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MedKoo Cat#: 597853 | Name: Probestin

Description:

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

Probestin is an inhibitor of aminopeptidase M; from Streptomyces azureus MH663-2F6.

Chemical Structure

Probestin
CAS#123652-87-9

Theoretical Analysis

MedKoo Cat#: 597853

Name: Probestin

CAS#: 123652-87-9

Chemical Formula: C26H38N4O6

Exact Mass: 502.2791

Molecular Weight: 502.61

Elemental Analysis: C, 62.13; H, 7.62; N, 11.15; O, 19.10

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 #
No Data
Synonym
Probestin;
IUPAC/Chemical Name
((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)-L-leucyl-L-prolyl-L-proline
InChi Key
CEQMEILRVSCKGT-FXTUREPZSA-N
InChi Code
InChI=1S/C26H38N4O6/c1-16(2)14-19(28-23(32)22(31)18(27)15-17-8-4-3-5-9-17)24(33)29-12-6-10-20(29)25(34)30-13-7-11-21(30)26(35)36/h3-5,8-9,16,18-22,31H,6-7,10-15,27H2,1-2H3,(H,28,32)(H,35,36)/t18-,19+,20+,21+,22+/m1/s1
SMILES Code
O=C(O)[C@H]1N(C([C@H]2N(C([C@H](CC(C)C)NC([C@@H](O)[C@H](N)CC3=CC=CC=C3)=O)=O)CCC2)=O)CCC1
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 502.61 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: Pathuri G, Hedrick AF, Awasthi V, Ihnat MA, Gali H. Evaluation of 99mTc-probestin for imaging APN expressing tumors by SPECT. Bioorg Med Chem Lett. 2013 Sep 15;23(18):5049-52. doi: 10.1016/j.bmcl.2013.07.046. Epub 2013 Jul 29. PubMed PMID: 23937983. 2: Pathuri G, Madka V, Hedrick AF, Lightfoot SA, Awasthi V, Cowley BD Jr, Rao CV, Gali H. Evaluation of (99m)Tc-probestin SPECT as a novel technique for noninvasive imaging of kidney aminopeptidase N expression. Mol Pharm. 2014 Aug 4;11(8):2948-53. doi: 10.1021/mp5002872. Epub 2014 Jul 10. PubMed PMID: 24988047; PubMed Central PMCID: PMC4144757. 3: Pathuri G, Thorpe JE, Disch BC, Bailey-Downs LC, Ihnat MA, Gali H. Solid phase synthesis and biological evaluation of probestin as an angiogenesis inhibitor. Bioorg Med Chem Lett. 2013 Jun 15;23(12):3561-4. doi: 10.1016/j.bmcl.2013.04.031. Epub 2013 Apr 23. PubMed PMID: 23664876. 4: Pathuri G, Hedrick AF, Disch BC, Doan JT, Ihnat MA, Awasthi V, Gali H. Synthesis and evaluation of novel Tc-99m labeled probestin conjugates for imaging APN/CD13 expression in vivo. Bioconjug Chem. 2012 Jan 18;23(1):115-24. doi: 10.1021/bc200546b. Epub 2011 Dec 20. PubMed PMID: 22148582; PubMed Central PMCID: PMC3261373. 5: Aoyagi T, Yoshida S, Nakamura Y, Shigihara Y, Hamada M, Takeuchi T. Probestin, a new inhibitor of aminopeptidase M, produced by Streptomyces azureus MH663-2F6. I. Taxonomy, production, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 1990 Feb;43(2):143-8. PubMed PMID: 1968900. 6: Yoshida S, Nakamura Y, Naganawa H, Aoyagi T, Takeuchi T. Probestin, a new inhibitor of aminopeptidase M, produced by Streptomyces azureus MH663-2F6. II. Structure determination of probestin. J Antibiot (Tokyo). 1990 Feb;43(2):149-53. PubMed PMID: 1968901. 7: Leung K. (99m)TcO-N,N-Dimethylglycyl-l-lysinyl-l-cysteinylamide-8-amino-3,6-dioxaoctanoic- probestin. 2012 Jan 15 [updated 2012 Apr 12]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK91527/ PubMed PMID: 22514807. 