Tyroserleutide

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

MedKoo CAT#: 205931

CAS#: 138168-48-6

Description: Tyroserleutide is a tripeptide consisting of tyrosine, serine, and leucine with potential antineoplastic activity. Although the mechanism of its antitumor activity has yet to be fully elucidated, tyroserleutide appears to inhibit the expression of ICAM-1 (CD54), a cell adhesion factor of the immunoglobulin (Ig) superfamily that plays an important role in the invasion, adhesion, and metastasis of tumor cells. In addition, this agent may influence the Ca2+/calmodulin pathway, inhibiting phosphatidylinositol 3 kinase (PI3K); PI3K is upregulated in tumor cells and is involved in cellular proliferation.


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Tyroserleutide is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205931
Name: Tyroserleutide
CAS#: 138168-48-6
Chemical Formula: C18H27N3O6
Exact Mass: 381.18999
Molecular Weight: 381.42
Elemental Analysis: C, 56.68; H, 7.13; N, 11.02; O, 25.17


Synonym: Tyroserleutide; YSL; CMS 024. HTyrSerLeuOH.

IUPAC/Chemical Name: (S)-2-((S)-2-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)-3-hydroxypropanamido)-4-methylpentanoic acid

InChi Key: MQGGXGKQSVEQHR-KKUMJFAQSA-N

InChi Code: InChI=1S/C18H27N3O6/c1-10(2)7-14(18(26)27)20-17(25)15(9-22)21-16(24)13(19)8-11-3-5-12(23)6-4-11/h3-6,10,13-15,22-23H,7-9,19H2,1-2H3,(H,20,25)(H,21,24)(H,26,27)/t13-,14-,15-/m0/s1

SMILES Code: CC(C)C[C@H](NC([C@@H](NC([C@@H](N)CC1=CC=C(O)C=C1)=O)CO)=O)C(O)=O


Technical Data

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, not soluble in water.

Shelf Life:
>5 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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Jian X, Fu Z, Zhang Y, Che X, Lu R, Yao Z. Subcellular location of antitumor tripeptide-tyroserleutide in human hepatocellular carcinoma cells. Exp Ther Med. 2012 Feb;3(2):195-199. Epub 2011 Dec 1. PubMed PMID: 22969868; PubMed Central PMCID: PMC3438698.

2: Wang HY, Yi WJ, Qin SY, Li C, Zhuo RX, Zhang XZ. Tyroserleutide-based gene vector for suppressing VEGF expression in cancer therapy. Biomaterials. 2012 Nov;33(33):8685-94. doi: 10.1016/j.biomaterials.2012.08.022. Epub 2012 Aug 24. PubMed PMID: 22925816.

3: Xiao ZY, Jia JB, Chen L, Zou W, Chen XP. Phase I clinical trial of continuous infusion of tyroserleutide in patients with advanced hepatocellular carcinoma. Med Oncol. 2012 Sep;29(3):1850-8. doi: 10.1007/s12032-011-0081-z. Epub 2011 Oct 11. PubMed PMID: 21987077.

4: Jia JB, Wang WQ, Sun HC, Liu L, Zhu XD, Kong LQ, Chai ZT, Zhang W, Zhang JB, Xu HX, Zeng ZC, Wu WZ, Wang L, Tang ZY. A novel tripeptide, tyroserleutide, inhibits irradiation-induced invasiveness and metastasis of hepatocellular carcinoma in nude mice. Invest New Drugs. 2011 Oct;29(5):861-72. doi: 10.1007/s10637-010-9435-1. Epub 2010 Apr 23. PubMed PMID: 20414698.

5: Wang C, Wang S, Lu R, Zhao L, Zhu ZF, Xu Q, Lv JQ, Wang LL, Fu Z, Lin G, Yao Z. Effects of a novel tripeptide, tyroserleutide (YSL), on cell cycle progression of human hepatocellular carcinoma. Anticancer Drugs. 2009 Aug;20(7):534-42. doi: 10.1097/CAD.0b013e32832ced93. PubMed PMID: 19491661.

