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Volumn 46, Issue 8, 2003, Pages 1429-1439

Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: Requirements for subtype selectivity and intrinsic activity modulation

Author keywords

[No Author keywords available]

Indexed keywords

3 METHOXYBENZYLBENZOFURAN; BENZOFURAN DERIVATIVE; MELATONIN 1 RECEPTOR; MELATONIN 2 RECEPTOR; MELATONIN DERIVATIVE; MELATONIN RECEPTOR AGONIST; MELATONIN RECEPTOR ANTAGONIST; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

EID: 0037431390     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020982d     Document Type: Article
Times cited : (58)

References (69)
  • 1
    • 0025166184 scopus 로고
    • Effects of melatonin on vertebrate circadian system
    • Cassone, V. M. Effects of melatonin on vertebrate circadian system. Trends Neurosci. 1990, 13, 457-464.
    • (1990) Trends Neurosci. , vol.13 , pp. 457-464
    • Cassone, V.M.1
  • 2
    • 0031968965 scopus 로고    scopus 로고
    • Melatonin - The key to the gate of sleep
    • Shochat, T.; Haimov, I.; Lavie, P. Melatonin - the key to the gate of sleep. Ann. Med. 1998, 30, 109-114.
    • (1998) Ann. Med. , vol.30 , pp. 109-114
    • Shochat, T.1    Haimov, I.2    Lavie, P.3
  • 4
    • 0032510504 scopus 로고    scopus 로고
    • Melatonin mediates two distinct responses in vascular smooth muscle
    • Doolen, S.; Krause, D. N.; Dubocovich, M. L.; Duckles, S. P. Melatonin mediates two distinct responses in vascular smooth muscle. Eur. J. Pharmacol. 1998, 345, 67-69.
    • (1998) Eur. J. Pharmacol. , vol.345 , pp. 67-69
    • Doolen, S.1    Krause, D.N.2    Dubocovich, M.L.3    Duckles, S.P.4
  • 5
    • 0033135083 scopus 로고    scopus 로고
    • Effects of melatonin on vascular reactivity, catecholamine levels, and blood pressure in healthy men
    • Arangino, S.; Cagnacci, A,; Angiolucci, M.; Vacca, A. M.; Longu, G.; Volpe, A.; Melis, G. B. Effects of melatonin on vascular reactivity, catecholamine levels, and blood pressure in healthy men. Am. J. Cardiol. 1999, 83, 1417-1419.
    • (1999) Am. J. Cardiol. , vol.83 , pp. 1417-1419
    • Arangino, S.1    Cagnacci, A.2    Angiolucci, M.3    Vacca, A.M.4    Longu, G.5    Volpe, A.6    Melis, G.B.7
  • 6
    • 0034933071 scopus 로고    scopus 로고
    • New issues about melatonin and its effects on the digestive System
    • Motilva, V.; Cabeza, J.; Alarcón de la Lastra, C. New issues about melatonin and its effects on the digestive System. Curr. Pharm. Des. 2001, 7, 909-931.
    • (2001) Curr. Pharm. Des. , vol.7 , pp. 909-931
    • Motilva, V.1    Cabeza, J.2    Alarcón de la Lastra, C.3
  • 7
    • 0031942551 scopus 로고    scopus 로고
    • Melatonin and its physiological and therapeutic properties
    • Nowak, J. Z.; Zawilska, J. B. Melatonin and its physiological and therapeutic properties. Pharm. World Sci. 1998, 20, 18-27.
    • (1998) Pharm. World Sci. , vol.20 , pp. 18-27
    • Nowak, J.Z.1    Zawilska, J.B.2
  • 8
    • 0033389698 scopus 로고    scopus 로고
    • Melatonin and clinical application
    • Wetterberg, L. Melatonin and clinical application. Reprod., Nutr., Dev. 1999, 39, 367-382.
    • (1999) Reprod., Nutr., Dev. , vol.39 , pp. 367-382
    • Wetterberg, L.1
  • 9
    • 0033740169 scopus 로고    scopus 로고
    • Melatonin receptors as potential targets for drug discovery
    • Li, P.-K.; Witt-Enderby, P. A. Melatonin receptors as potential targets for drug discovery. Drugs Future 2000, 25, 945-957.
