Wikipedia

Valorphin

(Redirected from VV-Hemorphin-5)

Valorphin, also known as VV-hemorphin-5, is a naturally occurring, endogenous opioid heptapeptide of the hemorphin family with the amino acid sequence H-Val-Val-Tyr-Pro-Trp-Thr-Gln-OH (VVYPWTQ).[1][2][3] It is produced in the body via proteolyic cleavage of residues 33-39 of the β-chain of hemoglobin.[2][4] Valorphin binds preferentially to the μ-opioid receptor and produces effects such as analgesia and self-administration in animals.[1][2] It also possesses cytotoxic and antiproliferative properties against tumor cells,[3][4][5][6] the mediation of which, because they are reversed by naloxone, appears to be dependent on the opioid receptors.[5]

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 mass 892.024 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

See also

edit

References

edit
  1. ^ a b Maurer 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 46078832.4–6&rft.pages=387-90&rft.date=1985-02&rft_id=https://api.semanticscholar.org/CorpusID:46078832#id-name=S2CID&rft_id=info:pmid/2860596&rft_id=info:doi/10.1016/0143-4179(85)90035-6&rft.aulast=Maurer&rft.aufirst=R&rft.au=Römer, D&rft.au=Büscher, HH&rft.au=Gähwiler, BH&rft.au=Thies, PW&rft.au=David, S&rfr_id=info:sid/en.wikipedia.org:Valorphin" class="Z3988">
  2. ^ a b c Erchegyi 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 1356941.477-84&rft.date=1992-06&rft_id=info:doi/10.1111/j.1399-3011.1992.tb00277.x&rft_id=info:pmid/1356941&rft.aulast=Erchegyi&rft.aufirst=J&rft.au=Kastin, AJ&rft.au=Zadina, JE&rft.au=Qiu, XD&rfr_id=info:sid/en.wikipedia.org:Valorphin" class="Z3988">
  3. ^ a b Blishchenko 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 44834813.903-10&rft.date=2002-05&rft_id=https://api.semanticscholar.org/CorpusID:44834813#id-name=S2CID&rft_id=info:pmid/12084521&rft_id=info:doi/10.1016/S0196-9781(02)50017-7&rft.aulast=Blishchenko&rft.aufirst=EY&rft.au=Sazonova, OV&rft.au=Kalinina, OA&rfr_id=info:sid/en.wikipedia.org:Valorphin" class="Z3988">
  4. ^ a b Blishchenko 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 46177846.438-52&rft.date=2002-08&rft_id=https://api.semanticscholar.org/CorpusID:46177846#id-name=S2CID&rft_id=info:pmid/12212807&rft_id=info:doi/10.1002/psc.402&rft.aulast=Blishchenko&rft.aufirst=E&rft.au=Sazonova, O&rft.au=Surovoy, A&rfr_id=info:sid/en.wikipedia.org:Valorphin" class="Z3988">
  5. ^ a b Blishchenko 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 11332853.79-85&rft.date=1997&rft_id=https://api.semanticscholar.org/CorpusID:11332853#id-name=S2CID&rft_id=info:pmid/9114456&rft_id=info:doi/10.1016/S0196-9781(96)00248-3&rft.au=Blishchenko EYu&rft.au=Mernenko OA&rft.au=Mirkina II&rfr_id=info:sid/en.wikipedia.org:Valorphin" class="Z3988">
  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 15662114.118-24&rft.date=2005-01&rft_id=info:doi/10.4161/cbt.4.1.1474&rft_id=info:pmid/15662114&rft.aulast=Blishchenko&rft.aufirst=EY&rft.au=Sazonova, OV&rft.au=Kalinina, OA&rft_id=http://www.landesbioscience.com/journals/cbt/abstract.php?id=1474&rfr_id=info:sid/en.wikipedia.org:Valorphin" class="Z3988">
Retrieved from "https://en.wikipedia.org/w/index.php?title=Valorphin&oldid=1033043256"