Fluorophore-mediated Photooxidation of the Guanine Heterocycle.


Journal

Journal of physical organic chemistry
ISSN: 0894-3230
Titre abrégé: J Phys Org Chem
Pays: England
ID NLM: 9883685

Informations de publication

Date de publication:
Nov 2022
Historique:
entrez: 17 11 2022
pubmed: 18 11 2022
medline: 18 11 2022
Statut: ppublish

Résumé

Fluorescent dyes are routinely used to visualize DNA or RNA in various experiments, and some dyes also act as photosensitizers capable of catalyzing oxidation reactions. The present studies explored whether the common labeling dyes fluorescein, rhodamine, BODIPY, or cyanine3 (Cy3) can function as photosensitizers to oxidize nucleic acid polymers. Photoirradiation of each dye in the presence of the guanine (G) heterocycle, which is the most sensitive toward oxidation, identified slow rates of nucleobase oxidation in the nucleoside and DNA contexts. For all four fluorophores studied, the only product detected was spiroiminodihydantoin (Sp) suggesting the dyes functioned as Type II photosensitizers and generate singlet oxygen (

Identifiants

pubmed: 36388261
doi: 10.1002/poc.4325
pmc: PMC9642976
mid: NIHMS1772256
pii:
doi:

Types de publication

Journal Article

Langues

eng

Subventions

Organisme : NCI NIH HHS
ID : P30 CA042014
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM129267
Pays : United States

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Auteurs

Aaron M Fleming (AM)

315 South 1400 East, Dept. of Chemistry, University of Utah, Salt Lake City, UT 84112-0850.

Songjun Xiao (S)

315 South 1400 East, Dept. of Chemistry, University of Utah, Salt Lake City, UT 84112-0850.

Michael B Chabot (MB)

315 South 1400 East, Dept. of Chemistry, University of Utah, Salt Lake City, UT 84112-0850.

Cynthia J Burrows (CJ)

315 South 1400 East, Dept. of Chemistry, University of Utah, Salt Lake City, UT 84112-0850.

Classifications MeSH