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Bioconjugate Chemistry

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https://www.readbyqxmd.com/read/28650634/reversible-and-versatile-on-tether-modification-of-chiral-center-induced-helical-peptides
#1
Kuan Hu, Chengjie Sun, Zigang Li
Modification of the cross-linker of constrained peptides has recently received considerable attention. Here, we present a versatile approach to modify the cross-linking tether of chiral center-induced helical (CIH) peptides via S-alkylation reac-tion. The alkylation process displayed high conversion efficiency, selectivity and substrate tolerance. Notably, although on-tether S-alkylation could lead to a pair of peptide epimers, the major alkylated product retained the helical structure of its helical precursor peptide...
June 26, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28644614/role-of-the-protein-corona-derived-from-human-plasma-in-cellular-interactions-between-nanoporous-human-serum-albumin-particles-and-endothelial-cells
#2
Mikhail Valeryevich Zyuzin, Yan Yan, Raimo Hartmann, Katelyn T Gause, Moritz Nazarenus, Jiwei Cui, Frank Caruso, Wolfgang J Parak
The presence of a protein corona on various synthetic nanomaterials has been shown to strongly influence how they interact with cells. However, it is unclear if the protein corona also exists on protein particles, and if so, its role in particle-cell interactions. In this study, pure human serum albumin (HSA) particles were fabricated via mesoporous silica particle templating. Our data reveal that various serum proteins adsorbed on the particles. The presence of a corona from human plasma was shown to decrease particle binding to cell membrane, increase the residence time of particles in early endosomes, and reduce the amount of internalized particles within the first hours of cell exposure to particles...
June 23, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28644608/targeting-cpg-adjuvant-to-lymph-node-via-dextran-conjugate-enhances-anti-tumor-immunotherapy
#3
Weidong Zhang, Myunggi An, Jingchao Xi, Haipeng Liu
Nucleic acids based adjuvants recognized by Toll-like receptors (TLR) are potent immune system stimulants that can augment the anti-tumor immune responses in an antigen-specific manner. However, their clinical uses as vaccine adjuvants are limited primarily due to lack of accumulation in the lymph nodes, the anatomic sites where the immune responses are initiated. Here, we showed that chemical conjugation of type B CpG DNA, a TLR9 agonist to dextran polymer dramatically enhanced CpG's lymph node accumulation in mice...
June 23, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28482148/bacteriophages-as-factories-for-eu2o3-nanoparticle-synthesis
#4
Piotr Golec, Kamila Żelechowska, Joanna Karczewska-Golec, Jakub Karczewski, Adam Leśniewski, Marcin Łoś, Grzegorz Węgrzyn, Andrzej M Kłonkowski
The use of phage display to identify peptides with an ability to bind and synthesize Eu2O3 nanoparticles is demonstrated in this report. This is the first report of modified phages specifically binding a lanthanide. The peptides exposed on virions revealed very strong binding to Eu2O3 nanoparticles and the ability to catalyze Eu2O3 nanoparticles' formation from Eu(OH)3 and Eu(NO3)3 solutions. The luminescence emission spectrum of Eu(3+) ions indicated that these ions existed mostly in sites deviated from the inversion symmetry in crystalline Eu2O3 aggregates and gelatinous Eu(OH)3 precipitate...
June 22, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28636382/development-of-efficient-chemistry-to-generate-site-specific-disulfide-linked-protein-and-peptide-payload-conjugates-application-to-thiomab%C3%A2-antibody-drug-conjugates
#5
Jack David Sadowsky, Thomas H Pillow, Jinhua Chen, Fang Fan, Changrong He, Yanli Wang, Gang Yan, Hui Yao, Zijin Xu, Shanique Martin, Donglu Zhang, Phillip Chu, Josefa Dela Cruz-Chuh, Aimee O'Donohue, Guangmin Li, Geoffrey Del Rosario, Jintang He, Luna Liu, Carl K Ng, Dian Su, Gail D Lewis Phillips, Katherine Ruth Kozak, Shang-Fan Yu, Keyang Xu, Douglas Leipold, John S Wai
Conjugation of small molecule payloads to specific cysteine residues on proteins via a disulfide bond represents an attractive strategy to generate redox-sensitive bioconjugates, which have value as potential diagnostic reagents or therapeutics. Advancement of such "direct-disulfide" bioconjugates to the clinic necessitates chemical methods to form disulfide connections efficiently, without byproducts. The disulfide connection must also be resistant to premature cleavage by thiols prior to arrival at the targeted tissue...