    • (2000) Drugs Future , vol.25 , pp. 945-957
    • Li, P.-K.1    Witt-Enderby, P.A.2
  • 12
    • 0033368290 scopus 로고    scopus 로고
    • Melatonin mediates seasonal adjustments in immune function
    • Nelson, R. J.; Drazen, D. L. Melatonin mediates seasonal adjustments in immune function. Reprod., Nutr., Dev. 1999, 39, 383-398.
    • (1999) Reprod., Nutr., Dev. , vol.39 , pp. 383-398
    • Nelson, R.J.1    Drazen, D.L.2
  • 13
    • 0032901972 scopus 로고    scopus 로고
    • Decreased melatonin levels in postmortem cerebrospinal fluid in relation to ageing, Alzheimer's desease, and apolipoprotein E-epsilon4/4 genotype
    • Liu, R. Y.; Zhou, J. N.; van Heerikhuize, J.; Hofman, M. A.; Swaab, D. F. Decreased melatonin levels in postmortem cerebrospinal fluid in relation to ageing, Alzheimer's desease, and apolipoprotein E-epsilon4/4 genotype. J. Clin. Endocrinol. Metab. 1999, 84, 323-327.
    • (1999) J. Clin. Endocrinol. Metab. , vol.84 , pp. 323-327
    • Liu, R.Y.1    Zhou, J.N.2    Van Heerikhuize, J.3    Hofman, M.A.4    Swaab, D.F.5
  • 15
    • 0035221189 scopus 로고    scopus 로고
    • Nuclear melatonin receptors
    • Smirnov, A. N. Nuclear Melatonin Receptors. Biochemistry (Moscow) 2001, 66, 19-26.
    • (2001) Biochemistry (Moscow) , vol.66 , pp. 19-26
    • Smirnov, A.N.1
  • 16
    • 3543128199 scopus 로고    scopus 로고
    • Membrane-bound calmodulin in Xenopus Laevis oocytes as a novel binding site for melatonin
    • Paz Romero, M.; García-Pergañeda, A.; Guerrero, J. M.; Osuna, C. Membrane-bound calmodulin in Xenopus Laevis oocytes as a novel binding site for melatonin. FASEB J. 1998, 12, 1401-1408.
    • (1998) FASEB J. , vol.12 , pp. 1401-1408
    • Paz Romero, M.1    García-Pergañeda, A.2    Guerrero, J.M.3    Osuna, C.4
  • 17
    • 0028909154 scopus 로고
    • Structural requirements at the melatonin receptor
    • Sugden, D.; Chong, N. W. S.; Lewis, D. F. V. Structural requirements at the melatonin receptor. Br. J. Pharmacol. 1995, 114, 618-623.
    • (1995) Br. J. Pharmacol. , vol.114 , pp. 618-623
    • Sugden, D.1    Chong, N.W.S.2    Lewis, D.F.V.3
  • 18
    • 0030220790 scopus 로고    scopus 로고
    • The high affinity melatonin binding site probed with conformationally restricted ligands-II. Homology modeling of the receptor
    • Grol, C. J.; Jansen, J. M. The high affinity melatonin binding site probed with conformationally restricted ligands-II. Homology modeling of the receptor. Bioorg. Med. Chem. 1996, 4, 1333-1339.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 1333-1339
    • Grol, C.J.1    Jansen, J.M.2
  • 19
    • 0030598632 scopus 로고    scopus 로고
    • A rhodopsin-based model for melatonin recognition at its G protein-coupled receptor
    • Navajas, C.; Kokkola, T.; Poso, A.; Honka, N.; Gynther, J.; Laitinen, J. T. A rhodopsin-based model for melatonin recognition at its G protein-coupled receptor. Eur. J. Pharmacol. 1996, 304, 173-183.
