Msh (11-13)

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

MedKoo CAT#: 530703

CAS#: 67727-97-3

Description: Msh (11-13) is a bioactive chemical.


Chemical Structure

img
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 not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Msh (11-13)

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

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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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. PubMed PMID: 11256945; PubMed Central
PMCID: PMC1221708.