6: Zhu ZF, Chen LJ, Lu R, Jia J, Liang Y, Xu Q, Zhou CL, Wang L, Wang S, Yao Z. Tripeptide tyroserleutide plus doxorubicin: therapeutic synergy and side effect attenuation. BMC Cancer. 2008 Nov 25;8:342. doi: 10.1186/1471-2407-8-342. PubMed PMID: 19025669; PubMed Central PMCID: PMC2601048.

7: Li XL, Liu JY, Lu R, Xu Q, Zhu ZF, Wang L, Zhou CL, Jia J, Fu Z, Yao Z. Evaluation of the therapeutic efficacy of tripeptide tyroserleutide (YSL) for human hepatocarcinoma by in vivo hollow fiber assay. Invest New Drugs. 2008 Dec;26(6):525-9. doi: 10.1007/s10637-008-9121-8. Epub 2008 Feb 9. PubMed PMID: 18264678.

8: Li PC, Li Y, Tang ZY, Wang L, Lu R, Xue Q. Study on the inhibitory effect of tyroserleutide on tumor growth and metastasis in nude mice model of human hepatocellular carcinoma metastasis. Hepatogastroenterology. 2007 Jul-Aug;54(77):1359-63. PubMed PMID: 17708254.

9: Zhao L, Zhao Q, Lu R, Fu Z, Zhu Z, Jia J, Wang S, Shi L, Jian X, Yao Z. Effects of tyroserleutide on gene expression of calmodulin and PI3K in hepatocellular carcinoma. J Cell Biochem. 2008 Feb 1;103(2):471-8. PubMed PMID: 17546603.

10: Yao Z, Che XC, Lu R, Zheng MN, Zhu ZF, Li JP, Jian X, Shi LX, Liu JY, Gao WY. Inhibition by tyroserleutide (YSL) on the invasion and adhesion of the mouse melanoma cell. Mol Med. 2007 Jan-Feb;13(1-2):14-21. PubMed PMID: 17515953; PubMed Central PMCID: PMC1869621.

11: Fu Z, Lu R, Li G, Zhao L, Gao W, Che X, Jian X, Zhou C, Yao Z. Tyroserleutide tripeptide affects calcium homeostasis of human hepatocarcinoma BEL-7402 cells. Sci China C Life Sci. 2005 Oct;48(5):523-30. PubMed PMID: 16315604.

12: Yao Z, Lu R, Jia J, Zhao P, Yang J, Zheng M, Lu J, Jin M, Yang H, Gao W. The effect of tripeptide tyroserleutide (YSL) on animal models of hepatocarcinoma. Peptides. 2006 Jun;27(6):1167-72. Epub 2005 Aug 29. PubMed PMID: 16129512.

13: Yao Z, Qiu S, Wang L, Lu R, Zhou CL, Zhao PP, Li HQ, Gao WY. Tripeptide tyroserleutide enhances the antitumor effects of macrophages and stimulates macrophage secretion of IL-1beta, TNF-alpha, and NO in vitro. Cancer Immunol Immunother. 2006 Jan;55(1):56-60. Epub 2005 Oct 27. PubMed PMID: 16091933.

14: Lu R, Jia J, Bao L, Fu Z, Li G, Wang S, Wang Z, Jin M, Gao W, Yao Z. Experimental study of the inhibition of human hepatocarcinoma Bel7402 cells by the tripeptide tyroserleutide(YSL). Cancer Chemother Pharmacol. 2006 Jan;57(2):248-56. Epub 2005 Jul 19. PubMed PMID: 16028100.

15: Ding W, Zhang J, Yao Z, Lu R, Wu D, Li G, Shen Z, Sun Y, Lin G, Wang C, Zhao M, Peng S. The synthesis, distribution, and anti-hepatic cancer activity of YSL. Bioorg Med Chem. 2004 Sep 15;12(18):4989-94. PubMed PMID: 15336278.

16: Wang C, Ding W, Zhao M, Lin G, Peng S. Studies on the large scale synthesis and anti-tumor activity of YSL. Prep Biochem Biotechnol. 2003 Aug;33(3):189-95. PubMed PMID: 12916810.