ACS Chemical Biology p. 1098 - 1105 (2016)
Update date:2022-08-10
Topics:
Zhou, Pengcheng
Yao, Juan
Hu, Guodong
Fang, Jianguo
Reversible thiol modifications are fundamental of cellular redox regulation. Specific thiol detection, including thiol sensing and protein thiols labeling, is critical to study such modifications. We reported the discovery of 4-methylsulfonyl-N-n-butyl-1,8-naphthalimide (MSBN), a highly selective fluorogenic probe for thiols based on the 1,8-naphthalimide scaffold. Thiols react with MSBN nearly quantitatively via nucleophilic aromatic substitution to replace the methylsulfonyl group and restore the quenched fluorescence (>100-fold increase). MSBN was employed to selectively image thiols in live cells and specifically label protein thiols with a turn-on signal to determine diverse reversible protein thiol modifications. In addition, we introduced a bulky group into the MSBN as a mass tag to create a probe MSBN-TPP, which readily discriminates the reduced thioredoxin from the oxidized one. The specific reaction of MSBN with thiols and the easy manipulation of the naphthalimide unit enable MSBN a versatile scaffold in developing novel probes for thiol-based protein bioconjugation and studying various thiol modifications.
View MoreGuangxi Shanyun Biochemical Science and Technology Co., Ltd
Contact:+86-0772--6828887
Address:#2 Industrial Park of Luzhai County, Liuzhou, Guangxi, China
ZHEJIANG JIANYE CHEMICAL CO.,LTD.
Contact:86-571-64149273,64149234
Address:No. 48, Fuxi Road, Meicheng Town
ZHIJIANG ZENVA SINO COMMERCE AND TRADE CO., LTD.
website:http://www.zenvasino.com
Contact:+86-138-72658998
Address:Shibeishan Road,Zhijiang, Hubei, China
Contact:0086-22-23410962
Address:17-201, Ningfuli, Shuishanggongyuandong road,Nankai district, Tianjin, China
Shanghai Dynamic Industrial Co.,Ltd.
website:http://www.shdynamic.com
Contact:86-021 3392 6680
Address:Room 805 Information Tower, No.1403 Minsheng Road, Pudong New Area, Shanghai 200135, P. R. China
Doi:10.1039/c6cy00195e
(2016)Doi:10.1039/c4ra14771e
(2015)Doi:10.1016/S0040-4039(01)01415-0
(2001)Doi:10.1039/c6md00564k
(2017)Doi:10.1039/jr9560001603
(1956)Doi:10.1248/cpb.59.1227
(2011)