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Volumn 26, Issue 1, 2011, Pages 78-87

Prediction of the relationship between the structural features of andrographolide derivatives and αî±-glucosidase inhibitory activity: A quantitative structure-activity relationship (QSAR) Study

Author keywords

glucosidase inhibitory activity; andrographolide; petitjean; QSAR; volsurf

Indexed keywords

ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; ANDROGRAPHOLIDE; ANDROGRAPHOLIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79851474038     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756361003724760     Document Type: Article
Times cited : (16)

References (46)
  • 1
    • 0028981092 scopus 로고
    • Te α-glucosidase i inhibitor castanospermine alters endothelial cell glycosylation, prevents angiogenesis, and inhibits tumor growth
    • Pili R, Chang J, Partis RA, Mueller RA, Chrest FJ, Passaniti A. Te α-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, prevents angiogenesis, and inhibits tumor growth. Cancer Res 1995;55:2920-2926.
    • (1995) Cancer Res , vol.55 , pp. 2920-2926
    • Pili, R.1    Chang, J.2    Partis, R.A.3    Mueller, R.A.4    Chrest, F.J.5    Passaniti, A.6
  • 2
    • 0022475489 scopus 로고
    • Inhibition of experimental metastasis by castanospermine in mice: Blockage of two distinct stages of tumor colonization by oligosaccharide processing inhibitors
    • Humphries MJ, Matsumoto K, White SL, Olden K. Inhibition of experimental metastasis by castanospermine in mice: Blockage of two distinct stages of tumor colonization by oligosaccharide processing inhibitors. Cancer Res 1986;46:5215-5222. (Pubitemid 16008292)
    • (1986) Cancer Research , vol.46 , Issue.10 , pp. 5215-5222
    • Humphries, M.J.1    Matsumoto, K.2    White, S.L.3    Olden, K.4
  • 3
    • 0036141030 scopus 로고    scopus 로고
    • The α-glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step
    • DOI 10.1124/mol.61.1.186
    • Papandreou MJ, Barbouche R, Guieu R, Kieny MP, Fenouillet E. Te α-glucosidase inhibitor 1-deoxynojirimycin blocks human immunodefciency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step. Mol Pharmacol 2002;61:186-193. (Pubitemid 34049526)
    • (2002) Molecular Pharmacology , vol.61 , Issue.1 , pp. 186-193
    • Papandreou, M.-J.1    Barbouche, R.2    Guieu, R.3    Kieny, M.P.4    Fenouillet, E.5
  • 4
    • 0036753024 scopus 로고    scopus 로고
    • The combination of interferon α-2b and n-butyl deoxynojirimycin has a greater than additive antiviral effect upon production of infectious bovine viral diarrhea virus (BVDV) in vitro: Implications for hepatitis C virus (HCV) therapy
    • DOI 10.1016/S0166-3542(02)00075-X, PII S016635420200075X
    • Ouzounov S, Mehta A, Dwek RA, Block TM, Jordan R. Te combination of interferon α-2b and n-butyl deoxynojirimycin has a greater than additive antiviral efect upon production of infectious bovine viral diarrhea virus (BVDV) in vitro: Implications for hepatitis C virus (HCV) therapy. Antiviral Res 2002;55:425-435. (Pubitemid 35223098)
    • (2002) Antiviral Research , vol.55 , Issue.3 , pp. 425-435
    • Ouzounov, S.1    Mehta, A.2    Dwek, R.A.3    Block, T.M.4    Jordan, R.5
  • 5
    • 0021744391 scopus 로고
    • Valiolamine, a new α-glucosidase inhibiting aminocyclitol. produced by Streptomyces hygroscopicus
