메뉴 건너뛰기




Volumn 18, Issue 5, 2012, Pages 1819-1840

Development of multiple QSAR models for consensus predictions and unified mechanistic interpretations of the free-radical scavenging activities of chromone derivatives

Author keywords

3D pharmacophore; Antioxidant; Comparative molecular similarity indices; Group based quantitative structure activity relationship; Hologram quantitative structure activity relationship

Indexed keywords

CHROMONE DERIVATIVE; FREE RADICAL;

EID: 84861227331     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-011-1198-x     Document Type: Article
Times cited : (24)

References (65)
  • 2
    • 0027474868 scopus 로고
    • Oxygen free radicals and hypercholesterolemic atherosclerosis: Effect of vitamin E
    • DOI 10.1016/0002-8703(93)90102-F
    • Prasad K, Kalra J (1993) Oxygen free radicals and hypercholesterolemic atherosclerosis: effect of vitamin E. Am Heart J 125:958-973 (Pubitemid 23117326)
    • (1993) American Heart Journal , vol.125 , Issue.4 , pp. 958-973
    • Prasad, K.1    Kalra, J.2
  • 3
    • 0028129137 scopus 로고
    • Evidence of an oxidative challenge in the Alzheimer's brain
    • Balazas L, Leon M (1994) Evidence of an oxidative challange in the Alzheimer's brain. Neurochem Res 19:1131-1137 (Pubitemid 24284787)
    • (1994) Neurochemical Research , vol.19 , Issue.9 , pp. 1131-1137
    • Balazs, L.1    Leon, M.2
  • 4
    • 0038799736 scopus 로고    scopus 로고
    • Oxidative DNA damage: Mechanisms, mutation, and disease
    • DOI 10.1096/fj.02-0752rev
    • Cooke MS, Evans MD, Dizdaroglu M, Lunec J (2003) Oxidative DNA damage: mechanisms, mutation, and disease. FASEB J 17:1195-1214 (Pubitemid 36775767)
    • (2003) FASEB Journal , vol.17 , Issue.10 , pp. 1195-1214
    • Cooke, M.S.1    Evans, M.D.2    Dizdaroglu, M.3    Lunec, J.4
  • 6
    • 0033796250 scopus 로고    scopus 로고
    • Mitochondrial free radical generation, oxidative stress, and aging
    • Cadenas E, Davies KJ (2000) Mitochondrial free radical generation, oxidative stress, and aging. Free Radical Biol Med 29:222-230
    • (2000) Free Radical Biol Med , vol.29 , pp. 222-230
    • Cadenas, E.1    Davies, K.J.2
  • 7
    • 0031963619 scopus 로고    scopus 로고
    • Iron, free radicals, and oxidative injury
    • McCord JM (1998) Iron, free radicals, and oxidative injury. Semin Hematol 35:5-12 (Pubitemid 28047038)
    • (1998) Seminars in Hematology , vol.35 , Issue.1 , pp. 5-12
    • McCord, J.M.1
  • 8
    • 0001998594 scopus 로고
    • The mechanism of antioxidant action in vitro
    • Hudson BJF (ed) Elsevier, New York
    • GordonMH (1990) The mechanism of antioxidant action in vitro. In: Hudson BJF (ed) Food antioxidants. Elsevier, New York, pp 1-18
    • (1990) Food Antioxidants , pp. 1-18
    • Gordon, M.H.1
  • 9
    • 74649084497 scopus 로고    scopus 로고
    • Antioxidant enzymes in cabbage: Variability and inheritance of superoxide dismutase, peroxidase and catalase
    • Singh BK, Sharma SR, Singh B (2010) Antioxidant enzymes in cabbage: variability and inheritance of superoxide dismutase, peroxidase and catalase. Sci Hort 124:9-13
    • (2010) Sci Hort , vol.124 , pp. 9-13
    • Singh, B.K.1    Sharma, S.R.2    Singh, B.3
  • 10
    • 0035857407 scopus 로고    scopus 로고
    • Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants
    • DOI 10.1021/ja002455u
    • Wright JS, Johnson ER, DiLabio GA (2001) Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants. J Am Chem Soc 123:1173-1183 (Pubitemid 32148182)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.6 , pp. 1173-1183
    • Wright, J.S.1    Johnson, E.R.2    DiLabio, G.A.3
  • 11
    • 24344457135 scopus 로고    scopus 로고
    • A DFT study on the deprotonation antioxidant mechanistic step of ortho-substituted phenolic cation radicals
    • DOI 10.1016/j.chemphys.2005.05.015, PII S030101040500203X
