Studies on pyrylretinal analogues of bacteriorhodopsin

Photochemistry and Photobiology

Volumn 70, Issue 6, 1999, Pages 949-956

  Das, Joydip ^a   Crouch, Rosalie K ^a,c   Govindjee, Rajni ^b   Balashov, Sergei ^b   Ebrey, Thomas ^b  

^a MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYL 5 (1 PYRYL) 2,4 PENTADIENAL; 3,7 DIMETHYL 9 (1 PYRYL) 2,4,6,8 NONATETRAENAL; 3,7-DIMETHYL-9-(1-PYRYL)-2,4,6,8-NONATETRAENAL; 3-METHYL-5-(1-PYRYL)-2,4-PENTADIENAL; BACTERIORHODOPSIN; DRUG DERIVATIVE; RETINAL;

ARTICLE; CHEMISTRY; METABOLISM; PHYSIOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BACTERIORHODOPSINS; RETINALDEHYDE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033250750     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1999.tb08307.x     Document Type: Article

References (35)

1. Oesterhelt, D. and W. Stoeckenius (1971) Rhodopsin-like protein from the purple membrane of Halobacterium halobium. Nature (New Biol.) 233, 149-152.
2. Birge, R. R. (1990) Nature of the primary photochemical events in rhodopsin and bacteriorhodopsin. Biochim. Biophys. Acta 1016, 293-327.
3. Ebrey, T. G. (1993) Light energy transduction in bacteriorhodopsin. In Thermodynamics of Membrane Receptors und Channels (Edited by M. B. Jackson), pp. 353-387. CRC Press, Boca Raton, FL.
4. Ottolenghi, M. and M. Sheves (1989) Synthetic retinals as probes for the binding site and photoreactions of rhodopsins. J. Membrane Biol. 112, 193-212.
5. Nakanishi, K. and R. Crouch (1995) Application of artificial pigments to structure determination and study of photoinduced transformations of retinal proteins. Isr. J. Chem. 35, 253-272.
6. Bayley, H., R. Radhakrishnan, K. Huang and H. G. Khorana (1981) Light-driven proton translocation by bacteriorhodopsin reconstituted with phenyl analog of retinal. J. Biol. Chem. 256, 3797-3801.
7. Maeda, A., A. E. Asato, R. S. H. Liu and T. Yoshizawa (1984) Interaction of aromatic retinal analogues with apopurple membranes of Halobacterium halohium. Biochemistry 23, 2507-2513.
8. Balogh-Nair, V., J. D. Carriker, B. Honig, V. Kamat, M. G. Motto, K. Nakanishi, R. Sen, M. Sheves, M. A. Tanis and K. Tsujimoto (1981) The 'opsin shift' in bacteriorhodopsin: studies with artificial bacteriorhodopsin. Pholochem. Photobiol. 33, 483-488.
9. Crouch, R. K., R. Scott, S. Ghent, R. Govindjee, C. Chang and T. Ebrey (1986) Properties of synthetic bacteriorhodopsin pigments. Further probes of the chromophore binding site. Photochem. Photobiol. 43, 297-303.
10. Iwasa, T., M. Takao, K. Tsujimoto and F. Tokunaga (1988) Photochemical properties of naphthylbacteriorhodopsins differing in their protein-chromophore interactions. Biochemistry 27, 2416-2419.
11. Iwasa, T., M. Takao, M. Yamada, K. Tsujimoto and F. Tokunaga (1984) Properties of an analogue pigment of bacteriorhodopsin synthesized with naphthylretinal. Biochemistry 23, 838-843.
12. Akhtar, M., L. Jallo and A. H. Johnson (1982) Interaction of a conformationally rigid analogue of retinal with bacteriorhodopsin. J. Chem. Soc. Chem. Commun., 44-46.
13. Ivanova, D., V. Kolev, T. Lazarova and E. Padros (1999) Synthesis of new heterocyclic and polycyclic aromatic retinals and their bacteriorhodopsin analogues. Tetrahedron Lett. 40, 2645-2648.
14. Birge, R. R. (1994) Protein-based three-dimensional memory. Am. Scientist 82, 348-355.
15. Birge, R. R. (1992) Protein-based optical computing and memories. Computer 25, 56-67.
16. Birge, R. R. (1990) Photophysics and molecular electronic applications of rhodopsins. Annu. Rev. Phys. Chem. 41, 683-733.
17. Hampp, N. and C. Braeuchle (1990) Bacteriorhodopsin and its functional variants. Potential applications in modern optics. Stud. Org. Chem. (Amsterdam) 40, 954-975.
