Avanbulin

• CAT Number: I003905
• CAS Number: 798577-91-0
• Molecular Formula: C20H17N7O2
• Molecular Weight: 387.39
• Purity: ≥95%
• Synonyms: 3-[[4-[1-[2-(4-aminophenyl)-2-oxoethyl]benzimidazol-2-yl]-1,2,5-oxadiazol-3-yl]amino]propanenitrile
• InChI: 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)
• InChIKey: LSFOZQQVTWFMNS-UHFFFAOYSA-N
• SMILES: C1=CC=C2C(=C1)N=C(N2CC(=O)C3=CC=C(C=C3)N)C4=NON=C4NCCC#N

Avanbulin (BAL27862) is a potent, Colchicine site-binding, tubulin assembly inhibitor. Avanbulin inhibits tubulin assembly at 37 °C with an IC50 of 1.4 μM. Avanbulin binds to tubulin with an apparent Kd value of 244 nM. Avanbulin can be used for the research of cancer and cell division[1][2][3][4].
Avanbulin (0-4 μM) binds to tubulin in the site as Colchicine with an apparent Kd value of 244 nM.[1].
Avanbulin (50 μM; 0, 10, 20, 30, 60 min) induces the proteolysis of tubulin[1].
Avanbulin (33 nM; 0, 10, 20, 30, 60 min; HeLa-tubGFP cells) collapses the mitotic spindle and forms the tiny tubulin aggregates[1].
Avanbulin does not induce the formation of tubulin oligomers[1].
Avanbulin induces growth inhibition of 23 tumor cell lines with a median relative IC50 of 13.8 nM (96 hours) [2].
Avanbulin (6 nM and 20 nM) inhibits the migration of GBM6 and GBM9 cells[3].
Avanbulin (6 nM and 20 nM; GBM6-shEB1 and GBM6-sh0 cells) triggers astrocytic differentiation of GBM6 in an EB1-dependent manner[3].
Avanbulin (12  nM; 4  h) reduces kinetochore-microtubule (KT–MT) occupancy of MG132(10 μM; 2h) treated hTert-RPE1 eGFP-α-tubulin cells[4].
Avanbulin (12  nM; 4  h) reduces average inter-KT distances of cells, shows intact spindle morphology, and lacks obvious chromosome alignment defects[4].

Reference

[1]. Prota AE, et al. The novel microtubule-destabilizing drug avanbulin binds to the colchicine site of tubulin with distinct effects on microtubule organization. J Mol Biol. 2014 Apr 17;426(8):1848-60.
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[2]. Kolb EA, et al. Initial testing (stage 1) of BAL101553, a novel tubulin binding agent, by the pediatric preclinical testing program. Pediatr Blood Cancer. 2015 Jun;62(6):1106-9.
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[3]. Bergès R, et al. The Novel Tubulin-Binding Checkpoint Activator BAL101553 Inhibits EB1-Dependent Migration and Invasion and Promotes Differentiation of Glioblastoma Stem-like Cells. Mol Cancer Ther. 2016 Nov;15(11):2740-2749.
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[4]. Dudka D, et al. Complete microtubule-kinetochore occupancy favours the segregation of merotelic attachments. Nat Commun. 2018;9(1):2042. Published 2018 May 23.
 [Content Brief]