A Spin Labeled Retinal Pigment Analogue of the Purple Membrane

Renk, G.E.; Grover, Thomas A.; Crouch, Rosalie K.; Mao, Boryeu; Ebrey, Thomas G.

doi:10.1111/j.1751-1097.1981.tb05450.x

Cited by 16 publications

(8 citation statements)

References 15 publications

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“…All-trans-4-hydroxyretinal was synthesized by the method of Renk et al (1981). The firefly squids used in this study were captured at different times and places around Japan.…”

Section: Methodsmentioning

confidence: 99%

On the three visual pigments in the retina of the firefly squid, Watasenia scintillans

et al. 1990

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The deep-sea bioluminescent squid, Watasenia scintillans, has three visual pigments: The major one (A1 pigment) is based on retinal and has 2max=484 nm, the second one (A2 pigment) is based on 3-dehydroretinal and has 2m~x = 500 rim, and the third one (A4 pigment) is based on 4-hydroxyretinal and has )[m.x = 470 nm. The distribution of these 3 visual pigments in the retina was studied by HPLC analysis of the retinals in retina slices obtained by microdissection. It was found that A1 pigment was not located in the specific region of the ventral retina receiving the down-welling light which contains very long photoreceptor cells, forming two strata. A2 and A4 pigment were found exclusively in the proximal pinkish stratum and in the distal yellowish stratum. The role of these pigments in the retina is hypothesized to involve spectral discrimination. The extraction and analysis of retinoids to determine the origin of 3-dehydroretinal and 4-hydroxyretinal in the mature squid showed only a trace amount of 4-hydroxyretinol in the eggs. Similar analysis of other cephalopods collected near Japan showed the absence of A2 or A4 pigment in their eyes.

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“…All-trans-4-hydroxyretinal was synthesized by the method of Renk et al (1981). The firefly squids used in this study were captured at different times and places around Japan.…”

Section: Methodsmentioning

confidence: 99%

On the three visual pigments in the retina of the firefly squid, Watasenia scintillans

et al. 1990

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“…4-Hydroxyretinal (5). The 4-hydroxyretinal was prepared from all-trans retinal and selinium dioxide, purified, and characterized as previously described (Reedy, 1965;Renk et al, 1981).…”

Section: Methodsmentioning

confidence: 99%

“…The residual oil was redissolved in 50 pk methylene chloride and analyzed by hplc on k-Porasil column. 4-hydroxy retinal 5 is synthesized and purified as previously described (Reedy, 1965;Renk et al, 1981). The naphthyl derivatives 6-8 are prepared from 2-naphthyl aldehyde and the respective phosphonoacetate and phosphonobutenates in a series of Wittig-type reactions followed by reduction and oxidation to the corresponding aldehyde.…”

Section: Bacterioopsin Pigmentsmentioning

confidence: 99%

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Properties of Synthetic Bacteriorhodopsin Pigments. Further Probes of the Chromophore Binding Site

Crouch

Scott

Ghent

et al. 1986

Photochem & Photobiology

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Abstract— A series of retinals with specific structural alterations have been synthesized to probe the bacteriorhodopsin binding site. The 4‐chloro‐, 4‐bromo‐ and 4‐iodoretinals all form pigments with bacterioopsin but undergo an in situ displacement of the allylic halogen to form the 4‐hydroxyretinal pigment. Several naphthyl retinals were prepared which effectively extend the polyene chain and/or add bulk to the ring portion of the chromophore. All the naphthyl retinals form pigments with bacterioopsin but only the pigment containing the derivative with a polyene side chain identical to that of retinal pumps protons efficiently. The 12‐butyl‐13‐desmethylretinal was also synthesized but this analogue did not form a pigment with bacterioopsin. These results confirm the nonspecificity at the ring portion of the chromophore binding site and the importance of the role of the polyene chain in the proton pumping function of bacteriorhodopsin.

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“…11-cis-retinal was obtained as a gift from the National Eye Institute. 11-cis 4-OH retinal was synthesized and purified as previously described ( Renk et al, 1981 ). Working solutions containing these retinoids were prepared for exogenous delivery to bleached photoreceptors in physiological saline solution.…”

Section: Methodsmentioning

confidence: 99%

Low aqueous solubility of 11-cis-retinal limits the rate of pigment formation and dark adaptation in salamander rods

Frederiksen

Boyer

Nickle

et al. 2012

Journal of General Physiology

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We report experiments designed to test the hypothesis that the aqueous solubility of 11-cis-retinoids plays a significant role in the rate of visual pigment regeneration. Therefore, we have compared the aqueous solubility and the partition coefficients in photoreceptor membranes of native 11-cis-retinal and an analogue retinoid, 11-cis 4-OH retinal, which has a significantly higher solubility in aqueous medium. We have then correlated these parameters with the rates of pigment regeneration and sensitivity recovery that are observed when bleached intact salamander rod photoreceptors are treated with physiological solutions containing these retinoids. We report the following results: (a) 11-cis 4-OH retinal is more soluble in aqueous buffer than 11-cis-retinal. (b) Both 11-cis-retinal and 11-cis 4-OH retinal have extremely high partition coefficients in photoreceptor membranes, though the partition coefficient of 11-cis-retinal is roughly 50-fold greater than that of 11-cis 4-OH retinal. (c) Intact bleached isolated rods treated with solutions containing equimolar amounts of 11-cis-retinal or 11-cis 4-OH retinal form functional visual pigments that promote full recovery of dark current, sensitivity, and response kinetics. However, rods treated with 11-cis 4-OH retinal regenerated on average fivefold faster than rods treated with 11-cis-retinal. (d) Pigment regeneration from recombinant and wild-type opsin in solution is slower when treated with 11-cis 4-OH retinal than with 11-cis-retinal. Based on these observations, we propose a model in which aqueous solubility of cis-retinoids within the photoreceptor cytosol can place a limit on the rate of visual pigment regeneration in vertebrate photoreceptors. We conclude that the cytosolic gap between the plasma membrane and the disk membranes presents a bottleneck for retinoid flux that results in slowed pigment regeneration and dark adaptation in rod photoreceptors.

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A Spin Labeled Retinal Pigment Analogue of the Purple Membrane

Cited by 16 publications

References 15 publications

On the three visual pigments in the retina of the firefly squid, Watasenia scintillans

On the three visual pigments in the retina of the firefly squid, Watasenia scintillans

Properties of Synthetic Bacteriorhodopsin Pigments. Further Probes of the Chromophore Binding Site

Low aqueous solubility of 11-cis-retinal limits the rate of pigment formation and dark adaptation in salamander rods

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