variety of nanomaterials have been designed to mimic the characteristics of natural enzymes, which connects an important bridge between nanotechnology and biological science. Unlike natural enzymes, the nanoscale properties of nanozymes endow them the potential to regulate their enzymatic-like activity from different perspectives. The mechanisms behind those methods are intriguing. In this review, we introduce these mechanisms from the aspects of surface chemistry, surface modification, molecular imprinting and hybridization and then focus attention on some specific catalytic mechanisms of several representative nanozymes...
April 9, 2019: Bioconjugate Chemistry
Wenjuan Wang, Xiaoyan Dong, Yan Sun
Fibrillogenesis of amyloid β-protein (Aβ) have been thought to be implicated in the progression of Alzheimer's disease (AD). Therefore, development of high- efficiency inhibitors is one of the strategies for the prevention and treatment of AD. Serum albumin has been found to capture Aβ monomers through its hydrophobic groove and suppress amyloid formation, but the inhibition efficiency is limited. Inspired by the strong inhibition potency of a basic protein, human lysozyme, we have herein proposed to develop a basified serum albumin by converting carboxyl groups into amino groups with ethylenediamine conjugated on the protein surface...
April 9, 2019: Bioconjugate Chemistry
Aleksandra Tchoryk, Vincenzo Taresco, Richard Argent, Marianne B Ashford, Paul Gellert, Snow Stolnik, Anna M Grabowska, Martin C Garnett
Animal models are effective for assessing tumour localisation of nanosystems, but difficult to use for studying penetration beyond the vasculature. Here, we have used well-characterised HCT116 colorectal cancer spheroids to study the effect of nanoparticle (NP) physicochemical properties on penetration and uptake. Incubation of spheroids with Hoechst 33342 resulted in a dye gradient which facilitated discrimination between the populations of cells in the core and at the periphery of spheroids by flow cytometry...
April 4, 2019: Bioconjugate Chemistry
Sobhana Babu Boga, Shane W Krska, Songnian Lin, Dmitri Pissarnitski, Lin Yan, Ahmet Kekec, Weijuan Tang, Nicholas A Pierson, Christopher A Strulson, Eric Streckfuss, Xiaohong Zhu, Xiaoping Zhang, Terri Kelly, Craig A Parish
A synthetic method to access novel azido-insulin analogs directly from recombinant human insulin (RHI) was developed via diazo-transfer chemistry using imidazole-1-sulfonyl azide. Systematic optimization of reaction conditions led to site-selective azidation of amino acids B1-phenylalanine and B29-lysine present in RHI. Subsequently, the azido-insulin analogs were used in azide-alkyne [3 + 2] cycloaddition reactions to synthesize a diverse array of triazole-based RHI bioconjugates that were found to be potent human insulin receptor binders...
April 4, 2019: Bioconjugate Chemistry
Kevin Moulton, Amissi Sadiki, Bilyana Koleva, Lincoln Ombelets, Tina Tran, Shanshan Liu, Bryan Wang, Hongyan Chen, Emily Micheloni, Penny Beuning, George O'Doherty, Zhaohui Sunny Zhou
Dynamic photoswitches in proteins that impart spatial and temporal control are important to manipulate and study biotic and abiotic processes. Nonetheless, approaches to install these switches into proteins site-specifically are limited. Herein we describe a novel site-specific method to generate photo-removable protein conjugates. Amine-containing chromophores (e.g., venerable o-nitrobenzyl and less-explored o-nitrophenylethyl groups) were incorporated via transamidation into glutamine side-chain of alpha-gliadin, LCMV and TAT peptides, as well as beta-casein and UmuD proteins by transglutaminase (TGase, EC 2...
April 4, 2019: Bioconjugate Chemistry
Minori Okubo, Maiko Miyazaki, Eiji Yuba, Atsushi Harada
Induction of cancer-specific cytotoxic T lymphocytes is crucially important to complement therapeutic effects of immune checkpoint inhibitors and to achieve efficient cancer immunotherapy. To induce cancer-specific cytotoxic T lymphocytes, cancer antigen carriers must have multiple functions to deliver cancer antigens to antigen presenting cells, release antigens into cytosol, and promote the maturation of these cells. We earlier achieved cytosolic delivery of antigens and induction of antigen-specific cytotoxic T lymphocytes using carboxylated polyglycidol or polysaccharide derivative-modified liposomes that can induce membrane fusion with endosomes in response to weakly acidic pH...
April 4, 2019: Bioconjugate Chemistry
Zheng Han, Shuixing Zhang, Kenji Fujiwara, Jia Zhang, Yuguo Li, Jing Liu, Peter C M van Zijl, Zheng-Rong Lu, Lei Zheng, Guanshu Liu
A dextran-peptide conjugate was developed for MR molecular imaging of pancreatic ductal adenocarcinoma (PDAC) through its overexpressed microenvironment biomarker, extradomain-B fibronectin (EDB-FN). This new agent consists of diamagnetic and biocompatible dextran and a targeting peptide. Dextrans can be directly detected by chemical exchange saturation transfer (CEST) MRI without the need for radionuclide- or metallic labelling. In addition, large molecular weight dextran, dextran 10 (MW~ 10 kD), provides an approximately fifty times higher sensitivity per molecule than a single glucose unit...
April 2, 2019: Bioconjugate Chemistry
Shino Manabe, Yoshiki Yamaguchi, Kana Matsumoto, Hirobumi Fuchigami, Taiji Kawase, Kenji Hirose, Ai Mitani, Wataru Sumiyoshi, Takashi Kinoshita, Junpei Abe, Masahiro Yasunaga, Yasuhiro Matsumura, Yukishige Ito
Glycan engineering of antibody has received considerable attention. Although various endo-β-N-acetylglucosaminidase mutants have been developed for glycan remodeling, side-reaction has been reported between glycan oxazoline and amino groups. In this study, we performed a detailed characterization for antibody products obtained through enzymatic and non-enzymatic reactions with the aim of maximizing the efficiency of glycosylation reaction with fewer side products. The reactions were monitored by an ultra-performance liquid chromatography system using an amide-based wide pore column...
April 2, 2019: Bioconjugate Chemistry
Cyrille Sabot, Jean Wilfried Fredy, Giuliano Cutolo, Benjamin Poret, Reine Nehmé, Marie Hubert-Roux, Pierrick Gandolfo, Helene Castel, Marie Schuler, Arnaud Tatibouët, Pierre-Yves Renard
The fluorescein isothiocyanate FITC is one of the most extensively used fluorescent probe for the labelling of biomolecules. The isothiocyanate function reacts with lysine residues of proteins to provide a chemically stable thiourea linkage without releasing any by-product. However, diversification of isothiocyanate-based reagents is still hampered by the lack of mild conditions to generate isothiocyanate chemical functions, as well as by their poor stability and limited solutions available to increase water solubility, restricting the use of isothiocyanate labelling to highly water soluble fluorophores...
April 1, 2019: Bioconjugate Chemistry
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