ABT-510 acetate | CAS#442526-87-6 | thrombospondin analog

MedKoo Cat#: 597843 | Name: ABT-510 acetate

Description:

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

ABT-510 acetate is a synthetic analog of thrombospondin, an endogenous angiogenesis inhibitor.

Chemical Structure

ABT-510 acetate

CAS#442526-87-6 (acetate)

Theoretical Analysis

MedKoo Cat#: 597843

Name: ABT-510 acetate

CAS#: 442526-87-6 (acetate)

Chemical Formula: C48H87N13O13

Exact Mass:

Molecular Weight: 1054.30

Elemental Analysis: C, 54.68; H, 8.32; N, 17.27; O, 19.73

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 #

251579-55-2 (free base) 442526-87-6 (acetate)

Synonym

ABT-510 acetate; ABT 510 acetate; ABT510 acetate;

IUPAC/Chemical Name

(S)-N-ethyl-1-(((S)-2-((2S,3R)-3-hydroxy-2-((2R,3S)-3-methyl-2-((S)-3-methyl-2-(2-(2-(N-methylacetamido)acetamido)acetamido)butanamido)pentanamido)butanamido)pentanoyl)-L-isoleucyl-L-arginyl)pyrrolidine-2-carboxamide acetate

InChi Key

VNYUZURIJSGETB-WVDYPPGZSA-N

InChi Code

InChI=1S/C46H83N13O11.C2H4O2/c1-12-18-30(39(64)55-36(26(7)13-2)42(67)53-31(19-16-21-50-46(47)48)45(70)59-22-17-20-32(59)40(65)49-15-4)52-44(69)38(28(9)60)57-43(68)37(27(8)14-3)56-41(66)35(25(5)6)54-33(62)23-51-34(63)24-58(11)29(10)61;1-2(3)4/h25-28,30-32,35-38,60H,12-24H2,1-11H3,(H,49,65)(H,51,63)(H,52,69)(H,53,67)(H,54,62)(H,55,64)(H,56,66)(H,57,68)(H4,47,48,50);1H3,(H,3,4)/t26-,27-,28+,30-,31-,32-,35-,36-,37+,38-;/m0./s1

SMILES Code

O=C(NCC)[C@H]1N(C([C@H](CCCNC(N)=N)NC([C@H]([C@@H](C)CC)NC([C@H](CCC)NC([C@H]([C@H](O)C)NC([C@@H]([C@@H](C)CC)NC([C@H](C(C)C)NC(CNC(CN(C(C)=O)C)=O)=O)=O)=O)=O)=O)=O)=O)CCC1.CC(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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,054.30 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.

