Photoswitchable 2‐phenyldiazenyl‐purines and their influence on DNA hybridization

  • Recently, photochromic derivatives of nucleobases have drawn attention for regulating oligonucleotide hybridization with light for photopharmacological applications. The nucleobase moiety provides attractive interaction for hybridization, whereas the photochromic moiety can alter the interaction upon irradiation due to conformational changes. Herein we report the synthesis of 2‐phenyldiazenyl‐substituted 2’‐deoxyadenosine (dAAzo) and 2’‐deoxyguanosine (dGAzo) and investigate their influence in a DNA context by UV/Vis absorption, fluorescence and CD spectroscopies. For comparison, the literature‐known azobenzene C‐nucleoside DNAzo was used as a reference system. It could be shown that photochromic purines improve overall hybridization affinity compared to azobenzene C‐nucleosides. In particular, 2’‐deoxyadenosine analogue dAAzo increases melting temperatures by 7.5 °C in the favored trans state with 86 % of the switching efficiency of the reference system.

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Author:Nikolai Michal Grebenovsky, Volker HermannsGND, Alexander HeckelORCiDGND
Parent Title (German):ChemPhotoChem
Publisher:Wiley-VCH GmbH
Place of publication:Weinheim
Document Type:Article
Date of Publication (online):2020/07/22
Date of first Publication:2020/07/22
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2020/12/07
Tag:DNA; azo compounds; hotochromism; oligonucleotides; photopharmacology
Page Number:4
First Page:5245
Last Page:5248
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
5 Naturwissenschaften und Mathematik / 57 Biowissenschaften; Biologie / 570 Biowissenschaften; Biologie
Licence (German):License LogoCreative Commons - Namensnennung 4.0