메뉴 건너뛰기




Volumn 72, Issue 6, 2008, Pages 575-584

QSAR study of 2-(1-propylpiperidin-4-yl)-1H-benzimidazole-4-carboxamide as PARP inhibitors for treatment of cancer

Author keywords

Chemometrics; Genetic algorithms; Multiple linear regression; PARP inhibitors; QSAR

Indexed keywords

2 (1 PROPYLPIPERIDIN 4 YL) 1H BENZIMIDAZOLE 4 CARBOXAMIDE; AMIDE; ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE INHIBITOR; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 56649103442     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2008.00739.x     Document Type: Article
Times cited : (26)

References (53)
  • 1
    • 0036447366 scopus 로고    scopus 로고
    • Potential clinical applications of poly(ADP-ribose) polymerase (PARP) inhibitors
    • Tentori L., Portarena I., Graziani G. (2002) Potential clinical applications of poly(ADP-ribose) polymerase (PARP) inhibitors. Pharmacol Res 45 : 73 85.
    • (2002) Pharmacol Res , vol.45 , pp. 73-85
    • Tentori, L.1    Portarena, I.2    Graziani, G.3
  • 2
    • 0029080684 scopus 로고
    • The role of inhibitors of poly(ADP-ribose) polymerase as resistance modifying agents in cancer therapy
    • Griffin R.J., Curtin N.J., Newell D.R., Golding B.T., Durkacz B.W., Calvert A.H. (1995) The role of inhibitors of poly(ADP-ribose) polymerase as resistance modifying agents in cancer therapy. Biochimie 77 : 408 422.
    • (1995) Biochimie , vol.77 , pp. 408-422
    • Griffin, R.J.1    Curtin, N.J.2    Newell, D.R.3    Golding, B.T.4    Durkacz, B.W.5    Calvert, A.H.6
  • 3
    • 0031913158 scopus 로고    scopus 로고
    • DNA repair mechanisms associated with cellular resistance to antitumor drugs: Potential novel targets
    • Barret J.M., Hill B.T. (1998) DNA repair mechanisms associated with cellular resistance to antitumor drugs: potential novel targets. Anticancer Drug 9 : 105 123.
    • (1998) Anticancer Drug , vol.9 , pp. 105-123
    • Barret, J.M.1    Hill, B.T.2
  • 4
    • 0000102949 scopus 로고
    • Poly(ADP-ribose) polymerase: A molecular nick-sensor
    • Demurcia G., Demurcia J.M. (1994) Poly(ADP-ribose) polymerase: a molecular nick-sensor. Trends Biochem Sci 19 : 172 176.
    • (1994) Trends Biochem Sci , vol.19 , pp. 172-176
    • Demurcia, G.1    Demurcia, J.M.2
  • 5
    • 0026507413 scopus 로고
    • Role of poly(ADP-ribose) formation in DNA repair
    • Satoh M.S., Lindahl T. (1992) Role of poly(ADP-ribose) formation in DNA repair. Nature 356 : 356 358.
    • (1992) Nature , vol.356 , pp. 356-358
    • Satoh, M.S.1    Lindahl, T.2
  • 7
    • 0027253141 scopus 로고
    • Overproduction of the poly(ADP-ribose) polymerase DNA-binding domain blocks alkylation-induced DNA repair synthesis in mammalian cells
    • Molinete M., Vermeulen W., Burkle A., Menissier-de M.J., Kupper J.H., Hoeijmakers J.H. (1993) Overproduction of the poly(ADP-ribose) polymerase DNA-binding domain blocks alkylation-induced DNA repair synthesis in mammalian cells. EMBO J 12 : 2109 2117.
    • (1993) EMBO J , vol.12 , pp. 2109-2117
    • Molinete, M.1    Vermeulen, W.2    Burkle, A.3    Menissier-De, M.J.4    Kupper, J.H.5    Hoeijmakers, J.H.6
  • 8
    • 0028145365 scopus 로고
    • Depletion of nuclear poly(ADP-ribose) polymerase by antisense RNA expression: Influences on genomic stability, chromatin organization, and carcinogen cytotoxicity
    • Ding R., Smulson M. (1994) Depletion of nuclear poly(ADP-ribose) polymerase by antisense RNA expression: influences on genomic stability, chromatin organization, and carcinogen cytotoxicity. Cancer Res 54 : 4627 4634.
