Prediction model of human ABCC2/MRP2 efflux pump inhibitors: a QSAR study
The overexpression of ABCC2/MRP2, an ATP-binding cassette transporter, contributes to multidrug resistance in cancer cells. In this study, a quantitative structure–activity relationship (QSAR) analysis on ABCC2 inhibitors has been carried out, aiming to establish a computational prediction model for...
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| Published in | Molecular diversity Vol. 25; no. 2; pp. 741 - 751 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Cham
Springer International Publishing
01.05.2021
Springer Nature B.V Springer Verlag |
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| Abstract | The overexpression of ABCC2/MRP2, an ATP-binding cassette transporter, contributes to multidrug resistance in cancer cells. In this study, a quantitative structure–activity relationship (QSAR) analysis on ABCC2 inhibitors has been carried out, aiming to establish a computational prediction model for ABCC2 modulators. Seven classification models and two regression models were built by SONNIA 4.2, and two other regression models were built by MOE 2008.10 based on a data set comprising 372 compounds collected from 16 relevant publications. The CPG-C iABCC2 model for classifying ABCC2 inhibitors has total accuracy of 0.88 and Matthews correlation coefficient MCC = 0.75. The CPG-C iEG model for classifying ABCC2 inhibitors (substrate EG: β-estradiol 17-β-
d
-glucuronide) has total accuracy of 0.91 and MCC = 0.82. The regression model PLS EG-IC
50
for predicting ABCC2 inhibitors (substrate EG) gave root-mean-square error RMSE = 0.26,
Q
2
= 0.73 and
R
pred
2
=
0.63
. The regression model PLS CDCF-IC
50
for predicting ABCC2 inhibitors [substrate CDCF: 5(6)-carboxy-2′,7′-dichlorofluorescein] gave RMSE = 0.31,
Q
2
= 0.74 and
R
pred
2
=
0.67
. Four 2D-QSAR models were applied to 1661 compounds, with results indicating 369 compounds having the ability to reverse the efflux of both EG and CDCF by ABCC2, 152 among them having IC
50
< 100 µM.
Graphic abstract |
|---|---|
| AbstractList | The overexpression of ABCC2/MRP2, an ATP-binding cassette transporter, contributes to multidrug resistance in cancer cells. In this study, a quantitative structure-activity relationship (QSAR) analysis on ABCC2 inhibitors has been carried out, aiming to establish a computational prediction model for ABCC2 modulators. Seven classification models and two regression models were built by SONNIA 4.2, and two other regression models were built by MOE 2008.10 based on a data set comprising 372 compounds collected from 16 relevant publications. The CPG-C iABCC2 model for classifying ABCC2 inhibitors has total accuracy of 0.88 and Matthews correlation coefficient MCC = 0.75. The CPG-C iEG model for classifying ABCC2 inhibitors (substrate EG: β-estradiol 17-β-D-glucuronide) has total accuracy of 0.91 and MCC = 0.82. The regression model PLS EG-IC
for predicting ABCC2 inhibitors (substrate EG) gave root-mean-square error RMSE = 0.26, Q
= 0.73 and [Formula: see text]. The regression model PLS CDCF-IC
for predicting ABCC2 inhibitors [substrate CDCF: 5(6)-carboxy-2',7'-dichlorofluorescein] gave RMSE = 0.31, Q
= 0.74 and [Formula: see text]. Four 2D-QSAR models were applied to 1661 compounds, with results indicating 369 compounds having the ability to reverse the efflux of both EG and CDCF by ABCC2, 152 among them having IC