18. Hampp, N., R. Thoma, D. Oesterhelt and C. Braeuchle (1992) Biological photochrome bacteriorhodopsin and its genetic variant Asp 96 - Asn as media for optical pattern recognition. Appl. Opt. 31, 1834-41.
19. Druzhko, A. B. and H. H. Weetall (1997) Photoinduced transformation of wild-type and D96N-mutant 4-keto-bacteriorhodopsin gelatin films. Thin Solid Films 293, 281-284.
20. Druzhko, A. B., B. Robertson, R. Alvarez, A. R. deLera and H. H. Weetall (1998) Phototransformation and proton pumping activity of the 14-fluoro bacteriorhodopsin derivatives. Biochem. Biophys. Acta 1371, 371-381.
21. Renk, G. E., Y. S. Or and R. K. Crouch (1987) A rhodopsin pigment containing a spin-labeled retinal. J. Am. Chem. Soc. 109, 6163-6168.
22. Torrado, A., B. Iglesias, S. Lopez and A. R. deLera (1995) The Suzuki reaction in stereocontrolled polyene synthesis: retinal (vitamin A), its 9- and/or 13-demethyl didydro retinol. Tetrahedron 51, 2435-2454.
23. Tokunaga, F., R. Govindjee, T. G. Ebrey and R. K. Crouch (1977) Synthetic pigment analogues of the purple membrane. Biophys. J. 19, 191-198.
24. Misra, S., R. Govindjee, T. G. Ebrey, N. Chen, J.-X. Ma and R. K. Crouch (1997) Proton uptake and release are rate-limiting steps in the photocycle of the bacteriorhodopsin mutant E204Q. Biochemistry 36, 4875-4883.
25. a of the group responsible for the light-driven proton release in bacteriorhodopsin. Biophys. J. 71, 1011-1023.
26. 17 aldehyde. Photochem. Photobiol. 33, 495-499.
27. Honig, B., B. Hudson, B. D. Sykes and M. Karplus (1971) Ring orientation in β-ionone and retinals. Proc. Natl. Acad. Sci. USA 68, 1289-1293.
28. Motto, M. G., M. Sheves, K. Tsujimoto, V. Balogh-Nair and K. Nakanishi (1980) Opsin shifts in bovine rhodopsin and bacteriorhodopsin. Comparison of two external point-charge models. J. Am. Chem. Soc. 102, 7947-7949.
29. Henderson, R., J. M. Baldwin, T. A. Ceska, F. ZemLin, E. Beckmann and K. H. Downing (1990) Model for the structure of bacteriorhodopsin based on high resolution electron cryomicroscopy. J. Mol. Biol. 213, 899-929.
30. Liu, R. S. H., E. Krogh, X.-Y. Li, D. Mead, R. U. Colmenares, J. R. Thiel, J. Ellis, D. Wong and A. E. Asato (1993) Analyzing the red-shift characteristics of azulenic, naphthyl, other ringfused and retinyl pigment analogs of bacteriorhodopsin. Photochem. Photobiol. 58, 701-705.
31. Dioumaaev, A. K., H. T. Richter, L. S. Brown, M. Tanio, S. Tuzi, H. Saito, Y. Kimura, R. Needleman and J. K. Lanyi (1998) Existence of a proton transfer chain in bacteriorhodopsin - participation of Glu-194 in the release of protons to the extracellular surface. Biochemistry 37, 2496-2506.
32. Balashov, S. P., M. Lu, E. S. Imasheva, R. Govindjee, T. G. Ebrey, B. Othersen III, Y. Chen, R. K. Crouch and D. R. Menick (1999) The proton release group of bacteriorhodopsin controls the rate of the final step of its photocycle at low pH. Biochemistry 38, 2026-2039.
33. Brown, L. S., J. Sasaki, H. Kandori, A. Maeda, R. Needleman and J. K. Lanyi (1995) Glutamic acid is the terminal proton release group at the extracellular surface of bacteriohodopsin. J. Biol. Chem. 270, 27122-27126.
34. Govindjee, R., E. S. Emasheva, S. Misra, S. P. Balashov, T. G. Ebrey, N. Chen, D. R. Menick and R. K. Crouch (1997) Mutation of a surface residue lysine-129, reverses the order of proton release and uptake in bacteriorhodopsin; guanidinium hydrochloride reverses it. Biophys. J. 72, 886-898.
35. Balashov, S. P., E. S. Imasheva, T. G. Ebrey, N. Chen, D. R. Menick and R. K. Crouch (1997) Glutamate-194 to cysteine mutation inhibits fast light-induced proton release in bacteriorhodopsin. Biochemistry 36, 8671-8676.