A methyl group at C7 of 11-cis-retinal allows chromophore formation but affects rhodopsin activation

被引:4
作者
Bosch, Laia
Cordomi, Arnau
Dominguez, Marta
Toledo, Darwin
Morillo, Margarita
Perez, Juan J.
Alvarez, Rosana
de Lera, Angel R.
Garriga, Pere [1 ]
机构
[1] Univ Politecn Catalunya, Dept Engn Quim, Terrassa 08222, Catalonia, Spain
[2] Univ Politecn Catalunya, Dept Engn Quim, E-08028 Barcelona, Catalonia, Spain
[3] Univ Vigo, Fac Quim, Dept Quim Organ, Vigo 36310, Spain
关键词
retinal analogues; chromophore regeneration; photobleaching; rhodopsin photoactivation; transducin activation;
D O I
10.1016/j.visres.2006.07.031
中图分类号
Q189 [神经科学];
学科分类号
071006 [神经生物学];
摘要
The newly synthesized 11-cis-7-methylretinal can form an artificial visual pigment with kinetic and spectroscopic properties similar to the native pigment in the dark-state. However, its photobleaching behavior is altered, showing a Meta I-like photoproduct. This behavior reflects a steric constraint imposed by the 7-methyl group that affects the conformational change in the binding pocket as a result of retinal photoisomerization. Transducin activation is reduced, when compared to the native pigment with 11-cis-retinal. Molecular dynamics simulations suggest coupling of the C7 methyl group and the beta-ionone ring with Met207 in transmembrane helix 5 in agreement with recent experimental results. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4472 / 4481
页数:10
相关论文
共 70 条
[1]
PHOTOLYSIS INTERMEDIATES OF THE ARTIFICIAL VISUAL PIGMENT CIS-5,6-DIHYDRO-ISORHODOPSIN [J].
ALBECK, A ;
FRIEDMAN, N ;
OTTOLENGHI, M ;
SHEVES, M ;
EINTERZ, CM ;
HUG, SJ ;
LEWIS, JW ;
KLIGER, DS .
BIOPHYSICAL JOURNAL, 1989, 55 (02) :233-241
[2]
(9Z)- and (11Z)-8-methylretinals for artificial visual pigment studies:: Stereoselective synthesis, structure, and binding models [J].
Alvarez, R ;
Domínguez, M ;
Pazos, Y ;
Sussman, F ;
de Lera, AR .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (23) :5821-5831
[3]
FTIR spectroscopy of complexes formed between metarhodopsin II and C-terminal peptides from the G-protein α- and γ-subunits [J].
Bartl, F ;
Ritter, E ;
Hofmann, KP .
FEBS LETTERS, 2000, 473 (02) :259-264
[4]
Partial agonism in a g protein-coupled receptor - Role of the retinal ring structure in rhodopsin activation [J].
Bartl, FJ ;
Fritze, O ;
Ritter, E ;
Herrmann, R ;
Kuksa, V ;
Palczewski, K ;
Hofmann, KP ;
Ernst, OP .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (40) :34259-34267
[5]
GROMACS - A MESSAGE-PASSING PARALLEL MOLECULAR-DYNAMICS IMPLEMENTATION [J].
BERENDSEN, HJC ;
VANDERSPOEL, D ;
VANDRUNEN, R .
COMPUTER PHYSICS COMMUNICATIONS, 1995, 91 (1-3) :43-56
[6]
Molecular dynamics simulations of a fluid bilayer of dipalmitoylphosphatidylcholine at full hydration, constant pressure, and constant temperature [J].
Berger, O ;
Edholm, O ;
Jahnig, F .
BIOPHYSICAL JOURNAL, 1997, 72 (05) :2002-2013
[7]
CLONING AND STRUCTURE-FUNCTION OF THE H-2 HISTAMINE-RECEPTOR [J].
BIRDSALL, NJM .
TRENDS IN PHARMACOLOGICAL SCIENCES, 1991, 12 (01) :9-10
[8]
Structural and functional role of helices I and II in rhodopsin - A novel interplay evidenced by mutations at Gly-51 and Gly-89 in the transmembrane domain [J].
Bosch, L ;
Ramon, E ;
del Valle, LJ ;
Garriga, P .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (22) :20203-20209
[9]
Buss V, 1998, ANGEW CHEM INT EDIT, V37, P1893, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1893::AID-ANIE1893>3.0.CO
[10]
2-M