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DAMGO

DAMGO
Names
IUPAC name
(2S)-2-[[2-[[(2R)-2-[[(2S)-2-Amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]-methylamino]-N-(2-hydroxyethyl)-3-phenylpropanamide
Other names
Ala2-MePhe4-Glyol5-Enkephalin, DAGO, DAMGE
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C26H35N5O6/c1-17(30-25(36)21(27)14-19-8-10-20(33)11-9-19)24(35)29-16-23(34)31(2)22(26(37)28-12-13-32)15-18-6-4-3-5-7-18/h3-11,17,21-22,32-33H,12-16,27H2,1-2H3,(H,28,37)(H,29,35)(H,30,36)/t17-,21+,22+/m1/s1 ☒N
    Key: HPZJMUBDEAMBFI-WTNAPCKOSA-N ☒N
  • InChI=1/C26H35N5O6/c1-17(30-25(36)21(27)14-19-8-10-20(33)11-9-19)24(35)29-16-23(34)31(2)22(26(37)28-12-13-32)15-18-6-4-3-5-7-18/h3-11,17,21-22,32-33H,12-16,27H2,1-2H3,(H,28,37)(H,29,35)(H,30,36)/t17-,21+,22+/m1/s1
    Key: HPZJMUBDEAMBFI-WTNAPCKOBV
  • C[C@@H](NC([C@@H](N)CC1=CC=C(O)C=C1)=O)C(NCC(N([C@H](C(NCCO)=O)CC2=CC=CC=C2)C)=O)=O
Properties
C26H35N5O6
Molar mass 513.595 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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DAMGO ([D-Ala2, N-MePhe4, Gly-ol]-enkephalin) is a synthetic opioid peptide with high μ-opioid receptor specificity. It was synthesized as a biologically stable analog of δ-opioid receptor-preferring endogenous opioids, leu- and met-enkephalin.[1] Structures of DAMGO bound to the μ opioid receptor reveal a very similar binding pose to morphinans.[2][3]

Its structure is H-Tyr-D-Ala-Gly-N-MePhe-Gly-ol.

DAMGO has been used in experimental settings for the possibility of alleviating or reducing opiate tolerance for patients under the treatment of an opioid. Such treatment on rats, adding DAMGO to morphine administration, showed that after seven days morphine had as much of an effect at the same dosage as the first day when administered together with DAMGO to the rats, whereas a separate control group of rats that were administered the same dosage of morphine over the course of the same week, but without DAMGO, displayed an increased tolerance and lessened analgesic efficacy toward the end of that week.[4][5][6]

See also

References

  1. ^ Handa BK, Land AC, Lord JA, Morgan BA, Rance MJ, Smith CF (April 1981). "Analogues of β-LPH61–64 possessing selective agonist activity at μ-opiate receptors". European Journal of Pharmacology. 70 (4): 531–40. doi:10.1016/0014-2999(81)90364-2. PMID 6263640.
  2. ^ Koehl A, Hu H, Maeda S, Zhang Y, Qu Q, Paggi JM, Latorraca NR, Hilger D, Dawson R, Matile H, Schertler GF, Granier S, Weis WI, Dror RO, Manglik A, Skiniotis G, Kobilka BK (June 2018). "Structure of the μ-opioid receptor–Gi". Nature. 558 (7711): 547–552. doi:10.1038/s41586-018-0219-7. PMC 6317904. PMID 29899455.
  3. ^ Zhuang Y, Wang Y, He B, He X, Zhou XE, Guo S, Rao Q, Yang J, Liu J, Zhou Q, Wang X, Liu M, Liu W, Jiang X, Yang D (2022-11-10). "Molecular recognition of morphine and fentanyl by the human μ-opioid receptor". Cell. 185 (23): 4361–4375.e19. doi:10.1016/j.cell.2022.09.041. PMID 36368306. S2CID 253426623.
  4. ^ Radler D (25 January 2002). "Reducing Tolerance To Morphine Could Aid Pain Therapy". Daily University Science News (UniSci). UniScience News Net, Inc.
  5. ^ Finn AK, Whistler JL (December 2001). "Endocytosis of the Mu Opioid Receptor Reduces Tolerance and a Cellular Hallmark of Opiate Withdrawal". Neuron. 32 (5): 829–839. doi:10.1016/S0896-6273(01)00517-7. PMID 11738029. S2CID 16396686.
  6. ^ He L, Fong J, von Zastrow M, Whistler JL (January 2002). "Regulation of Opioid Receptor Trafficking and Morphine Tolerance by Receptor Oligomerization". Cell. 108 (2): 271–82. doi:10.1016/S0092-8674(02)00613-X. PMID 11832216. S2CID 15933405.
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