A highly acidic acridine for efficient site-selective activation of RNA leading to an eminent ribozyme mimic

被引:22
作者
Kuzuya, A [1 ]
Machida, K [1 ]
Komiyama, M [1 ]
机构
[1] Univ Tokyo, Adv Sci & Technol Res Ctr, Meguro Ku, Tokyo 1538904, Japan
关键词
acridine; oligonucleotides; site-selective scission; lanthanide; acid catalysis;
D O I
10.1016/S0040-4039(02)02017-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
9-Amino-2-methoxy-6-nitroacridine (1a) is conjugated with oligonucleotide for site-selective RNA hydrolysis. When this conjugate forms a duplex with complementary RNA, the phosphodiester linkage of the RNA in front of la is activated and selectively hydrolyzed by Lu(III) ion. Covalent fixation of the metal ion to sequence-recognizing moiety is unnecessary. The site-selective hydrolysis by this conjugate is 2.2 times as fast as that by the oligonucleotide bearing 9-amino-6-chloro-2-methoxyacridine (1b), which hitherto has been the most active for the RNA activation. The acridine derivative 1a is more acidic than 1b, and thus is more effective as acid catalyst for the RNA hydrolysis. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8249 / 8252
页数:4
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