beta-Casomorphin 5 | CAS#72122-63-5 | opioid receptor agonist

MedKoo Cat#: 597808 | Name: beta-Casomorphin 5

Description:

WARNING: This product is for research use only, not for human or veterinary use.

beta-Casomorphin 5 is an opioid receptor agonist, is a member of the β-casomorphin peptide family derived from β-casein. β-casomorphins are used to study their differential effects on processes such as hyperglycemia, oxidative stress, opioid signalling and immunosuppression.

Chemical Structure

beta-Casomorphin 5

CAS#72122-63-5

Theoretical Analysis

MedKoo Cat#: 597808

Name: beta-Casomorphin 5

CAS#: 72122-63-5

Chemical Formula: C30H37N5O7

Exact Mass: 579.2693

Molecular Weight: 579.65

Elemental Analysis: C, 62.16; H, 6.43; N, 12.08; O, 19.32

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Synonym

beta-Casomorphin 5; 4-Pro-casomorphin; Deprolorphin; L-Pro(4)-casomorphin; Tyr-pro-phe-pro-gly;

IUPAC/Chemical Name

L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolylglycine

InChi Key

PKKIDZFGRQACGB-QORCZRPOSA-N

InChi Code

InChI=1S/C30H37N5O7/c31-22(16-20-10-12-21(36)13-11-20)29(41)34-14-5-9-25(34)28(40)33-23(17-19-6-2-1-3-7-19)30(42)35-15-4-8-24(35)27(39)32-18-26(37)38/h1-3,6-7,10-13,22-25,36H,4-5,8-9,14-18,31H2,(H,32,39)(H,33,40)(H,37,38)/t22-,23-,24-,25-/m0/s1

