Page last updated: 2024-11-10

deltorphin

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

Description

deltorphin: isolated from skin of Phyllomedusa sauvagei; has affinity to opioid receptor; note deltorphin I and deltorphin II are available, they have Ala in position 2 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3035060
CHEMBL ID20775
CHEBI ID81455
MeSH IDM0165662

Synonyms (27)

Synonym
deltorphin
chebi:81455 ,
CHEMBL20775 ,
C18010
dermenkephalin
119975-64-3
deltorphin a
(3s)-4-amino-3-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-phenylpropanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]
3-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxy-phenyl)-propionylamino]-4-methylsulfanyl-butyrylamino}-3-phenyl-propionylamino)-3-(3h-imidazol-4-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyrylamino)-succinamic acid
3-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxy-phenyl)-propionylamino]-4-methylsulfanyl-butyrylamino}-3-phenyl-propionylamino)-3-(3h-imidazol-4-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyrylamino)-succinamic acid (deltorphin a)
bdbm50000518
tyr-met-phe-his-leu-met-asp-nh2
l-alpha-asparagine, n2-(n-(n-(n-(n-(n-l-tyrosyl-d-methionyl)-l-phenylalanyl)-l-histidyl)-l-leucyl)-l-methionyl)-
tyrosyl-methionyl-phenylalanyl-histidyl-leucyl-methionyl-aspartamide
DTXSID60152630
AS-74086
mfcd00133249
Q5254878
h-tyr-d-met-phe-his-leu-met-asp-nh2
h-tyr-(d)met-phe-his-leu-met-asp-nh2
l-alpha-asparagine, l-tyrosyl-d-methionyl-l-phenylalanyl-l-histidyl-l-leucyl-l-methionyl-
(5r,8s,11s,14s,17s,20s)-11-((1h-imidazol-4-yl)methyl)-5-((s)-2-amino-3-(4-hydroxyphenyl)propanamido)-8-benzyl-20-carbamoyl-14-isobutyl-17-(2-(methylthio)ethyl)-6,9,12,15,18-pentaoxo-2-thia-7,10,13,16,19-pentaazadocosan-22-oic acid
AKOS037647558
GLXC-25917
CS-0104599
HY-129271
AKOS040744531

Research Excerpts

Overview

The deltorphins are a class of highly selective delta-opioid heptapeptides from the skin of the Amazonian frogs Phyllomedusa sauvagei and P. bicolor. Deltorphin I is an opioid peptide of sequence H-Tyr-D-Ala-Phe-Asp- Val-Val-Gly-NH2.

ExcerptReferenceRelevance
"The deltorphins are a class of highly selective delta-opioid heptapeptides from the skin of the Amazonian frogs Phyllomedusa sauvagei and P. "( What peptides these deltorphins be.
Bryant, SD; Cooper, PS; Lazarus, LH; Salvadori, S, 1999
)
1.19
"Deltorphin I is an opioid peptide of sequence H-Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2, recently isolated from the skin of Phyllomedusa bicolor. "( New features of the delta opioid receptor: conformational properties of deltorphin I analogues.
Balboni, G; Marastoni, M; Picone, D; Salvadori, S; Tancredi, T; Temussi, PA; Tomatis, R, 1990
)
1.95
"Deltorphin is an opioid peptide with the sequence H-Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2, recently isolated from the skin of Phyllomedusa sauvagei. "( Conformational properties of deltorphin: new features of the delta-opioid receptor.
Balboni, G; Marastoni, M; Picone, D; Salvadori, S; Tancredi, T; Temussi, PA; Tomatis, R, 1989
)
2.01

