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Valorphin

From Wikipedia, the free encyclopedia
Valorphin
Names
IUPAC name
L-Valyl-L-valyl-L-tyrosyl-L-prolyl-L-tryptophyl-L-threonyl-L-glutamine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C44H60N8O12/c1-22(2)35(45)40(59)50-36(23(3)4)41(60)49-32(19-25-12-14-27(54)15-13-25)43(62)52-18-8-11-33(52)39(58)48-31(20-26-21-46-29-10-7-6-9-28(26)29)38(57)51-37(24(5)53)42(61)47-30(44(63)64)16-17-34(55)56/h6-7,9-10,12-15,21-24,30-33,35-37,46,53-54H,8,11,16-20,45H2,1-5H3,(H,47,61)(H,48,58)(H,49,60)(H,50,59)(H,51,57)(H,55,56)(H,63,64)/t24-,30+,31+,32+,33+,35+,36+,37+/m1/s1
    Key: CNYWVXYFCKFXLL-NMUVPRMFSA-N
  • C[C@H]([C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H]3CCCN3C(=O)[C@H](Cc4ccc(cc4)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N)O
Properties
C44H61N9O11
Molar mass892.024 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Valorphin, also known asVV-hemorphin-5, is anaturally occurring,endogenousopioidheptapeptide of thehemorphin family with theamino acid sequence H-Val-Val-Tyr-Pro-Trp-Thr-Gln-OH (VVYPWTQ).[1][2][3] It is produced in the body viaproteolyiccleavage ofresidues 33-39 of the β-chain ofhemoglobin.[2][4] Valorphin binds preferentially to theμ-opioid receptor and produces effects such asanalgesia andself-administration in animals.[1][2] It also possessescytotoxic andantiproliferative properties againsttumorcells,[3][4][5][6] the mediation of which, because they are reversed bynaloxone, appears to be dependent on theopioid receptors.[5]

See also

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References

[edit]
  1. ^abMaurer R, Römer D, Büscher HH, Gähwiler BH, Thies PW, David S (February 1985). "Valorphin: a novel chemical structure with opioid activity".Neuropeptides.5 (4–6):387–90.doi:10.1016/0143-4179(85)90035-6.PMID 2860596.S2CID 46078832.
  2. ^abcErchegyi J, Kastin AJ, Zadina JE, Qiu XD (June 1992). "Isolation of a heptapeptide Val-Val-Tyr-Pro-Trp-Thr-Gln (valorphin) with some opiate activity".International Journal of Peptide and Protein Research.39 (6):477–84.doi:10.1111/j.1399-3011.1992.tb00277.x.PMID 1356941.
  3. ^abBlishchenko EY, Sazonova OV, Kalinina OA, et al. (May 2002). "Family of hemorphins: co-relations between amino acid sequences and effects in cell cultures".Peptides.23 (5):903–10.doi:10.1016/S0196-9781(02)00017-7.PMID 12084521.S2CID 44834813.
  4. ^abBlishchenko E, Sazonova O, Surovoy A, et al. (August 2002). "Antiproliferative action of valorphin in cell cultures".Journal of Peptide Science.8 (8):438–52.doi:10.1002/psc.402.PMID 12212807.S2CID 46177846.
  5. ^abBlishchenko EYu; Mernenko OA; Mirkina II; et al. (1997). "Tumor cell cytolysis mediated by valorphin, an opioid-like fragment of hemoglobin beta-chain".Peptides.18 (1):79–85.doi:10.1016/S0196-9781(96)00248-3.PMID 9114456.S2CID 11332853.
  6. ^Blishchenko EY, Sazonova OV, Kalinina OA, et al. (January 2005)."Antitumor effect of valorphin in vitro and in vivo: combined action with cytostatic drugs".Cancer Biology & Therapy.4 (1):118–24.doi:10.4161/cbt.4.1.1474.PMID 15662114.
Hormones
Opioid peptides
Dynorphins
Endomorphins
Endorphins
Enkephalins
Others
Other
neuropeptides
Kinins
Neuromedins
Orexins
Other
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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