June 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28636368/probing-the-mechanism-of-lal-32-a-gold-nanoparticle-based-antibiotic-discovered-through-small-molecule-variable-ligand-display
#6
Rose Byrne-Nash, Danielle Lucero, Niki Osbaugh, Roberta J Melander, Christian Melander, Daniel L Feldheim
The unrelenting rise of antimicrobial resistant bacteria has necessitated the search for novel antibiotic solutions. Herein we describe further mechanistic studies on a 2.0 nm diameter gold nanoparticle-based antibiotic (designated LAL-32). This antibiotic exhibits bactericidal activity against the Gram-negative bacterium Escherichia coli at 1.0 μΜ, a concentration significantly lower than several clinically available antibiotics (such as ampicillin and gentamicin), and acute treatment with LAL-32 does not give rise to spontaneous resistant mutants...
June 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28636335/a2b-miktoarm-glycopolymer-fibers-and-their-interactions-with-tenocytes
#7
Renjie Liu, Dharmesh Patel, Hazel R C Screen, C Remzi Becer
Electrospun biodegradable membranes have attracted great attention for a range of tissue engineering applications. Among them, poly (ε-caprolactone) (PCL) is one of the most widely used polymers, owing to its well-controlled biocompatibility and biodegradability. However, PCL also has a number of limitations, such as its hydrophobic nature and the lack of functional groups on its side chain, limiting its ability to interact with cells. Herein, we have designed and prepared a series of well-defined A2B-miktoarm copolymers with PCL and glycopolymer segments to address these limitations...
June 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28635265/metabolic-oligosaccharide-engineering-with-alkyne-sialic-acids-confers-neuraminidase-resistance-and-inhibits-influenza-reproduction
#8
Torben Heise, Christian Büll, Daniëlle M H Beurskens, Emiel Rossing, Marien de Jonge, Gosse J Adema, Thomas J Boltje, Jeroen Langereis
Metabolic incorporation of azide or alkyne modified sialic acids into the cellular glycosylation pathway enables the study of sialoglycan expression, localization and trafficking via bioorthogonal chemistry. Herein we report that such modifications of the sialic acid sugar can have a profound influence on their hydrolysis by neuraminidases (sialidase). Azidoacetyl modified sialic acids were prone to neuraminidase cleavage, whereas propargyloxycarbonyl (Poc) modified sialic acids were largely resistent to cleavage...
June 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28635259/a-delivery-system-targeting-haemagglutinin-of-influenza-virus-a-to-facilitate-antisense-based-anti-h1n1-therapy
#9
Xiaoran Ding, Jing Yang, Dandan Lu, Qingjun Li, Zhaoyan Zhang, Zhe Zhou, Shengqi Wang
Antisense oligonucleotides (ODNs) are therapeutic molecules that hybridize to complementary target mRNA sequences. To further overcome the poor cellular uptake of ODNs, we proposed a novel strategy to deliver ODNs by conjugating the anti-influenza A virus (IAV) ODN with a peptide showing high affinity to the haemagglutinin (HA) on the surface of IAV particles or the IAV infected host cells. The HA-specific binding peptides were selected by phage display and the individual binding clones are characterized by DNA sequencing, and the selected phage was further assayed by ELISA...
June 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28558204/development-and-application-of-synthetic-affinity-ligands-for-the-purification-of-ferritin-based-influenza-antigens
#10
Shaleem I Jacob, Basmah Khogeer, Nick Bampos, Tom Sheppard, Richard Schwartz, Christopher R Lowe
A recently developed novel recombinant influenza antigen vaccine has shown great success in preclinical studies in ferrets and mice. It provides broader protection, and is efficient to manufacture compared to the conventional trivalent influenza vaccines (TIV). Each strain of the recombinant antigen has a constant self-assembled bacterial ferritin core which, if used as a target for affinity chromatography, could lead to a universal purification method. Ferritin in silico models were used to explore potential target binding sites against ligands synthesized by the four-component Ugi reaction...
June 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28581724/targeting-tumor-associated-phosphatidylserine-with-new-zinc-dipicolylamine-based-drug-conjugates
#11
Yu-Wei Liu, Kak-Shan Shia, Chien-Huang Wu, Kuan-Liang Liu, Yu-Cheng Yeh, Chen-Fu Lo, Chiung-Tong Chen, Yun-Yu Chen, Teng-Kuang Yeh, Wei-Han Chen, Jiing-Jyh Jan, Yu-Chen Huang, Chen-Lung Huang, Ming-Yu Fang, Brian D Gray, Koon Y Pak, Tsu-An Hsu, Kuan-Hsun Huang, Lun K Tsou
A series of zinc(II) dipicolylamine (ZnDPA)-based drug conjugates have been synthesized to probe the potential of phosphatidylserine (PS) as a new antigen for small molecule drug conjugate (SMDC) development. Using in vitro cytotoxicity and plasma stability studies, PS-binding assay, in vivo pharmacokinetic studies, and maximum tolerated dose profiles, we provided a roadmap and the key parameters required for the development of the ZnDPA based drug conjugate. In particular, conjugate 24 induced tumor regression in the COLO 205 xenograft model and exhibited a more potent antitumor effect with a 70% reduction of cytotoxic payload compared to that of the marketed irinotecan when dosed at the same regimen...