    • Vafiadis AP, Bakalbassis EG (2005) A DFT study on the deprotonation antioxidant mechanistic step of ortho-substituted phenolic cation radicals. Chem Phys 316:195-204 (Pubitemid 41253585)
    • (2005) Chemical Physics , vol.316 , Issue.1-3 , pp. 195-204
    • Vafiadis, A.P.1    Bakalbassis, E.G.2
  • 12
    • 27644539327 scopus 로고    scopus 로고
    • • radicals by vitamin E is accelerated by its partial ionization: The role of sequential proton loss electron transfer
    • DOI 10.1021/ol051962j
    • Musialik M, Litwinienko G (2005) Scavenging of DPPH· radicals by vitamin E is accelerated by its partial ionization: the role of sequential proton loss electron transfer. Org Lett 7:4951-4954 (Pubitemid 41579901)
    • (2005) Organic Letters , vol.7 , Issue.22 , pp. 4951-4954
    • Musialik, M.1    Litwinienko, G.2
  • 13
    • 34447631168 scopus 로고    scopus 로고
    • Oxyl radicals, redox-sensitive signalling cascades and antioxidants
    • DOI 10.1016/j.cellsig.2007.04.009, PII S0898656807001258
    • Genestra M (2007) Oxyl radicals, redox-sensitive signaling cascades and antioxidants. Cell Signal 19:1807-1819 (Pubitemid 47090178)
    • (2007) Cellular Signalling , vol.19 , Issue.9 , pp. 1807-1819
    • Genestra, M.1
  • 14
    • 0036591855 scopus 로고    scopus 로고
    • Free radical-induced damage to DNA: Mechanisms and measurement
    • DOI 10.1016/S0891-5849(02)00826-2, PII S0891584902008262
    • Dizdaroglu M, Jaruga P, Birincioglu M, Rodriguez H (2002) Free radical-induced damage to DNA: mechanisms and measurement. Free Radic Biol Med 32:1102-1115 (Pubitemid 34603348)
    • (2002) Free Radical Biology and Medicine , vol.32 , Issue.11 , pp. 1102-1115
    • Dizdaroglu, M.1    Jaruga, P.2    Birincioglu, M.3    Rodriguez, H.4
  • 17
    • 34447521097 scopus 로고
    • Correlation of biological activity of phenoxyacetic acids with Hammett substituent constants and partition coefficients
    • Hansch C, Maloney PP, Fujita T, Muir RM (1962) Correlation of biological activity of phenoxyacetic acids with Hammett substituent constants and partition coefficients. Nature 194:178-180
    • (1962) Nature , vol.194 , pp. 178-180
    • Hansch, C.1    Maloney, P.P.2    Fujita, T.3    Muir, R.M.4
  • 18
    • 0036973247 scopus 로고    scopus 로고
    • Study on the multiple mechanisms underlying the reaction between hydroxyl radical and phenolic compounds by qualitative structure and activity relationship
    • DOI 10.1016/S0968-0896(02)00267-5, PII S0968089602002675
    • Cheng Z, Ren J, Li Y, Chang W, Chen Z (2002) Study on the multiple mechanisms underlying the reaction between hydroxyl radical and phenolic compounds by qualitative structure and activity relationship. Bioorg Med Chem 10:4067-4073 (Pubitemid 36164707)
    • (2002) Bioorganic and Medicinal Chemistry , vol.10 , Issue.12 , pp. 4067-4073
    • Cheng, Z.1    Ren, J.2    Li, Y.3    Chang, W.4    Chen, Z.5
  • 19
    • 33745786642 scopus 로고    scopus 로고
    • Computation of relative bond dissociation enthalpies (ΔBDE) of phenolic antioxidants from Quantum Topological Molecular Similarity (QTMS)
    • DOI 10.1021/jp0553885
    • Singh N, Loader RJ, O'Malley PJ, Popelier PLA (2006) Computation of relative bond dissociation enthalpies (DBDE) of phenolic antioxidants from quantum topological molecular similarity (QTMS). J Phys Chem A 110:6498-6503 (Pubitemid 44020303)
    • (2006) Journal of Physical Chemistry A , vol.110 , Issue.20 , pp. 6498-6503
    • Singh, N.1    Loader, R.J.2    O'Malley, P.J.3    Popelier, P.L.A.4
  • 21
    • 64249110197 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship modeling of antioxidant activities of hydroxybenzalacetones using quantum chemical, physicochemical and spatial descriptors
    • Mitra I, Saha A, Roy K (2009) Quantitative structure-activity relationship modeling of antioxidant activities of hydroxybenzalacetones using quantum chemical, physicochemical and spatial descriptors. Chem Biol Drug Des 73:526-536
