AG14361   Click here for help

GtoPdb Ligand ID: 8094

Synonyms: AG 14361 | AG-14361
Compound class: Synthetic organic
Comment: AG14361 is a potent experimental inhibitor of poly (ADP-ribose) polymerase 1 (PARP1) [7]. Its discovery is described in [5], where it is compound 22.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 50.16
Molecular weight 320.16
XLogP 3.42
No. Lipinski's rules broken 0
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Canonical SMILES CN(Cc1ccc(cc1)c1nc2c3n1CCNC(=O)c3ccc2)C
Isomeric SMILES CN(Cc1ccc(cc1)c1nc2c3n1CCNC(=O)c3ccc2)C
InChI InChI=1S/C19H20N4O/c1-22(2)12-13-6-8-14(9-7-13)18-21-16-5-3-4-15-17(16)23(18)11-10-20-19(15)24/h3-9H,10-12H2,1-2H3,(H,20,24)
1. Buisson R, Dion-Côté AM, Coulombe Y, Launay H, Cai H, Stasiak AZ, Stasiak A, Xia B, Masson JY. (2010)
Cooperation of breast cancer proteins PALB2 and piccolo BRCA2 in stimulating homologous recombination.
Nat Struct Mol Biol, 17 (10): 1247-54. [PMID:20871615]
2. Calabrese CR, Almassy R, Barton S, Batey MA, Calvert AH, Canan-Koch S, Durkacz BW, Hostomsky Z, Kumpf RA, Kyle S et al.. (2004)
Anticancer chemosensitization and radiosensitization by the novel poly(ADP-ribose) polymerase-1 inhibitor AG14361.
J Natl Cancer Inst, 96 (1): 56-67. [PMID:14709739]
3. Curtin NJ, Wang LZ, Yiakouvaki A, Kyle S, Arris CA, Canan-Koch S, Webber SE, Durkacz BW, Calvert HA, Hostomsky Z et al.. (2004)
Novel poly(ADP-ribose) polymerase-1 inhibitor, AG14361, restores sensitivity to temozolomide in mismatch repair-deficient cells.
Clin Cancer Res, 10 (3): 881-9. [PMID:14871963]
4. Murai J, Huang SY, Das BB, Renaud A, Zhang Y, Doroshow JH, Ji J, Takeda S, Pommier Y. (2012)
Trapping of PARP1 and PARP2 by Clinical PARP Inhibitors.
Cancer Res, 72 (21): 5588-99. [PMID:23118055]
5. Skalitzky DJ, Marakovits JT, Maegley KA, Ekker A, Yu XH, Hostomsky Z, Webber SE, Eastman BW, Almassy R, Li J et al.. (2003)
Tricyclic benzimidazoles as potent poly(ADP-ribose) polymerase-1 inhibitors.
J Med Chem, 46 (2): 210-3. [PMID:12519059]
6. Smith LM, Willmore E, Austin CA, Curtin NJ. (2005)
The novel poly(ADP-Ribose) polymerase inhibitor, AG14361, sensitizes cells to topoisomerase I poisons by increasing the persistence of DNA strand breaks.
Clin Cancer Res, 11 (23): 8449-57. [PMID:16322308]
7. Veuger SJ, Curtin NJ, Richardson CJ, Smith GC, Durkacz BW. (2003)
Radiosensitization and DNA repair inhibition by the combined use of novel inhibitors of DNA-dependent protein kinase and poly(ADP-ribose) polymerase-1.
Cancer Res, 63 (18): 6008-15. [PMID:14522929]