title: 1-(Hydroxyacetyl)pyrene a new fluorescent phototrigger for cell imaging and caging of alcohols, phenol and adenosine.
abstract: 1-(Hydroxyacetyl)pyrene has been introduced as a new fluorescent phototrigger for alcohols and phenols. Alcohols and phenols were protected as their corresponding carbonate esters by coupling with fluorescent phototrigger, 1-(hydroxyacetyl)pyrene. Photophysical studies of caged carbonates showed that they all exhibited strong fluorescence properties. Irradiation of the caged carbonates by visible light (≥410 nm) in aqueous acetonitrile released the corresponding alcohols or phenols in high chemical (95-97%) and quantum (0.17-0.21) yields. The mechanism for the photorelease was proposed based on Stern-Volmer quenching experiments and solvent effect studies. Importantly, 1-(hydroxyacetyl)pyrene showed as a phototrigger for rapid photorelease of the biologically active molecule adenosine. In vitro biological studies revealed that 1-(hydroxyacetyl)pyrene has good biocompatibility, cellular uptake property and cell imaging ability.
authors: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur-721302, India.
authors: Avijit
authors: A
authors: Jana
authors: Biswajit
authors: B
authors: Saha
authors: Mohammed
authors: M
authors: Ikbal
authors: Sudip Kumar
authors: SK
authors: Ghosh
authors: N D Pradeep
authors: ND
authors: Singh
mesh_terms: D000241:Adenosine / Q000032:analysis*; D000438:Alcohols / Q000032:analysis*; D000818:Animals; D001692:Biological Transport; D002254:Carbonates / Q000737:chemistry; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D005453:Fluorescence; D008027:Light; D051379:Mice; D057054:Molecular Imaging / Q000379:methods*; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D019800:Phenol / Q000032:analysis*; D010782:Photolysis; D011721:Pyrenes / Q000138:chemical synthesis* / Q000494:pharmacology; D012997:Solvents; D013050:Spectrometry, Fluorescence
chemical_list: C578179:1-(hydroxyacetyl)pyrene; D000438:Alcohols; D002254:Carbonates; D015335:Molecular Probes; D011721:Pyrenes; D012997:Solvents; D019800:Phenol; D000241:Adenosine