DNA Binding and Recognition of a CC Mismatch in a DNA Duplex by Water-Soluble Peptidocalix[4]arenes: Synthesis and Applications

被引：9

作者：

Alavijeh, Nahid S. ^{[1
]}

Zadmard, Reza ^{[1
]}

Balalaie, Saeed ^{[2
]}

Alavijeh, Mohammad S. ^{[3
]}

Soltani, Nima ^{[4
]}

机构：

[1] Chem & Chem Engn Res Ctr Iran, POB 14335-186, Tehran 1496813151, Iran

[2] KN Toosi Univ Technol, Peptide Chem Res Ctr, POB 15875-4416, Tehran 1969764499, Iran

[3] Pharmidex Pharmaceut Serv Ltd, London W1S 1YH, England

[4] Sharif Univ Technol, Dept Chem, POB 11155-3516, Tehran 1458889694, Iran

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

关键词：

PROTEIN; CALIXARENES; SPECIFICITY; DELIVERY; COMPLEX;

D O I：

10.1021/acs.orglett.6b01995

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Water-soluble peptidocalix[4]arenes were synthesized by the introduction of arginine-rich narrow groove binding residues at lower rims through solid-phase synthesis. The study of binding of these water-soluble bidentate ligands to well-matched and mismatched DNA duplexes by fluorescent titrations, ethidium bromide (EB) displacement assays, DNA-melting experiments, and circular dichroism (CD) analysis revealed a sequence-dependent groove-binding mechanism.

引用

页码：4766 / 4769

页数：4

共 26 条

[1] Efficient synthesis of lower rim α-hydrazino tetrazolocalix[4]arenes via an Ugi-azide multicomponent reaction
Alavijeh, Nahid S.
Zadmard, Reza
Ramezanpour, Sorour
Balalaie, Saeed
Alavijeh, Mohammad S.
Rominger, Frank
[J]. NEW JOURNAL OF CHEMISTRY, 2015, 39 (08) : 6578 - 6584
[2] DNA binders in clinical trials and chemotherapy
Ali, Asfa
Bhattacharya, Santanu
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (16) : 4506 - 4521
[3] Arginine clustering on calix[4]arene macrocycles for improved cell penetration and DNA delivery
Bagnacani, Valentina
Franceschi, Valentina
Bassi, Michele
Lomazzi, Michela
Donofrio, Gaetano
Sansone, Francesco
Casnati, Alessandro
Ungaro, Rocco
[J]. NATURE COMMUNICATIONS, 2013, 4
[4] Calixarene-based multivalent ligands
Baldini, L.
Casnati, A.
Sansone, F.
Ungaro, R.
[J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) : 254 - 266
[5] Histidine-Based Lipopeptides Enhance Cleavage of Nucleic Acids: Interactions with DNA and Hydrolytic Properties
Belieres, M.
Dejugnat, C.
Chouini-Lalanne, N.
[J]. BIOCONJUGATE CHEMISTRY, 2015, 26 (12) : 2520 - 2529
[6] Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]arenes
Bois, Joackim
Bonnamour, Isabelle
Duchamp, Christian
Parrot-Lopez, Helene
Darbost, Ulrich
Felix, Caroline
[J]. NEW JOURNAL OF CHEMISTRY, 2009, 33 (10) : 2128 - 2135
[7] DNA recognition with large calixarene dimers and varying spacers
Breitkreuz, Caroline J.
Zadmard, Reza
Schrader, T.
[J]. SUPRAMOLECULAR CHEMISTRY, 2008, 20 (1-2) : 109 - 115
[8] Demeunynck M, 2006, DNA RNA BINDERS SMAL
[9] Recognition of specific DNA sequences
Garvie, CW
Wolberger, C
[J]. MOLECULAR CELL, 2001, 8 (05) : 937 - 946
[10] Monomeric complex of human orphan estrogen related receptor-2 with DNA: A pseudo-dimer interface mediates extended half-site recognition
Gearhart, MD
Holmbeck, SMA
Evans, RM
Dyson, HJ
Wright, PE
[J]. JOURNAL OF MOLECULAR BIOLOGY, 2003, 327 (04) : 819 - 832

← 1 2 3 →