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 × 104 M−1, although the value is somewhat lower than that obtained for retinol (3.06 × 105 M−1). Pyrylretinol (1) also quenches the BSA intrinsic fluorescence with the quenching rate constant of 1.67 × 1013 M−1 s−1 and the value is lower than that obtained for retinol (4.06 × 1013 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.
How to translate text using browser tools
1 September 2000
Fluorescence Properties of Pyrylretinol
Joydip Das,
Rosalie K. Crouch,
Parkson Lee-Gau Chong
ACCESS THE FULL ARTICLE
It is not available for individual sale.
This article is only available to subscribers.
It is not available for individual sale.
It is not available for individual sale.
<
Previous Article
|
Photochemistry and Photobiology
Vol. 72 • No. 3
September 2000
Vol. 72 • No. 3
September 2000