Dynorphin B

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Dynorphin B[1]
Names
Other names
Dynorphin B-13; Rimorphin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C74H115N21O17/c1-40(2)34-53(91-68(107)54(36-44-18-10-8-11-19-44)86-58(100)39-84-57(99)38-85-62(101)48(76)35-46-25-27-47(97)28-26-46)67(106)89-51(24-17-33-83-74(80)81)63(102)87-50(23-16-32-82-73(78)79)64(103)90-52(29-30-56(77)98)65(104)92-55(37-45-20-12-9-13-21-45)69(108)88-49(22-14-15-31-75)66(105)93-59(41(3)4)70(109)94-60(42(5)6)71(110)95-61(43(7)96)72(111)112/h8-13,18-21,25-28,40-43,48-55,59-61,96-97H,14-17,22-24,29-39,75-76H2,1-7H3,(H2,77,98)(H,84,99)(H,85,101)(H,86,100)(H,87,102)(H,88,108)(H,89,106)(H,90,103)(H,91,107)(H,92,104)(H,93,105)(H,94,109)(H,95,110)(H,111,112)(H4,78,79,82)(H4,80,81,83)/t43-,48+,49+,50+,51+,52+,53+,54+,55+,59+,60+,61+/m1/s1 ☒N
    Key: AGTSSZRZBSNTGQ-ITZCFHCWSA-N ☒N
  • InChI=1/C74H115N21O17/c1-40(2)34-53(91-68(107)54(36-44-18-10-8-11-19-44)86-58(100)39-84-57(99)38-85-62(101)48(76)35-46-25-27-47(97)28-26-46)67(106)89-51(24-17-33-83-74(80)81)63(102)87-50(23-16-32-82-73(78)79)64(103)90-52(29-30-56(77)98)65(104)92-55(37-45-20-12-9-13-21-45)69(108)88-49(22-14-15-31-75)66(105)93-59(41(3)4)70(109)94-60(42(5)6)71(110)95-61(43(7)96)72(111)112/h8-13,18-21,25-28,40-43,48-55,59-61,96-97H,14-17,22-24,29-39,75-76H2,1-7H3,(H2,77,98)(H,84,99)(H,85,101)(H,86,100)(H,87,102)(H,88,108)(H,89,106)(H,90,103)(H,91,107)(H,92,104)(H,93,105)(H,94,109)(H,95,110)(H,111,112)(H4,78,79,82)(H4,80,81,83)/t43-,48+,49+,50+,51+,52+,53+,54+,55+,59+,60+,61+/m1/s1
    Key: AGTSSZRZBSNTGQ-ITZCFHCWBN
  • [H]/N=C(\N)/NCCC[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)O)NC(=O)[C@H](CCCN/C(=N/[H])/N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc2ccccc2)NC(=O)CNC(=O)CNC(=O)[C@H](Cc3ccc(cc3)O)N
Properties
C74H115N21O17
Molar mass 1570.8354
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dynorphin B, also known as rimorphin,[2] is a form of dynorphin and an endogenous opioid peptide with the amino acid sequence Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Gln-Phe-Lys-Val-Val-Thr. Dynorphin B is generated as a proteolytic cleavage product of leumorphin, which in turn is a cleavage product of preproenkephalin B (prodynorphin).[citation needed]


Dynorphin B has an identical N-terminal sequence, but different C-terminal sequence to dynorphin A. In an alanine scan of the non-glycine residues of dynorphin B, it was discovered that Tyr1 and Phe4 residues are critical for both opioid receptor affinity and κ-opioid receptor agonist potency, Arg6 and Arg7 promote κ-opioid affinity and Lys10 contributes to the opioid receptor affinity.[3]

Inducers of dynorphin B

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Cannabinoid CP55,940 and △9-tetrahydrocannabinol (△9-THC) can induce the release of dynorphin B, which in return acts as an agonist of κ-opioid receptors, resulting in the production of antinociception.[4] Similarly, Tyr-D-Arg-Phe-Sar (TAPS) is capable of promoting a release of dynorphin B through the simulation of μ1-opioid receptors, causing a production of antinociception.[5] The antinociceptive effect produced by dynorphin B allows for spinal analgesia.

See also

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References

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  1. ^ Dynorphin B - Compound Summary, PubChem.
  2. ^ Paul V. Malven (12 January 1993). Mammalian Neuroendocrinology. CRC Press. p. 70. ISBN 978-0-8493-8757-9. Retrieved 22 April 2012.
  3. ^ Joshi, Anand A.; Murray, Thomas F.; Aldrich, Jane V. (September 2017). "Alanine scan of the opioid peptide dynorphin B amide". Biopolymers. 108 (5): e23026. doi:10.1002/bip.23026. PMC 6003702. PMID 28464209.
  4. ^ Houser, Susan J; Eads, Micah; Embrey, James P; Welch, Sandra P (February 2000). "Dynorphin B and spinal analgesia: induction of antinociception by the cannabinoids CP55,940, Δ9-THC and anandamide1Published on the World Wide Web on 18 January 2000.1". Brain Research. 857 (1–2): 337–342. doi:10.1016/S0006-8993(00)01981-8. PMID 10700588. S2CID 8616013.
  5. ^ Mizoguchi, Hirokazu; Ito, Kanenori; Watanabe, Hiroyuki; Watanabe, Chizuko; Katsuyama, Sou; Fujimura, Tsutomu; Sakurada, Tsukasa; Sakurada, Shinobu (November 2006). "Contribution of spinal μ1-opioid receptors and dynorphin B to the antinociception induced by Tyr-d-Arg-Phe-Sar". Peptides. 27 (11): 2786–2793. doi:10.1016/j.peptides.2006.07.006. PMID 16919848. S2CID 1770295.


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