    • (1994) Cancer Res , vol.54 , pp. 4627-4634
    • Ding, R.1    Smulson, M.2
  • 10
    • 33745876586 scopus 로고    scopus 로고
    • Inhibition of poly(ADP-ribose) pollyrnerase in cancer
    • Plummer E.R. (2006) Inhibition of poly(ADP-ribose) pollyrnerase in cancer. Curr Opin Pharmacol 6 : 364 368.
    • (2006) Curr Opin Pharmacol , vol.6 , pp. 364-368
    • Plummer, E.R.1
  • 11
    • 34250370941 scopus 로고    scopus 로고
    • Poly(ADP-ribose) polymerase as a drug target for cardiovascular disease and cancer: An update
    • Horvath E.M., Szabo C. (2007) Poly(ADP-ribose) polymerase as a drug target for cardiovascular disease and cancer: an update. Drug News Perspect 20 : 171 181.
    • (2007) Drug News Perspect , vol.20 , pp. 171-181
    • Horvath, E.M.1    Szabo, C.2
  • 12
    • 33947380240 scopus 로고    scopus 로고
    • Current development of clinical inhibitors of poly (ADP-ribose) polymerase in oncology
    • Ratnam K., Low J.A. (2007) Current development of clinical inhibitors of poly (ADP-ribose) polymerase in oncology. Clin Cancer Res 13 : 1383 1388.
    • (2007) Clin Cancer Res , vol.13 , pp. 1383-1388
    • Ratnam, K.1    Low, J.A.2
  • 13
    • 34249006299 scopus 로고    scopus 로고
    • ABT-888, an orallyactive poly(ADP-ribose) polymerase inhibitor that potentiates DNA-damaging agents in preclinical tumor models
    • Donawho C.K., Luo Y., Penning T.D., Bauch J.L., Bouska J.J., Bontcheva-Diaz V.D., Cox B.F. et al. (2007) ABT-888, an orallyactive poly(ADP-ribose) polymerase inhibitor that potentiates DNA-damaging agents in preclinical tumor models. Clin Cancer Res 13 : 2728 2737.
    • (2007) Clin Cancer Res , vol.13 , pp. 2728-2737
    • Donawho, C.K.1    Luo, Y.2    Penning, T.D.3    Bauch, J.L.4    Bouska, J.J.5    Bontcheva-Diaz, V.D.6    Cox, B.F.7
  • 14
    • 56649112153 scopus 로고    scopus 로고
    • Oral administration of PARP inhibitor GPI
    • 18180 increases the anti-tumor activity of temozolomide against intracranial melanoma in mice.
    • Lapidus R.G., Tentori L., Graziani G., Leonetti C., Scarsella M., Vergati M., Muzi A., Zhang J. (2005) Oral administration of PARP inhibitor GPI 18180 increases the anti-tumor activity of temozolomide against intracranial melanoma in mice. J Clin Oncol 23 : 225S 225S.
    • (2005) J Clin Oncol , vol.23
    • Lapidus, R.G.1    Tentori, L.2    Graziani, G.3    Leonetti, C.4    Scarsella, M.5    Vergati, M.6    Muzi, A.7    Zhang, J.8
  • 16
    • 10744233684 scopus 로고    scopus 로고
    • Systemic administration of GPI
    • 15427, a novel Poly(ADP-Ribose) polymerase-1 inhibitor, increases the antitumor activity of temozolomide against intracranial melanoma, glioma, lymphoma.
    • Tentori L., Leonetti C., Scarsella M., d'Amati G., Vergati M., Portarena I., Xu W., Kalish V., Zupi G., Zhang J., Graziani G. (2003) Systemic administration of GPI 15427, a novel Poly(ADP-Ribose) polymerase-1 inhibitor, increases the antitumor activity of temozolomide against intracranial melanoma, glioma, lymphoma. Clin Cancer Res 9 : 5370 5379.