8: Herranz R, Vinuesa S, Pérez C, García-López MT, De Ceballos ML, Murillo FM, del Río J. Aminopeptidase inhibitory properties and analgesic activity of (2S,3R)-3,7-diamino-2-hydroxy-heptanoic acid containing tripeptide analogues of the N-terminal tripeptide of probestin. Arch Pharm (Weinheim). 1992 Aug;325(8):515-8. PubMed PMID: 1417460. 9: Pathuri G, Hedrick AF, Disch BC, Ihnat MA, Awasthi V, Gali H. Synthesis and biodistribution studies of technetium-99m-labeled aminopeptidase N inhibitor conjugates. Bioorg Med Chem Lett. 2012 Jul 15;22(14):4567-70. doi: 10.1016/j.bmcl.2012.05.106. Epub 2012 Jun 6. PubMed PMID: 22727671. 10: Lendeckel U, Kähne T, Arndt M, Frank K, Ansorge S. Inhibition of alanyl aminopeptidase induces MAP-kinase p42/ERK2 in the human T cell line KARPAS-299. Biochem Biophys Res Commun. 1998 Nov 9;252(1):5-9. PubMed PMID: 9813136. 11: Kunz D, Bühling F, Hütter HJ, Aoyagi T, Ansorge S. Aminopeptidase N (CD13, EC 3.3.4.11.2) occurs on the surface of resting and concanavalin A-stimulated lymphocytes. Biol Chem Hoppe Seyler. 1993 Apr;374(4):291-6. PubMed PMID: 8101091. 12: Lendeckel U, Wex T, Reinhold D, Kähne T, Frank K, Faust J, Neubert K, Ansorge S. Induction of the membrane alanyl aminopeptidase gene and surface expression in human T-cells by mitogenic activation. Biochem J. 1996 Nov 1;319 ( Pt 3):817-21. PubMed PMID: 8920985; PubMed Central PMCID: PMC1217861. 13: Kocha T, Ohtsuka E, Funahashi T, Fukuda T, Aoyagi T, Wanda T, Takeuchi T. Suppression of splenic enzyme activities by administration of aminopeptidase N (CD13) inhibitors: relationship between actions in vivo and in vitro. J Enzyme Inhib. 1994;8(3):187-95. PubMed PMID: 7539487. 14: Ansorge S, Schön E, Kunz D. Membrane-bound peptidases of lymphocytes: functional implications. Biomed Biochim Acta. 1991;50(4-6):799-807. PubMed PMID: 1686972. 15: Abramić M, Schleuder D, Dolovcak L, Schröder W, Strupat K, Sagi D, Peter-Katalini J, Vitale L. Human and rat dipeptidyl peptidase III: biochemical and mass spectrometric arguments for similarities and differences. Biol Chem. 2000 Dec;381(12):1233-43. PubMed PMID: 11209758. 16: Nishimura K, Ueki M, Kaneto H, Hazato T. [Study of a new endogenous inhibitor of enkephalin-degrading enzymes; pharmacological function and metabolism of spinorphin]. Masui. 1993 Nov;42(11):1663-70. Japanese. PubMed PMID: 8267798. 17: Yanagisawa J, Tsuda M, Ohkubo T, Hiyoshi M, Kamiguchi H, Tsukamoto H, Yamamura M, Kocha T, Aoyagi T. A new type of major aminopeptidase in bovine brain. Biochem Mol Med. 1996 Dec;59(2):161-8. PubMed PMID: 8986639. 18: Tieku S, Hooper NM. Inhibition of aminopeptidases N, A and W. A re-evaluation of the actions of bestatin and inhibitors of angiotensin converting enzyme. Biochem Pharmacol. 1992 Nov 3;44(9):1725-30. PubMed PMID: 1360211. 19: Navarrete Santos A, Langner J, Riemann D. Enzymatic activity is not a precondition for the intracellular calcium increase mediated by mAbs specific for aminopeptidase N/CD13. Adv Exp Med Biol. 2000;477:43-7. PubMed PMID: 10849729. 20: Aoyagi T, Yoshida S, Matsuda N, Ikeda T, Hamada M, Takeuchi T. Leuhistin, a new inhibitor of aminopeptidase M, produced by Bacillus laterosporus BMI156-14F1. I. Taxonomy, production, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 1991 Jun;44(6):573-8. PubMed PMID: 1676997.