June 19, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28603971/enhanced-and-prolonged-cell-penetrating-abilities-of-arginine-rich-peptides-by-introducing-cyclic-%C3%AE-%C3%AE-disubstituted-%C3%AE-amino-acids-with-stapling
#12
Makoto Oba, Masayuki Kunitake, Takuma Kato, Atsushi Ueda, Masakazu Tanaka
Cell-penetrating peptides are receiving increasing attention as drug delivery tools, and the search for peptides with high cell-penetrating ability and negligible cytotoxicity has become a critical research topic. Herein, cyclic α,α-disubstituted α-amino acids were introduced into arginine-rich peptides and an additional staple was provided in the side chain. The peptides designed in the present study showed more enhanced and prolonged cell-penetrating abilities than an arginine nonapeptide due to high resistance to protease and conformationally stable helical structures...
June 16, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28616969/ph-driven-actuation-of-dna-origami-via-parallel-i-motif-sequences-in-solution-and-on-surfaces
#13
Jacob M Majikes, Lucas C C Ferraz, Thomas H LaBean
As bottom up DNA nanofabrication creates increasingly complex and dynamic mechanisms, the implementation of actuators within the DNA nanotechnology toolkit has grown increasingly important. One such actuator, the I-motif, is fairly simple in that it consists solely of standard DNA sequences and does not require any modification chemistry or special purification beyond that typical for DNA oligomer synthesis. This study presents a new implementation of parallel I-motif actuators, emphasizing their future potential as drivers of complex internal motion between substructures...
June 15, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28570043/fabrication-of-polymeric-micelles-with-aggregation-induced-emission-and-forster-resonance-energy-transfer-for-anticancer-drug-delivery
#14
Na Hao, Changzhen Sun, Zhengfei Wu, Long Xu, Wenxia Gao, Jun Cao, Li Li, Bin He
With the aim of obtaining effective cancer therapy with simultaneous cellular imaging, dynamic drug-release monitoring, and chemotherapeutic treatment, a polymeric micelle with aggregation-induced emission (AIE) imaging and a Forster resonance energy transfer (FRET) effect was fabricated as the drug carrier. An amphiphilic conjugate of 1H-pyrrole-1-propanoicacid (MAL)-poly(ethylene glycol) (PEG)-Tripp-bearing AIE molecules were synthesized and self-assembled into micelles to load the anticancer drug doxorubicin (DOX)...
June 15, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28613834/amino-functionalized-5-cap-analogs-as-tools-for-site-specific-sequence-independent-labeling-of-messenger-rna
#15
Marcin Warminski, Pawel J Sikorski, Zofia Warminska, Maciej Lukaszewicz, Anna Kropiwnicka, Joanna Zuberek, Edward Darzynkiewicz, Joanna Kowalska, Jacek Jemielity
mRNA is a template for protein biosynthesis, and consequently mRNA transport, translation, and turnover are key elements in the overall regulation of gene expression. Along with growing interest in the mechanisms regulating mRNA decay and localization, there is an increasing need for tools enabling convenient fluorescent labelling or affinity tagging of mRNA. We report new mRNA 5' cap analog-based tools that enable site-specific labelling of RNA within the cap using N-hydroxysuccinimide (NHS) chemistry. We explored two complementary methods: a co-transcriptional labelling method, in which the label is first attached to cap analog and then incorporated into RNA by transcription in vitro, and post-transcriptional labelling method, in which an amino-functionalized cap analog is incorporated into RNA followed by chemical labelling of the resulting transcript...
