24367-44-0Relevant articles and documents
Synthesis and biological evaluation of disulfides as anticancer agents with thioredoxin inhibition
Wei, Xiangxu,Zhong, Miao,Wang, Song,Li, Lexun,Song, Zi-Long,Zhang, Junmin,Xu, Jianqiang,Fang, Jianguo
, (2021/03/24)
Altered redox homeostasis as a hallmark of cancer cells is exploited by cancer cells for growth and survival. The thioredoxin (Trx), an important regulator in maintaining the intracellular redox homeostasis, is cumulatively recognized as a promising target for the development of anticancer drugs. Herein, we synthesized 72 disulfides and evaluated their inhibition for Trx and antitumor activity. First, we established an efficient and fast method to screen Trx inhibitors by using the probe NBL-SS that was developed by our group to detect Trx function in living cells. After an initial screening of the Trx inhibitory activity of these compounds, 8 compounds showed significant inhibition activity against Trx. We then evaluated the cytotoxicity of these 8 disulfides, compounds 68 and 69 displayed high cytotoxicity to HeLa cells, but less sensitive to normal cell lines. Next, we performed kinetic studies of both two disulfides, 68 had faster inhibition of Trx than 69. Further studies revealed that 68 led to the accumulation of reactive oxygen species and eventually induced apoptosis of Hela cells via inhibiting Trx. The establishment of a method for screening Trx inhibitors and the discovery of 68 with remarkable Trx inhibition provide support for the development of anticancer candidates with Trx inhibition.
Visible-light photocatalytic selective aerobic oxidation of thiols to disulfides on anatase TiO2
Xu, Hui,Shi, Ji-Long,Lyu, Shaoshuai,Lang, Xianjun
, p. 1468 - 1473 (2020/04/29)
This work presents the visible-light photocatalytic selective oxidation of thiols to disulfides with molecular oxygen (O2) on anatase TiO2. The high specific surface area of anatase TiO2 proved to be especially critical in
TEMPO visible light photocatalysis: The selective aerobic oxidation of thiols to disulfides
Xu, Hui,Zhang, Yu-Fei,Lang, Xianjun
supporting information, p. 1520 - 1524 (2019/12/09)
TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) is well-established in orangocatalysis that usually work in synergy with transition-metal catalysis or semiconductor photocatalysis. Here, TEMPO was turned into a visible light photocatalyst to conduct the selective aerobic oxidation of thiols into disulfides. With O2 as an oxidant, a mild and efficient protocol for the selective oxidation of thiols into disulfides including symmetrical and unsymmetrical ones with 5 molpercent of TEPMO as a photocatalyst was developed at room temperature under the irradiation of 460 nm blue LEDs. It was found that a complex formed between TEMPO and thiols underpinned the visible light activity and disulfides were obtained in very high isolated yields. This work suggests that TEMPO takes diverse roles in for photocatalytic selective oxidative transformations with O2 as the oxidant.
Phototropin-Inspired Chemoselective Synthesis of Unsymmetrical Disulfides: Aerobic Oxidative Heterocoupling of Thiols Using Flavin Photocatalysis
Iida, Hiroki,Katsube, Daichi,Oka, Marina,Tsuji, Takeshi
supporting information, p. 9244 - 9248 (2020/12/21)
Inspired by the photochemical mechanism of a plant blue-light receptor, a unique flavin-based photocatalytic system was developed for the chemoselective heterocoupling of two different thiols, which enabled the facile synthesis of unsymmetrical disulfides. Owing to the redox- and photo-organocatalysis of flavin, the coupling reaction took place under mild metal-free conditions and visible light irradiation with the use of air, which is recognized as the ideal green oxidant.
Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water
Song, Lijuan,Li, Wenhao,Duan, Wenxue,An, Jichao,Tang, Shanyu,Li, Longjia,Yang, Guanyu
supporting information, p. 1432 - 1438 (2019/03/26)
The formation of S-S bonds has great significance and value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various symmetrical and unsymmetrical disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrates the practicability of our method.
Electro-Oxidative S?H/S?H Cross-Coupling with Hydrogen Evolution: Facile Access to Unsymmetrical Disulfides
Huang, Pengfei,Wang, Pan,Tang, Shan,Fu, Zhuangjiong,Lei, Aiwen
supporting information, p. 8115 - 8119 (2018/06/04)
Sulfur is an essential element because it exists widely in proteins. The disulfide bond is an important moiety in many different types of significant organic molecules. A new approach for oxidant- and catalyst-free S?H/S?H cross-coupling, with hydrogen ev
POLYNUCLEOTIDE CONSTRUCTS HAVING BIOREVERSIBLE AND NON-BIOREVERSIBLE GROUPS
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Page/Page column 103, (2016/02/19)
The invention features a hybridized polynucleotide construct containing a passenger strand, a guide strand loadable into a RISC complex, and (i) a 3'-terminal or an internucleotide non-bioreversible group in the guide strand; or (ii) a 5'-terminal, a 3'-terminal, or an internucleotide non-bioreversible group in the passenger strand, and a 5'-terminal, a 3'-terminal, or an internucleotide disulfide bioreversible group in the guide strand or the passenger strand. The invention also features methods of delivering a polynucleotide to a cell using the hybridized polynucleotide construct. The invention further features methods of reducing the expression of a polypeptide in a cell using the hybridized polynucleotide construct.
Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole
Hunter, Roger,Caira, Mino,Stellenboom, Nashia
, p. 8268 - 8271 (2007/10/03)
A new synthesis of unsymmetrical disulfides is described. The reaction of a thiol R1SH with 1-chlorobenzotriazole (BtCl) at -78 °C in DCM affords a high-yielding conversion to R1SBt without appreciable formation of the symmetrical disulfide R1SSR1. R1SBt is then reacted with R2SH to form the unsymmetrical disulfide in a one-pot sequence with green character that avoids the use of toxic and harsh oxidizing agents. The methodology has been developed for synthesis of various types of disulfides.
beta-scission of the N-O bond in alkyl hydroxamate radicals: a fast radical trap.
Wu,Begley
, p. 1345 - 1348 (2007/10/03)
[reaction--see text ] The rate of the beta-scission of the N-O bond in the alkyl hydroxamate radical is faster than 2 x 10(8) s(-)(1). This reaction may be useful as a radical trap.