Dosage Studied

ExcerptRelevanceReference
"3 nmol/rat of DADELT II and shifted the dose-response curve to the right, without decreasing the maximum effect."( Behavioural effects of deltorphins in rats.
Angelucci, F; Negri, L; Noviello, V, 1991
)
0.59
"03 microgram of DAMGO resulting in a steeper dose-response relationship."( Evidence for delta opioid receptor subtypes in rat spinal cord: studies with intrathecal naltriben, cyclic[D-Pen2, D-Pen5] enkephalin and [D-Ala2, Glu4]deltorphin.
Hammond, DL; Stewart, PE, 1993
)
0.48
" The decreases in labeling index evoked by OGF were blocked by concomitant administration of the opioid antagonist, naloxone (10 mg/kg); naloxone alone at the dosage utilized had no influence on cell replicative processes."( The opioid growth factor, [Met5]-enkephalin, and the zeta opioid receptor are present in human and mouse skin and tonically act to inhibit DNA synthesis in the epidermis.
McLaughlin, PJ; Wu, Y; Zagon, IS, 1996
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
peptideAmide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another with formal loss of water. The term is usually applied to structures formed from alpha-amino acids, but it includes those derived from any amino carboxylic acid. X = OH, OR, NH2, NHR, etc.
[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]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta-type opioid receptorMus musculus (house mouse)IC50 (µMol)0.04950.00010.729810.0000AID132686
Delta-type opioid receptorRattus norvegicus (Norway rat)Ki0.08360.00000.60689.2330AID149804; AID149926; AID220517
Mu-type opioid receptorRattus norvegicus (Norway rat)Ki0.31470.00000.38458.6000AID149298; AID151758; AID151888
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID229963IC50 ratio (GPI/MVD)1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID76094Inhibition of electrically evoked contractions in Guinea pig ileum1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID220517Compound was tested for its binding affinity against opioid receptor delta using [3H]DPDPE as radioligand.1992Journal of medicinal chemistry, Apr-03, Volume: 35, Issue:7
Stereospecificity of amino acid side chains in deltorphin defines binding to opioid receptors.
AID234885Potency to inhibit GPI relative to [Leu]enkephalin1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID151888Inhibition of [3H]- ]DAMGO binding to mu receptor from rat brain membrane1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID149926Inhibition of [3H]- ]DSLET binding to delta receptor from rat brain membrane1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID149804Binding affinity against Opioid receptor delta 1 in P2 membrane preparation of rat brain by [3H]DADLE displacement.1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Function of negative charge in the "address domain" of deltorphins.
AID233402Opioid receptor delta selectivity was defined as the ratio between Ki(opioid receptor mu)/Ki(opioid receptor delta)1992Journal of medicinal chemistry, Apr-03, Volume: 35, Issue:7
Stereospecificity of amino acid side chains in deltorphin defines binding to opioid receptors.
AID151923Potency to inhibit 3H ]DAMGO binding to mu receptor relative to [Leu]enkephalin1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID151758Binding affinity against Opioid receptor mu 1 in P2 membrane preparation of rat brain by [3H]DAGO displacement.1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Function of negative charge in the "address domain" of deltorphins.
AID132686Inhibition of electrically evoked contractions in mouse vas deferens1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID229665Selectivity ratio (mu/delta)1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID234886Potency to inhibit MVD relative to [Leu]enkephalin1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID149956Potency to inhibit [3H]- ]DSLET binding to delta receptor relative to [Leu]enkephalin1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Conformationally restricted deltorphin analogues.
AID228347Ratio of Ki values for mu and delta opioid receptors.1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Function of negative charge in the "address domain" of deltorphins.
AID149298Compound was tested for its binding affinity against opioid receptor mu using [3H]DAGO as radioligand.1992Journal of medicinal chemistry, Apr-03, Volume: 35, Issue:7
Stereospecificity of amino acid side chains in deltorphin defines binding to opioid receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (165)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (3.64)18.7374
1990's93 (56.36)18.2507
2000's45 (27.27)29.6817
2010's18 (10.91)24.3611
2020's3 (1.82)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.09

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.09 (24.57)
Research Supply Index5.17 (2.92)
Research Growth Index5.77 (4.65)
Search Engine Demand Index33.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.57%)5.53%
Reviews7 (4.02%)6.00%
Case Studies1 (0.57%)4.05%
Observational0 (0.00%)0.25%
Other165 (94.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]