    • (1996) Eur. J. Pharmacol. , vol.304 , pp. 173-183
    • Navajas, C.1    Kokkola, T.2    Poso, A.3    Honka, N.4    Gynther, J.5    Laitinen, J.T.6
  • 23
    • 0032161469 scopus 로고    scopus 로고
    • Selective MT2 melatonin receptor antagonists block melatonin-mediated phase advances of circadian rhythms
    • Dubocovich, M. L.; Yun, K.; Al-Ghoul, W. M.; Benloucif, S.; Masana, M. I. Selective MT2 melatonin receptor antagonists block melatonin-mediated phase advances of circadian rhythms. FASEB J. 1998, 12, 1211-1220.
    • (1998) FASEB J. , vol.12 , pp. 1211-1220
    • Dubocovich, M.L.1    Yun, K.2    Al-Ghoul, W.M.3    Benloucif, S.4    Masana, M.I.5
  • 24
    • 0035008125 scopus 로고    scopus 로고
    • Activation of MT2 melatonin receptors in rat suprachiasmatic nucleus phase advances the circadian clock
    • Hunt, A. E.; Al-Ghoul, W. M.; Gillitte, M. U.; Dubocovich, M. L. Activation of MT2 melatonin receptors in rat suprachiasmatic nucleus phase advances the circadian clock. Am. J. Physiol.: Cell Physiol. 2001, 280, C110-C118.
    • (2001) Am. J. Physiol.: Cell Physiol. , vol.280
    • Hunt, A.E.1    Al-Ghoul, W.M.2    Gillitte, M.U.3    Dubocovich, M.L.4
  • 25
    • 0034877393 scopus 로고    scopus 로고
    • Melatonin receptor subtype MT2 (Mel1b) and not mt1 (Mel1a) is associated with melatonin-induced enhancement of cell-mediated and humoral immunity
    • Drazen, D. L.; Nelson, R. J. Melatonin receptor subtype MT2 (Mel1b) and not mt1 (Mel1a) is associated with melatonin-induced enhancement of cell-mediated and humoral immunity. Neuroendocrinology 2001, 74, 178-184.
    • (2001) Neuroendocrinology , vol.74 , pp. 178-184
    • Drazen, D.L.1    Nelson, R.J.2
  • 28
    • 0027482462 scopus 로고
    • 2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents
    • Copinga, S.; Tepper, P. G.; Grol, C. J.; Horn, A. S.; Dubocovich, M. L. 2-Amido-8-methoxytetralins: a series of nonindolic melatonin-like agents. J. Med. Chem. 1993, 36, 2891-2898.
    • (1993) J. Med. Chem. , vol.36 , pp. 2891-2898
    • Copinga, S.1    Tepper, P.G.2    Grol, C.J.3    Horn, A.S.4    Dubocovich, M.L.5
  • 30
    • 0028300079 scopus 로고
    • N-Acyl-3-amino-5-methoxychromans: A new series of non-indolic melatonin analogues
    • Sugden, D. N-Acyl-3-amino-5-methoxychromans: a new series of non-indolic melatonin analogues. Eur. J. Pharmacol. 1994, 254, 271-275.
    • (1994) Eur. J. Pharmacol. , vol.254 , pp. 271-275
    • Sugden, D.1
  • 33
    • 0029930956 scopus 로고    scopus 로고
    • Mapping the melatonin receptor. 4. Comparison of the binding affinities of a series of substituted phenylalkyl amides
    • Garratt, P. J.; Travard, S.; Vonhoff, S.; Tsotinis, A.; Sugden, D. Mapping the melatonin receptor. 4. Comparison of the binding affinities of a series of substituted phenylalkyl amides. J. Med. Chem. 1996, 39, 1797-1805.
