Synonym
Hemorphin 5; Tyr-pro-trp-thr-gln;
IUPAC/Chemical Name
L-tyrosyl-L-prolyl-L-tryptophyl-L-threonyl-L-glutamine
InChi Key
DFRFZNQVSGGPAY-OOTSGESESA-N
InChi Code
InChI=1S/C34H43N7O9/c1-18(42)29(32(47)38-25(34(49)50)12-13-28(36)44)40-30(45)26(16-20-17-37-24-6-3-2-5-22(20)24)39-31(46)27-7-4-14-41(27)33(48)23(35)15-19-8-10-21(43)11-9-19/h2-3,5-6,8-11,17-18,23,25-27,29,37,42-43H,4,7,12-16,35H2,1H3,(H2,36,44)(H,38,47)(H,39,46)(H,40,45)(H,49,50)/t18-,23+,25+,26+,27+,29+/m1/s1
SMILES Code
O=C(N)CC[C@@H](C(O)=O)NC([C@H]([C@H](O)C)NC([C@H](CC1=CNC2=C1C=CC=C2)NC([C@H]3N(C([C@H](CC4=CC=C(O)C=C4)N)=O)CCC3)=O)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
693.75
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Cohen M, Fruitier-Arnaudin I, Sauvan R, Birnbaum D, Piot JM. Serum levels of Hemorphin-7 peptides in patients with breast cancer. Clin Chim Acta. 2003 Nov;337(1-2):59-67. PubMed PMID: 14568181.
2: Yamamoto Y, Ono H, Ueda A, Shimamura M, Nishimura K, Hazato T. Spinorphin as an endogenous inhibitor of enkephalin-degrading enzymes: roles in pain and inflammation. Curr Protein Pept Sci. 2002 Dec;3(6):587-99. Review. PubMed PMID: 12470213.
3: Jinsmaa Y, Yoshikawa M. Release of hemorphin-5 from human hemoglobin by pancreatic elastase. Biosci Biotechnol Biochem. 2002 May;66(5):1130-2. PubMed PMID: 12092829.
4: Blishchenko EY, Sazonova OV, Kalinina OA, Yatskin ON, Philippova MM, Surovoy AY, Karelin AA, Ivanov VT. Family of hemorphins: co-relations between amino acid sequences and effects in cell cultures. Peptides. 2002 May;23(5):903-10. PubMed PMID: 12084521.
5: Yatskin ON, Philippova MM, Blishchenko EYu, Karelin AA, Ivanov VT. LVV- and VV-hemorphins: comparative levels in rat tissues. FEBS Lett. 1998 May 29;428(3):286-90. PubMed PMID: 9654150.
6: Zhao Q, Piot JM. Investigation of inhibition angiotensin-converting enzyme (ACE) activity and opioid activity of two hemorphins, LVV-hemorphin-5 and VV-hemorphin-5, isolated from a defined peptic hydrolysate of bovine hemoglobin. Neuropeptides. 1997 Apr;31(2):147-53. PubMed PMID: 9179868.
7: Zhao Q, Sannier F, Piot JM. Kinetics of appearance of four hemorphins from bovine hemoglobin peptic hydrolysates by HPLC coupled with photodiode array detection. Biochim Biophys Acta. 1996 Jun 7;1295(1):73-80. PubMed PMID: 8679676.
8: Davis TP, Gillespie TJ, Porreca F. Peptide fragments derived from the beta-chain of hemoglobin (hemorphins) are centrally active in vivo. Peptides. 1989 Jul-Aug;10(4):747-51. PubMed PMID: 2587417.
9: Brantl V, Gramsch C, Lottspeich F, Mertz R, Jaeger KH, Herz A. Novel opioid peptides derived from hemoglobin: hemorphins. Eur J Pharmacol. 1986 Jun 17;125(2):309-10. PubMed PMID: 3743640.
