Page last updated: 2024-12-10

11-cis-retinal

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 11-cis-retinal: The Key to Sight

11-cis-retinal is a crucial molecule in the human eye, playing a fundamental role in **vision**. It's a derivative of **vitamin A** and exists within **rhodopsin**, a light-sensitive protein found in **rod cells** of the retina.

**Here's why it's important for research:**

**1. Understanding Vision:**

* **Light absorption:** 11-cis-retinal absorbs light, specifically in the **blue-green range**.
* **Shape change:** Upon light absorption, 11-cis-retinal undergoes a **conformational change** to its all-trans isomer. This change triggers a series of events within rhodopsin, eventually sending a signal to the brain that is interpreted as vision.
* **Visual cycle:** The all-trans isomer is converted back to 11-cis-retinal through a series of enzymatic reactions, allowing the process to repeat and sustain vision.

**2. Research into eye diseases:**

* **Retinitis pigmentosa:** Research focuses on the role of 11-cis-retinal in **retinal degeneration** associated with this disease. Understanding its behavior could lead to potential treatments.
* **Age-related macular degeneration:** This condition affects the central part of the retina, and research investigates the relationship between 11-cis-retinal and the disease's progression.

**3. Potential applications in other fields:**

* **Optogenetics:** 11-cis-retinal's ability to change shape upon light exposure makes it attractive for **optogenetic research**. This field explores the use of light to control neuronal activity, potentially leading to new treatments for neurological conditions.
* **Bio-imaging:** 11-cis-retinal's fluorescent properties have led to its use as a **probe** for bio-imaging applications, helping researchers visualize biological processes in real time.

**In summary, 11-cis-retinal is a fascinating molecule with significant implications for understanding vision, developing treatments for eye diseases, and exploring novel applications in bio-imaging and optogenetics.** Its research continues to reveal its vital role in human health and offer exciting possibilities for the future.

Rhodopsin: A purplish-red, light-sensitive pigment found in RETINAL ROD CELLS of most vertebrates. It is a complex consisting of a molecule of ROD OPSIN and a molecule of 11-cis retinal (RETINALDEHYDE). Rhodopsin exhibits peak absorption wavelength at about 500 nm. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

11-cis-retinal : A retinal having 2E,4Z,6E,8E-double bond geometry. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5280490
CHEMBL ID1255087
CHEBI ID16066
SCHEMBL ID8325392
MeSH IDM0018958

Synonyms (33)

Synonym
564-87-4
CHEBI:16066 ,
(2e,4z,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
LMPR01090003
rhodopsin
11-cis-retinal
11-cis-vitamin a aldehyde
C02110
11-cis-retinene
cis-retinal
(11z)-retinal
11-cis-retinaldehyde
neoretinene b
(2e,4z,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
CHEMBL1255087
11-cis retinal
gtpl6669
(2e,4z,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenal
3HX3
SCHEMBL8325392
11-cis-retinal [mi]
retinal, (11z)-
unii-91058v6hch
91058v6hch ,
DTXSID80415057
cis-11-retinal
NCYCYZXNIZJOKI-IOUUIBBYSA-N
Q17002962
11-cis-retinal (>65%)
11-cis-retinal (>65per cent)
AKOS040756294
CS-0066342
HY-116711