    • (1996) J. Med. Chem. , vol.39 , pp. 1797-1805
    • Garratt, P.J.1    Travard, S.2    Vonhoff, S.3    Tsotinis, A.4    Sugden, D.5
  • 34
    • 0030967890 scopus 로고    scopus 로고
    • Synthesis and receptor binding studies of quinolinic derivatives as melatonin receptor ligands
    • Li, P.-K.; Chu, G.-H.; Gillen, M. L.; Witt-Enderby, P. A. Synthesis and receptor binding studies of quinolinic derivatives as melatonin receptor ligands. Bioorg. Med. Chem. Lett. 1997, 7, 2177-2180.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 2177-2180
    • Li, P.-K.1    Chu, G.-H.2    Gillen, M.L.3    Witt-Enderby, P.A.4
  • 35
    • 0032510073 scopus 로고    scopus 로고
    • Mapping the melatonin receptor. 5. Melatonin agonists and antagonists derived from tetrahydrocyclopent[b]indoles, tetrahydrocarbazoles and hexahydrocyclohept-[b]indoles
    • Davies, D. J.; Garratt, P. J.; Tocher, D. A.; Vonhoff, S.; Davies, J.; Teh, M. T.; Sugden, D. Mapping the melatonin receptor. 5. Melatonin agonists and antagonists derived from tetrahydrocyclopent[b]indoles, tetrahydrocarbazoles and hexahydrocyclohept-[b]indoles. J. Med. Chem. 1998, 41, 451-467.
    • (1998) J. Med. Chem. , vol.41 , pp. 451-467
    • Davies, D.J.1    Garratt, P.J.2    Tocher, D.A.3    Vonhoff, S.4    Davies, J.5    Teh, M.T.6    Sugden, D.7
  • 38
    • 0034704888 scopus 로고    scopus 로고
    • Mapping the melatonin receptor. 6. Melatonin agonists and antagonists derived from 6H-isoindolo[2,1-a]indoles, 5,6-dihydroindolo[2,1-a]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]indoles
    • Faust, R.; Garratt, P. J.; Jones, R.; Yeh, L.-K.; Tsotinis, A.; Panoussopoulou, M.; Calogeropoulou, T.; Teh, M.-T.; Sugden, D. Mapping the melatonin receptor. 6. Melatonin agonists and antagonists derived from 6H-isoindolo[2,1-a]indoles, 5,6-dihydroindolo[2,1-a]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]indoles. J. Med. Chem. 2000, 43, 1050-1061.
    • (2000) J. Med. Chem. , vol.43 , pp. 1050-1061
    • Faust, R.1    Garratt, P.J.2    Jones, R.3    Yeh, L.-K.4    Tsotinis, A.5    Panoussopoulou, M.6    Calogeropoulou, T.7    Teh, M.-T.8    Sugden, D.9
  • 40
    • 0030201178 scopus 로고    scopus 로고
    • The high affinity melatonin binding site probed with conformationally restricted ligands - I. Pharmacophore and minireceptor models
    • Jansen, J. M.; Copinga, S.; Gruppen, G.; Molinari, E. J.; Dubocovich, M. L.; Grol, C. J. The high affinity melatonin binding site probed with conformationally restricted ligands - I. Pharmacophore and minireceptor models. Bioorg. Med. Chem. 1996, 4, 1321-1332.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 1321-1332
    • Jansen, J.M.1    Copinga, S.2    Gruppen, G.3    Molinari, E.J.4    Dubocovich, M.L.5    Grol, C.J.6
  • 41
    • 0032487939 scopus 로고    scopus 로고
    • Pharmacophoric search and 3D-QSAR comparative molecular field analysis studies on agonists of melatonin sheep receptors
    • Marot, C.; Chavatte, P.; Morin-Allory, L.; Viaud, M. C.; Guillaumet, G.; Renard, P.; Lesieur, D.; Michel, A. Pharmacophoric search and 3D-QSAR comparative molecular field analysis studies on agonists of melatonin sheep receptors. J. Med. Chem. 1998, 41, 4453-4465.
    • (1998) J. Med. Chem. , vol.41 , pp. 4453-4465
    • Marot, C.1    Chavatte, P.2    Morin-Allory, L.3    Viaud, M.C.4    Guillaumet, G.5    Renard, P.6    Lesieur, D.7    Michel, A.8
  • 42
    • 0031771553 scopus 로고    scopus 로고
    • Comparison of the structure-activity relationships of melatonin receptor agonists and antagonists: Lengthening the N-acyl side-chain has differing effects on potency on Xenopus melanophores
    • Teh, M. T.; Sugden, D. Comparison of the structure-activity relationships of melatonin receptor agonists and antagonists: lengthening the N-acyl side-chain has differing effects on potency on Xenopus melanophores. Naunyn.Schmiedeberg's Arch. Pharmacol. 1998, 358, 522-528.