< 100 µM. The overexpression of ABCC2/MRP2, an ATP-binding cassette transporter, contributes to multidrug resistance in cancer cells. In this study, a quantitative structure–activity relationship (QSAR) analysis on ABCC2 inhibitors has been carried out, aiming to establish a computational prediction model for ABCC2 modulators. Seven classification models and two regression models were built by SONNIA 4.2, and two other regression models were built by MOE 2008.10 based on a data set comprising 372 compounds collected from 16 relevant publications. The CPG-C iABCC2 model for classifying ABCC2 inhibitors has total accuracy of 0.88 and Matthews correlation coefficient MCC = 0.75. The CPG-C iEG model for classifying ABCC2 inhibitors (substrate EG: β-estradiol 17-β-d-glucuronide) has total accuracy of 0.91 and MCC = 0.82. The regression model PLS EG-IC50 for predicting ABCC2 inhibitors (substrate EG) gave root-mean-square error RMSE = 0.26, Q2 = 0.73 and Rpred2=0.63. The regression model PLS CDCF-IC50 for predicting ABCC2 inhibitors [substrate CDCF: 5(6)-carboxy-2′,7′-dichlorofluorescein] gave RMSE = 0.31, Q2 = 0.74 and Rpred2=0.67. Four 2D-QSAR models were applied to 1661 compounds, with results indicating 369 compounds having the ability to reverse the efflux of both EG and CDCF by ABCC2, 152 among them having IC50 < 100 µM.Graphic abstract The overexpression of ABCC2/MRP2, an ATP-binding cassette transporter, contributes to multidrug resistance in cancer cells. In this study, a quantitative structure–activity relationship (QSAR) analysis on ABCC2 inhibitors has been carried out, aiming to establish a computational prediction model for ABCC2 modulators. Seven classification models and two regression models were built by SONNIA 4.2, and two other regression models were built by MOE 2008.10 based on a data set comprising 372 compounds collected from 16 relevant publications. The CPG-C iABCC2 model for classifying ABCC2 inhibitors has total accuracy of 0.88 and Matthews correlation coefficient MCC = 0.75. The CPG-C iEG model for classifying ABCC2 inhibitors (substrate EG: β-estradiol 17-β- d -glucuronide) has total accuracy of 0.91 and MCC = 0.82. The regression model PLS EG-IC 50 for predicting ABCC2 inhibitors (substrate EG) gave root-mean-square error RMSE = 0.26, Q 2 = 0.73 and R pred 2 = 0.63 . The regression model PLS CDCF-IC 50 for predicting ABCC2 inhibitors [substrate CDCF: 5(6)-carboxy-2′,7′-dichlorofluorescein] gave RMSE = 0.31, Q 2 = 0.74 and R pred 2 = 0.67 . Four 2D-QSAR models were applied to 1661 compounds, with results indicating 369 compounds having the ability to reverse the efflux of both EG and CDCF by ABCC2, 152 among them having IC 50 < 100 µM. Graphic abstract The overexpression of ABCC2/MRP2, an ATP-binding cassette transporter, contributes to multidrug resistance in cancer cells. In this study, a quantitative structure-activity relationship (QSAR) analysis on ABCC2 inhibitors has been carried out, aiming to establish a computational prediction model for ABCC2 modulators. Seven classification models and two regression models were built by SONNIA 4.2, and two other regression models were built by MOE 2008.10 based on a data set comprising 372 compounds collected from 16 relevant publications. The CPG-C iABCC2 model for classifying ABCC2 inhibitors has total accuracy of 0.88 and Matthews correlation coefficient MCC = 0.75. The CPG-C iEG model for classifying ABCC2 inhibitors (substrate EG: β-estradiol 