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" In the proposed system the time courses of the concentrations of certain photoproducts turn out to be equal to the quantal absorption rate passed through various linear filters."( Linking quantal absorption rate to the visual response.
Dawis, SM, 1981
)
0.26
" Since this rate of absorption is sufficient to saturate the rod, one possible purpose of photostasis is to maintain the rod system in a saturated state during daylight hours."( Distribution of photon absorption rates across the rat retina.
Giordano, L; Henderson, RP; Webbers, JP; Williams, TP, 1998
)
0.3
" However, orgovyx has demonstrated poor pharmacokinetic profile with low oral bioavailability and high efflux."( Discovery of the thieno[2,3-d]pyrimidine-2,4-dione derivative 21a: A potent and orally bioavailable gonadotropin-releasing hormone receptor antagonist.
Gao, Y; Jiang, W; Liu, C; Lu, J; Ma, M; Tian, J; Wang, W; Wang, Y; Ye, L; Yu, D; Zhang, J; Zhang, R; Zhao, M; Zou, F, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" Rats maintained under these conditions were treated with DMTU at different concentrations and dosing schedules and then exposed for various times to intense visible light, either intermittently (1 hr light and 2 hr dark) or continuously."( Protection by dimethylthiourea against retinal light damage in rats.
Blanks, JC; Darrow, RM; Jiang, YI; Marak, GE; Organisciak, DT, 1992
)
0.28
" Under regimen 1, dexamethasone was given at a daily dosage of 1 mg kg-1 for 8 days, starting 6 days before light exposure."( Dexamethasone ameliorates retinal photic injury in albino rats.
Fu, J; Lam, TT; Tso, MO, 1992
)
0.28
" The dose-response profiles for the effects of the beta gamma T complex on the rate and extent of the GTP gamma S-stimulated fluorescence enhancement of alpha T have also been examined."( The intrinsic fluorescence of the alpha subunit of transducin. Measurement of receptor-dependent guanine nucleotide exchange.
Cerione, RA; Phillips, WJ, 1988
)
0.27
"The general modeling of dose-response curves to very low stimuli in a photosensory-effector system is critically reshaped starting from basic assumptions on the fluctuations of chemical signals inside the receptor cell, which add to those of the stimulus itself, both arising from their granular (or quantal) structure."( Photoreceptor sensitivity and the shot noise of chemical processes.
Cercignani, G; Lucia, S; Petracchi, D, 1996
)
0.29
" The dose-response curve for stimulation by betagamma subunits of the m2 and rhodopsin phosphorylation was shifted to the higher concentration of betagamma subunits by addition of Ca2+-calmodulin."( Ca2+-dependent inhibition of G protein-coupled receptor kinase 2 by calmodulin.
Haga, K; Haga, T; Tsuga, H, 1997
)
0.3
" A ligand dose-response curve with the photoactivatable agonist 11-cis-retinal showed a half-maximal signal at 120 nM."( Micropatterned immobilization of a G protein-coupled receptor and direct detection of G protein activation.
Bieri, C; Ernst, OP; Heyse, S; Hofmann, KP; Vogel, H, 1999
)
0.54
"(1) These results demonstrated that rod biochemistry, physiology and synaptic signaling are compromised in a gene dosage dependent manner when the expression of trkB is reduced in transgenic mice."( Gene dosage effect of the TrkB receptor on rod physiology and biochemistry in juvenile mouse retina.
Rohrer, B, 2001
)
0.31
" αT*(S43N) activated the cGMP phosphodiesterase (PDE) with a dose-response similar to wild-type αT*."( A dominant-negative Galpha mutant that traps a stable rhodopsin-Galpha-GTP-betagamma complex.
Cerione, RA; Ramachandran, S, 2011
)
0.37
" There was a significant dose-response effect for lutein supplementation, and the changes in MPOD from baseline to 48 weeks were correlated negatively with baseline MPOD in all active treatment groups (r = -0."( Effect of lutein and zeaxanthin on macular pigment and visual function in patients with early age-related macular degeneration.
Dong, PC; Dou, HL; Huang, YM; Lin, XM; Lu, XR; Ma, L; Pang, HL; Qian, F; Sun, TT; Wang, X; Xiao, X; Xu, XR; Yan, SF; Zou, ZY, 2012
)
0.38
" By screening multiple compound concentrations, dose-response curves can be generated, and the false negative rate minimized."( A high content screening approach to identify molecules neuroprotective for photoreceptor cells.
Berlinicke, CA; Bonnet-Wersinger, D; Fuller, JA; Hansen, BS; Inglese, J; Shaw, GC; Zack, DJ, 2014
)
0.4
" Dosing with LA protected photoreceptors, decreasing the numbers of TUNEL-positive photoreceptors and increasing the number of surviving photoreceptors."( Systemic administration of the antioxidant/iron chelator α-lipoic acid protects against light-induced photoreceptor degeneration in the mouse retina.
Dunaief, JL; Li, Y; Song, D; Song, Y; Su, G; Wang, C; Zhao, L, 2014
)
0.4
" Daily dosing of wild-type mice from postnatal day P17 to P28 resulted in smaller increases in Bdnf and Gdnf expression, normal Cntf expression, and reduced Fgf2 expression (25%)."( Different effects of valproic acid on photoreceptor loss in Rd1 and Rd10 retinal degeneration mice.
Byrd, D; DeLooff, C; Deshpande, M; Guzman, AE; Laux, K; Metcalf, B; Mitton, KP; Mkoyan, K; Sotzen, J; Tran, T; Wallace, A; Zlojutro, P, 2014
)
0.4
" Histological analysis using plastic sections showed dosing with BBR preserved photoreceptors."( Berberine protects against light-induced photoreceptor degeneration in the mouse retina.
Dunaief, JL; Li, Y; Song, D; Song, J; Wang, C, 2016
)
0.43
" Here we present a comprehensive study of the 8 Tg lines, including the time course of PR degeneration from the onset to one year of age, retinal structure by light and electron microscopy (EM), hemispheric asymmetry and gradients of rod and cone degeneration, rhodopsin content, gene dosage effect, rapid activation and invasion of the outer retina by presumptive microglia, rod outer segment disc shedding and phagocytosis by the retinal pigmented epithelium (RPE), and retinal function by the electroretinogram (ERG)."( Phenotypic characterization of P23H and S334ter rhodopsin transgenic rat models of inherited retinal degeneration.
Chen, J; Duncan, JL; Flannery, JG; Lau-Villacorta, C; LaVail, MM; Matthes, MT; Naash, MI; Nishikawa, S; Peterson, WM; Steinberg, RH; Trautmann, N; Yang, H; Yasumura, D, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
chromophoreThe part (atom or group of atoms) of a molecular entity in which the electronic transition responsible for a given spectral band is approximately localized.
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
retinalAn enal that consists of 3,7-dimethyl-9-nona-2,4,6,8-tetraenal (double bond geometry unspecified) carrying a 2,6,6-trimethylcyclohex-1-en-1-yl group at the 9-position.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (17)