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: Uronis HE, Cushman SM, Bendell JC, Blobe GC, Morse MA, Nixon AB, Dellinger A, Starr MD, Li H, Meadows K, Gockerman J, Pang H, Hurwitz HI. A phase I study of ABT-510 plus bevacizumab in advanced solid tumors. Cancer Med. 2013 Jun;2(3):316-24. doi: 10.1002/cam4.65. Epub 2013 Mar 21. PubMed PMID: 23930208; PubMed Central PMCID: PMC3699843. 2: Matsumoto E, Fujita Y, Okada Y, Kauppinen EI, Kamiya H, Chiba K. Hydrophobic benzyl amines as supports for liquid-phase C-terminal amidated peptide synthesis: application to the preparation of ABT-510. J Pept Sci. 2015 Sep;21(9):691-5. doi: 10.1002/psc.2791. Epub 2015 Jul 22. PubMed PMID: 26200065. 3: Recouvreux MV, Camilletti MA, Rifkin DB, Becu-Villalobos D, Díaz-Torga G. Thrombospondin-1 (TSP-1) analogs ABT-510 and ABT-898 inhibit prolactinoma growth and recover active pituitary transforming growth factor-β1 (TGF-β1). Endocrinology. 2012 Aug;153(8):3861-71. doi: 10.1210/en.2012-1007. Epub 2012 Jun 14. PubMed PMID: 22700773; PubMed Central PMCID: PMC3404347. 4: Sahora AI, Rusk AW, Henkin J, McKeegan EM, Shi Y, Khanna C. Prospective study of thrombospondin-1 mimetic peptides, ABT-510 and ABT-898, in dogs with soft tissue sarcoma. J Vet Intern Med. 2012 Sep-Oct;26(5):1169-76. doi: 10.1111/j.1939-1676.2012.00966.x. Epub 2012 Jul 21. PubMed PMID: 22816494. 5: Ebbinghaus S, Hussain M, Tannir N, Gordon M, Desai AA, Knight RA, Humerickhouse RA, Qian J, Gordon GB, Figlin R. Phase 2 study of ABT-510 in patients with previously untreated advanced renal cell carcinoma. Clin Cancer Res. 2007 Nov 15;13(22 Pt 1):6689-95. PubMed PMID: 18006769. 6: Markovic SN, Suman VJ, Rao RA, Ingle JN, Kaur JS, Erickson LA, Pitot HC, Croghan GA, McWilliams RR, Merchan J, Kottschade LA, Nevala WK, Uhl CB, Allred J, Creagan ET. A phase II study of ABT-510 (thrombospondin-1 analog) for the treatment of metastatic melanoma. Am J Clin Oncol. 2007 Jun;30(3):303-9. PubMed PMID: 17551310. 7: Campbell NE, Greenaway J, Henkin J, Moorehead RA, Petrik J. The thrombospondin-1 mimetic ABT-510 increases the uptake and effectiveness of cisplatin and paclitaxel in a mouse model of epithelial ovarian cancer. Neoplasia. 2010 Mar;12(3):275-83. PubMed PMID: 20234821; PubMed Central PMCID: PMC2838444. 8: Nabors LB, Fiveash JB, Markert JM, Kekan MS, Gillespie GY, Huang Z, Johnson MJ, Meleth S, Kuo H, Gladson CL, Fathallah-Shaykh HM. A phase 1 trial of ABT-510 concurrent with standard chemoradiation for patients with newly diagnosed glioblastoma. Arch Neurol. 2010 Mar;67(3):313-9. doi: 10.1001/archneurol.2010.16. PubMed PMID: 20212229. 9: Rusk A, McKeegan E, Haviv F, Majest S, Henkin J, Khanna C. Preclinical evaluation of antiangiogenic thrombospondin-1 peptide mimetics, ABT-526 and ABT-510, in companion dogs with naturally occurring cancers. Clin Cancer Res. 2006 Dec 15;12(24):7444-55. PubMed PMID: 17189418. 10: Hoekstra R, de Vos FY, Eskens FA, de Vries EG, Uges DR, Knight R, Carr RA, Humerickhouse R, Verweij J, Gietema JA. Phase I study of the thrombospondin-1-mimetic angiogenesis inhibitor ABT-510 with 5-fluorouracil and leucovorin: a safe combination. Eur J Cancer. 2006 Mar;42(4):467-72. Epub 2006 Jan 10. PubMed PMID: 16406507. 11: Yang Q, Tian Y, Liu S, Zeine R, Chlenski A, Salwen HR, Henkin J, Cohn SL. Thrombospondin-1 peptide ABT-510 combined with valproic acid is an effective antiangiogenesis strategy in neuroblastoma. Cancer Res. 2007 Feb 15;67(4):1716-24. PubMed PMID: 17308113. 12: Hasina R, Martin LE, Kasza K, Jones CL, Jalil A, Lingen MW. ABT-510 is an effective chemopreventive agent in the mouse 4-nitroquinoline 1-oxide model of oral carcinogenesis. Cancer Prev Res (Phila). 2009 Apr;2(4):385-93. doi: 10.1158/1940-6207.CAPR-08-0211. Epub 2009 Mar 31. PubMed PMID: 19336725; PubMed Central PMCID: PMC2702843. 13: Greenaway J, Henkin J, Lawler J, Moorehead R, Petrik J. ABT-510 induces tumor cell apoptosis and inhibits ovarian tumor growth in an orthotopic, syngeneic model of epithelial ovarian cancer. Mol Cancer Ther. 2009 Jan;8(1):64-74. doi: 10.1158/1535-7163.MCT-08-0864. PubMed PMID: 19139114; PubMed Central PMCID: PMC3383797. 14: Isenberg JS, Yu C, Roberts DD. Differential effects of ABT-510 and a CD36-binding peptide derived from the type 1 repeats of thrombospondin-1 on fatty acid uptake, nitric oxide signaling, and caspase activation in vascular cells. Biochem Pharmacol. 2008 Feb 15;75(4):875-82. Epub 2007 Nov 1. PubMed PMID: 18068687; PubMed Central PMCID: PMC2267764. 15: Westphal JR. Technology evaluation: ABT-510, Abbott. Curr Opin Mol Ther. 2004 Aug;6(4):451-7. PubMed PMID: 15468604. 16: Yap R, Veliceasa D, Emmenegger U, Kerbel RS, McKay LM, Henkin J, Volpert OV. Metronomic low-dose chemotherapy boosts CD95-dependent antiangiogenic effect of the thrombospondin peptide ABT-510: a complementation antiangiogenic strategy. Clin Cancer Res. 2005 Sep 15;11(18):6678-85. PubMed PMID: 16166447. 17: Baker LH, Rowinsky EK, Mendelson D, Humerickhouse RA, Knight RA, Qian J, Carr RA, Gordon GB, Demetri GD. Randomized, phase II study of the thrombospondin-1-mimetic angiogenesis inhibitor ABT-510 in patients with advanced soft tissue sarcoma. J Clin Oncol. 2008 Dec 1;26(34):5583-8. doi: 10.1200/JCO.2008.17.4706. Epub 2008 Nov 3. PubMed PMID: 18981463. 18: Anderson JC, Grammer JR, Wang W, Nabors LB, Henkin J, Stewart JE Jr, Gladson CL. ABT-510, a modified type 1 repeat peptide of thrombospondin, inhibits malignant glioma growth in vivo by inhibiting angiogenesis. Cancer Biol Ther. 2007 Mar;6(3):454-62. Epub 2007 Mar 26. PubMed PMID: 17384534. 19: Tolle JC, Becker CL, Califano JC, Chang JL, Gernhardt K, Napier JJ, Wittenberger SJ, Yuan J. Impurity rejection in the crystallization of ABT-510 as a method to establish starting material specifications. Adv Exp Med Biol. 2009;611:595-6. PubMed PMID: 19400326. 20: Sheikh AY, Pal A, Viswanath S, Tolle JC. Agglomerative crystallization of ABT-510 in a partially miscible solvent system. J Pharm Sci. 2008 Mar;97(3):1202-12. PubMed PMID: 17683060.