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Bioconjugate Chemistry

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https://www.readbyqxmd.com/read/28445034/dual-in-tether-chiral-centers-modulate-peptide-helicity
#1
Kuan Hu, Chengjie Sun, Mengying Yu, Wenjun Li, Huacan Lin, Jialin Guo, Yixiang Jiang, Chengxiang Lei, Zigang Li
The facile chemical modification on the peptide cross-linking moiety is an important strategy to improve the physico-chemical properties of a peptide. Herein, peptides were contrained into helical conformations using a dual in-tether chiral center strategy that induced synergistic effects between two chiral centers. A pentapeptide minimalistic model was used to determine a correlation between the absolute configurations of the dual in-tether chiral centers and the secondary structures of the peptides. This strategy provides an on-tether modification site that does not interrupt the secondary structure of the peptide...
April 26, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28443656/acyl-fluorides-fast-efficient-and-versatile-lysine-based-protein-conjugation-via-plug-and-play-strategy
#2
Igor Dovgan, Sylvain Ursuegui, Stéphane Erb, Chloé Michel, Sergii Kolodych, Sarah Cianférani, Alain Wagner
We report a plug-and-play strategy for the preparation of functionally enhanced antibodies with a defined average degree of conjugation (DoC). The first stage (plug) allows the controllable and efficient installation of azide groups on lysine residues of a native antibody using 4-azidobenzoyl fluoride. The second step (play) allows for versatile antibody functionalization with a single payload or combination of payloads, such as a toxin, a fluorophore, or an oligonucleotide, via copper-free strain-promoted azide-alkyne cycloaddition (SPAAC)...
April 26, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28443328/correction-to-l-rhamnose-enhances-the-immunogenicity-of-melanoma-associated-antigen-a3for-stimulating-antitumor-immune-responses
#3
Huajie Zhang, Bin Wang, Zhongrui Ma, Mohui Wei, Jun Liu, Dong Li, Houcheng Zhang, Peng George Wang, Min Chen
No abstract text is available yet for this article.
April 26, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28402621/specific-imaging-of-intracellular-lipid-droplets-using-a-benzothiadiazole-derivative-with-solvatochromic-properties
#4
Hanna Appelqvist, Kati Stranius, Karl Börjesson, K Peter R Nilsson, Christine Dyrager
Altered lipid metabolism and extensive lipid storage in cells have been associated with various medical disorders, including cancer. The development of fluorescent probes that specifically accumulate in lipid deposits is therefore of great interest in order to study pathological processes that are linked to dysregulated lipogenesis. In the present study, we present a small fluorescent benzothiadiazole dye that specifically stains lipid droplets in living and fixated cells. The photophysical characterization of the probe revealed strong solvatochromic behavior, large Stokes shifts, and high fluorescent quantum yields in hydrophobic solvents...
April 26, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28441501/hooked-on-cryogels-a-carbamate-linker-based-depot-for-slow-drug-release
#5
Duygu Aydin, Mehmet Arslan, Amitav Sanyal, Rana Sanyal
Poly(ethylene glycol) (PEG) based bulk hydrogels and cryogels containing activated carbonate groups as amine reactive handles to facilitate drug conjugations through carbamate linkages were fabricated and evaluated as slow releasing drug reservoirs. As an initial approach, photopolymerization of N-hydroxysuccinimide (NHS)-activated carbonate functional group containing monomer and PEG-methacrylate in the presence of a crosslinker was utilized to obtain bulk hydrogels with high gel conversions. The resultant hydrogels possessed moderate water uptake (170-340 %) which was dependent on the monomer ratios...
April 25, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28441471/gemcitabine-integrated-nano-prodrug-carrier-system
#6
Seren Hamsici, Melis Sardan Ekiz, Goksu Cinar Ciftci, Ayse Begum Tekinay, Mustafa O Guler
Peptide nanomaterials have received a great deal of interest in drug delivery applications due to their biodegradability, biocompatibility, suitability for large scale synthesis, high drug loading capacities, targeting ability and ordered structural organization. The covalent conjugation of drugs to peptide backbone results in prolonged circulation time and improved stability of drugs. Therapeutic efficacy of gemcitabine, which is used for breast cancer treatment, is severely compromised due to its rapid plasma degradation...
