Detection of Cysteine Sulfenic Acid on E. coli Proteins with a Biotin-Benzoboroxole Probe

被引:3
作者
Niu, Yaxin [1 ]
Chen, Zhenzhen [1 ]
Jiang, Zhongyao [1 ]
Yang, Yanmei [1 ]
Liu, Guangzhao [1 ]
Cheng, Xiufen [1 ]
Jiang, Zhenhao [1 ]
Zhang, Guanglu [1 ]
Tong, Lili [1 ]
Tang, Bo [1 ,2 ]
机构
[1] Shandong Normal Univ, Coll Chem Chem Engn & Mat Sci, Collaborat Innovat Ctr Functionalized Probes Chem, Key Lab Mol & Nano Probes,Minist Educ, Jinan 250014, Peoples R China
[2] Qingdao Natl Lab Marine Sci & Technol, Qingdao 266237, Peoples R China
基金
中国国家自然科学基金;
关键词
REACTIVITY; CHEMISTRY;
D O I
10.1021/acschembio.3c00073
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
S-sulfenylationof cysteine residues on proteins can effectivelychange protein structures and accordingly regulate their functionsin vivo. Investigation of S-sulfenylation in different biologicalenvironments is thus vital for a systematic understanding of cellularredox regulation. In this work, a functional probe, biotin-benzoboroxole(Bio-ben), was designed for the detection of cysteine sulfenic acid(Cys-SOH). The performance of Bio-ben was characterized by small-moleculesulfenic acid, protein models, and proteome tests via mass spectraand western blotting. The results showed that Bio-ben was validatedfor cysteine sulfenic acid on proteins with good capture efficiencyeven at low concentrations. Compared with commonly used probes suchas dimedone, the current probe has significantly shortened labelingtime and exhibited comparable sensitivity. The proposed method providesa new approach for exploring S-sulfenylation in the oxidative modificationof proteins and is helpful for related biological and clinical applications.
引用
收藏
页码:1351 / 1359
页数:9
相关论文
共 46 条
[1]   SYNTHESIS AND PH-DEPENDENT STABILITY OF PURINE-6-SULFENIC ACID, A PUTATIVE REACTIVE METABOLITE OF 6-THIOPURINE [J].
ABRAHAM, RT ;
BENSON, LM ;
JARDINE, I .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (10) :1523-1526
[2]   Proteome-Wide Survey of Cysteine Oxidation by Using a Norbornene Probe [J].
Alcock, Lisa J. ;
Langini, Maike ;
Stuehler, Kai ;
Remke, Marc ;
Perkins, Michael, V ;
Bernardes, Goncalo J. L. ;
Chalker, Justin M. .
CHEMBIOCHEM, 2020, 21 (09) :1329-1334
[3]   Norbornene Probes for the Detection of Cysteine Sulfenic Acid in Cells [J].
Alcock, Lisa J. ;
Oliveira, Bruno L. ;
Deery, Michael J. ;
Pukala, Tara L. ;
Perkins, Michael V. ;
Bernardes, Goncalo J. L. ;
Chalker, Justin M. .
ACS CHEMICAL BIOLOGY, 2019, 14 (04) :594-598
[4]   Norbornene probes for the study of cysteine oxidation [J].
Alcock, Lisa J. ;
Farrell, Kyle D. ;
Akol, Mawey T. ;
Jones, Gregory H. ;
Tierney, Matthew M. ;
Kramer, Holger B. ;
Pukala, Tara L. ;
Bernardes, Goncalo J. L. ;
Perkins, Michael V. ;
Chalker, Justin M. .
TETRAHEDRON, 2018, 74 (12) :1220-1228
[5]  
BENITEZ LV, 1974, J BIOL CHEM, V249, P6234
[6]  
Benkovic S., 2016, BORONIC BORINIC ACID, V9, P309
[7]   Large-scale analysis of post-translational modifications in E. coli under glucose-limiting conditions [J].
Brown, Colin W. ;
Sridhara, Viswanadham ;
Boutz, Daniel R. ;
Person, Maria D. ;
Marcotte, Edward M. ;
Barrick, Jeffrey E. ;
Wilke, Claus O. .
BMC GENOMICS, 2017, 18
[8]   Characterizing posttranslational modifications in prokaryotic metabolism using a multiscale workflow [J].
Brunk, Elizabeth ;
Chang, Roger L. ;
Xia, Jing ;
Hefzi, Hooman ;
Yurkovich, James T. ;
Kim, Donghyuk ;
Buckmiller, Evan ;
Wang, Harris H. ;
Cho, Byung-Kwan ;
Yang, Chen ;
Palsson, Bernhard O. ;
Church, George M. ;
Lewis, Nathan E. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2018, 115 (43) :11096-11101
[9]   Genomic Diversity and Fitness of E. coli Strains Recovered from the Intestinal and Urinary Tracts of Women with Recurrent Urinary Tract Infection [J].
Chen, Swaine L. ;
Wu, Meng ;
Henderson, Jeffrey P. ;
Hooton, Thomas M. ;
Hibbing, Michael E. ;
Hultgren, Scott J. ;
Gordon, Jeffrey I. .
SCIENCE TRANSLATIONAL MEDICINE, 2013, 5 (184)
[10]   Target discovery of ebselen with a biotinylated probe [J].
Chen, Zhenzhen ;
Jiang, Zhongyao ;
Chen, Nan ;
Shi, Qian ;
Tong, Lili ;
Kong, Fanpeng ;
Cheng, Xiufen ;
Chen, Hao ;
Wang, Chu ;
Tang, Bo .
CHEMICAL COMMUNICATIONS, 2018, 54 (68) :9506-9509