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使用带有d-苏糖醇连接子的吡喃咔唑修饰的寡脱氧核苷酸进行DNA光交联。

DNA photo-cross-linking using a pyranocarbazole-modified oligodeoxynucleotide with a d-threoninol linker.

作者信息

Fujimoto Kenzo, Yamaguchi Tsubasa, Inatsugi Takahiro, Takamura Masahiko, Ishimaru Isao, Koto Ayako, Nakamura Shigetaka

机构信息

Department of Advanced Institute Science and Technology, Japan Advanced Institute of Science and Technology Asahidai 1-1 Nomi Ishikawa 923-1292 Japan

Advanced Materials Research Laboratory, Advanced Technology Research Department, In statute of Surface Science and Technology, NICCA CHEMICAL CO., LTD. 23-1, 4-Chome, Bunkyo Fukui-City 910-8670 Japan.

出版信息

RSC Adv. 2019 Sep 27;9(53):30693-30697. doi: 10.1039/c9ra06145b. eCollection 2019 Sep 26.

Abstract

An alternative photo-cross-linker having a d-threoninol skeleton instead of the 2'-deoxyribose backbone in 3-cyanovinylcarbazole (K) was investigated to improve the photoreactivity of photo-cross-linkers; the photo-cross-linking rate of 3-cyanovinylcarbazole with d-threoninol (D) was found to be greater than that of K. Therefore, in this study, a novel photo-cross-linker having pyranocarbazole (X) and d-threoninol instead of the 2'-deoxyribose backbone in X (D) was developed. The D in double-stranded DNA photo-cross-linked to a pyrimidine base at the -1 position of a complementary strand similar to X. Furthermore, the photoreactivity of D was significantly higher than that of X. The introduction of d-threoninol improved the reactivity of pyranocarbazole to cytosine, the use of D may extend the applicability of the photo-cross-linking reaction for DNA manipulation. In particular, this novel photo-cross-linker can contribute to the photochemical regulation of gene expression or biological events in a living cell.

摘要

研究了一种替代的光交联剂,其在3-氰基乙烯基咔唑(K)中具有d-苏糖醇骨架而非2'-脱氧核糖主链,以提高光交联剂的光反应活性;发现3-氰基乙烯基咔唑与d-苏糖醇(D)的光交联速率大于K。因此,在本研究中,开发了一种新型光交联剂,其具有吡喃并咔唑(X)和d-苏糖醇,而非X(D)中的2'-脱氧核糖主链。双链DNA中的D在互补链的-1位与嘧啶碱基发生光交联,类似于X。此外,D的光反应活性显著高于X。d-苏糖醇的引入提高了吡喃并咔唑对胞嘧啶的反应活性,D的使用可能会扩展光交联反应在DNA操作中的适用性。特别是,这种新型光交联剂可有助于对活细胞中的基因表达或生物事件进行光化学调控。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d6/9072208/2f8c9041c016/c9ra06145b-f1.jpg

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