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Literature DB >> 22681565

Methylsulfonyl benzothiazole (MSBT): a selective protein thiol blocking reagent.

Dehui Zhang¹, Nelmi O Devarie-Baez, Qian Li, Jack R Lancaster, Ming Xian.

Abstract

A new thiol blocking reagent, methylsulfonyl benzothiazole, was discovered. This reagent showed good selectivity and high reactivity for protein thiols.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2012 PMID： 22681565 PMCID： PMC3391333 DOI： 10.1021/ol301370s

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

28 in total

Review 1. Sulfur and selenium: the role of oxidation state in protein structure and function.

Authors: Claus Jacob; Gregory I Giles; Niroshini M Giles; Helmut Sies
Journal: Angew Chem Int Ed Engl Date: 2003-10-13 Impact factor: 15.336

2. Structure-activity relationships of 2-(benzothiazolylthio)acetamide class of CCR3 selective antagonist.

Authors: Akira Naya; Kensuke Kobayashi; Makoto Ishikawa; Kenji Ohwaki; Toshihiko Saeki; Kazuhito Noguchi; Norikazu Ohtake
Journal: Chem Pharm Bull (Tokyo) Date: 2003-06 Impact factor: 1.645

3. Differential reactivity of maleimide and bromoacetyl functions with thiols: application to the preparation of liposomal diepitope constructs.

Authors: P Schelté; C Boeckler; B Frisch; F Schuber
Journal: Bioconjug Chem Date: 2000 Jan-Feb Impact factor: 4.774

4. Synthetic chemotherapeutic agents. II. Synthesis of 2-substituted thiazolo(5,4-f)quinoline derivatives.

Authors: S Kadoya; I Takamura; N Suzuki; R Dohmori
Journal: Chem Pharm Bull (Tokyo) Date: 1976-01 Impact factor: 1.645

5. Studies on cardiotonic agents. VI. Synthesis of novel 4,5-dihydro-3(2H)-pyridazinone derivatives carrying some benzoheterocycles at the 6-position.

Authors: Y Nomoto; H Takai; T Ohno; K Kubo
Journal: Chem Pharm Bull (Tokyo) Date: 1991-02 Impact factor: 1.645

Review 6. Mapping the cysteine proteome: analysis of redox-sensing thiols.

Authors: Dean P Jones; Young-Mi Go
Journal: Curr Opin Chem Biol Date: 2011-01-07 Impact factor: 8.822

7. The local electrostatic environment determines cysteine reactivity of tubulin.

Authors: P J Britto; Leslie Knipling; J Wolff
Journal: J Biol Chem Date: 2002-05-21 Impact factor: 5.157

8. Reactivity and pH dependence of thiol conjugation to N-ethylmaleimide: detection of a conformational change in chalcone isomerase.

Authors: R A Bednar
Journal: Biochemistry Date: 1990-04-17 Impact factor: 3.162

9. Reactivity of small thiolate anions and cysteine-25 in papain toward methyl methanethiosulfonate.

Authors: D D Roberts; S D Lewis; D P Ballou; S T Olson; J A Shafer
Journal: Biochemistry Date: 1986-09-23 Impact factor: 3.162

10. Heteroaromatic thioether-organostannane cross-coupling.

Authors: Masahiro Egi; Lanny S Liebeskind
Journal: Org Lett Date: 2003-03-20 Impact factor: 6.005

24 in total

Review 1. Arylation Chemistry for Bioconjugation.

Authors: Chi Zhang; Ekaterina V Vinogradova; Alexander M Spokoyny; Stephen L Buchwald; Bradley L Pentelute
Journal: Angew Chem Int Ed Engl Date: 2019-02-15 Impact factor: 15.336

2. Rapid, stable, chemoselective labeling of thiols with Julia-Kocieński-like reagents: a serum-stable alternative to maleimide-based protein conjugation.

Authors: Narihiro Toda; Shigehiro Asano; Carlos F Barbas
Journal: Angew Chem Int Ed Engl Date: 2013-10-02 Impact factor: 15.336

Review 3. Mass spectrometry in studies of protein thiol chemistry and signaling: opportunities and caveats.

Authors: Nelmi O Devarie Baez; Julie A Reisz; Cristina M Furdui
Journal: Free Radic Biol Med Date: 2014-09-28 Impact factor: 7.376

4. H₂O₂ oxidation of cysteine residues in c-Jun N-terminal kinase 2 (JNK2) contributes to redox regulation in human articular chondrocytes.