April 25, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28441015/-bottom-up-construction-of-multi-polyprodrug-arm-hyperbranched-amphiphiles-for-cancer-therapy
#7
Pei Sun, Dong Chen, Hongping Deng, Nan Wang, Ping Huang, Xin Jin, Xinyuan Zhu
Despite of great advantages of polymer-drug conjugates (PDC) in cancer therapy, the controlling of drug loading site and degree via a facile approach remains a great challenge. Herein, combination the controllability of the "bottom-up" strategy and the stability of multi-arm hyperbranched amphiphiles, we have developed a novel multi-polyprodrug-arm hyperbranched amphiphiles (H40-star-(PHCPTMA-b-PMPC), hPCM) via reversible addition-fragmentation chain transfer (RAFT) polymerization for cancer therapy. The hPCM was constructed via two-step polymerization of an acid-labile prodrug monomer and a zwitterionic monomer, respectively...
April 25, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28441009/bisazide-cyanine-dyes-as-fluorogenic-probes-for-bis-cyclooctynylated-peptide-tags-and-as-fluorogenic-crosslinkers-of-cyclooctynylated-proteins
#8
Orsolya Demeter, Attila Kormos, Christine Koehler, Gábor Mezõ, Krisztina Németh, Eszter Kozma, Levente Takacs, Edward A Lemke, Peter Kele
Herein we present the synthesis and fluorogenic characterization of a series of double-quenched bisazide cyanine probes with emission maxima between 565-580 nm that can participate in covalent, two-point binding bioorthogonal tagging schemes in combination with bis-cyclooctynylated peptides. Compared to other fluorogenic cyanines these double-quenched systems showed remarkable fluorescence intensity increase upon formation of cyclic dye-peptide conjugates. Furthermore, we also demonstrated that these bisazides are useful fluorogenic crosslinking platforms that are able to form a covalent linkage between monocyclooctynylated proteins...
April 25, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28437092/facile-quenching-and-spatial-patterning-of-cylooctynes-via-strain-promoted-alkyne-azide-cycloaddition-of-inorganic-azides
#9
Matthew Bjerknes, Hazel Cheng, Christopher D McNitt, Vladimir V Popik
Little is known about the reactivity of strain-promoted alkyne-azide cycloaddition (SPAAC) reagents with inorganic azides. We explore the reactions of a variety of popular SPAAC reagents with sodium azide and hydrozoic acid. We find that the reactions proceed in water at rates comparable to those with organic azides, yielding in all cases a triazole adduct. The azide ion's utility as a cyclooctyne quenching reagent is demonstrated by using it to spatially pattern uniformly-doped hydrogels. The facile quenching of cyclooctynes demonstrated here should be useful in other bioorthogonal ligation techniques in which cyclooctynes are employed, including SPANC, Diels-Alder, and thiol-yne...
April 24, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28437083/dual-plug-and-display-synthetic-assembly-using-orthogonal-reactive-proteins-for-twin-antigen-immunization
#10
Karl Brune, Can Buldun, Yuanyuan Li, Iona Taylor, Florian Brod, Sumi Biswas, Mark Howarth
Engineering modular platforms to control biomolecular architecture can advance both the understanding and manipulation of biological systems. Icosahedral particles uniformly displaying single antigens stimulate potent immune activation and have been successful in various licensed vaccines. However, it remains challenging to display multiple antigens on a single particle, to induce broader immunity protective across strains or even against distinct diseases. Here we design a dually-addressable synthetic nanoparticle, by engineering the multimerizing coiled-coil IMX313 and two orthogonally-reactive split proteins...