    • (1998) Naunyn.Schmiedeberg's Arch. Pharmacol. , vol.358 , pp. 522-528
    • Teh, M.T.1    Sugden, D.2
  • 43
    • 0033002220 scopus 로고    scopus 로고
    • Structure-affinity relationships of indole-based melatonin analogs
    • Spadoni, G.; Mor, M.; Tarzia, G. Structure-affinity relationships of indole-based melatonin analogs. Biol. Signals Recept. 1999, 8, 15-23.
    • (1999) Biol. Signals Recept. , vol.8 , pp. 15-23
    • Spadoni, G.1    Mor, M.2    Tarzia, G.3
  • 46
    • 0031052115 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationship of melatonin receptor ligands: A comparative molecular field analysis study
    • Sicsic, S.; Serraz, I.; Andrieux, J.; Brémont, B.; Mathé-Allainmat, M.; Poncet, A.; Shen, S.; Langlois, M. Three-dimensional quantitative structure-activity relationship of melatonin receptor ligands: a comparative molecular field analysis study. J. Med. Chem. 1997, 40, 739-748.
    • (1997) J. Med. Chem. , vol.40 , pp. 739-748
    • Sicsic, S.1    Serraz, I.2    Andrieux, J.3    Brémont, B.4    Mathé-Allainmat, M.5    Poncet, A.6    Shen, S.7    Langlois, M.8
  • 50
    • 0035371006 scopus 로고    scopus 로고
    • Comparative pharmacological studies of melatonin receptors: MT1, MT2 and MT3/QR2. Tissue distribution of MT3/QR2
    • Nosjean, O.; Nicolas, J.-P.; Klupsch, F.; Delagrange, P.; Canet, E.; Boutin, J. A. Comparative pharmacological studies of melatonin receptors: MT1, MT2 and MT3/QR2. Tissue distribution of MT3/QR2. Biochem. Pharmacol. 2001, 61, 1369-1379.
    • (2001) Biochem. Pharmacol. , vol.61 , pp. 1369-1379
    • Nosjean, O.1    Nicolas, J.-P.2    Klupsch, F.3    Delagrange, P.4    Canet, E.5    Boutin, J.A.6
  • 55
    • 0031801678 scopus 로고    scopus 로고
    • Pharmacological characterization of the human melatonin Mel1a receptor following stable transfection into NIH3T3 cells
    • Nonno, R.; Lucini, V.; Pannacci, M.; Mazzucchelli, C.; Angeloni, D.; Fraschini, F.; Stankov, B. M. Pharmacological characterization of the human melatonin Mel1a receptor following stable transfection into NIH3T3 cells. Br. J. Pharmacol. 1998, 124, 485-492.
    • (1998) Br. J. Pharmacol. , vol.124 , pp. 485-492
    • Nonno, R.1    Lucini, V.2    Pannacci, M.3    Mazzucchelli, C.4    Angeloni, D.5    Fraschini, F.6    Stankov, B.M.7
  • 56
    • 0032812567 scopus 로고    scopus 로고
    • Ligand efficacy and potency at recombinant human MT2 melatonin receptors: Evidence for agonist activity of some mt1-antagonists
    • Nonno, R.; Pannacci, M.; Lucini, V.; Angeloni, D.; Fraschini, F.; Stankov, B. M. Ligand efficacy and potency at recombinant human MT2 melatonin receptors: evidence for agonist activity of some mt1-antagonists. Br. J. Pharmacol. 1999, 127, 1288-1294.
    • (1999) Br. J. Pharmacol. , vol.127 , pp. 1288-1294
    • Nonno, R.1    Pannacci, M.2    Lucini, V.3    Angeloni, D.4    Fraschini, F.5    Stankov, B.M.6
  • 58
    • 0003797555 scopus 로고    scopus 로고
    • Tripos Inc. (1699 South Hanley Rd): St. Louis, MO 63144
    • Sybyl, version 6.8; Tripos Inc. (1699 South Hanley Rd): St. Louis, MO 63144; 2001.
