Premium
Fluorescence Properties of Pyrylretinol
Author(s) -
Das Joydip,
Crouch Rosalie K.,
Chong Parkson LeeGau
Publication year - 2000
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1562/0031-8655(2000)0720415fpop2.0.co2
Subject(s) - chemistry , fluorescence , quantum yield , binding constant , quenching (fluorescence) , fluorescence anisotropy , liposome , photochemistry , bovine serum albumin , fluorescence spectroscopy , analytical chemistry (journal) , crystallography , membrane , binding site , organic chemistry , chromatography , biochemistry , physics , quantum mechanics
A fluorescent analog of retinol, 3,7‐dimethyl‐9‐(1‐pyryl)‐2E,4E,6E,8E‐nonatetraene‐1‐ol (referred to as pyrylretinol, or 1) has been synthesized. The fluorescence properties ( e.g. quantum yield, lifetime, steady‐state anisotropy, and excitation/emission spectra) of this compound in various organic solvents and in dimyristoylphosphatidylcholine (DMPC) liposomes have been studied, and the results are compared with those obtained from 3‐methyl‐5‐(1‐pyryl)‐2E,4E‐pentadiene‐1‐ol (2), which has the same fused aromatic ring system but a much shorter acyclic chain. 1 and 2 form excimer in aqueous media and fluorescence anisotropies of both 1 and 2 in DMPC liposomes exhibit an abrupt decrease at ∼21–23°C, which coincides with the main phase transition temperature of DMPC liposomes, indicating that both compounds may be a useful membrane probe. In addition, the binding and quenching capability of pyrylretinol (1) to bovine serum albumin has been investigated. Pyrylretinol (1) binds with BSA with a binding constant of 3.6 × 10 4 M −1 , although the value is somewhat lower than that obtained for retinol (3.06 × 10 5 M −1 ). Pyrylretinol (1) also quenches the BSA intrinsic fluorescence with the quenching rate constant of 1.67 × 10 13 M −1 s −1 and the value is lower than that obtained for retinol (4.06 × 10 13 M −1 s −1 ). The binding and quenching studies suggest that pyrylretinol ( 1 ) may serve as a useful fluorescence probe for structure/function studies of different retinoid binding proteins.