DNA sequence recognition in the minor groove by hairpin pyrrole polyamide-Hoechst 33258 analogue conjugate

被引：14

作者：

Reddy, PM ^{[1
]}

Dexter, R ^{[1
]}

Bruice, TC ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 14期

关键词：

D O I：

10.1016/j.bmcl.2004.04.089

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A hairpin pyrrole polyamide conjugated to a Hoechst 33258 (Ht) analogue, PyPyPy-gamma-PyPyPy-gamma-Ht, was synthesized on solid-phase by adaptation of an Fmoc technique using a series of PyBOP/HOBt mediated coupling reactions. Sequence selectivity and complex stabilities were characterized by spectrofluorometric titrations and thermal melting studies. The polyamide of the conjugate was observed to bind in a hairpin motif forming 1: 1 conjugate:dsDNA complexes. The conjugate is able to recognize nine contiguous A/T bps, discriminating from the sequences containing fewer than nine contiguous A/T bps. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3803 / 3807

页数：5

共 28 条

[1] MULTIVARIATE CHROMOSOME ANALYSIS AND COMPLETE KARYOTYPING USING DUAL LABELING AND FLUORESCENCE DIGITAL IMAGING MICROSCOPY [J].

ARNDTJOVIN, DJ ;

JOVIN, TM .

CYTOMETRY, 1990, 11 (01) :80-93

[2] Sequence-specific DNA minor groove binders. Design and synthesis of netropsin and distamycin analogues [J].

Bailly, C ;

Chaires, JB .

BIOCONJUGATE CHEMISTRY, 1998, 9 (05) :513-538

[3] DNA minor groove recognition by bis-benzimidazole analogues of Hoechst 33258:: insights into structure-DNA affinity relationships assessed by fluorescence titration measurements [J].

Bostock-Smith, CE ;

Searle, MS .

NUCLEIC ACIDS RESEARCH, 1999, 27 (07) :1619-1624

[4] MICROGONOTROPENS AND THEIR INTERACTIONS WITH DNA .2. QUANTITATIVE-EVALUATION OF EQUILIBRIUM-CONSTANTS FOR 1/1 AND 2/1 BINDING OF DIEN-MICROGONOTROPEN-A, DIEN-MICROGONTROPEN-B, AND DIEN-MICROGONTROPEN-C AS WELL AS DISTAMYCIN AND HOECHST-33258 TO D(GGCGCAAATTTGGCGG)/D(CCGCCAATTTGCGCC) [J].

BROWNE, KA ;

HE, GX ;

BRUICE, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) :7072-7079

[5] Targeting E2F1-DNA complexes with microgonotropen DNA binding agents [J].

Chiang, SY ;

Bruice, TC ;

Azizkhan, JC ;

Gawron, L ;

Beerman, TA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (07) :2811-2816

[6] Targeting the Ets binding site of the HER2/neu promoter with pyrrole-imidazole polyamides [J].

Chiang, SY ;

Bürli, RW ;

Benz, CC ;

Gawron, L ;

Scott, GK ;

Dervan, PB ;

Beerman, TA .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (32) :24246-24254

[7] Recognition of the DNA minor groove by pyrrole-imidazole polyamides [J].

Dervan, PB ;

Edelson, BS .

CURRENT OPINION IN STRUCTURAL BIOLOGY, 2003, 13 (03) :284-299

[8] Sequence-specific DNA recognition by polyamides [J].

Dervan, PB ;

Bürli, RW .

CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (06) :688-693

[9] Molecular recognition of DNA by small molecules [J].

Dervan, PB .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (09) :2215-2235

[10]

Frau S, 1996, B SOC CHIM FR, V133, P1053

← 1 2 3 →