Water soluble extended naphthalene diimides as pH fluorescent sensors and G-quadruplex ligands

被引：68

作者：

Doria, Filippo ^{[2
]}

Nadai, Matteo ^{[1
]}

Sattin, Giovanna ^{[1
]}

Pasotti, Luca ^{[2
]}

Richter, Sara N. ^{[1
]}

Freccero, Mauro ^{[2
]}

机构：

[1] Univ Padua, Dipartimento Med Mol, I-35121 Padua, Italy

[2] Univ Pavia, Dipartimento Chim, I-27100 Pavia, Italy

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 19期

关键词：

TELOMERIC G-QUADRUPLEXES; OPTICAL-PROPERTIES; ALKYLATING-AGENTS; CORE; BINDING; CANCER; DNA; SELECTIVITY; DUPLEX; PROBES;

D O I：

10.1039/c2ob07006e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Extended naphthalene diimides (NDIs) fused to 1,4-dihydropyrazine-2,3-dione, containing two solubilizing moieties, have been synthesized. Fluorescence spectra of the new NDIs were remarkably affected by pH, as the second deprotonation of the dihydropyrazinedione moiety (pK(a) 6.9) switched off the emission. Binding to a G-quadruplex folded oligonucleotide and stoichiometry were evaluated by FRET melting assay and CD analysis. G-quadruplex binding was strongly enhanced shifting from pH 7.4 to pH 6.0 as a consequence of the dihydropyrazinedione moiety protonation. Cytotoxicity studies using two human telomerase-positive cell lines (HT29 and A549) revealed that the best G-quadruplex ligand was very active against the colon cell line, with an EC50 of 300 nM.

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收藏

页码：3830 / 3840

页数：11

相关论文

共 37 条

[1] pH-Mediated Fluorescence and G-Quadruplex Binding of Amido Phthalocyanines [J].

Alzeer, Jawad ;

Luedtke, Nathan W. .

BIOCHEMISTRY, 2010, 49 (20) :4339-4348

[2] Guanidinium-Modified Phthalocyanines as High-Affinity G-Quadruplex Fluorescent Probes and Transcriptional Regulators [J].

Alzeer, Jawad ;

Vummidi, Balayeshwanth R. ;

Roth, Phillipe J. C. ;

Luedtke, Nathan W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9362-9365

[3] Interaction of malachite green with guanine-rich single-stranded DNA: preferential binding to a G-quadruplex [J].

Bhasikuttan, Achikanath C. ;

Mohanty, Jyotirmayee ;

Pal, Haridas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9305-9307

[4] RETRACTED: A Core-Substituted Naphthalene Diimide Fluoride Sensor (Retracted Article) [J].

Bhosale, Sheshanath V. ;

Bhosale, Sidhanath V. ;

Kalyankar, Mohan B. ;

Langford, Steven J. .

ORGANIC LETTERS, 2009, 11 (23) :5418-5421

[5] Making sense of G-quadruplex and i-motif functions in oncogene promoters [J].

Brooks, Tracy A. ;

Kendrick, Samantha ;

Hurley, Laurence .

FEBS JOURNAL, 2010, 277 (17) :3459-3469

[6] Tri- and tetra-substituted naphthalene diimides as potent G-quadruplex ligands [J].

Cuenca, Francisco ;

Greciano, Olga ;

Gunaratnam, Mekala ;

Haider, Shozeb ;

Munnur, Deeksha ;

Nanjunda, Rupesh ;

Wilson, W. David ;

Neidle, Stephen .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (05) :1668-1673

[7] Quinone Methides Tethered to Naphthalene Diimides as Selective G-Quadruplex Alkylating Agents [J].

Di Antonio, Marco ;

Doria, Filippo ;

Richter, Sara N. ;

Bertipaglia, Carolina ;

Mella, Mariella ;

Sissi, Claudia ;

Palumbo, Manlio ;

Freccero, Mauro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :13132-13141

[8] Hybrid ligand-alkylating agents targeting telomeric G-quadruplex structures [J].

Doria, Filippo ;

Nadai, Matteo ;

Folini, Marco ;

Di Antonio, Marco ;

Germani, Luca ;

Percivalle, Claudia ;

Sissi, Claudia ;

Zaffaroni, Nadia ;

Alcaro, Stefano ;

Artese, Anna ;

Richter, Sara N. ;

Freccero, Mauro .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (14) :2798-2806

[9] Substituted Heterocyclic Naphthalene Diimides with Unexpected Acidity. Synthesis, Properties, and Reactivity [J].

Doria, Filippo ;

di Antonio, Marco ;

Benotti, Michele ;

Verga, Daniela ;

Freccero, Mauro .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) :8616-8625

[10] N-phenyl-carbazole-based two-photon fluorescent probes: Strong sequence dependence of the duplex vs quadruplex selectivity [J].

Dumat, B. ;

Bordeau, G. ;

Faurel-Paul, E. ;

Mahuteau-Betzer, F. ;

Saettel, N. ;

Bombled, M. ;

Metge, G. ;

Charra, F. ;

Fiorini-Debuisschert, C. ;

Teulade-Fichou, M. -P. .

BIOCHIMIE, 2011, 93 (08) :1209-1218

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