    • (2003) Clin Cancer Res , vol.9 , pp. 5370-5379
    • Tentori, L.1    Leonetti, C.2    Scarsella, M.3    D'Amati, G.4    Vergati, M.5    Portarena, I.6    Xu, W.7    Kalish, V.8    Zupi, G.9    Zhang, J.10    Graziani, G.11
  • 17
    • 0001176135 scopus 로고    scopus 로고
    • PARP inhibitors
    • Li J.-H., Zhang J. (2001) PARP inhibitors. IDrugs 4 : 804 812.
    • (2001) IDrugs , vol.4 , pp. 804-812
    • Li, J.-H.1    Zhang, J.2
  • 20
    • 34447335391 scopus 로고    scopus 로고
    • ANN-QSAR model of drug-binding to human serum albumin
    • Deeb O., Hemmateenejad B. (2007) ANN-QSAR model of drug-binding to human serum albumin. Chem Biol Drug Des 70 : 19 29.
    • (2007) Chem Biol Drug des , vol.70 , pp. 19-29
    • Deeb, O.1    Hemmateenejad, B.2
  • 22
    • 34547758418 scopus 로고    scopus 로고
    • QSAR study on the relaxant agents from some mexican medicinal plants and synthetic related organic compounds
    • Ramirez-Galicia G., Garduno-Juarez R., Hemmateenejad B., Deeb O., Estrada-Soto S. (2007) QSAR study on the relaxant agents from some mexican medicinal plants and synthetic related organic compounds. Chem Biol Drug Des 70 : 143 153.
    • (2007) Chem Biol Drug des , vol.70 , pp. 143-153
    • Ramirez-Galicia, G.1    Garduno-Juarez, R.2    Hemmateenejad, B.3    Deeb, O.4    Estrada-Soto, S.5
  • 24
    • 34250745945 scopus 로고    scopus 로고
    • A mechanistic QSAR study on the leishmanicidal activity of some 5-substituted-1,3,4-thiadiazole derivatives
    • Hemmateenejad B., Miri R., Niroomand U., Foroumadi A., Shafiee A. (2007) A mechanistic QSAR study on the leishmanicidal activity of some 5-substituted-1,3,4-thiadiazole derivatives. Chem Biol Drug Des 69 : 435 443.
    • (2007) Chem Biol Drug des , vol.69 , pp. 435-443
    • Hemmateenejad, B.1    Miri, R.2    Niroomand, U.3    Foroumadi, A.4    Shafiee, A.5
  • 25
    • 32844465022 scopus 로고    scopus 로고
    • Effect of cholesterol on DMPC phospholipid membranes and QSAR model construction in membrane-interaction QSAR study through molecular dynamics simulation
    • Liu J., Yang L. (2006) Effect of cholesterol on DMPC phospholipid membranes and QSAR model construction in membrane-interaction QSAR study through molecular dynamics simulation. Bioorg Med Chem 14 : 2225 2234.
    • (2006) Bioorg Med Chem , vol.14 , pp. 2225-2234
    • Liu, J.1    Yang, L.2
  • 26
    • 9644268924 scopus 로고    scopus 로고
    • On the role of polarizability in QSAR
    • Verma R.P., Kurup A., Hansch C. (2005) On the role of polarizability in QSAR. Bioorg Med Chem 13 : 237 255.
    • (2005) Bioorg Med Chem , vol.13 , pp. 237-255
    • Verma, R.P.1    Kurup, A.2    Hansch, C.3
  • 27
    • 0033813236 scopus 로고    scopus 로고
    • A QSAR study investigating the effect of l-alanine ester variation on the anti-HIV activity of some phosphoramidate derivatives of d4T
    • Knaggs M.H., McGuigan C., Harris S.A., Heshmati P., Cahard D., Gilbert I.H., Balzarini J. (2000) A QSAR study investigating the effect of l-alanine ester variation on the anti-HIV activity of some phosphoramidate derivatives of d4T. Bioorg Med Chem Lett 10 : 2075 2078.