April 24, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28437080/comparison-of-tumor-penetration-of-podophyllotoxin-carboxymethylcellulose-conjugates-with-various-chemical-compositions-in-tumor-spheroid-culture-and-in-vivo-solid-tumor
#11
Yang Yang, Aniruddha Roy, Yucheng Zhao, Elijus Undzys, Shyh-Dar Li
Polymer conjugation is an attractive approach for delivering insoluble and highly toxic drugs to tumors. However, most reports in the literature only disclose the optimal composition without emphasizing rational design or composition optimization to achieve maximized biological effects. In this study, we aimed to demonstrate that composition of a polymer conjugate would determine its physiochemical characteristics, tumor penetration and, ultimately, the in vivo efficacy. We also aimed to examine whether the tumor spheroid model could generate comparable results with the in vivo tumor model in terms of tumor penetration and efficacy of the various polymer conjugates...
April 24, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28436674/general-dialdehyde-click-chemistry-for-amine-bioconjugation
#12
Sina Elahipanah, Paul J O'Brien, Dmitry Rogozhnikov, Muhammad N Yousaf
The development of methods for conjugating a range of molecules to primary amine functional groups has revolutionized the fields of chemistry, biology, and material science. The primary amine is a key functional group and one of the most important nucleophiles and bases used in all of synthetic chemistry. Therefore, tremendous interest in the synthesis of molecules containing primary amines and strategies to devise chemical reactions to react with primary amines has been at the core of chemical research. In particular, primary amines are a ubiquitous functional group found in biological systems as free amino acids, as key side chain lysines in proteins, and in signaling molecules and metabolites and are also present in many natural product classes...
April 24, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28431209/drug-delivery-systems-based-on-hydroxyethyl-starch
#13
Constantinos M Paleos, Zili Sideratou, Dimitris Tsiourvas
Τhe advantageous biological properties of hydroxyethyl starch (HES) triggered research interest towards design and synthesis of Drug Delivery Systems (DDSs) based on this polysaccharide. Convenient reaction schemes, including one-step reactions, led to the synthesis of HES conjugates with selected anticancer molecules or therapeutic proteins. Nanocapsules and hydrogels based on HES were also prepared and studied as prospective drug delivery systems. Formulations originating from these drug conjugates and also from nanocapsules and hydrogels loaded with drugs were characterized, highlighting on the extension of their half-life in plasma which is a critical property as far as their efficacy is concerned...
April 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28430413/bioimaging-with-macromolecular-probes-incorporating-multiple-bodipy-fluorophores
#14
Ek Raj Thapaliya, Yang Zhang, Pravat Dhakal, Adrienne S Brown, James N Wilson, Kevin Collins, Françisco M Raymo
Seven macromolecular constructs incorporating multiple borondipyrromethene (BODIPY) fluorophores along a common poly(methacrylate) backbone with decyl and oligo(ethylene glycol) side chains were synthesized. The hydrophilic oligo(ethylene glycol) components impose solubility in aqueous environment on the overall assembly. The hydrophobic decyl chains insulate effectively the fluorophores from each other to prevent detrimental interchromophoric interactions and preserve their photophysical properties. As a result, the brightness of these multicomponent assemblies is approximately three times greater than that of a model BODIPY monomer...
April 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28381088/tuning-thermoresponsive-properties-of-cationic-elastin-like-polypeptides-by-varying-counterions-and-side-chains
#15
Rosine Petitdemange, Elisabeth Garanger, Laure Bataille, Katell Bathany, Bertrand Garbay, Timothy J Deming, Sébastien Lecommandoux
We report the synthesis of methionine-containing recombinant elastin-like polypeptides (ELPs) of different lengths that contain periodically spaced methionine residues. These ELPs were chemoselectively alkylated at all methionine residues to give polycationic derivatives. Some of these samples were found to possess solubility transitions in water, where the temperature of these transitions varied with ELP concentration, nature of the methionine alkylating group, and nature of the sulfonium counterions. These studies show that introduction and controlled spacing of methionine sulfonium residues into ELPs can be used as a means both to tune their solubility transition temperatures in water using a variety of different parameters and to introduce new side-chain functionality...
