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MedKoo Cat#: 597788 | Name: Biphalin

Description:

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

Biphalin is a synthetic opioid octapeptide with a palindromic sequence has high analgesic activity. Biphalin displays a strong affinity for μ and δ-opioid receptors, and a significant to κ-receptor.

Chemical Structure

Biphalin
Biphalin
CAS#83916-01-2

Theoretical Analysis

MedKoo Cat#: 597788

Name: Biphalin

CAS#: 83916-01-2

Chemical Formula: C46H56N10O10

Exact Mass: 908.4181

Molecular Weight: 909.01

Elemental Analysis: C, 60.78; H, 6.21; N, 15.41; O, 17.60

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Biphalin; D-Enk-O; D-ENK; Dala(2);
IUPAC/Chemical Name
(2S,2'S)-N,N'-((2R,8S,13S,19R)-8,13-dibenzyl-3,6,9,12,15,18-hexaoxo-4,7,10,11,14,17-hexaazaicosane-2,19-diyl)bis(2-amino-3-(4-hydroxyphenyl)propanamide)
InChi Key
DESSEGDLRYOPTJ-VRANXALZSA-N
InChi Code
InChI=1S/C46H56N10O10/c1-27(51-43(63)35(47)21-31-13-17-33(57)18-14-31)41(61)49-25-39(59)53-37(23-29-9-5-3-6-10-29)45(65)55-56-46(66)38(24-30-11-7-4-8-12-30)54-40(60)26-50-42(62)28(2)52-44(64)36(48)22-32-15-19-34(58)20-16-32/h3-20,27-28,35-38,57-58H,21-26,47-48H2,1-2H3,(H,49,61)(H,50,62)(H,51,63)(H,52,64)(H,53,59)(H,54,60)(H,55,65)(H,56,66)/t27-,28-,35+,36+,37+,38+/m1/s1
SMILES Code
O=C(NNC([C@H](CC1=CC=CC=C1)NC(CNC([C@@H](C)NC([C@H](CC2=CC=C(O)C=C2)N)=O)=O)=O)=O)[C@H](CC3=CC=CC=C3)NC(CNC([C@@H](C)NC([C@H](CC4=CC=C(O)C=C4)N)=O)=O)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 909.01 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.

