Literature DB >> 33128946

A modular template for the design of thiol-triggered sensors and prodrugs.

Jessica Renee Knight1, Yingying Wang1, Shi Xu2, Wei Chen1, Clifford E Berkman1, Ming Xian3.   

Abstract

A unique reaction between thiols (RSH) and alkyl sulfonylbenzothiazole was discovered. This reaction was specific for thiols and produced a sulfinic acid (RSO2H) as the intermediate, which further triggered an intramolecular cyclization to release a -OH containing payload. This reaction was used to develop thiol-triggered fluorescent sensors and prodrugs. The modular design of this template provides tunability of the release profiles of the payloads.
Copyright © 2020 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  Biothiols; Fluorescent probe; Prodrug; Sulfinic acid

Mesh:

Substances:

Year:  2020        PMID: 33128946      PMCID: PMC7736145          DOI: 10.1016/j.saa.2020.119072

Source DB:  PubMed          Journal:  Spectrochim Acta A Mol Biomol Spectrosc        ISSN: 1386-1425            Impact factor:   4.098


  29 in total

1.  Glutathione deficiency is associated with impaired survival in HIV disease.

Authors:  L A Herzenberg; S C De Rosa; J G Dubs; M Roederer; M T Anderson; S W Ela; S C Deresinski; L A Herzenberg
Journal:  Proc Natl Acad Sci U S A       Date:  1997-03-04       Impact factor: 11.205

2.  Synthesis of CDDO-amino acid-nitric oxide donor trihybrids as potential antitumor agents against both drug-sensitive and drug-resistant colon cancer.

Authors:  Yong Ai; Fenghua Kang; Zhangjian Huang; Xiaowen Xue; Yisheng Lai; Sixun Peng; Jide Tian; Yihua Zhang
Journal:  J Med Chem       Date:  2015-02-23       Impact factor: 7.446

3.  The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides.

Authors:  Wei Chen; Ethan W Rosser; Tetsuro Matsunaga; Armando Pacheco; Takaaki Akaike; Ming Xian
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-18       Impact factor: 15.336

Review 4.  The role of glutathione in cancer.

Authors:  Ganesaratnam K Balendiran; Rajesh Dabur; Deborah Fraser
Journal:  Cell Biochem Funct       Date:  2004 Nov-Dec       Impact factor: 3.685

5.  Critical roles of intracellular thiols and calcium in parthenolide-induced apoptosis in human colorectal cancer cells.

Authors:  Siyuan Zhang; Choon-Nam Ong; Han-Ming Shen
Journal:  Cancer Lett       Date:  2004-05-28       Impact factor: 8.679

6.  Rational Design of a Dual-Reactivity-Based Fluorescent Probe for Visualizing Intracellular HSNO.

Authors:  Wei Chen; Tetsuro Matsunaga; Deshka L Neill; Chun-Tao Yang; Takaaki Akaike; Ming Xian
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-24       Impact factor: 15.336

Review 7.  Glutathione in cancer biology and therapy.

Authors:  José M Estrela; Angel Ortega; Elena Obrador
Journal:  Crit Rev Clin Lab Sci       Date:  2006       Impact factor: 6.250

Review 8.  Cysteine regulation of protein function--as exemplified by NMDA-receptor modulation.

Authors:  Stuart A Lipton; Yun-Beom Choi; Hiroto Takahashi; Dongxian Zhang; Weizhong Li; Adam Godzik; Laurie A Bankston
Journal:  Trends Neurosci       Date:  2002-09       Impact factor: 13.837

9.  Naphthalimide Scaffold Provides Versatile Platform for Selective Thiol Sensing and Protein Labeling.

Authors:  Pengcheng Zhou; Juan Yao; Guodong Hu; Jianguo Fang
Journal:  ACS Chem Biol       Date:  2016-02-09       Impact factor: 5.100

Review 10.  Thiol reactive probes and chemosensors.

Authors:  Hanjing Peng; Weixuan Chen; Yunfeng Cheng; Lovemore Hakuna; Robert Strongin; Binghe Wang
Journal:  Sensors (Basel)       Date:  2012-11-19       Impact factor: 3.576

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