    • (2009) Chem Biol Drug des , vol.73 , pp. 526-536
    • Mitra, I.1    Saha, A.2    Roy, K.3
  • 22
    • 70349757130 scopus 로고    scopus 로고
    • QSAR of antilipid peroxidative activity of substituted benzodioxoles using chemometric tools
    • Mitra I, Roy K, Saha A (2009) QSAR of antilipid peroxidative activity of substituted benzodioxoles using chemometric tools. J Comput Chem 30:2712-2722
    • (2009) J Comput Chem , vol.30 , pp. 2712-2722
    • Mitra, I.1    Roy, K.2    Saha, A.3
  • 23
    • 77958059491 scopus 로고    scopus 로고
    • Pharmacophore mapping of arylamino-substituted benzo[b]thiophenes as free radical scavengers
    • Mitra I, Saha A, Roy K (2010) Pharmacophore mapping of arylamino-substituted benzo[b]thiophenes as free radical scavengers. J Mol Model 16:1585-1596
    • (2010) J Mol Model , vol.16 , pp. 1585-1596
    • Mitra, I.1    Saha, A.2    Roy, K.3
  • 24
    • 72949124487 scopus 로고    scopus 로고
    • Advances in quantitative structure-activity relationship models of antioxidants
    • Roy K, Mitra I (2009) Advances in quantitative structure-activity relationship models of antioxidants. Expert Opin Drug Discov 4:1157-1175
    • (2009) Expert Opin Drug Discov , vol.4 , pp. 1157-1175
    • Roy, K.1    Mitra, I.2
  • 25
    • 41649088617 scopus 로고    scopus 로고
    • 3D-QSAR investigation of synthetic antioxidant chromone derivatives by molecular field analysis
    • DOI 10.3390/ijms9030235
    • Samee W, Nunthanavanit P, Ungwitayatorn J (2008) 3D-QSAR investigation of synthetic antioxidant chromone derivatives by molecular field analysis. Int J Mol Sci 9:235-246 (Pubitemid 351482112)
    • (2008) International Journal of Molecular Sciences , vol.9 , Issue.3 , pp. 235-246
    • Samee, W.1    Nunthanavanit, P.2    Ungwitayatorn, J.3
  • 26
    • 41649090083 scopus 로고    scopus 로고
    • Structure-radical scavenging activity relationships of the synthesized chromone derivatives
    • Samee W, Sae-Lee N, Ungwitayatorn J (2004) Structure-radical scavenging activity relationships of the synthesized chromone derivatives. J Pharm Sci 9:36-42
    • (2004) J Pharm Sci , vol.9 , pp. 36-42
    • Samee, W.1    Sae-Lee, N.2    Ungwitayatorn, J.3
  • 27
    • 33645028278 scopus 로고    scopus 로고
    • On selection of training and test sets for the development of predictive QSAR models
    • Leonard JT, Roy K (2006) On selection of training and test sets for the development of predictive QSAR models. QSAR Comb Sci 25:235-251
    • (2006) QSAR Comb Sci , vol.25 , pp. 235-251
    • Leonard, J.T.1    Roy, K.2
  • 28
    • 36749045167 scopus 로고    scopus 로고
    • Exploring the impact of size of training sets for the development of predictive QSAR models
    • DOI 10.1016/j.chemolab.2007.07.004, PII S0169743907001529
    • Roy PP, Leonard JT, Roy K (2008) Exploring the impact of the size of training sets for the development of predictive QSAR models. Chemom Intell Lab Sys 90:31-42 (Pubitemid 350213175)
    • (2008) Chemometrics and Intelligent Laboratory Systems , vol.90 , Issue.1 , pp. 31-42
    • Roy, P.P.1    Leonard, J.T.2    Roy, K.3
  • 29
    • 84861229133 scopus 로고    scopus 로고
    • SPSS Inc Chicago.
    • SPSS Inc. (2011) SPSS. SPSS Inc., Chicago. http://www.spss.com
    • (2011) SPSS
  • 30
    • 84986522856 scopus 로고
    • Poling: Promoting conformational variation
    • Smellie A, Teig SL, Towbin P (1995) Poling: promoting conformational variation. J Comput Chem 16:171-187
    • (1995) J Comput Chem , vol.16 , pp. 171-187
    • Smellie, A.1    Teig, S.L.2    Towbin, P.3
  • 31
    • 77958054159 scopus 로고    scopus 로고
    • Accelrys Inc. Accelrys Inc., San Diego
    • Accelrys Inc (2010) Cerius 2, v.4.10. Accelrys Inc., San Diego
    • (2010) Cerius 2, v.4.10
  • 33
    • 78649543896 scopus 로고    scopus 로고
