The aggregation and G-quadruplex DNA selectivity of charged 3,4,9,10-perylenetetracarboxylic acid diimides

被引：57

作者：

Kern, JT ^{[1
]}

Kerwin, SM ^{[1
]}

机构：

[1] Univ Texas, Coll Pharm, Div Med Chem, Austin, TX 78712 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 23期

关键词：

D O I：

10.1016/S0960-894X(02)00763-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Two N,N"-disubstituted perylene diimide G-quadruplex DNA ligands. Tel11 (N,N'-bis-[3-(4-methyl-morpholin-4-yl)-propyl]-3.4.9.10-perylenetetracarboxylic acid diimide diiodide) and Tel12 (N,N'-bis-[(3-phosphono)-propyl]-3,4,9,10-perylene-tetracarboxylic acid diimide tetrapotassium salt) were synthesized and studied. Visible absorbance spectroscopy, resonance light scattering. and fluorescence spectroscopy were utilized to explore the aggregation state, affinity for various DNA structures, and G-quadruplex selectivity of these ligands. The water-soluble ligands exist in a monomer-dimer equilibrium with the cationic Tel11 exhibiting a greater affinity for various DNA structures than the anionic Tel12. Tel12 has greater selectivity for G-quadruplex DNA over double-stranded DNA than Tel11. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3395 / 3398

页数：4

共 18 条

[1] Benzoindoloquinolines interact with DNA tetraplexes and inhibit telomerase
Alberti, P
Schmitt, P
Nguyen, CH
Rivalle, C
Hoarau, M
Grierson, DS
Mergny, JL
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (07) : 1071 - 1074
[2] Naphthalene- and perylene-based linkers for the stabilization of hairpin triplexes
Bevers, S
Schutte, S
McLaughlin, LW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (25) : 5905 - 5915
[3] SYNTHESIS AND PROPERTIES OF FLUORESCENT BIS-QUATERNIZED PERYLENE DYES
DELIGEORGIEV, T
ZANEVA, D
PETKOV, I
TIMCHEVA, I
SABNIS, R
[J]. DYES AND PIGMENTS, 1994, 24 (01) : 75 - 81
[4] Duan WH, 2001, MOL CANCER THER, V1, P103
[5] NMR-based model of a telomerase-inhibiting compound bound to G-quadruplex DNA
Fedoroff, OY
Salazar, M
Han, HY
Chemeris, VV
Kerwin, SM
Hurley, LH
[J]. BIOCHEMISTRY, 1998, 37 (36) : 12367 - 12374
[6] PHOTOCHEMISTRY OF 3,4,9,10-PERYLENETETRACARBOXYLIC DIANHYDRIDE DYES - VISIBLE ABSORPTION AND FLUORESCENCE OF THE DI(GLYCYL)IMIDE DERIVATIVE MONOMER AND DIMER IN BASIC AQUEOUS-SOLUTIONS
FORD, WE
[J]. JOURNAL OF PHOTOCHEMISTRY, 1987, 37 (01): : 189 - 204
[7] Helical aggregation of cyanine dyes on DNA templates: Effect of dye structure on formation of homo- and heteroaggregates
Garoff, RA
Litzinger, EA
Connor, RE
Fishman, I
Armitage, BA
[J]. LANGMUIR, 2002, 18 (16) : 6330 - 6337
[8] Accelerated assembly of G-quadruplex structures by a small molecule
Han, HY
Cliff, CL
Hurley, LH
[J]. BIOCHEMISTRY, 1999, 38 (22) : 6981 - 6986
[9] Inhibition of unwinding of G-quadruplex structures by Sgs1 helicase in the presence of N,N′-bis[2-(1-piperidino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide, a G-quadruplex-interactive ligand
Han, HY
Bennett, RJ
Hurley, LH
[J]. BIOCHEMISTRY, 2000, 39 (31) : 9311 - 9316
[10] The relationship between ligand aggregation and G-quadruplex DNA selectivity in a series of 3,4,9,10-perylenetetracarboxylic acid diimides
Kern, JT
Thomas, PW
Kerwin, SM
[J]. BIOCHEMISTRY, 2002, 41 (38) : 11379 - 11389

← 1 2 →