17-β-D-glucuronide) has total accuracy of 0.91 and MCC = 0.82. The regression model PLS EG-IC50 for predicting ABCC2 inhibitors (substrate EG) gave root-mean-square error RMSE = 0.26, Q2 = 0.73 and [Formula: see text]. The regression model PLS CDCF-IC50 for predicting ABCC2 inhibitors [substrate CDCF: 5(6)-carboxy-2',7'-dichlorofluorescein] gave RMSE = 0.31, Q2 = 0.74 and [Formula: see text]. Four 2D-QSAR models were applied to 1661 compounds, with results indicating 369 compounds having the ability to reverse the efflux of both EG and CDCF by ABCC2, 152 among them having IC50 < 100 µM. |
| Author | Le, Minh-Tri Tran-Nguyen, Viet-Khoa Tran, Thanh-Dao Thai, Khac-Minh Phan, Thien-Vy |
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| CitedBy_id | crossref_primary_10_1016_j_tips_2023_11_001 crossref_primary_10_1080_07391102_2023_2175381 crossref_primary_10_1097_MD_0000000000028869 crossref_primary_10_1007_s11030_023_10758_9 |
| Cites_doi | 10.1002/0471140856.tx2304s54 10.1023/A:1011064806507 10.1016/j.bmcl.2008.07.127 10.1021/jm7015683 10.1186/1471-2105-8-380 10.1517/17425255.2.3.351 10.1177/1087057108316702 10.1016/j.ijpharm.2011.08.009 10.1016/S1359-6446(01)00173-8 10.1007/s01869-005-1869-8 10.1016/j.chemolab.2015.04.013 10.1096/fj.08-121855 10.1021/tx034101x 10.1208/s12248-009-9117-0 10.1016/j.ejps.2008.11.014 10.1016/j.ejpb.2007.10.003 10.1016/j.ejps.2012.02.016 10.1124/dmd.106.013250 10.1016/j.bmc.2015.04.029 10.1111/j.1747-0285.2008.00705.x 10.1124/jpet.106.110379 10.1016/j.bcp.2004.11.002 10.1007/BF02174528 10.1016/j.chemolab.2011.03.011 10.1042/bj3270305 10.1124/dmd.107.019661 10.1038/clpt.2013.74 10.1364/AO.26.004979 |
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| Keywords | Virtual screening Regression Inhibitor ABCC2 QSAR Classification |
| Language | English |
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| References | Zhang, Xiang, Zhao, Wei, Yang (CR4) 2009; 36 Heredi-Szabo, Kis, Molnar, Gyorfi, Krajcsi (CR9) 2008; 13 Hecht-Nielsen (CR28) 1987; 26 van Zanden, Wortelboer, Bijlsma, Punt, Usta, van Bladeren, Rietjens, Cnubben (CR17) 2005; 69 Wissel, Kudryavtsev, Ghemtio, Tammela, Wipf, Yliperttula, Finel, Urtti, Kidron, Xhaard (CR2) 2015; 23 Pedersen, Matsson, Bergström, Norinder, Hoogstraate, Artursson (CR13) 2008; 51 CR33 Thai, Ecker (CR30) 2008; 72 El-Sheikh, van den Heuvel, Koenderink, Russel (CR6) 2007; 320 Procko, O’Mara, Bennett, Tieleman, Gaudet (CR14) 2009; 23 Kidron, Wissel, Manevski, Häkli, Ketola, Finel, Yliperttula, Xhaard, Urtti (CR11) 2012; 46 Hillgren, Keppler, Zur, Giacomini, Stieger, Cass, Zhang (CR5) 2013; 94 Cramer (CR25) 1993; 1 Roy, Kar, Ambure (CR29) 2015; 145 Jedlitschky, Leier, Buchholz, Hummel-Eisenbeiss, Burchell, Keppler (CR10) 1997; 327 Jedlitschky, Hoffmann, Kroemer (CR1) 2006; 2 Terfloth, Gasteiger (CR27) 2001; 6 Carugo (CR31) 2007; 8 Förster, Volz, Fricker (CR7) 2008; 69 Leyers, Häcker, Wiendlocha, Gütschow, Wiese (CR12) 2008; 18 CR24 CR23 CR22 Xing, Hu, Lai (CR3) 2009; 11 Vadlapatla, Vadlapudi, Kwatra, Pal, Mitra (CR16) 2011; 420 Lai, Xing, Poda, Hu (CR21) 2007; 35 Ajith (CR26) 2005 Ojha, Mitra, Das, Roy (CR32) 2011; 107 Han, Kato, Haramura, Ohta, Matsuoka, Sugiyama (CR8) 2001; 18 Slot, Wise, Deeley, Monks, Cole (CR15) 2008; 36 Hirono, Nakagome, Imai, Maeda, Kusuhara, Sugiyama (CR19) 2005; 22 Wortelboer, Usta, van der Velde, Boersma, Spenkelink, van Zanden, Rietjens, van Bladeren, Cnubben (CR18) 2003; 16 Herédi-Szabó, Kis, Krajcsi (CR20) 2012; 54 G Wissel (10047_CR2) 2015; 23 G Jedlitschky (10047_CR10) 1997; 327 K Roy (10047_CR29) 2015; 145 PK Ojha (10047_CR32) 2011; 107 HM Wortelboer (10047_CR18) 2003; 16 R Hecht-Nielsen (10047_CR28) 1987; 26 10047_CR24 O Carugo (10047_CR31) 2007; 8 YH Han (10047_CR8) 2001; 18 JJ van Zanden (10047_CR17) 2005; 69 10047_CR22 10047_CR23 S Hirono (10047_CR19) 2005; 22 H Zhang (10047_CR4) 2009; 36 H Kidron (10047_CR11) 2012; 46 Y Lai (10047_CR21) 2007; 35 KM Hillgren (10047_CR5) 2013; 94 A Ajith (10047_CR26) 2005 G Jedlitschky (10047_CR1) 2006; 2 AJ Slot (10047_CR15) 2008; 36 10047_CR33 L Xing (10047_CR3) 2009; 11 RK Vadlapatla (10047_CR16) 2011; 420 S Leyers (10047_CR12) 2008; 18 L Terfloth (10047_CR27) 2001; 6 AA El-Sheikh (10047_CR6) 2007; 320 JM Pedersen (10047_CR13) 2008; 51 K Herédi-Szabó (10047_CR20) 2012; 54 F Förster (10047_CR7) 2008; 69 K Heredi-Szabo (10047_CR9) 2008; 13 E Procko (10047_CR14) 2009; 23 RD Cramer (10047_CR25) 1993; 1 KM Thai (10047_CR30) 2008; 72 |
| References_xml | – ident: CR22 – volume: 54 start-page: 23.4.1 year: 2012 end-page: 23.4.16 ident: CR20 article-title: The vesicular transport assay: validated in vitro methods to study drug-mediated inhibition of canalicular efflux transporters ABCB11/BSEP and ABCC2/MRP2 publication-title: Curr Protoc Toxicol doi: 10.1002/0471140856.tx2304s54 contributor: fullname: Krajcsi – volume: 18 start-page: 579 year: 2001 end-page: 586 ident: CR8 article-title: Physicochemical parameters responsible for the affinity of methotrexate analogs for rat canalicular multispecific organic anion transporter (cMOAT/MRP2) publication-title: Pharm Res doi: 10.1023/A:1011064806507 contributor: fullname: Sugiyama – volume: 18 start-page: 4761 year: 2008 end-page: 4763 ident: CR12 article-title: A 4-aminobenzoic acid derivative as novel lead for selective inhibitors of multidrug resistance-associated proteins publication-title: Bioorg Med Chem Lett doi: 10.1016/j.bmcl.2008.07.127 contributor: fullname: Wiese – volume: 51 start-page: 3275 year: 2008 end-page: 3287 ident: CR13 article-title: Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2) publication-title: J Med Chem doi: 10.1021/jm7015683 contributor: fullname: Artursson – year: 2005 ident: CR26 publication-title: Artificial neural networks handbook of measuring system design contributor: fullname: Ajith – volume: 8 start-page: 380 year: 2007 ident: CR31 article-title: Detailed estimation of bioinformatics prediction reliability through the fragmented prediction performance plots publication-title: BMC Bioinform doi: 10.1186/1471-2105-8-380 contributor: fullname: Carugo – ident: CR33 – volume: 2 start-page: 351 year: 2006 end-page: 366 ident: CR1 article-title: Structure and function of the MRP2 (ABCC2) protein and its role in drug disposition publication-title: Expert Opin Drug Metab Toxicol doi: 10.1517/17425255.2.3.351 contributor: fullname: Kroemer – volume: 13 start-page: 295 year: 2008 end-page: 301 ident: CR9 article-title: Characterization of 5(6)-carboxy-2′,7′-dichlorofluorescein transport by MRP2 and utilization of this substrate as a fluorescent surrogate for LTC4 publication-title: J Biomol Screen doi: 10.1177/1087057108316702 contributor: fullname: Krajcsi – volume: 420 start-page: 26 year: 2011 end-page: 33 ident: CR16 article-title: Differential effect of P-gp and MRP2 on cellular translocation of gemifloxacin publication-title: Int J Pharm doi: 10.1016/j.ijpharm.2011.08.009 