ABT-510

• CAT Number: I000872
• CAS Number: 251579-55-2
• Molecular Formula: C46H83N13O11
• Molecular Weight: 994.25
• Purity: ≥95%
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4°Cfor short term (days to weeks), or -20 °C for long term (months).
• IUPAC Name: (2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2R,3S)-2-[[(2S)-2-[[2-[[2-[acetyl(methyl)amino]acetyl]amino]acetyl]amino]-3-methylbutanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]pentanoyl]amino]-3-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]-N-ethylpyrrolidine-2-carboxamide
• InChI: InChI=1S/C46H83N13O11/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/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)/t26-,27-,28+,30-,31-,32-,35-,36-,37+,38-/m0/s1
• InChIKey: RIWLPSIAFBLILR-WVNGMBSFSA-N
• SMILES: CCCC(C(=O)NC(C(C)CC)C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC)NC(=O)C(C(C)O)NC(=O)C(C(C)CC)NC(=O)C(C(C)C)NC(=O)CNC(=O)CN(C)C(=O)C

ABT-510 (Cat.No:I000872) is synthetic peptide that mimics the anti-angiogenic activity of the endogenous protein thrombospondin-1 (TSP-1). ABT-510 inhibits the actions of several pro-angiogenic growth factors important to tumor neovascularization; these pro-angiogenic growth factors include vascular endothelial growth factor (VEGF), basic fibroblast growth factor (bFGF)), hepatocyte growth factor (HGF), and interleukin 8 (IL-8).

Reference

1:Hydrophobic benzyl amines as supports for liquid-phase C-terminal amidated peptide synthesis: application to the preparation of ABT-510. Matsumoto E, Fujita Y, Okada Y, Kauppinen EI, Kamiya H, Chiba K.J Pept Sci. 2015 Sep;21(9):691-5. doi: 10.1002/psc.2791. Epub 2015 Jul 22. PMID: 26200065 2:A phase I study of ABT-510 plus bevacizumab in advanced solid tumors. 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.Cancer Med. 2013 Jun;2(3):316-24. doi: 10.1002/cam4.65. Epub 2013 Mar 21. PMID: 23930208 Free PMC Article3:Prospective study of thrombospondin-1 mimetic peptides, ABT-510 and ABT-898, in dogs with soft tissue sarcoma. Sahora AI, Rusk AW, Henkin J, McKeegan EM, Shi Y, Khanna C.J Vet Intern Med. 2012 Sep-Oct;26(5):1169-76. doi: 10.1111/j.1939-1676.2012.00966.x. Epub 2012 Jul 21. PMID: 22816494 Free Article4:Thrombospondin-1 (TSP-1) analogs ABT-510 and ABT-898 inhibit prolactinoma growth and recover active pituitary transforming growth factor-β1 (TGF-β1). Recouvreux MV, Camilletti MA, Rifkin DB, Becu-Villalobos D, Díaz-Torga G.Endocrinology. 2012 Aug;153(8):3861-71. doi: 10.1210/en.2012-1007. Epub 2012 Jun 14. PMID: 22700773 Free PMC Article5:The thrombospondin-1 mimetic ABT-510 increases the uptake and effectiveness of cisplatin and paclitaxel in a mouse model of epithelial ovarian cancer. Campbell NE, Greenaway J, Henkin J, Moorehead RA, Petrik J.Neoplasia. 2010 Mar;12(3):275-83. PMID: 20234821 Free PMC Article6:A phase 1 trial of ABT-510 concurrent with standard chemoradiation for patients with newly diagnosed glioblastoma. Nabors LB, Fiveash JB, Markert JM, Kekan MS, Gillespie GY, Huang Z, Johnson MJ, Meleth S, Kuo H, Gladson CL, Fathallah-Shaykh HM.Arch Neurol. 2010 Mar;67(3):313-9. doi: 10.1001/archneurol.2010.16. PMID: 20212229 7:Impurity rejection in the crystallization of ABT-510 as a method to establish starting material specifications. Tolle JC, Becker CL, Califano JC, Chang JL, Gernhardt K, Napier JJ, Wittenberger SJ, Yuan J.Adv Exp Med Biol. 2009;611:595-6. PMID: 19400326 8:Evolution of the synthetic process to prepare the tripeptide segment of ABT-510. Becker CL, Califano JC, Tolle JC, Napier JJ, Kolaczkowski L, Chang SJ, Tian Z, Manna S.Adv Exp Med Biol. 2009;611:575-6. No abstract available. PMID: 19400320 9:ABT-510 is an effective chemopreventive agent in the mouse 4-nitroquinoline 1-oxide model of oral carcinogenesis. Hasina R, Martin LE, Kasza K, Jones CL, Jalil A, Lingen MW.Cancer Prev Res (Phila). 2009 Apr;2(4):385-93. doi: 10.1158/1940-6207.CAPR-08-0211. Epub 2009 Mar 31. PMID: 19336725 Free PMC Article10:ABT-510 induces tumor cell apoptosis and inhibits ovarian tumor growth in an orthotopic, syngeneic model of epithelial ovarian cancer. Greenaway J, Henkin J, Lawler J, Moorehead R, Petrik J.Mol Cancer Ther. 2009 Jan;8(1):64-74. doi: 10.1158/1535-7163.MCT-08-0864. PMID: 19139114 Free PMC Article