    • (2000) Bioorg Med Chem Lett , vol.10 , pp. 2075-2078
    • Knaggs, M.H.1    McGuigan, C.2    Harris, S.A.3    Heshmati, P.4    Cahard, D.5    Gilbert, I.H.6    Balzarini, J.7
  • 28
    • 33644766870 scopus 로고    scopus 로고
    • QSAR models for Daphnia toxicity of pesticides based on combinations of topological parameters of molecular structures
    • Toropov A.A., Benfenati E. (2006) QSAR models for Daphnia toxicity of pesticides based on combinations of topological parameters of molecular structures. Bioorg Med Chem 14 : 2779 2788.
    • (2006) Bioorg Med Chem , vol.14 , pp. 2779-2788
    • Toropov, A.A.1    Benfenati, E.2
  • 29
    • 0036166633 scopus 로고    scopus 로고
    • QSAR study on toxicity to aqueous organisms using the PI index
    • Khadikar P.V., Phadnis A., Shrivastava A. (2002) QSAR study on toxicity to aqueous organisms using the PI index. Bioorg Med Chem 10 : 1181 1188.
    • (2002) Bioorg Med Chem , vol.10 , pp. 1181-1188
    • Khadikar, P.V.1    Phadnis, A.2    Shrivastava, A.3
  • 30
    • 0034801283 scopus 로고    scopus 로고
    • QSAR prediction of toxicity of nitrobenzenes
    • Agrawal V.K., Khadikar P.V. (2001) QSAR prediction of toxicity of nitrobenzenes. Bioorg Med Chem 9 : 3035 3040.
    • (2001) Bioorg Med Chem , vol.9 , pp. 3035-3040
    • Agrawal, V.K.1    Khadikar, P.V.2
  • 31
    • 33750692773 scopus 로고    scopus 로고
    • Synthesis and antiviral activity against tobacco mosaic virus and 3D-QSAR of alpha-substituted-1,2,3-thiadiazoleacetamides
    • Zhao W.G., Wang H.G., Li Z.M., Yang Z. (2006) Synthesis and antiviral activity against tobacco mosaic virus and 3D-QSAR of alpha-substituted-1,2,3- thiadiazoleacetamides. Bioorg Med Chem Let 16 : 6107 6111.
    • (2006) Bioorg Med Chem Let , vol.16 , pp. 6107-6111
    • Zhao, W.G.1    Wang, H.G.2    Li, Z.M.3    Yang, Z.4
  • 32
    • 0345707697 scopus 로고    scopus 로고
    • Synthesis of thiadiazolo-s-triazines for their antiviral activity based on QSAR studies
    • Pandey V.K., Tusi Z., Tandon M., Joshi M.N., Bajpai S.K. (2003) Synthesis of thiadiazolo-s-triazines for their antiviral activity based on QSAR studies. Indian J Chem B 42 : 2583 2588.
    • (2003) Indian J Chem B , vol.42 , pp. 2583-2588
    • Pandey, V.K.1    Tusi, Z.2    Tandon, M.3    Joshi, M.N.4    Bajpai, S.K.5
  • 33
    • 47549095368 scopus 로고    scopus 로고
    • Discovery and SAR of 2-(1-propylpiperidin-4-yl)-1H-benzimidazole-4- carboxamide: A potent inhibitor of poly(ADP-ribose) polymerase (PARP) for the treatment of cancer
    • Penning T.D., Zhu G.D., Gandhi V.B., Gong J.C., Thomas S., Lubisch W., Grandel R. et al. (2008) Discovery and SAR of 2-(1-propylpiperidin-4-yl)-1H- benzimidazole-4-carboxamide: a potent inhibitor of poly(ADP-ribose) polymerase (PARP) for the treatment of cancer. Bioorg Med Chem 16 : 6965 6975.
    • (2008) Bioorg Med Chem , vol.16 , pp. 6965-6975
    • Penning, T.D.1    Zhu, G.D.2    Gandhi, V.B.3    Gong, J.C.4    Thomas, S.5    Lubisch, W.6    Grandel, R.7
  • 36
    • 5244364136 scopus 로고    scopus 로고
    • The discrimination ability of some topological and information distance indices for graphs of unbranched hexagonal systems
    • Kostantinova E.V. (1996) The discrimination ability of some topological and information distance indices for graphs of unbranched hexagonal systems. J Chem Inf Comp Sci 36 : 54 57.
