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Deltorphin I

From Wikipedia, the free encyclopedia
Deltorphin I
Names
IUPAC names
(3S)-3-[(2S)-2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-3-phenylpropanamido]-3-{[(1S)-1-{[(1S)-1-[(carbamoylmethyl)carbamoyl]-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}propanoic acid
or
L-tyrosyl-D-alanyl-L-phenylalanyl-L-α-aspartyl-L-valyl-L-valylglycinamide
Other names
[D-Ala2]Deltorphin I; Deltorphin C
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C37H52N8O10/c1-19(2)30(36(54)40-18-28(39)47)45-37(55)31(20(3)4)44-35(53)27(17-29(48)49)43-34(52)26(16-22-9-7-6-8-10-22)42-32(50)21(5)41-33(51)25(38)15-23-11-13-24(46)14-12-23/h6-14,19-21,25-27,30-31,46H,15-18,38H2,1-5H3,(H2,39,47)(H,40,54)(H,41,51)(H,42,50)(H,43,52)(H,44,53)(H,45,55)(H,48,49)/t21-,25+,26+,27+,30+,31+/m1/s1
    Key: CJAORFIPPWIGPG-QXYJMILXSA-N
  • InChI=1/C37H52N8O10/c1-19(2)30(36(54)40-18-28(39)47)45-37(55)31(20(3)4)44-35(53)27(17-29(48)49)43-34(52)26(16-22-9-7-6-8-10-22)42-32(50)21(5)41-33(51)25(38)15-23-11-13-24(46)14-12-23/h6-14,19-21,25-27,30-31,46H,15-18,38H2,1-5H3,(H2,39,47)(H,40,54)(H,41,51)(H,42,50)(H,43,52)(H,44,53)(H,45,55)(H,48,49)/t21-,25+,26+,27+,30+,31+/m1/s1
    Key: CJAORFIPPWIGPG-QXYJMILXBS
  • O=C(N)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)C)Cc2ccccc2)CC(=O)O)C(C)C)C(C)C
Properties
C37H52N8O10
Molar mass768.856 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Deltorphin I, also known as[D-Ala2]deltorphin I ordeltorphin C, is anaturally occurring,exogenousopioidheptapeptide and hence,exorphin, with theamino acid sequence Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2.[1][2] While not known to beendogenous to humans or other mammals, deltorphin I, along with the otherdeltorphins and thedermorphins, is produced naturally in the skin of species ofPhyllomedusa,[1] a genus offrogs native toSouth andCentral America. Deltorphin possesses very highaffinity andselectivity as anagonist for theδ-opioid receptor,[1][2] and on account of its unusually highblood-brain-barrier penetration rate,[3] producescentrally-mediatedanalgesic effects in animals even when administeredperipherally.[4]

See also

[edit]

References

[edit]
  1. ^abcErspamer V, Melchiorri P, Falconieri-Erspamer G, et al. (July 1989)."Deltorphins: a family of naturally occurring peptides with high affinity and selectivity for delta opioid binding sites".Proceedings of the National Academy of Sciences of the United States of America.86 (13):5188–92.Bibcode:1989PNAS...86.5188E.doi:10.1073/pnas.86.13.5188.PMC 297583.PMID 2544892.
  2. ^abBalboni G, Marastoni M, Picone D, et al. (June 1990). "New features of the delta opioid receptor: conformational properties of deltorphin I analogues".Biochemical and Biophysical Research Communications.169 (2):617–22.doi:10.1016/0006-291X(90)90375-W.PMID 2162669.
  3. ^Fiori A, Cardelli P, Negri L, Savi MR, Strom R, Erspamer V (August 1997)."Deltorphin transport across the blood–brain barrier".Proceedings of the National Academy of Sciences of the United States of America.94 (17):9469–74.Bibcode:1997PNAS...94.9469F.doi:10.1073/pnas.94.17.9469.PMC 23226.PMID 9256506.
  4. ^Thomas SA, Abbruscato TJ, Hau VS, et al. (May 1997)."Structure-activity relationships of a series of [D-Ala2]deltorphin I and II analogues; in vitro blood–brain barrier permeability and stability".The Journal of Pharmacology and Experimental Therapeutics.281 (2):817–25.PMID 9152390.
Opioids
Opiates/opium
Semisynthetic
Synthetic
Paracetamol-type
NSAIDs
Propionates
Oxicams
Acetates
COX-2 inhibitors
Fenamates
Salicylates
Pyrazolones
Others
Cannabinoids
Ion channel
modulators
Calcium blockers
Sodium blockers
Potassium openers
Myorelaxants
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μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
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