INTERACTION OF DIBUCAINEHCl LOCAL ANESTHETICS WITH BACTERIORHODOPSIN IN PURPLE MEMBRANE: A SPECTROSCOPIC STUDY

作者: C. T. LIN , Y. G. CHYAN , G. C. KRESHECK , HERBERT C. BITTING JR , M. A. EL-SAYED

DOI: 10.1111/J.1751-1097.1989.TB08436.X

关键词:

摘要: Several spectroscopic techniques (absorption, emission, transient absorption and differential scanning calorimetry--DSC) were used to investigate the deprotonation of dibucaine.HCl in a hydrophobic environment, interaction sites mechanisms local anesthetic on bacteriorhodopsin (bR) purple membrane. The important results are summarized as follows: (1) visible features native (lambda max = 568 nm) deionized 608 bR sensitive amount added; (2) emission spectrum embedded retinal-free mutant is similar that dibucaine free base Triton X-100 micellar solutions; (3) phosphorescence at 77 K completely quenched by fluorescence quenching rate for incorporated was determined kq 4.09 x 10(13) M-1 s-1; (4) incorporation inhibits slow component formation M412 decreases photochemical cycle bR; (5) thermal stability measured DSC presence absence yielded an endothermic transition 95.9 +/- 1.0 degrees C with 13.6 J/g (3.25 0.12 cal/g) enthalpy changes. All observations suggest action site anesthetic, dibucaine.HCl, near or chromophore, i.e. retinal Schiff bR. membrane probably via specific binding, but not conformational mechanism.

参考文章(51)
Dieter Oesterhelt, Walther Stoeckenius, Isolation of the cell membrane of Halobacterium halobium and its fractionation into red and purple membrane Methods in Enzymology. ,vol. 31, pp. 667- 678 ,(1974) , 10.1016/0076-6879(74)31072-5
Maria MURADIN-SZWEYKOWSKA, Johannes A. PARDOEN, Dick DOBBELSTEIN, AMSTERDAM, Johan LUGTENBURG, Bacteriorhodopsins with chromophores modified at the β‐ionone site FEBS Journal. ,vol. 140, pp. 173- 176 ,(1984) , 10.1111/J.1432-1033.1984.TB08082.X
J. Cerbón, NMR Evidence for the hydrophobic interaction of local anaesthetics Biochimica et Biophysica Acta (BBA) - Biomembranes. ,vol. 290, pp. 51- 57 ,(1972) , 10.1016/0005-2736(72)90051-X
T Frazier, T Narahashi, M Yamada, THE SITE OF ACTION AND ACTIVE FORM OF LOCAL ANESTHETICS. I. THEORY AND pH EXPERIMENTS WITH TERTIARY COMPOUNDS Journal of Pharmacology and Experimental Therapeutics. ,vol. 171, pp. 32- 44 ,(1970)
H. Bayley, K. S. Huang, R. Radhakrishnan, A. H. Ross, Y. Takagaki, H. G. Khorana, Site of attachment of retinal in bacteriorhodopsin. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 78, pp. 2225- 2229 ,(1981) , 10.1073/PNAS.78.4.2225
C.- H. Chang, J.- G. Chen, R. Govindjee, T. Ebrey, Cation binding by bacteriorhodopsin. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 82, pp. 396- 400 ,(1985) , 10.1073/PNAS.82.2.396
M. Braiman, R. Mathies, Resonance Raman spectra of bacteriorhodopsin's primary photoproduct: evidence for a distorted 13-cis retinal chromophore. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 79, pp. 403- 407 ,(1982) , 10.1073/PNAS.79.2.403
Yoshiya Shinagawa, Charles Gravis, Shinpei Ohki, Mode of action of tertiary amine local anesthetics on axon membrane excitability Biochimica et Biophysica Acta. ,vol. 507, pp. 395- 407 ,(1978) , 10.1016/0005-2736(78)90349-8
C. T. Lin, M. Malak, G. Vanderkooi, W. R. Mason, Solvent effects on the photophysical properties of dibucaine: a quinoline analogue Photochemistry and Photobiology. ,vol. 45, pp. 749- 755 ,(1987) , 10.1111/J.1751-1097.1987.TB07877.X
E. L. Chronister, T. C. Corcoran, L. Song, M. A. El-Sayed, On the molecular mechanisms of the Schiff base deprotonation during the bacteriorhodopsin photocycle Proceedings of the National Academy of Sciences of the United States of America. ,vol. 83, pp. 8580- 8584 ,(1986) , 10.1073/PNAS.83.22.8580