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MedKoo Cat#: 530703 | Name: Msh (11-13)

Description:

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

Msh (11-13) is a bioactive chemical.

Chemical Structure

Msh (11-13)
Msh (11-13)
CAS#67727-97-3

Theoretical Analysis

MedKoo Cat#: 530703

Name: Msh (11-13)

CAS#: 67727-97-3

Chemical Formula: C16H30N4O4

Exact Mass: 342.2267

Molecular Weight: 342.44

Elemental Analysis: C, 56.12; H, 8.83; N, 16.36; O, 18.69

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
Msh (11-13); ACTH-(11-13); L-Lysyl-L-prolyl-L-valine;
IUPAC/Chemical Name
L-Valine, N-(1-L-lysyl-L-prolyl)-
InChi Key
YSPZCHGIWAQVKQ-AVGNSLFASA-N
InChi Code
InChI=1S/C16H30N4O4/c1-10(2)13(16(23)24)19-14(21)12-7-5-9-20(12)15(22)11(18)6-3-4-8-17/h10-13H,3-9,17-18H2,1-2H3,(H,19,21)(H,23,24)/t11-,12-,13-/m0/s1
SMILES Code
CC(C)[C@@H](C(O)=O)NC([C@H]1N(C([C@H](CCCCN)N)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 342.44 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: Song DH, Jo YH, Ahn JH, Kim SB, Yun CY, Kim Y, Hwang BY, Lee MK. Sesquiterpenes from fruits of Torilis japonica with inhibitory activity on melanin synthesis in B16 cells. J Nat Med. 2018 Jan;72(1):155-160. doi: 10.1007/s11418-017-1123-4. Epub 2017 Aug 19. PubMed PMID: 28823078. 2: Xiao B, Xu Z, Viennois E, Zhang Y, Zhang Z, Zhang M, Han MK, Kang Y, Merlin D. Orally Targeted Delivery of Tripeptide KPV via Hyaluronic Acid-Functionalized Nanoparticles Efficiently Alleviates Ulcerative Colitis. Mol Ther. 2017 Jul 5;25(7):1628-1640. doi: 10.1016/j.ymthe.2016.11.020. Epub 2017 Jan 28. PubMed PMID: 28143741; PubMed Central PMCID: PMC5498804. 3: Schaible EV, Steinsträßer A, Jahn-Eimermacher A, Luh C, Sebastiani A, Kornes F, Pieter D, Schäfer MK, Engelhard K, Thal SC. Single administration of tripeptide α-MSH(11-13) attenuates brain damage by reduced inflammation and apoptosis after experimental traumatic brain injury in mice. PLoS One. 2013 Aug 5;8(8):e71056. doi: 10.1371/journal.pone.0071056. Print 2013. PubMed PMID: 23940690; PubMed Central PMCID: PMC3733710. 4: Singh M, Mukhopadhyay K. C-terminal amino acids of alpha-melanocyte-stimulating hormone are requisite for its antibacterial activity against Staphylococcus aureus. Antimicrob Agents Chemother. 2011 May;55(5):1920-9. doi: 10.1128/AAC.00957-10. Epub 2011 Jan 31. PubMed PMID: 21282427; PubMed Central PMCID: PMC3088230. 5: Laroui H, Dalmasso G, Nguyen HT, Yan Y, Sitaraman SV, Merlin D. Drug-loaded nanoparticles targeted to the colon with polysaccharide hydrogel reduce colitis in a mouse model. Gastroenterology. 2010 Mar;138(3):843-53.e1-2. doi: 10.1053/j.gastro.2009.11.003. Epub 2009 Nov 10. PubMed PMID: 19909746. 6: Wallingford N, Perroud B, Gao Q, Coppola A, Gyengesi E, Liu ZW, Gao XB, Diament A, Haus KA, Shariat-Madar Z, Mahdi F, Wardlaw SL, Schmaier AH, Warden CH, Diano S. Prolylcarboxypeptidase regulates food intake by inactivating alpha-MSH in rodents. J Clin Invest. 2009 Aug;119(8):2291-303. doi: 10.1172/JCI37209. Epub 2009 Jul 20. PubMed PMID: 19620781; PubMed Central PMCID: PMC2719925. 7: Charnley M, Moir AJ, Douglas CW, Haycock JW. Anti-microbial action of melanocortin peptides and identification of a novel X-Pro-D/L-Val sequence in Gram-positive and Gram-negative bacteria. Peptides. 2008 Jun;29(6):1004-9. doi: 10.1016/j.peptides.2008.02.004. Epub 2008 Feb 15. PubMed PMID: 18355945. 