Site-selective DNA photocleavage involving unusual photoinitiated tautomerization of chiral tridentate vanadyl(V) complexes derived from N-salicylidene α-amino acids

被引:57
作者
Chen, CT [1 ]
Lin, JS
Kuo, JH
Weng, SS
Cuo, TS
Lin, YW
Cheng, CC
Huang, YC
Yu, JK
Chou, PT
机构
[1] Natl Taiwan Normal Univ, Dept Chem, Taipei, Taiwan
[2] Tamkang UNiv, Dept Chem, Taipei, Taiwan
[3] Natl Taiwan Univ, Dept Chem, Taipei 10764, Taiwan
关键词
D O I
10.1021/ol048156h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The titled vanadyl(V) complexes serve as efficient reagents for cleaving supercoiled plasmid DNA by photoinitiation. Complex 3d, derived from 2-hydroxy-1-naphthaldehyde and L-phenylalanine, exhibits a unique wedge feature, inducing a site-selective photocleavage at the C22-T23 of the bulge backbone for a HIV-27 DNA system at 0.1-5 muM. Transient absorption experiments for 3d indicate the involvement of LMCT with concomitant tautomerization, leading to an o-quinone-methide V-bound hydroxyl species responsible for the cleavage profiles.
引用
收藏
页码:4471 / 4474
页数:4
相关论文
共 35 条
[1]   Highly selective DNA modification by ambient O2-activated Co(II)•Lys-Gly-His metallopeptides [J].
Ananias, DC ;
Long, EC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) :10460-10461
[2]   Photocleavage of nucleic acids [J].
Armitage, B .
CHEMICAL REVIEWS, 1998, 98 (03) :1171-1200
[3]   Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates [J].
Barhate, NB ;
Chen, CT .
ORGANIC LETTERS, 2002, 4 (15) :2529-2532
[4]   Photohydration and photosolvolysis of biphenyl alkenes and alcohols via biphenyl quinone methide-type intermediates and diarylmethyl carbocations [J].
Brousmiche, DW ;
Xu, MS ;
Lukeman, M ;
Wan, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12961-12970
[5]   Effects of secondary structure on DNA and RNA cleavage by diplatinum(II) [J].
Carter, PJ ;
Breiner, KM ;
Thorp, HH .
BIOCHEMISTRY, 1998, 37 (39) :13736-13743
[6]   Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate [J].
Chen, CT ;
Kuo, JH ;
Li, CH ;
Barhate, NB ;
Hon, SW ;
Li, TW ;
Chao, SD ;
Liu, CC ;
Li, YC ;
Chang, IH ;
Lin, JS ;
Liu, CJ ;
Chou, YC .
ORGANIC LETTERS, 2001, 3 (23) :3729-3732
[7]  
Chen CT, 1999, SYNLETT, P816
[8]   CONFORMATION-SPECIFIC DETECTION OF GUANINE IN DNA - ENDS, MISMATCHES, BULGES, AND LOOPS [J].
CHEN, XY ;
BURROWS, CJ ;
ROKITA, SE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :322-325
[9]   Mechanistic aspects of CoII(HAPP)(TFA)2 in DNA bulge-specific recognition [J].
Cheng, CC ;
Huang-Fu, WC ;
Hung, KC ;
Chen, PJ ;
Wang, WJ ;
Chen, YJ .
NUCLEIC ACIDS RESEARCH, 2003, 31 (08) :2227-2233
[10]  
Cheng CC, 1999, ANGEW CHEM INT EDIT, V38, P1255, DOI 10.1002/(SICI)1521-3773(19990503)38:9<1255::AID-ANIE1255>3.0.CO