1095-85-8Relevant academic research and scientific papers
A sulfanyl-PEG derivative of relaxin-like peptide utilizable for the conjugation with KLH and the antibody production
Katayama, Hidekazu,Mita, Masatoshi
, p. 3596 - 3602 (2016)
A small peptide–keyhole limpet hemocyanin (KLH) conjugate is generally used as an antigen for producing specific antibodies. However, preparation of a disulfide-rich heterodimeric peptide–KLH conjugates is difficult. In this study, we developed a novel method for preparation of the conjugate, and applied it to the production of specific antibodies against the relaxin-like gonad-stimulating peptide (RGP) from the starfish. In this method, a sulfanyl group necessary for the conjugation with KLH was site-specifically introduced to the peptide after regioselective disulfide bond formation reactions. Using the conjugate, we could obtain specific antibodies with a high antibody titer. This method might also be useful for the production of antibodies against other heterodimeric peptides with disulfide cross-linkages, such as vertebrate relaxins.
Synthesis and biological evaluation of technetium-99m labeled galactose derivatives as potential asialoglycoprotein receptor probes in a hepatic fibrosis mouse model
Chang, Wen-Yi,Kao, Hao-Wen,Wang, Hsin-Ell,Chen, Jenn-Tzong,Lin, Wuu-Jyh,Wang, Shyh-Jen,Chen, Chuan-Lin
, p. 6486 - 6491 (2013)
Two galactose derivatives, a monovalent 99mTc-MAMA-MGal galactoside and a divalent 99mTc-MAMA-DGal galactoside, were synthesized and radiolabeled in high radiochemical purity (>98%). Dynamic microSPECT imaging and biodistribution stu
Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
Vishwanatha, Thimmalapura M.,Bergamaschi, Enrico,D?mling, Alexander
, p. 3195 - 3198 (2017)
A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.
Dynamic covalent diblock copolymers: Instructed coupling, micellation and redox responsiveness
Yang, Qinglai,Bai, Ling,Zhang, Yuanqing,Zhu, Fangxia,Xu, Yuhong,Shao, Zhifeng,Shen, Yu-Mei,Gong, Bing
, p. 7431 - 7441 (2014)
Instructed by association units that allow reversible and unsymmetrical disulfide bond formation, hydrophilic (PEG) and hydrophobic (PLA) polymer chains are efficiently coupled into amphiphilic diblock copolymers. The desymmetrization of otherwise symmetrical reversible disulfide bond formation is achieved with amide association units that integrate both directional H-bonding and reversible disulfide bond formation, which ensure the connection of different polymer blocks while minimizing self-coupling. The resultant amphiphilic block copolymers self-assemble into long-lasting spherical micelles that are responsive to free thiols.
Bulky toroidal and vesicular self-assembled nanostructures from fullerene end-capped rod-like polymers
Mazzier,Mba,Zerbetto,Moretto
, p. 4571 - 4574 (2014)
In this work, we present novel fullerene (C60) end-capped rod-like polypeptide-polymers, obtained by one-pot thiol-ene chemistry. These systems are able to self-assemble in water creating precise bulky microstructures of toroidal or vesicular shapes. Independent molecular dynamics simulations supported the observed experimental results. the Partner Organisations 2014.
Synthesis of the molecular hybrid inspired by Largazole and Psammaplin A
Yu, Xiaoling,Zhang, Bingbing,Shan, Guangsheng,Wu, Yue,Yang, Feng-Ling,Lei, Xinsheng
, p. 549 - 555 (2018)
One important class of HDAC (histone deacetylation enzymes) inhibitors is the sulfur-containing marine natural products with structural diversity. Inspired by two structurally distinguishing examples, Largazole and Psammaplin A, which possess macrocyclic depsipeptide and simple linear amide scaffold respectively, we designed one novel molecular hybrid by replacing the alkene moiety in Largazole with a semirigid amide bond. This hybrid compound has been synthesized from L-malic acid in 10 steps with an overall yield of 7%. The preliminary biological assays suggest that the replacement of trans olefin moiety with amide bond will lead to an unbeneficial effect on the inhibition against HDACs.