8: Kannengiesser K, Maaser C, Heidemann J, Luegering A, Ross M, Brzoska T, Bohm M, Luger TA, Domschke W, Kucharzik T. Melanocortin-derived tripeptide KPV has anti-inflammatory potential in murine models of inflammatory bowel disease. Inflamm Bowel Dis. 2008 Mar;14(3):324-31. PubMed PMID: 18092346. 9: Dalmasso G, Charrier-Hisamuddin L, Nguyen HT, Yan Y, Sitaraman S, Merlin D. PepT1-mediated tripeptide KPV uptake reduces intestinal inflammation. Gastroenterology. 2008 Jan;134(1):166-78. Epub 2007 Oct 17. PubMed PMID: 18061177; PubMed Central PMCID: PMC2431115. 10: Carotenuto A, Saviello MR, Auriemma L, Campiglia P, Catania A, Novellino E, Grieco P. Structure-function relationships and conformational properties of alpha-MSH(6-13) analogues with candidacidal activity. Chem Biol Drug Des. 2007 Jan;69(1):68-74. PubMed PMID: 17313459. 11: Bonfiglio V, Camillieri G, Avitabile T, Leggio GM, Drago F. Effects of the COOH-terminal tripeptide alpha-MSH(11-13) on corneal epithelial wound healing: role of nitric oxide. Exp Eye Res. 2006 Dec;83(6):1366-72. Epub 2006 Sep 11. PubMed PMID: 16965771. 12: Elliott RJ, Szabo M, Wagner MJ, Kemp EH, MacNeil S, Haycock JW. alpha-Melanocyte-stimulating hormone, MSH 11-13 KPV and adrenocorticotropic hormone signalling in human keratinocyte cells. J Invest Dermatol. 2004 Apr;122(4):1010-9. PubMed PMID: 15102092. 13: Cantón I, Eves PC, Szabo M, Vidal-Vanaclocha F, Sisley K, Rennie IG, Haycock JW, MacNeil S. Tumor necrosis factor alpha increases and alpha-melanocyte-stimulating hormone reduces uveal melanoma invasion through fibronectin. J Invest Dermatol. 2003 Sep;121(3):557-63. PubMed PMID: 12925215. 14: Muceniece R, Krigere L, Süli-Vargha H, Wikberg JE. Effects of alpha-melanotropin C-terminal tripeptide analogues on macrophage NO production. Peptides. 2003 May;24(5):701-7. PubMed PMID: 12895656. 15: Luger TA, Scholzen TE, Brzoska T, Böhm M. New insights into the functions of alpha-MSH and related peptides in the immune system. Ann N Y Acad Sci. 2003 Jun;994:133-40. Review. PubMed PMID: 12851308. 16: Getting SJ, Schiöth HB, Perretti M. Dissection of the anti-inflammatory effect of the core and C-terminal (KPV) alpha-melanocyte-stimulating hormone peptides. J Pharmacol Exp Ther. 2003 Aug;306(2):631-7. Epub 2003 May 15. PubMed PMID: 12750433. 17: Grieco P, Rossi C, Colombo G, Gatti S, Novellino E, Lipton JM, Catania A. Novel alpha-melanocyte stimulating hormone peptide analogues with high candidacidal activity. J Med Chem. 2003 Feb 27;46(5):850-5. PubMed PMID: 12593664. 18: Chavatte P, Yous S, Lesieur D, Hénichart JP. Conformational analysis of tripeptide Ac-Lys-Pro-Val-NH2, COOH-terminal sequence of alpha-MSH. J Pharm Pharmacol. 2001 Jul;53(7):949-53. PubMed PMID: 11480545. 19: Ichiyama T, Sato S, Okada K, Catania A, Lipton JM. The neuroimmunomodulatory peptide alpha-MSH. Ann N Y Acad Sci. 2000;917:221-6. Review. PubMed PMID: 11268347. 20: Haddad JJ, Lauterbach R, Saadé NE, Safieh-Garabedian B, Land SC. Alpha-melanocyte-related tripeptide, Lys-d-Pro-Val, ameliorates endotoxin-induced nuclear factor kappaB translocation and activation: evidence for involvement of an interleukin-1beta193-195 receptor antagonism in the alveolar epithelium. Biochem J. 2001 Apr 1;355(Pt 1):29-38. 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