Authors: Kimberly J Nelson; Jesalyn A Bolduc; Hanzhi Wu; John A Collins; Elizabeth A Burke; Julie A Reisz; Chananat Klomsiri; Scott T Wood; Raghunatha R Yammani; Leslie B Poole; Cristina M Furdui; Richard F Loeser
Journal: J Biol Chem Date: 2018-09-06 Impact factor: 5.157

5. Highly selective fluorescence off-on probes for biothiols and imaging in live cells.

Authors: Di Zhang; Wei Chen; Jianming Kang; Yong Ye; Yufen Zhao; Ming Xian
Journal: Org Biomol Chem Date: 2014-09-21 Impact factor: 3.876

6. Overexpression of Cystathionine γ-Lyase Suppresses Detrimental Effects of Spinocerebellar Ataxia Type 3.

Authors: Pauline M Snijder; Madina Baratashvili; Nicola A Grzeschik; Henri G D Leuvenink; Lucas Kuijpers; Sippie Huitema; Onno Schaap; Ben N G Giepmans; Jeroen Kuipers; Jan Lj Miljkovic; Aleksandra Mitrovic; Eelke M Bos; Csaba Szabó; Harm H Kampinga; Pascale F Dijkers; Eelke M Bos; Csaba Szabó; Harm H Kampinga; Pascale F Dijkers; Wilfred F A den Dunnen; Milos R Filipovic; Harry van Goor; Ody C M Sibon
Journal: Mol Med Date: 2015-10-13 Impact factor: 6.354

Methylsulfonyl benzothiazole (MSBT): a selective protein thiol blocking reagent.

Review 1. Sulfur and selenium: the role of oxidation state in protein structure and function.

2. Structure-activity relationships of 2-(benzothiazolylthio)acetamide class of CCR3 selective antagonist.

3. Differential reactivity of maleimide and bromoacetyl functions with thiols: application to the preparation of liposomal diepitope constructs.

4. Synthetic chemotherapeutic agents. II. Synthesis of 2-substituted thiazolo(5,4-f)quinoline derivatives.

5. Studies on cardiotonic agents. VI. Synthesis of novel 4,5-dihydro-3(2H)-pyridazinone derivatives carrying some benzoheterocycles at the 6-position.

Review 6. Mapping the cysteine proteome: analysis of redox-sensing thiols.

7. The local electrostatic environment determines cysteine reactivity of tubulin.

8. Reactivity and pH dependence of thiol conjugation to N-ethylmaleimide: detection of a conformational change in chalcone isomerase.

9. Reactivity of small thiolate anions and cysteine-25 in papain toward methyl methanethiosulfonate.

10. Heteroaromatic thioether-organostannane cross-coupling.

Review 1. Arylation Chemistry for Bioconjugation.

2. Rapid, stable, chemoselective labeling of thiols with Julia-Kocieński-like reagents: a serum-stable alternative to maleimide-based protein conjugation.

Review 3. Mass spectrometry in studies of protein thiol chemistry and signaling: opportunities and caveats.

4. H₂O₂ oxidation of cysteine residues in c-Jun N-terminal kinase 2 (JNK2) contributes to redox regulation in human articular chondrocytes.

5. Highly selective fluorescence off-on probes for biothiols and imaging in live cells.

6. Overexpression of Cystathionine γ-Lyase Suppresses Detrimental Effects of Spinocerebellar Ataxia Type 3.

7. Introduction to approaches and tools for the evaluation of protein cysteine oxidation.

8. Detection of protein S-sulfhydration by a tag-switch technique.

Review 9. Chemical Biology of H₂S Signaling through Persulfidation.

10. Thiol-blocking electrophiles interfere with labeling and detection of protein sulfenic acids.

Review 1. Sulfur and selenium: the role of oxidation state in protein structure and function.

Review 6. Mapping the cysteine proteome: analysis of redox-sensing thiols.

Review 1. Arylation Chemistry for Bioconjugation.

Review 3. Mass spectrometry in studies of protein thiol chemistry and signaling: opportunities and caveats.

Review 9. Chemical Biology of H2S Signaling through Persulfidation.

Review 9. Chemical Biology of H₂S Signaling through Persulfidation.