Second Generation G-Quadruplex Stabilizing Trimethine Cyanines Article Swipe

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Eric A. Owens , Hang T Huynh , Ekaterina Stroeva , Arghya Barman , Kostiantyn Ziabrev , Ananya Paul , Sarah V. Nguyen , Matthew Laramie , Donald Hamelberg , Markus W. Germann , W. David Wilson , Maged Henary ·

YOU? · · 2019 · Open Access · · DOI: https://doi.org/10.1021/acs.bioconjchem.9b00571

G-quadruplex DNA has been recognized as a highly appealing target for the development of new selective chemotherapeutics, which could result in markedly reduced toxicity towards normal cells. In particular, the cyanine dyes that bind selectively to G-quadruplex structures without targeting duplex DNA have attracted attention due to their high amenability to structural modifications that allows fine tuning of their biomolecular interactions. We have previously reported pentamethine and symmetric trimethine cyanines designed to effectively bind G-quadruplexes through end stacking interactions. Herein, we are reporting a second generation of drug candidates, the asymmetric trimethine cyanines. These have been synthesized and evaluated for their quadruplex binding properties. Incorporating a benz[c,d]indolenine heterocyclic unit increased overall quadruplex binding and elongating the alkyl length increases the quadruplex-to-duplex binding specificity.

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Chemistry Cyanine Stacking G-quadruplex Duplex (building) DNA Biophysics Combinatorial chemistry Stereochemistry Biochemistry Organic chemistry Physics Quantum mechanics Biology Fluorescence

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Type: article
Language: en
Landing Page: https://doi.org/10.1021/acs.bioconjchem.9b00571
OA Status: green
Cited By: 8
References: 36
Related Works: 10
OpenAlex ID: https://openalex.org/W2972986983

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DOI: https://doi.org/10.1021/acs.bioconjchem.9b00571

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Title: Second Generation G-Quadruplex Stabilizing Trimethine Cyanines

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Type: article

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Language: en

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Publication year: 2019

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Publication date: 2019-09-13

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Authors: Eric A. Owens, Hang T Huynh, Ekaterina Stroeva, Arghya Barman, Kostiantyn Ziabrev, Ananya Paul, Sarah V. Nguyen, Matthew Laramie, Donald Hamelberg, Markus W. Germann, W. David Wilson, Maged Henary

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Landing page: https://doi.org/10.1021/acs.bioconjchem.9b00571

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OA status: green

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OA URL: https://www.ncbi.nlm.nih.gov/pmc/articles/7032661

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Concepts: Chemistry, Cyanine, Stacking, G-quadruplex, Duplex (building), DNA, Biophysics, Combinatorial chemistry, Stereochemistry, Biochemistry, Organic chemistry, Physics, Quantum mechanics, Biology, Fluorescence

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Cited by: 8

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