MedKoo Cat#: 205822 Name: BAL27862 CAS#: 798577-91-0 Chemical Formula: C20H17N7O2 Exact Mass: 387.14437 Molecular Weight: 387.39 Elemental Analysis: C, 62.01; H, 4.42; N, 25.31; O, 8.26
Synonym: BAL27862; BAL-27862; BAL 27862
IUPAC/Chemical Name: 3-((4-(1-(2-(4-aminophenyl)-2-oxoethyl)-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-yl)amino)propanenitrile
InChi Key: LSFOZQQVTWFMNS-UHFFFAOYSA-N
InChi Code: InChI=1S/C20H17N7O2/c21-10-3-11-23-19-18(25-29-26-19)20-24-15-4-1-2-5-16(15)27(20)12-17(28)13-6-8-14(22)9-7-13/h1-2,4-9H,3,11-12,22H2,(H,23,26)
SMILES Code: N#CCCNC1=NON=C1C2=NC3=CC=CC=C3N2CC(C4=CC=C(N)C=C4)=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 in water
Shelf Life: >2 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
BAL27862 is a novel MTA that triggers apoptosis in cancer cells. In vitro, BAL27862 destabilizes microtubules to produce a microtubule phenotype distinct from that observed with other MTAs, and retains its antiproliferative activity against P-gp overexpressing tumor cells. BAL27862, when administered intravenously or orally, induces significant antitumor responses in a range of animal models of human cancer, including tumors refractory to conventional treatments. BAL27862 overcomes P-gp overexpression-mediated resistance, and demonstrate that Bcl-2 status and tubulin modifications do not necessarily affect its antitumor activity. Analysis of MDs shows that BAL27862 elicited effects consistent with its destabilizing activity; suppression of MDs was 2-fold lower than observed with PTX. Strikingly, BAL27862 displayed a unique microtubule severing activity. Conclusions: Besides its microtubule-targeting activity, BAL27862 displays unique features in its mechanism of action that make it a promising compound for clinical investigation. (source: J Clin Oncol 28, 2010 (suppl; abstr e13589)
References
1: Prota AE, Danel F, Bachmann F, Bargsten K, Buey RM, Pohlmann J, Reinelt S, Lane H, Steinmetz MO. The novel microtubule-destabilizing drug BAL27862 binds to the colchicine site of tubulin with distinct effects on microtubule organization. J Mol Biol. 2014 Apr 17;426(8):1848-60. doi: 10.1016/j.jmb.2014.02.005. Epub 2014 Feb 11. PubMed PMID: 24530796.