    • Exploring quantitative structure- activity relationship (QSAR) studies of antioxidant phenolic compounds obtained from traditional Chinese medicinal plants
    • Mitra I, Saha A, Roy K (2010) Exploring quantitative structure- activity relationship (QSAR) studies of antioxidant phenolic compounds obtained from traditional Chinese medicinal plants. Mol Simul 36:1067-1079
    • (2010) Mol Simul , vol.36 , pp. 1067-1079
    • Mitra, I.1    Saha, A.2    Roy, K.3
  • 35
    • 41949116226 scopus 로고    scopus 로고
    • On some aspects of variable selection for partial least squares regressionmodels
    • Roy PP, Roy K (2008) On some aspects of variable selection for partial least squares regressionmodels.QSAR Comb Sci 27:302-313
    • (2008) QSAR Comb Sci , vol.27 , pp. 302-313
    • Roy, P.P.1    Roy, K.2
  • 36
    • 67249129284 scopus 로고    scopus 로고
    • On two novel parameters for validation of predictive QSAR models
    • Roy PP, Paul S, Mitra I, Roy K (2009) On two novel parameters for validation of predictive QSAR models. Molecules 14:1660-1701
    • (2009) Molecules , vol.14 , pp. 1660-1701
    • Roy, P.P.1    Paul, S.2    Mitra, I.3    Roy, K.4
  • 37
    • 74349118668 scopus 로고    scopus 로고
    • On further application of r2 m as a metric for validation of QSAR models
    • Mitra I, Roy PP, Kar S, Ojha PK, Roy K (2010) On further application of r2 m as a metric for validation of QSAR models. J Chemometrics 24:22-33
    • (2010) J Chemometrics , vol.24 , pp. 22-33
    • Mitra, I.1    Roy, P.P.2    Kar, S.3    Ojha, P.K.4    Roy, K.5
  • 38
    • 79955650139 scopus 로고    scopus 로고
    • Further exploring r2 m metrics for validation of QSPR models
    • Ojha PK, Mitra I, Das RN, Roy K (2011) Further exploring r2 m metrics for validation of QSPR models. Chemom Intell Lab Syst 107:194-205
    • (2011) Chemom Intell Lab Syst , vol.107 , pp. 194-205
    • Ojha, P.K.1    Mitra, I.2    Das, R.N.3    Roy, K.4
  • 39
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). Effect of shape on binding of steroids to carrier proteins
    • Cramer RD III, Patterson DE, Bunce JD (1988) Comparative molecular field analysis (CoMFA). Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959-5967
    • (1988) J Am Chem Soc , vol.110 , pp. 5959-5967
    • Cramer Iii, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 40
    • 0027944195 scopus 로고
    • Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity
    • DOI 10.1021/jm00050a010
    • Klebe G, Abraham U,Mietzner T (1994) Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 37:4130-4146 (Pubitemid 24379702)
    • (1994) Journal of Medicinal Chemistry , vol.37 , Issue.24 , pp. 4130-4146
    • Klebe, G.1    Abraham, U.2    Mietzner, T.3
  • 42
    • 0011872065 scopus 로고
    • The principles and practice of molecular mechanics calculations
    • White DNJ (1977) The principles and practice of molecular mechanics calculations. Comput Chem 1:225-233
    • (1977) Comput Chem , vol.1 , pp. 225-233
    • White, D.N.J.1
  • 44
    • 43749099504 scopus 로고    scopus 로고
    • Tripos Inc., St. Louis.
    • Tripos Inc. (2006) SYBYL 7.3. Tripos Inc., St. Louis. http://www. tripos.com
    • (2006) SYBYL 7.3
  • 46
    • 85162676194 scopus 로고
    • PLS regression methods
    • Hoskuldsson A (1987) PLS regression methods. J Chemometrics 2:211-228
    • (1987) J Chemometrics , vol.2 , pp. 211-228
    • Hoskuldsson, A.1
  • 47
    • 20844450385 scopus 로고    scopus 로고
    • Statistical variation in progressive scrambling
    • Clark RD, Fox PC (2004) Statistical variation in progressive scrambling. J Comput Aided Mol Des 18:563-576
    • (2004) J Comput Aided Mol des , vol.18 , pp. 563-576
    • Clark, R.D.1    Fox, P.C.2
  • 50
    • 66149095480 scopus 로고    scopus 로고
    • Group-based QSAR (G-QSAR): Mitigating interpretation challenges in QSAR
