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798577-91-0

798577-91-0 structure
798577-91-0 structure
  • Name: BAL-27862
  • Chemical Name: 3-[(4-{1-[2-(4-Aminophenyl)-2-oxoethyl]-1H-benzimidazol-2-yl}-1,2,5-oxadiazol-3-yl)amino]propanenitrile
  • CAS Number: 798577-91-0
  • Molecular Formula: C20H17N7O2
  • Molecular Weight: 387.395
  • Catalog: Signaling Pathways Cell Cycle/DNA Damage Microtubule/Tubulin
  • Create Date: 2018-06-27 19:19:23
  • Modify Date: 2025-08-25 05:19:39
  • 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].

Name 3-[(4-{1-[2-(4-Aminophenyl)-2-oxoethyl]-1H-benzimidazol-2-yl}-1,2,5-oxadiazol-3-yl)amino]propanenitrile
Synonyms Propanenitrile, 3-[[4-[1-[2-(4-aminophenyl)-2-oxoethyl]-1H-benzimidazol-2-yl]-1,2,5-oxadiazol-3-yl]amino]-
MFCD28502222
3-[(4-{1-[2-(4-Aminophenyl)-2-oxoethyl]-1H-benzimidazol-2-yl}-1,2,5-oxadiazol-3-yl)amino]propanenitrile
Description 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].
Related Catalog
In Vitro Avanbulin (0-4 μM) binds to tubulin with an apparent Kd value of 244 nM[1]. Avanbulin (0-20 μM) and Colchicine (0-10 μM) are competitive for binding to tubulin with an apparent Ki value of 1.8 μM[1]. Avanbulin binds to the same site as Colchicine at the intradimer interface[1]. Avanbulin (50 μM; 0, 10, 20, 30, 60 min) induces the proteolysis of tubulin[1]. Avanbulin (1-100 nM; 72 h; HeLa-tubGFP cells) has anti-proliferative effects[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 (0.1 nM-1.0 μM; 96 hours) induces growth inhibition of cells with a median relative IC50 of 13.8 nM[2]. Avanbulin (0-1,000 nM; 3 days) inhibits the growth of glioblastoma cancer stem-like cells, GBM6 (EC50=20.8 nM) and GBM9 (EC50=21.7 nM) [3]. 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[4]. Avanbulin-treated (12  nM; 4  h) cells show intact spindle morphology and lack of obvious chromosome alignment defects[4]. Cell Cytotoxicity Assay[2] Cell Line: 23 cell lines, including RD, TC-71, SJ-GBM2, NB-1643. Concentration: 0.1 nM-1.0 μM Incubation Time: 96 hours Result: Induced growth inhibition of cells with a median relative IC50 of 13.8 nM.
References

[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.

[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.

[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.

[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.

Density 1.4±0.1 g/cm3
Boiling Point 771.5±70.0 °C at 760 mmHg
Molecular Formula C20H17N7O2
Molecular Weight 387.395
Flash Point 420.4±35.7 °C
Exact Mass 387.144379
LogP 4.25
Vapour Pressure 0.0±2.6 mmHg at 25°C
Index of Refraction 1.731
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