    • (2001) Sybyl, Version 6.8
  • 59
    • 84988115618 scopus 로고
    • Validation of the general purpose Tripos 5.2 force field
    • Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. Validation of the general purpose Tripos 5.2 force field. J. Comput. Chem. 1989, 10, 982-1012.
    • (1989) J. Comput. Chem. , vol.10 , pp. 982-1012
    • Clark, M.1    Cramer R.D. III2    Van Opdenbosch, N.3
  • 60
    • 33846446220 scopus 로고
    • Restart procedures for the conjugate gradient method
    • Powell, M. J. D. Restart procedures for the conjugate gradient method. Math. Program. 1977, 12, 241-254.
    • (1977) Math. Program , vol.12 , pp. 241-254
    • Powell, M.J.D.1
  • 61
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer R.D. III1    Patterson, D.E.2    Bunce, J.D.3
  • 62
    • 0027944195 scopus 로고
    • Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity
    • Klebe, G.; Abraham, U.; Mietzner, T. Molecular Similarity Indices in a Comparative Analysis (CoMSIA) of Drug Molecules To Correlate and Predict Their Biological Activity. J. Med. Chem. 1994, 37, 4130-4146.
    • (1994) J. Med. Chem. , vol.37 , pp. 4130-4146
    • Klebe, G.1    Abraham, U.2    Mietzner, T.3
  • 63
    • 0033022163 scopus 로고    scopus 로고
    • Comparative Molecular Similarity Index Analysis (CoMSIA) to study hydrogen-bonding properties and to score combinatorial libraries
    • Klebe, G.; Abraham, U. Comparative Molecular Similarity Index Analysis (CoMSIA) To Study Hydrogen-Bonding Properties and To Score Combinatorial Libraries. J. Comput.-Aided Mol. Des. 1999, 13, 1-10.
    • (1999) J. Comput.-Aided Mol. Des. , vol.13 , pp. 1-10
    • Klebe, G.1    Abraham, U.2
  • 64
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity - Rapid access to atomic charges
    • Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity-Rapid access to atomic charges. Tetrahedron 1980, 36, 3219-3228.
    • (1980) Tetrahedron , vol.36 , pp. 3219-3228
    • Gasteiger, J.1    Marsili, M.2
  • 65
    • 0001059278 scopus 로고
    • Quanten theoretische beiträge zum benzolproblem. I. Die electron enkonfiguration des benzols
    • Hückel, Z. Quanten theoretische beiträge zum benzolproblem. I. Die electron enkonfiguration des benzols. Z. Phys. 1931, 70, 203-286.
    • (1931) Z. Phys. , vol.70 , pp. 203-286
    • Hückel, Z.1
  • 66
    • 0001681052 scopus 로고
    • The covariance problem in linear regression. The partial least squares (PLS) approach to generalized inverses
    • Wold, S.; Ruhe, A.; Wold, H.; Dunn, W. J. The covariance problem in linear regression. The partial least squares (PLS) approach to generalized inverses. SIAM J. Sci. Stat. Comput. 1984, 5, 735-743.
    • (1984) SIAM J. Sci. Stat. Comput. , vol.5 , pp. 735-743
    • Wold, S.1    Ruhe, A.2    Wold, H.3    Dunn, W.J.4
  • 67
    • 84987100711 scopus 로고
    • Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies
    • Cramer, R. D., III; Bunce, J. D.; Patterson, D. E. Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quantum Struct.-Act. Relat. 1988, 7, 18-25.
    • (1988) Quantum Struct.-Act. Relat. , vol.7 , pp. 18-25
    • Cramer R.D. III1    Bunce, J.D.2    Patterson, D.E.3
  • 68
    • 0027672324 scopus 로고
    • Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA
    • Bush, B. L.; Nachbar, R. B. Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA. J. Comput.-Aided Mol. Des. 1993, 7, 587-619.
    • (1993) J. Comput.-Aided Mol. Des. , vol.7 , pp. 587-619
    • Bush, B.L.1    Nachbar, R.B.2


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