    • Ajmani S, Jadhav K, Kulkarni SA (2009) Group-based QSAR (G-QSAR): mitigating interpretation challenges in QSAR. QSAR Comb Sci 28:36-51
    • (2009) QSAR Comb Sci , vol.28 , pp. 36-51
    • Ajmani, S.1    Jadhav, K.2    Kulkarni, S.A.3
  • 51
    • 84861228292 scopus 로고    scopus 로고
    • VLife Sciences Technologies Pvt. Ltd., Pune.
    • VLife Sciences Technologies Pvt. Ltd. (2007) VLife MDS 3.5. VLife Sciences Technologies Pvt. Ltd., Pune. http://www. vlifesciences.com
    • (2007) VLife MDS 3.5
  • 54
    • 0001237510 scopus 로고
    • Asymptotic results for goodness-of-fit statistics with unknown parameters
    • Stephens MA (1976) Asymptotic results for goodness-of-fit statistics with unknown parameters. Ann Stat 4:357-369
    • (1976) Ann Stat , vol.4 , pp. 357-369
    • Stephens, M.A.1
  • 55
    • 84941871856 scopus 로고
    • The Kolmogorov-Smirnov test for goodness of fit
    • Massey FJ Jr (1951) The Kolmogorov-Smirnov test for goodness of fit. J Am Stat Assoc 46:68-78
    • (1951) J Am Stat Assoc , vol.46 , pp. 68-78
    • Massey Jr., F.J.1
  • 56
    • 34247990255 scopus 로고
    • On the Kolmogorov-Smirnov test for normality with mean and variance unknown
    • Lilliefors HW (1967) On the Kolmogorov-Smirnov test for normality with mean and variance unknown. J Am Stat Assoc 64:399-402
    • (1967) J Am Stat Assoc , vol.64 , pp. 399-402
    • Lilliefors, H.W.1
  • 57
    • 34250628103 scopus 로고    scopus 로고
    • Principles of QSAR models validation: Internal and external
    • DOI 10.1002/qsar.200610151
    • Gramatica P (2007) Principles of QSAR models validation: internal and external. QSAR Comb Sci 26:694-701 (Pubitemid 46932857)
    • (2007) QSAR and Combinatorial Science , vol.26 , Issue.5 , pp. 694-701
    • Gramatica, P.1
  • 58
    • 0043132440 scopus 로고    scopus 로고
    • Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs
    • Eriksson L, Jaworska J, Worth AP, Cronin MT, McDowell RM, Gramatica P (2003) Methods for reliability and uncertainty assessment and for applicability evaluations of classificationand regression-based QSARs. Environ Health Perspect 111:1361-1375 (Pubitemid 37021142)
    • (2003) Environmental Health Perspectives , vol.111 , Issue.10 , pp. 1361-1375
    • Eriksson, L.1    Jaworska, J.2    Worth, A.P.3    Cronin, M.T.D.4    McDowell, R.M.5    Gramatica, P.6
  • 60
    • 0033820007 scopus 로고    scopus 로고
    • Calculating partition coefficient by atom-additive method
    • Wang R, Gao Y, Lai L (2000) Calculating partition coefficient by atom-additive method. Perspect Drug Discov 19:47-66
    • (2000) Perspect Drug Discov , vol.19 , pp. 47-66
    • Wang, R.1    Gao, Y.2    Lai, L.3
  • 61
    • 0033557262 scopus 로고    scopus 로고
    • The K correlation index: Theory development and its application in chemometrics
    • DOI 10.1016/S0169-7439(98)00124-5, PII S0169743998001245
    • Todeschini R, Consonni V, Maiocchi A (1999) The K correlation index: theory development and its applications in chemometrics. Chemom Intell Lab Syst 46:13-29 (Pubitemid 29071096)
    • (1999) Chemometrics and Intelligent Laboratory Systems , vol.46 , Issue.1 , pp. 13-29
    • Todeschini, R.1    Consonni, V.2    Maiocchi, A.3
  • 62
    • 0030922822 scopus 로고    scopus 로고
    • Data correlation, number of significant principal components and shape of molecules. The K correlation index
    • DOI 10.1016/S0003-2670(97)00290-0, PII S0003267097002900
    • Todeschini R (1997) Data correlation, number of significant principal components and shape of molecules. The K correlation index. Anal Chim Acta 348:419-430 (Pubitemid 27398522)
    • (1997) Analytica Chimica Acta , vol.348 , Issue.1-3 , pp. 419-430
    • Todeschini, R.1
  • 63
    • 21244473739 scopus 로고    scopus 로고
    • Umetrics AB, Umea.
    • Umetrics AB (2002) SIMCA-P 10.0. Umetrics AB, Umea. http://www.umetrics. com
    • (2002) SIMCA-P 10.0


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.