    • (1996) J Chem Inf Comp Sci , vol.36 , pp. 54-57
    • Kostantinova, E.V.1
  • 37
    • 0027658970 scopus 로고
    • Counts of all walks as atomic and molecular descriptors
    • Rucker G., Rucker C. (1993) Counts of all walks as atomic and molecular descriptors. J Chem Inf Comp Sci 33 : 683 695.
    • (1993) J Chem Inf Comp Sci , vol.33 , pp. 683-695
    • Rucker, G.1    Rucker, C.2
  • 39
    • 0021363878 scopus 로고
    • Molecular structures: Perception, autocorrelation descriptor and sar studies
    • Broto P., Moreau G., Vandicke C. (1984) Molecular structures: perception, autocorrelation descriptor and sar studies. Eur J Med Chem 19 : 66 70.
    • (1984) Eur J Med Chem , vol.19 , pp. 66-70
    • Broto, P.1    Moreau, G.2    Vandicke, C.3
  • 40
    • 30744458142 scopus 로고    scopus 로고
    • Linear and nonlinear modeling of antifungal activity of some heterocyclic ring derivatives using multiple linear regression and Bayesian-regulated neural networks
    • Caballero J., Fernandez M. (2006) Linear and nonlinear modeling of antifungal activity of some heterocyclic ring derivatives using multiple linear regression and Bayesian-regulated neural networks. J Mol Model 12 : 168 181.
    • (2006) J Mol Model , vol.12 , pp. 168-181
    • Caballero, J.1    Fernandez, M.2
  • 41
    • 33750495370 scopus 로고    scopus 로고
    • Bayesian-regularized genetic neural networks applied to the modeling of non-peptide antagonists for the human luteinizing hormone-releasing hormone receptor
    • Fernandez M., Caballero J. (2006) Bayesian-regularized genetic neural networks applied to the modeling of non-peptide antagonists for the human luteinizing hormone-releasing hormone receptor. J Mol Graph Model 25 : 410 422.
    • (2006) J Mol Graph Model , vol.25 , pp. 410-422
    • Fernandez, M.1    Caballero, J.2
  • 42
    • 13844316617 scopus 로고    scopus 로고
    • Toward an optimal procedure for PC-ANN model building: Prediction of the carcinogenic activity of a large set of drug
    • Hemmateenejad B., Safarpour M.A., Miri R., Nesari N. (2005) Toward an optimal procedure for PC-ANN model building: prediction of the carcinogenic activity of a large set of drug. J Chem Inf Model 45 : 190 199.
    • (2005) J Chem Inf Model , vol.45 , pp. 190-199
    • Hemmateenejad, B.1    Safarpour, M.A.2    Miri, R.3    Nesari, N.4
  • 43
    • 0000994201 scopus 로고    scopus 로고
    • Optimization and analysis of force field parameters by combination of genetic algorithms and neural networks
    • Hunger J., Huttner G. (1999) Optimization and analysis of force field parameters by combination of genetic algorithms and neural networks. J Comput Chem 20 : 455 471.
    • (1999) J Comput Chem , vol.20 , pp. 455-471
    • Hunger, J.1    Huttner, G.2
  • 44
    • 0038454608 scopus 로고    scopus 로고
    • Design and training of a neural network for predicting the solvent accessibility of proteins
    • Ahmad S., Gromiha M.M. (2003) Design and training of a neural network for predicting the solvent accessibility of proteins. J Comput Chem 24 : 1313 1320.
    • (2003) J Comput Chem , vol.24 , pp. 1313-1320
    • Ahmad, S.1    Gromiha, M.M.2
  • 45
    • 0000481568 scopus 로고    scopus 로고
    • Development and validation of a novel variable selection technique with application to multidimensional quantitative structure-activity relationship studies
    • Waller C.L., Bradley M.P. (1999) Development and validation of a novel variable selection technique with application to multidimensional quantitative structure-activity relationship studies. J Chem Inf Comput Sci 39 : 345 355.