SMILES Code

O=C(O)CNC([C@H]1N(C([C@H](CC2=CC=CC=C2)NC([C@H]3N(C([C@H](CC4=CC=C(O)C=C4)N)=O)CCC3)=O)=O)CCC1)=O

Appearance

Solid powder

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 579.65 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: Nguyen DD, Solah VA, Johnson SK, Charrois JW, Busetti F. Isotope dilution liquid chromatography-tandem mass spectrometry for simultaneous identification and quantification of beta-casomorphin 5 and beta-casomorphin 7 in yoghurt. Food Chem. 2014 Mar 1;146:345-52. doi: 10.1016/j.foodchem.2013.09.057. Epub 2013 Sep 18. PubMed PMID: 24176353. 2: Sakaguchi M, Murayama K, Yabe K, Satoh M, Takeuchi M, Matsumura E. Beta-casomorphin-5 stimulates neurite outgrowth in a mouse neuroblastoma cell line (Neuro-2a). Neurosci Lett. 1998 Jul 24;251(2):97-100. PubMed PMID: 9718983. 3: Dalziel JE, Spencer NJ, Dunstan KE, Lynch AT, Haggarty NW, Gopal PK, Roy NC. An in vitro rat model of colonic motility to determine the effect of β-casomorphin-5 on propagating contractions. Food Funct. 2014 Nov;5(11):2768-74. doi: 10.1039/c4fo00193a. PubMed PMID: 25093576. 4: Liebmann C, Mentz P, Schnittler M, Schrader U, Neubert K, Barth A. Nonopioid effects of beta-casomorphin-5 in guinea pig heart: alterations to the beta-adrenoceptor-G-protein complex and inhibition of myocardial responses to isoproterenol. Peptides. 1991 Mar-Apr;12(2):265-70. PubMed PMID: 1648711. 5: Ul Haq MR, Kapila R, Kapila S. Release of β-casomorphin-7/5 during simulated gastrointestinal digestion of milk β-casein variants from Indian crossbred cattle (Karan Fries). Food Chem. 2015 Feb 1;168:70-9. doi: 10.1016/j.foodchem.2014.07.024. Epub 2014 Jul 11. PubMed PMID: 25172685. 6: Sakaguchi M, Koseki M, Wakamatsu M, Matsumura E. Effects of systemic administration of beta-casomorphin-5 on learning and memory in mice. Eur J Pharmacol. 2006 Jan 13;530(1-2):81-7. Epub 2005 Dec 15. PubMed PMID: 16360145. 7: Sakaguchi M, Koseki M, Wakamatsu M, Matsumura E. Effects of beta-casomorphin-5 on passive avoidance response in mice. Biosci Biotechnol Biochem. 2003 Nov;67(11):2501-4. PubMed PMID: 14646221. 8: Schmidt R, Neubert K, Barth A, Liebmann C, Schnittler M, Chung NN, Schiller PW. Structure-activity relationships of cyclic beta-casomorphin-5 analogues. Peptides. 1991 Nov-Dec;12(6):1175-80. PubMed PMID: 1667685. 9: Ermisch A, Rühle HJ, Neubert K, Hartrodt B, Landgraf R. On the blood-brain barrier to peptides: [3H]beta-casomorphin-5 uptake by eighteen brain regions in vivo. J Neurochem. 1983 Nov;41(5):1229-33. PubMed PMID: 6619862. 10: Hartrodt B, Neubert K, Fischer G, Schulz H, Barth A. [Synthesis and enzymatic degradation of beta-casomorphin-5 (author's transl)]. Pharmazie. 1982 Mar;37(3):165-9. German. PubMed PMID: 7100234. 11: Svedberg J, de Haas J, Leimenstoll G, Paul F, Teschemacher H. Demonstration of beta-casomorphin immunoreactive materials in in vitro digests of bovine milk and in small intestine contents after bovine milk ingestion in adult humans. Peptides. 1985 Sep-Oct;6(5):825-30. PubMed PMID: 4080604. 12: Delaet NG, Verheyden PM, Tourwe D, Van Binst G, Davis P, Burks TF. Morphiceptin and beta-casomorphin-5 analogues containing a reduced peptide bond: selective mu-receptor agonists and a novel mu antagonist, H-Tyr-Pro psi (CH2-NH)Phe-Pro-Gly-OH. Biopolymers. 1992 Aug;32(8):957-69. PubMed PMID: 1330047. 13: Blass EM, Blom J. beta-Casomorphin causes hypoalgesia in 10-day-old rats: evidence for central mediation. Pediatr Res. 1996 Feb;39(2):199-203. PubMed PMID: 8825787. 14: Akhmedov NA. [Theoretical conformation analysis of beta-casomorphin-5 molecule]. Mol Biol (Mosk). 1986 Nov-Dec;20(6):1547-9. Russian. PubMed PMID: 3807911. 15: Rüthrich HL, Grecksch G, Schmidt R. Phe1-substituted beta-casomorphin-5 analogues with analgesic activity. Peptides. 1994;15(3):457-60. PubMed PMID: 7937319. 16: Delaet NG, Verheyden PM, Tourwé D, Van Binst G. Assignment of the 1H-NMR resonances of the four rotamers of beta-casomorphin-5 in DMSO. Biopolymers. 1991 Oct 15;31(12):1409-16. PubMed PMID: 1816877. 17: Carpenter KA, Schiller PW, Schmidt R, Wilkes BC. Distinct conformational preferences of three cyclic beta-casomorphin-5 analogs determined using NMR spectroscopy and theoretical analysis. Int J Pept Protein Res. 1996 Jul;48(1):102-11. PubMed PMID: 8844269. 18: Mentz P, Neubert K, Hoffmann S, Liebmann C, Barth A. Effects of beta-casomorphin in isolated heart preparations. Pharmazie. 1988 Apr;43(4):271-3. PubMed PMID: 3413218. 19: Reymann KG, Chepkova AN, Schulzeck K, Ott T. Effects of beta-casomorphin on dentate hippocampal field potentials in freely moving rats. Biomed Biochim Acta. 1985;44(5):749-54. PubMed PMID: 2998350. 20: Furkert J, Rathsack R, Schmidt HE. [Development of a radioimmunoassay for beta-casomorphin (1-5)]. Radiobiol Radiother (Berl). 1986;27(2):205-13. German. PubMed PMID: 3714988.