Self-assembly of a thymine quartet and quadruplex via an organic template

被引:4
作者
Hui, Wei-Qiang Benjamin [1 ]
Sherman, John C. [1 ]
机构
[1] Univ British Columbia, Vancouver, BC V6T 1Z1, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
Cavitands; Supramolecular chemistry; Template synthesis; Thymine quartet; Thymine quadruplex; MAGNETIC-RESONANCE; BASE-STACKING; RNA TETRAPLEX; IMINO PROTON; DNA; TELOMERE; TARGETS; TETRADS; GUANINE; COMPLEXATION;
D O I
10.1016/j.tetlet.2014.01.058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of two hydrophobic cavitands bearing four (1) and eight (2) thymidine residues covalently linked with triazole moieties is reported. Spectral evidence indicates the adoption of a hydrogen-bonded T-quartet assembly by 1 in chloroform at low temperature and a pi-stacked quadruplex by 2 in DMSO under ambient conditions. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1479 / 1485
页数:7
相关论文
共 51 条
[1]   Stabilisation of G-Quadruplex DNA by Small Molecules [J].
Arola, Anna ;
Vilar, Ramon .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2008, 8 (15) :1405-1415
[2]   Targeting G-quadruplexes in gene promoters: a novel anticancer strategy? [J].
Balasubramanian, Shankar ;
Hurley, Laurence H. ;
Neidle, Stephen .
NATURE REVIEWS DRUG DISCOVERY, 2011, 10 (04) :261-275
[3]   G-quadruplex nucleic acids as therapeutic targets [J].
Balasubramanian, Shankar ;
Neidle, Stephen .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2009, 13 (03) :345-353
[4]   A Thymine Tetrad Assembly Templated from Thymidylic Acid [J].
Bare, Grant A. L. ;
Sherman, John C. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (16) :8198-8202
[5]   Synthesis of a Single G-Quartet Platform in Water [J].
Bare, Grant A. L. ;
Liu, Bo ;
Sherman, John C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11985-11989
[6]   A thymine tetrad in d(TGGGGT) quadruplexes stabilized with Tl+/Na+ ions [J].
Cáceres, C ;
Wright, G ;
Gouyette, C ;
Parkinson, G ;
Subirana, JA .
NUCLEIC ACIDS RESEARCH, 2004, 32 (03) :1097-1102
[7]   SOLUTION STRUCTURE OF AN UNUSUALLY STABLE RNA TETRAPLEX CONTAINING G-QUARTET AND U-QUARTET STRUCTURES [J].
CHEONG, CJ ;
MOORE, PB .
BIOCHEMISTRY, 1992, 31 (36) :8406-8414
[8]   HOST-GUEST COMPLEXATION .65. HEMICARCERANDS THAT ENCAPSULATE HYDROCARBONS WITH MOLECULAR-WEIGHTS GREATER-THAN 200 [J].
CRAM, DJ ;
JAEGER, R ;
DESHAYES, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10111-10116
[9]   An improved synthesis of 5′-amino-5′-deoxyguanosine [J].
Dean, DK .
SYNTHETIC COMMUNICATIONS, 2002, 32 (10) :1517-1521
[10]   X-ray analysis of an RNA tetraplex (UGGGGU)4 with divalent Sr2+ ions at subatomic resolution (0.61Å) [J].
Deng, JP ;
Xiong, Y ;
Sundaralingam, M .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (24) :13665-13670