    • (1999) J Chem Inf Comput Sci , vol.39 , pp. 345-355
    • Waller, C.L.1    Bradley, M.P.2
  • 46
    • 0036006953 scopus 로고    scopus 로고
    • Prediction of H-1 NMR chemical shifts using neural networks
    • Aires-de-Sousa J., Hemmer M.C., Casteiger J. (2002) Prediction of H-1 NMR chemical shifts using neural networks. Anal Chem 74 : 80 90.
    • (2002) Anal Chem , vol.74 , pp. 80-90
    • Aires-De-Sousa, J.1    Hemmer, M.C.2    Casteiger, J.3
  • 47
    • 0002906202 scopus 로고
    • History and objectives of quantitative drug design in advances in drug research
    • In: Sammes, P., Taylor, J., editors. Vol. 4, Oxford: Pergamon. p.
    • Tute M. 1990) History and objectives of quantitative drug design in advances in drug research. In : Sammes P., Taylor J., editors. Comprehensive Medicinal Chemistry, Vol. 4, Oxford : Pergamon p. 1 32.
    • (1990) Comprehensive Medicinal Chemistry , pp. 1-32
    • Tute, M.1
  • 49
    • 28944449555 scopus 로고    scopus 로고
    • Modeling of cyclin-dependent kinase inhibition by 1H-pyrazolo[3,4-d] pyrimidine derivatives using artificial neural network ensembles
    • Fernandez M., Tundidor-Camba A., Caballero J. (2005) Modeling of cyclin-dependent kinase inhibition by 1H-pyrazolo[3,4-d] pyrimidine derivatives using artificial neural network ensembles. J Chem Inf Model 45 : 1884 1895.
    • (2005) J Chem Inf Model , vol.45 , pp. 1884-1895
    • Fernandez, M.1    Tundidor-Camba, A.2    Caballero, J.3
  • 50
    • 33846815342 scopus 로고    scopus 로고
    • Modeling of the inhibition constant (Ki) of some cruzain ketone-based inhibitors using 2D spatial autocorrelation vectors and data-diverse ensembles of Bayesian-regularized genetic neural networks
    • Caballero J., Tundidor-Camba A., Fernandez M. (2007) Modeling of the inhibition constant (Ki) of some cruzain ketone-based inhibitors using 2D spatial autocorrelation vectors and data-diverse ensembles of Bayesian-regularized genetic neural networks. QSAR Comb Sci 26 : 27 40.
    • (2007) QSAR Comb Sci , vol.26 , pp. 27-40
    • Caballero, J.1    Tundidor-Camba, A.2    Fernandez, M.3
  • 51
    • 33751158192 scopus 로고
    • Molecular connectivity descriptors of the physicochemical properties of the alpha-amino-acids
    • Pogliani L. (1994) Molecular connectivity descriptors of the physicochemical properties of the alpha-amino-acids. J Phys Chem 98 : 1494 1499.
    • (1994) J Phys Chem , vol.98 , pp. 1494-1499
    • Pogliani, L.1
  • 52
    • 0034299377 scopus 로고    scopus 로고
    • From molecular connectivity indices to semiempirical connectivity terms: Recent trends in graph theoretical descriptors
    • Pogliani L. (2000) From molecular connectivity indices to semiempirical connectivity terms: recent trends in graph theoretical descriptors. Chem Rev 100 : 3827 3858.
    • (2000) Chem Rev , vol.100 , pp. 3827-3858
    • Pogliani, L.1
  • 53
    • 28444497469 scopus 로고    scopus 로고
    • Chance correlation in variable subset regression: Influence of the objective function, the selection mechanism, and ensemble averaging
    • Baumann K. (2005) Chance correlation in variable subset regression: Influence of the objective function, the selection mechanism, and ensemble averaging. QSAR Comb Sci 24 : 1033 1046.
    • (2005) QSAR Comb Sci , vol.24 , pp. 1033-1046
    • Baumann, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.