Recalculate based on batch purity %
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: Sobczak M, Pilarczyk A, Jonakowski M, Jarmuż A, Sałaga M, Lipkowski AW, Fichna J. Anti-inflammatory and antinociceptive action of the dimeric enkephalin peptide biphalin in the mouse model of colitis: new potential treatment of abdominal pain associated with inflammatory bowel diseases. Peptides. 2014 Oct;60:102-6. doi: 10.1016/j.peptides.2014.08.005. Epub 2014 Aug 20. PubMed PMID: 25151037. 2: Frączak O, Lasota A, Kosson P, Leśniak A, Muchowska A, Lipkowski AW, Olma A. Biphalin analogs containing β(3)-homo-amino acids at the 4,4' positions: Synthesis and opioid activity profiles. Peptides. 2015 Apr;66:13-8. doi: 10.1016/j.peptides.2015.02.004. Epub 2015 Feb 20. PubMed PMID: 25708417. 3: Zielińska M, Jarmuż A, Sałaga M, Lipkowski AW, Fichna J. Mixed MOP/DOP agonist biphalin elicits anti-transit effect in mouse models mimicking diarrhea-predominant irritable bowel syndrome symptoms. Pharmacol Rep. 2016 Feb;68(1):32-6. doi: 10.1016/j.pharep.2015.06.001. Epub 2015 Jun 12. PubMed PMID: 26721348. 4: Bądzyńska B, Lipkowski AW, Sadowski J. An antihypertensive opioid: Biphalin, a synthetic non-addictive enkephalin analog decreases blood pressure in spontaneously hypertensive rats. Pharmacol Rep. 2016 Feb;68(1):51-5. doi: 10.1016/j.pharep.2015.06.006. Epub 2015 Jun 26. PubMed PMID: 26721351. 5: Costante R, Pinnen F, Stefanucci A, Mollica A. Potent biphalin analogs with µ/δ mixed opioid activity: in vivo and in vitro biological evaluation. Arch Pharm (Weinheim). 2014 May;347(5):305-12. doi: 10.1002/ardp.201300380. Epub 2014 Feb 19. PubMed PMID: 24798820. 6: Feliciani F, Pinnen F, Stefanucci A, Costante R, Cacciatore I, Lucente G, Mollica A. Structure-activity relationships of biphalin analogs and their biological evaluation on opioid receptors. Mini Rev Med Chem. 2013 Jan;13(1):11-33. Review. PubMed PMID: 22512573. 7: Yang L, Islam MR, Karamyan VT, Abbruscato TJ. In vitro and in vivo efficacy of a potent opioid receptor agonist, biphalin, compared to subtype-selective opioid receptor agonists for stroke treatment. Brain Res. 2015 Jun 3;1609:1-11. doi: 10.1016/j.brainres.2015.03.022. Epub 2015 Mar 20. PubMed PMID: 25801116; PubMed Central PMCID: PMC4417435. 8: Mollica A, Costante R, Stefanucci A, Pinnen F, Lucente G, Fidanza S, Pieretti S. Antinociceptive profile of potent opioid peptide AM94, a fluorinated analogue of biphalin with non-hydrazine linker. J Pept Sci. 2013 Apr;19(4):233-9. doi: 10.1002/psc.2465. Epub 2012 Nov 8. PubMed PMID: 23136069. 9: Garbuz O, Gulea A, Dyniewicz J, Zablocka B, Lipkowski AW. The non-opioid receptor, antioxidant properties of morphine and the opioid peptide analog biphalin. Peptides. 2015 Jan;63:1-3. doi: 10.1016/j.peptides.2014.09.027. Epub 2014 Oct 23. PubMed PMID: 25453981. 10: Frączak O, Lasota A, Leśniak A, Lipkowski AW, Olma A. The biological consequences of replacing D-Ala in biphalin with amphiphilic α-alkylserines. Chem Biol Drug Des. 2014 Aug;84(2):199-205. doi: 10.1111/cbdd.12305. Epub 2014 Mar 24. PubMed PMID: 24674466. 11: Cowell SM, Lee YS. Biphalin: The Foundation of Bivalent Ligands. Curr Med Chem. 2016;23(29):3267-3284. Review. PubMed PMID: 27160537. 12: Mollica A, Carotenuto A, Novellino E, Limatola A, Costante R, Pinnen F, Stefanucci A, Pieretti S, Borsodi A, Samavati R, Zador F, Benyhe S, Davis P, Porreca F, Hruby VJ. Novel cyclic biphalin analogue with improved antinociceptive properties. ACS Med Chem Lett. 2014 Jul 14;5(9):1032-6. doi: 10.1021/ml500241n. eCollection 2014 Sep 11. PubMed PMID: 25221662; PubMed Central PMCID: PMC4160744. 13: Lesniak A, Bochynska-Czyz M, Sacharczuk M, Benhye S, Misicka A, Bujalska-Zadrozny M, Lipkowski AW. Biphalin preferentially recruits peripheral opioid receptors to facilitate analgesia in a mouse model of cancer pain - A comparison with morphine. Eur J Pharm Sci. 2016 Jun 30;89:39-49. doi: 10.1016/j.ejps.2016.04.014. Epub 2016 Apr 14. PubMed PMID: 27094782. 14: Lesniak A, Pick CG, Misicka A, Lipkowski AW, Sacharczuk M. Biphalin protects against cognitive deficits in a mouse model of mild traumatic brain injury (mTBI). Neuropharmacology. 2016 Feb;101:506-18. doi: 10.1016/j.neuropharm.2015.10.014. Epub 2015 Oct 22. PubMed PMID: 26474659. 15: Leone S, Chiavaroli A, Orlando G, Mollica A, Di Nisio C, Brunetti L, Vacca M. The analgesic activity of biphalin and its analog AM 94 in rats. Eur J Pharmacol. 2012 Jun 15;685(1-3):70-3. doi: 10.1016/j.ejphar.2012.04.026. Epub 2012 Apr 23. PubMed PMID: 22546229. 16: Mollica A, Pinnen F, Costante R, Locatelli M, Stefanucci A, Pieretti S, Davis P, Lai J, Rankin D, Porreca F, Hruby VJ. Biological active analogues of the opioid peptide biphalin: mixed α/β(3)-peptides. J Med Chem. 2013 Apr 25;56(8):3419-23. doi: 10.1021/jm301456c. Epub 2013 Apr 12. PubMed PMID: 23547584; PubMed Central PMCID: PMC3942533. 17: Kawalec M, Kowalczyk JE, Beresewicz M, Lipkowski AW, Zablocka B. Neuroprotective potential of biphalin, multireceptor opioid peptide, against excitotoxic injury in hippocampal organotypic culture. Neurochem Res. 2011 Nov;36(11):2091-5. doi: 10.1007/s11064-011-0568-1. Epub 2011 Aug 13. PubMed PMID: 21842273; PubMed Central PMCID: PMC3183243. 18: Yang L, Shah K, Wang H, Karamyan VT, Abbruscato TJ. Characterization of neuroprotective effects of biphalin, an opioid receptor agonist, in a model of focal brain ischemia. J Pharmacol Exp Ther. 2011 Nov;339(2):499-508. doi: 10.1124/jpet.111.184127. Epub 2011 Aug 19. PubMed PMID: 21856861; PubMed Central PMCID: PMC3199980. 19: Lazarczyk M, Matyja E, Lipkowski AW. A comparative study of morphine stimulation and biphalin inhibition of human glioblastoma T98G cell proliferation in vitro. Peptides. 2010 Aug;31(8):1606-12. doi: 10.1016/j.peptides.2010.05.002. Epub 2010 May 24. PubMed PMID: 20580757. 20: Hsieh JY, Chiang TY, Chen JL, Chen YW, Lin HC, Hwang CC. A molecular dynamics study on opioid activities of biphalin molecule. J Mol Model. 2011 Oct;17(10):2455-64. doi: 10.1007/s00894-010-0931-1. Epub 2010 Dec 23. PubMed PMID: 21181216.