Redox-responsive flower-like micelles of poly(l-lactic acid)-b-poly(ethylene glycol)-b-poly(l-lactic acid) for intracellular drug delivery
Yang, Qinglai,He, Changyu,Zhang, Zhen,Tan, Lianjiang,Liu, Bingya,Zhu, Zhenggang,Shao, Zhifeng,Gong, Bing,Shen, Yu-Mei
, p. 351 - 362 (2016)
Redox-responsive micelles self-assembled from triblock copolymers of poly(l-lactic acid)-poly(ethylene glycol)-poly(l-lactic acid) (PLA-PEG-PLA) with double-disulfide linkage in the backbone were synthesized and characterized by proton nuclear magnetic resonance (1H NMR) and size exclusion chromatography (SEC), in which both PEG (Mn = 1000, 2000 and 4000 g mol-1) and PLA (Mn = 1600 g mol-1) have different molecular weights respectively. The triblock copolymers PLA3000-PEG2000-PLA3000 and PLA3000-PEG4000-PLA3000 can self-assemble into flower-like micelles in aqueous media with average diameters 110 nm and 43 nm and lower critical micelle concentrations (CMC) 0.017 and 0.014 mg mL-1 respectively compared with that of diblock copolymers. Moreover, in vitro drug release analyses indicated that reductive environment can result in triggered drug release profiles. 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl- 2-H-tetrazolium bromide (MTT) assay in vitro showed no significant cytotoxicity as NIH 3T3 cells incubated in the micelles even when the concentrations up to 1000 μg/mL. Additionally fluorescence microscopy measurements and MTT assay demonstrated that the micelles exhibited a faster drug release and higher cellular proliferation inhibition due to the effect of intracellular reduction responsiveness compared with that of diblock copolymers. The above results suggest that the reduction-responsive, biodegradable and biocompatibility micelles could provide a platform to construct potential drug delivery systems for cancer therapy.
Molecular determinants of microbial resistance to thiopeptide antibiotics
Baumann, Sascha,Schoof, Sebastian,Bolten, Marcel,Haering, Claudia,Takagi, Motoki,Shin-Ya, Kazuo,Arndt, Hans-Dieter
, p. 6973 - 6981 (2010)
Ribosomally produced thiopeptide antibiotics are highly promising lead compounds targeting the GTPase-associated region (GAR) of the bacterial ribosome. A representative panel of GAR mutants suspected to confer resistance against thiopeptide antibiotics w
Clickable Nucleic Acids: Sequence-Controlled Periodic Copolymer/Oligomer Synthesis by Orthogonal Thiol-X Reactions
Xi, Weixian,Pattanayak, Sankha,Wang, Chen,Fairbanks, Benjamin,Gong, Tao,Wagner, Justine,Kloxin, Christopher J.,Bowman, Christopher N.
, p. 14462 - 14467 (2015)
Synthetic polymer approaches generally lack the ability to control the primary sequence, with sequence control referred to as the holy grail. Two click chemistry reactions were now combined to form nucleobase-containing sequence-controlled polymers in simple polymerization reactions. Two distinct approaches are used to form these click nucleic acid (CNA) polymers. These approaches employ thiol-ene and thiol-Michael reactions to form homopolymers of a single nucleobase (e.g., poly(A)n) or homopolymers of specific repeating nucleobase sequences (e.g., poly(ATC)n). Furthermore, the incorporation of monofunctional thiol-terminated polymers into the polymerization system enables the preparation of multiblock copolymers in a single reaction vessel; the length of the diblock copolymer can be tuned by the stoichiometric ratio and/or the monomer functionality. These polymers are also used for organogel formation where complementary CNA-based polymers form reversible crosslinks.
Synthesis of a β-CCT-lanthanide conjugate for binding the dopamine transporter
Naumiec, Gregory R.,Lincourt, Grace,Clever, Jeremy P.,McGregor, Michael A.,Kovoor, Abraham,Deboef, Brenton
, p. 2537 - 2540 (2015)
The development of a β-CCT-lanthanide conjugate that binds the dopamine transporter (DAT) with high affinity (Kd = 303 nM) is described. Contrast agents such as the one described herein could be used as molecular probes to directly study the binding of small molecules to receptors such as DAT via MRI, PET or SPECT. This journal is