PathwayProteinsCompounds
Signaling Pathways1269117
Visual phototransduction6241
The canonical retinoid cycle in rods (twilight vision)1415
The retinoid cycle in cones (daylight vision)712
Signaling by Nuclear Receptors15246
Signaling by Retinoic Acid2431
RA biosynthesis pathway1119
Retinol Metabolism3730
Vitamin A Deficiency3730
Disease1278231
Diseases associated with visual transduction710
Retinoid cycle disease events710
Diseases of the neuronal system710
Sensory Perception21568
10q22q23 copy number variation014
the visual cycle I (vertebrates)1410
Vitamin A and carotenoid metabolism020

Protein Targets (2)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Retinaldehyde-binding protein 1Homo sapiens (human)Kd0.01000.01000.01000.0100AID977611
Chain A, Retinaldehyde-binding protein 1Homo sapiens (human)Kd0.01000.01000.01000.0100AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2009Proceedings of the National Academy of Sciences of the United States of America, Nov-03, Volume: 106, Issue:44
Bothnia dystrophy is caused by domino-like rearrangements in cellular retinaldehyde-binding protein mutant R234W.
AID646177Inverse agonist activity at human red cone opsin expressed in COS1 cells assessed as transducer activity at 20 uM by radioactive filter binding assay2011Journal of natural products, Mar-25, Volume: 74, Issue:3
Probing human red cone opsin activity with retinal analogues.
AID515689Cytotoxicity against HEK293 cells by WST-1 assay2010Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19
Retinobenzaldehydes as proper-trafficking inducers of folding-defective P23H rhodopsin mutant responsible for retinitis pigmentosa.
AID515690Upregulation of HA-tagged rhodopsin P23H expression in HEK293 cell surface by ELISA2010Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19
Retinobenzaldehydes as proper-trafficking inducers of folding-defective P23H rhodopsin mutant responsible for retinitis pigmentosa.
AID591677Agonist activity at bovine rhodopsin assessed as opsin mediated cognate G protein transducer activation by fluorescence assay2011Journal of natural products, Mar-25, Volume: 74, Issue:3
Cyclopropyl and isopropyl derivatives of 11-cis and 9-cis retinals at C-9 and C-13: subtle steric differences with major effects on ligand efficacy in rhodopsin.
AID515688Induction of subcellular localization of HA-tagged human rhodopsin P23H mutant on HEK293 cell surface by immunofluorescence microscopy2010Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19
Retinobenzaldehydes as proper-trafficking inducers of folding-defective P23H rhodopsin mutant responsible for retinitis pigmentosa.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7,029)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901694 (24.10)18.7374
1990's1307 (18.59)18.2507
2000's1820 (25.89)29.6817
2010's1754 (24.95)24.3611
2020's454 (6.46)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 50.04

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index50.04 (24.57)
Research Supply Index8.89 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index86.38 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (50.04)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (0.05%)5.53%
Reviews685 (9.40%)6.00%
Case Studies63 (0.86%)4.05%
Observational2 (0.03%)0.25%
Other6,535 (89.66%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]