contributor: fullname: Mitra – volume: 6 start-page: 102 year: 2001 end-page: 108 ident: CR27 article-title: Neural networks and genetic algorithms in drug design publication-title: Drug Discov Today doi: 10.1016/S1359-6446(01)00173-8 contributor: fullname: Gasteiger – volume: 22 start-page: 260 year: 2005 end-page: 269 ident: CR19 article-title: Estimation of the three-dimensional pharmacophore of ligands for rat multidrug-resistance-associated protein 2 using ligand-based drug design techniques publication-title: Pharm Res doi: 10.1007/s01869-005-1869-8 contributor: fullname: Sugiyama – volume: 145 start-page: 22 year: 2015 end-page: 29 ident: CR29 article-title: On a simple approach for determining applicability domain of QSAR models publication-title: Chemom Intellig Lab Syst doi: 10.1016/j.chemolab.2015.04.013 contributor: fullname: Ambure – volume: 23 start-page: 1287 year: 2009 end-page: 1302 ident: CR14 article-title: The mechanism of ABC transporters: general lessons from structural and functional studies of an antigenic peptide transporter publication-title: FASEB J doi: 10.1096/fj.08-121855 contributor: fullname: Gaudet – volume: 16 start-page: 1642 year: 2003 end-page: 1651 ident: CR18 article-title: Interplay between MRP inhibition and metabolism of MRP inhibitors: the case of curcumin publication-title: Chem Res Toxicol doi: 10.1021/tx034101x contributor: fullname: Cnubben – ident: CR23 – volume: 11 start-page: 406 year: 2009 end-page: 413 ident: CR3 article-title: Advancement of structure-activity relationship of multidrug resistance-associated protein 2 interactions publication-title: AAPS J doi: 10.1208/s12248-009-9117-0 contributor: fullname: Lai – volume: 36 start-page: 451 year: 2009 end-page: 457 ident: CR4 article-title: Support vector machine and pharmacophore-based prediction models of multidrug-resistance protein 2 (MRP2) inhibitors publication-title: Eur J Pharm Sci doi: 10.1016/j.ejps.2008.11.014 contributor: fullname: Yang – volume: 69 start-page: 396 year: 2008 end-page: 403 ident: CR7 article-title: Compound profiling for ABCC2 (MRP2) using a fluorescent microplate assay system publication-title: Eur J Pharm Biopharm doi: 10.1016/j.ejpb.2007.10.003 contributor: fullname: Fricker – volume: 46 start-page: 100 year: 2012 end-page: 105 ident: CR11 article-title: Impact of probe compound in MRP2 vesicular transport assays publication-title: Eur J Pharm Sci doi: 10.1016/j.ejps.2012.02.016 contributor: fullname: Urtti – volume: 35 start-page: 937 year: 2007 end-page: 945 ident: CR21 article-title: Structure–activity relationships for interaction with multidrug resistance protein 2 (ABCC2/MRP2): the role of torsion angle for a series of biphenyl-substituted heterocycles publication-title: Drug Metab Dispos doi: 10.1124/dmd.106.013250 contributor: fullname: Hu – volume: 23 start-page: 3513 year: 2015 end-page: 3525 ident: CR2 article-title: Exploring the structure–activity relationships of ABCC2 modulators using a screening approach publication-title: Biorg Med Chem doi: 10.1016/j.bmc.2015.04.029 contributor: fullname: Xhaard – volume: 72 start-page: 279 year: 2008 end-page: 289 ident: CR30 article-title: Classification models for hERG inhibitors by counter-propagation neural networks publication-title: Chem Biol Drug Des doi: 10.1111/j.1747-0285.2008.00705.x contributor: fullname: Ecker – volume: 320 start-page: 229 year: 2007 end-page: 235 ident: CR6 article-title: Interaction of nonsteroidal anti-inflammatory drugs with multidrug resistance protein (MRP) 2/ABCC2- and MRP4/ABCC4-mediated methotrexate transport publication-title: J Pharmacol Exp Ther doi: 10.1124/jpet.106.110379 contributor: fullname: Russel – volume: 69 start-page: 699 year: 2005 end-page: 708 ident: CR17 article-title: Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2 publication-title: Biochem Pharmacol doi: 10.1016/j.bcp.2004.11.002 contributor: fullname: Cnubben – volume: 1 start-page: 269 year: 1993 end-page: 278 ident: CR25 article-title: Partial least squares (PLS): its strengths and limitations publication-title: Perspect Drug Discov Des doi: 10.1007/BF02174528 contributor: fullname: Cramer – volume: 107 start-page: 194 year: 2011 end-page: 205 ident: CR32 article-title: Further exploring metrics for validation of QSPR models publication-title: Chemom Intellig Lab Syst doi: 10.1016/j.chemolab.2011.03.011 contributor: fullname: Roy – volume: 327 start-page: 305 year: 1997 end-page: 310 ident: CR10 article-title: ATP-dependent transport of bilirubin glucuronides by the multidrug resistance protein MRP1 and its hepatocyte canalicular isoform MRP2 publication-title: Biochem J doi: 10.1042/bj3270305 contributor: fullname: Keppler – volume: 36 start-page: 552 year: 2008 end-page: 560 ident: CR15 article-title: Modulation of human multidrug resistance protein (MRP) 1 (ABCC1) and MRP2 (ABCC2) transport activities by endogenous and exogenous glutathione-conjugated catechol metabolites publication-title: Drug Metab Dispos doi: 10.1124/dmd.107.019661 contributor: fullname: Cole – volume: 94 start-page: 52 year: 2013 end-page: 63 ident: CR5 article-title: Emerging transporters of clinical importance: an update from the International Transporter Consortium publication-title: Clin Pharmacol Ther doi: 10.1038/clpt.2013.74 contributor: fullname: Zhang – ident: CR24 – volume: 26 start-page: 4979 year: 1987 end-page: 4984 ident: CR28 article-title: Counterpropagation networks publication-title: Appl Opt doi: 10.1364/AO.26.004979 contributor: fullname: Hecht-Nielsen – volume: 18 start-page: 4761 year: 2008 ident: 10047_CR12 publication-title: Bioorg Med Chem Lett doi: 10.1016/j.bmcl.2008.07.127 contributor: fullname: S Leyers – ident: 10047_CR22 – volume: 6 start-page: 102 year: 2001 ident: 10047_CR27 publication-title: Drug Discov Today doi: 10.1016/S1359-6446(01)00173-8 contributor: fullname: L Terfloth – volume: 13 start-page: 295 year: 2008 ident: 10047_CR9 publication-title: J Biomol Screen doi: 10.1177/1087057108316702 contributor: fullname: K Heredi-Szabo – volume: 327 start-page: 305 year: 1997 ident: 10047_CR10 publication-title: Biochem J doi: 10.1042/bj3270305 contributor: fullname: G Jedlitschky – volume: 16 start-page: 1642 year: 2003 ident: 10047_CR18 publication-title: Chem Res Toxicol doi: 10.1021/tx034101x contributor: fullname: HM Wortelboer – ident: 10047_CR24 – volume: 72 start-page: 279 year: 2008 ident: 10047_CR30 publication-title: Chem Biol Drug Des doi: 10.1111/j.1747-0285.2008.00705.x contributor: fullname: KM Thai – volume: 23 start-page: 1287 year: 2009 ident: 10047_CR14 publication-title: FASEB J doi: 10.1096/fj.08-121855 contributor: fullname: E Procko – volume: 1 start-page: 269 year: 1993 ident: 10047_CR25 publication-title: Perspect Drug Discov Des doi: 10.1007/BF02174528 contributor: fullname: RD Cramer – volume: 69 start-page: 396 year: 2008 ident: 10047_CR7 