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Issue 25, 2017
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Porphyrin-based photosensitizers and their DNA conjugates for singlet oxygen induced nucleic acid interstrand crosslinking

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Abstract

The development of methods for the generation of site-selective interstrand crosslinks (ICLs) in synthetic oligonucleotides provides a platform for the study of ICL repair mechanisms and the stabilisation of DNA-based materials. Our group has previously reported on the use of a furan moiety as a masked reactive functionality for ICL generation and recently introduced the use of 1O2 as an efficient light-induced oxidant. Here, the use of porphyrin-based photosensitizers (PSs) has been explored for ICL generation. The efficiency of the ICL reaction has been investigated using PSs added into solution as well as attached to oligonucleotide probes. Interestingly, even a highly hydrophobic phthalocyanine was able to produce ICLs. Either in solution or conjugated to an ON, chlorin e6 was the most efficient ICL generator for the current purpose.

Graphical abstract: Porphyrin-based photosensitizers and their DNA conjugates for singlet oxygen induced nucleic acid interstrand crosslinking

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Supplementary files

Article information


Submitted
13 Apr 2017
Accepted
02 Jun 2017
First published
07 Jun 2017

Org. Biomol. Chem., 2017,15, 5402-5409
Article type
Paper

Porphyrin-based photosensitizers and their DNA conjugates for singlet oxygen induced nucleic acid interstrand crosslinking

E. M. Llamas, J. P. C. Tome, J. M. M. Rodrigues, T. Torres and A. Madder, Org. Biomol. Chem., 2017, 15, 5402
DOI: 10.1039/C7OB01269A

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