June 14, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28612603/sortase-mediated-ligation-as-a-modular-approach-for-the-covalent-attachment-of-proteins-to-the-exterior-of-the-bacteriophage-p22-virus-like-particle
#16
Dustin P Patterson, Benjamin Schwarz, John Avera, Brian Western, Matthew Hicks, Paul Krugler, Matthew Terra, Masaki Uchida, Kimberly McCoy, Trevor Douglas
Virus-like particles are unique platforms well suited for the construction of nanomaterials with broad range applications. The research presented here describes the development of a modular approach for the covalent attachment of protein domains to the exterior of the versatile bacteriophage P22 virus-like particle (VLP) via a sortase-mediated ligation strategy. The bacteriophage P22 coat protein was genetically engineered to incorporate an LPETG amino acid sequence on the C-terminus, providing the peptide recognition sequence utilized by the sortase enzyme to catalyze peptide bond formation between the LPETG-tagged protein and a protein containing a poly-glycine sequence on the N-terminus...
June 14, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28590752/optimization-of-an-enzymatic-antibody-drug-conjugation-approach-based-on-coenzyme-a-analogs
#17
Jan Grünewald, Yunho Jin, Julie Vance, Jessica Read, Xing Wang, Yongqin Wan, Huanfang Zhou, Weijia Ou, Heath E Klock, Eric C Peters, Tetsuo Uno, Ansgar Brock, Bernhard H Geierstanger
Phosphopantetheine transferases (PPTases) can be used to efficiently prepare site-specific antibody-drug conjugates (ADCs) by enzymatically coupling coenzyme A (CoA)-linker payloads to 11-12 amino acid peptide substrates inserted into antibodies. Here, a two-step strategy is established wherein in a first step, CoA analogs with various bioorthogonal reactivities are enzymatically installed on the antibody for chemical conjugation with a cytotoxic payload in a second step. Because of the high structural similarity of these CoA analogs to the natural PPTase substrate CoA-SH, the first step proceeds very efficiently and enables the use of peptide tags as short as 6 amino acids compared to the 11-12 amino acids required for efficient one-step coupling of the payload molecule...
June 14, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28603974/evolution-of-new-bolaliposomes-using-novel-%C3%AF-tocopheryl-succinate-based-cationic-lipid-and-1-12-disubstituted-dodecane-based-bolaamphiphile-for-efficient-gene-delivery
#18
Mallikarjun Gosangi, Hithavani Rapaka, Venkatesh Ravula, Srilakshmi Venkata Patri
Non-viral lipid based vectors are promising transporting systems for the intracellular delivery of therapeutic gene sequences and directly influence the success of gene delivery. However, the associated drawbacks like lower transfection, toxicity and targetability with which demands further improvisation. Towards this goal, herein, we report a novel lipid formulation by mixing two distinct cationic surfactants such as tocopheryl succinate based cationic lipid and 1, 12 dodecane based bolaamphiphile and is proved as good transfection reagent with its competing potential with "golden" standard, Lipofectamine 3000 (L3K)...
June 12, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28598150/high-yield-site-specific-conjugation-of-fibroblast-growth-factor-1-with-monomethylauristatin-e-via-cysteine-flanked-by-basic-residues
#19
Michal Lobocki, Malgorzata Zakrzewska, Anna Szlachcic, Mateusz Adam Krzyscik, Aleksandra Sokolowska-Wedzina, Jacek Otlewski
Site-specific conjugation is a leading trend in the development of protein conjugates, including antibody-drug conjugates (ADCs), suitable for targeted cancer therapy. Here, we present a very efficient strategy for specific attachment of a cytotoxic drug to fibroblast growth factor 1 (FGF1), a natural ligand of FGF receptors (FGFRs), which are overexpressed in several types of lung, breast and gastric cancers and are therefore an attractive molecular target. Recently we showed that FGF1 fused to monomethylauristatin E (vcMMAE) was highly cytotoxic to cells presenting FGFRs on their surface and could be used as a targeting agent alternative to an antibody...
June 9, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28595014/a-chelator-free-and-biocompatible-melanin-nanoplatform-with-facile-loading-gadolinium-and-copper-64-for-bioimaging
#20
Su Hyun Hong, Yao Sun, Chu Tang, Kai Cheng, Ruiping Zhang, Quli Fan, Liying Xu, Daijuan Huang, Anthony Zhao, Zhen Cheng
Development of a chelator-free and biocompatible platform for facile construction of gadolinium3+ (Gd3+) loaded nanoparticle-based probe for in vivo magentic resonance imaging (MRI) is still challenging. Herein, a biocompatible Gd3+ loaded melanin dot (Gd-M-dot) has been easily preppared without the use of ay chelators, and the resulted nanoprobe exhibited good loading efficiency for Gd3+, high stability, and higher T1 relaxivity compared with the commercial contrast agent, Gd-DOTA. Furthermore, Gd-M-dot showed unique photoacoustic (PA) property, and high PA imaging signal could be observed after 1 h injection in small animal models...
June 8, 2017: Bioconjugate Chemistry
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