publication-title: Eur J Pharm Biopharm doi: 10.1016/j.ejpb.2007.10.003 contributor: fullname: F Förster – volume: 420 start-page: 26 year: 2011 ident: 10047_CR16 publication-title: Int J Pharm doi: 10.1016/j.ijpharm.2011.08.009 contributor: fullname: RK Vadlapatla – volume: 94 start-page: 52 year: 2013 ident: 10047_CR5 publication-title: Clin Pharmacol Ther doi: 10.1038/clpt.2013.74 contributor: fullname: KM Hillgren – ident: 10047_CR33 – volume: 11 start-page: 406 year: 2009 ident: 10047_CR3 publication-title: AAPS J doi: 10.1208/s12248-009-9117-0 contributor: fullname: L Xing – volume: 36 start-page: 552 year: 2008 ident: 10047_CR15 publication-title: Drug Metab Dispos doi: 10.1124/dmd.107.019661 contributor: fullname: AJ Slot – volume: 69 start-page: 699 year: 2005 ident: 10047_CR17 publication-title: Biochem Pharmacol doi: 10.1016/j.bcp.2004.11.002 contributor: fullname: JJ van Zanden – volume: 26 start-page: 4979 year: 1987 ident: 10047_CR28 publication-title: Appl Opt doi: 10.1364/AO.26.004979 contributor: fullname: R Hecht-Nielsen – volume: 23 start-page: 3513 year: 2015 ident: 10047_CR2 publication-title: Biorg Med Chem doi: 10.1016/j.bmc.2015.04.029 contributor: fullname: G Wissel – volume-title: Artificial neural networks handbook of measuring system design year: 2005 ident: 10047_CR26 contributor: fullname: A Ajith – volume: 18 start-page: 579 year: 2001 ident: 10047_CR8 publication-title: Pharm Res doi: 10.1023/A:1011064806507 contributor: fullname: YH Han – volume: 46 start-page: 100 year: 2012 ident: 10047_CR11 publication-title: Eur J Pharm Sci doi: 10.1016/j.ejps.2012.02.016 contributor: fullname: H Kidron – volume: 2 start-page: 351 year: 2006 ident: 10047_CR1 publication-title: Expert Opin Drug Metab Toxicol doi: 10.1517/17425255.2.3.351 contributor: fullname: G Jedlitschky – volume: 8 start-page: 380 year: 2007 ident: 10047_CR31 publication-title: BMC Bioinform doi: 10.1186/1471-2105-8-380 contributor: fullname: O Carugo – volume: 36 start-page: 451 year: 2009 ident: 10047_CR4 publication-title: Eur J Pharm Sci doi: 10.1016/j.ejps.2008.11.014 contributor: fullname: H Zhang – volume: 51 start-page: 3275 year: 2008 ident: 10047_CR13 publication-title: J Med Chem doi: 10.1021/jm7015683 contributor: fullname: JM Pedersen – ident: 10047_CR23 – volume: 320 start-page: 229 year: 2007 ident: 10047_CR6 publication-title: J Pharmacol Exp Ther doi: 10.1124/jpet.106.110379 contributor: fullname: AA El-Sheikh – volume: 107 start-page: 194 year: 2011 ident: 10047_CR32 publication-title: Chemom Intellig Lab Syst doi: 10.1016/j.chemolab.2011.03.011 contributor: fullname: PK Ojha – volume: 54 start-page: 23.4.1 year: 2012 ident: 10047_CR20 publication-title: Curr Protoc Toxicol doi: 10.1002/0471140856.tx2304s54 contributor: fullname: K Herédi-Szabó – volume: 145 start-page: 22 year: 2015 ident: 10047_CR29 publication-title: Chemom Intellig Lab Syst doi: 10.1016/j.chemolab.2015.04.013 contributor: fullname: K Roy – volume: 22 start-page: 260 year: 2005 ident: 10047_CR19 publication-title: Pharm Res doi: 10.1007/s01869-005-1869-8 contributor: fullname: S Hirono – volume: 35 start-page: 937 year: 2007 ident: 10047_CR21 publication-title: Drug Metab Dispos doi: 10.1124/dmd.106.013250 contributor: fullname: Y Lai |
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| Title | Prediction model of human ABCC2/MRP2 efflux pump inhibitors: a QSAR study |
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