April 18, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28381085/revisiting-boronate-diol-complexation-as-a-double-stimulus-responsive-bioconjugation
#16
Arianna Gennari, Chirag Gujral, Erwin Hohn, Enrique Lallana, Francesco Cellesi, Nicola Tirelli
This study presents a quantitative assessment of the complexation between boronic acids and diols as a reversible and double-stimulus (oxidation and acidification)-responsive bioconjugation reaction. First, by using a competition assay, we have evaluated the equilibrium constants (water, pH 7.4) of 34 boronate/diol pairs, using diols of both aliphatic and aromatic (catechols) nature; in general, catechols were characterized by constants 3 orders of magnitude higher than those of aliphatic diols. Second, we have demonstrated that successful complexation with diols generated in situ via enzymatic reactions, and the boronate complexation was also employed to calculate the Michaelis-Menten parameters for two catechol-producing reactions: the demethylation of 3-methoxytyramine and the 2-hydroxylation of estradiol, respectively, mediated by P4502D6 and P4501A2...
April 18, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28414915/tethered-fluorogen-assay-to-visualize-membrane-apposition-in-living-cells
#17
Daniel S Ackerman, Kalin V Vasilev, Brigitte F Schmidt, Lianne B Cohen, Jonathan W Jarvik
We describe proof-of-concept for a novel approach for visualizing regions of close apposition between the surfaces of living cells. A membrane-anchored protein with high affinity for a chemical ligand is expressed on the surface of one set of cells, and the cells are co-cultured with a second set of cells that express a membrane-anchored fluorogen-activating protein (FAP). The co-cultured cells are incubated with a bivalent reagent comprised of fluorogen linked to the high-affinity ligand, with the concentration of the bivalent reagent chosen to be less than the binding constant for the FAP/fluorogen pair, but greater than the binding constant for the ligand/high-affinity protein pair...
April 17, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28414435/synthesis-of-bodipy-peptide-conjugates-for-fluorescence-labeling-of-egfr-over-expressing-cells
#18
Ning Zhao, Tyrslai Williams, Zehua Zhou, Frank R Fronczek, Martha Sibrian-Vazquez, Seetharama Jois, M Graca Henriques Vicente
Regioselective functionalization of 2,3,5,6,8-pentachloro-BODIPY 1 produced unsymmetric BODIPY 5, bearing an isothiocyanate group suitable for conjugation, in only four steps. The X-ray structure of 5 reveals a nearly planar BODIPY core with aryl dihedral angles in the range 47.4° - 62.9°. Conjugation of 5 to two EGFR-targeting pegylated peptides, 3PEG-LARLLT (6) and 3PEG-GYHWYGYTPQNVI (7), under mild conditions (30 min at room temperature), afforded BODIPY conjugates 8 and 9 in 50-80% isolated yields. These conjugates show red-shifted absorption and emission spectra compared with 5, in the near-IR region, and were evaluated as potential fluorescence imaging agents for EGRF over-expressing cells...
April 17, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28379682/synthetic-random-copolymers-as-a-molecular-platform-to-mimic-host-defense-antimicrobial-peptides
#19
Haruko Takahashi, Gregory A Caputo, Satyavani Vemparala, Kenichi Kuroda
Synthetic polymers have been used as a molecular platform to develop host-defense antimicrobial peptide (AMP) mimetics which are effective in killing drug-resistant bacteria. In this topical review, we will discuss the AMP-mimetic design and chemical optimization strategies as well as the biological and biophysical implications of AMP mimicry by synthetic polymers. Traditionally, synthetic polymers have been used as a chemical means to replicate the chemical functionalities and physicochemical properties of AMPs (e...
April 17, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28406614/vinyluridine-as-a-versatile-chemoselective-handle-for-the-posttranscriptional-chemical-functionalization-of-rna
#20
Jerrin Thomas George, Seergazhi G Srivatsan
Development of modular and efficient methods to functionalize RNA with biophysical probes is very important to advance the understanding of the structural and functional relevance of RNA in various cellular events. Herein we demonstrate a two-step bioorthogonal chemical functionalization approach for the conjugation of multiple probes onto RNA transcripts using a 5-vinyl-modified uridine nucleotide analog (VUTP). VUTP, containing a structurally non-invasive and versatile chemoselective handle, was efficiently incorporated into RNA transcripts by in vitro transcription reactions...
April 13, 2017: Bioconjugate Chemistry
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