    • Kameda Y, Asano N, Yoshikawa M. Valiolamine, a new α-glucosidase inhibiting aminocyclitol produced by Streptomyces hygroscopicus. J Antibiotics 1984;37:1301-1307. (Pubitemid 15220687)
    • (1984) Journal of Antibiotics , vol.37 , Issue.11 , pp. 1301-1307
    • Kameda, Y.1    Asano, N.2    Yoshikawa, M.3
  • 7
    • 13844262949 scopus 로고    scopus 로고
    • Effect of two α-glucosidase inhibitors, voglibose and acarbose, on postprandial hyperglycemia correlates with subjective abdominal symptoms
    • DOI 10.1016/j.metabol.2004.10.004
    • Fujisawa T, Ikegami H, Inoue K, Kawabata Y, Ogihara T. Efect of two α-glucosidase inhibitors, voglibose and acarbose, on postprandial hyperglycemia correlates with subjective abdominal symptoms. Metab Clinic Exp 2005;54:387-390. (Pubitemid 40250100)
    • (2005) Metabolism: Clinical and Experimental , vol.54 , Issue.3 , pp. 387-390
    • Fujisawa, T.1    Ikegami, H.2    Inoue, K.3    Kawabata, Y.4    Ogihara, T.5
  • 9
    • 33645861668 scopus 로고    scopus 로고
    • Studies on the novel α-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues
    • Gui FD, Hai WX, Jun FW, Feng WL, Hong ML. Studies on the novel α-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues. Bioorg Med Chem Lett 2006;16:2710-2713.
    • (2006) Bioorg Med Chem Lett , vol.16 , pp. 2710-2713
    • Gui, F.D.1    Hai, W.X.2    Jun, F.W.3    Feng, W.L.4    Hong, M.L.5
  • 10
    • 4143138851 scopus 로고    scopus 로고
    • Computer-aided molecular design of novel glucosidase inhibitors for AIDS treatment
    • Silva CHTP, Taft CA. Computer aided molecular design of novel glucosidase inhibitors for AIDS treatment. J Biomol Struct Dyn 2004;22:59-63. (Pubitemid 39095283)
    • (2004) Journal of Biomolecular Structure and Dynamics , vol.22 , Issue.1 , pp. 59-63
    • Silva, C.H.T.P.1    Taft, C.A.2
  • 11
    • 0029112274 scopus 로고
    • Te α-glucosidase inhibitor N-butyldeoxynojirimycin inhibits human immunodefciency virus entry at the level of post-CD4 binding
    • Fischer PB, Colin M, Karlson GB, James W, Butters TD, Davis SJ, Gordon S, Dwek RA, Platt FM. Te α-glucosidase inhibitor N-butyldeoxynojirimycin inhibits human immunodefciency virus entry at the level of post-CD4 binding. J Virol 1995;69:5791-5797.
    • (1995) J Virol , vol.69 , pp. 5791-5797
    • Fischer, P.B.1    Colin, M.2    Karlson, G.B.3    James, W.4    Butters, T.D.5    Davis, S.J.6    Gordon, S.7    Dwek, R.A.8    Platt, F.M.9
  • 12
    • 0027959359 scopus 로고
    • Inhibition of α-glucosidase I of the glycoprotein-processing enzymes by 6-O-butanoyl castanospermine (MDL 28,574) and its consequences in human immunodeficiency virus-infected T cells
    • Taylor DL, Kang MS, Brennan TM, Bridges CG, Sunkara PS, Tyms AS. Inhibition of α-glucosidase I of the glycoprotein-processing enzymes by 6-O-butanoyl Castanospermine (MDL 28,574) and its consequences in human immunodefciency virus infected T cells. Antimicrob Agents Chemother 1994;38:1780-1787. (Pubitemid 24250724)
    • (1994) Antimicrobial Agents and Chemotherapy , vol.38 , Issue.8 , pp. 1780-1787
    • Taylor, D.L.1    Kang, M.S.2    Brennan, T.M.3    Bridges, C.G.4    Sunkara, P.S.5    Tyms, A.S.6
  • 13
    • 45149090787 scopus 로고    scopus 로고
    • Toward the virtual screening of α-glucosidase inhibitors with the homology-modelled protein structure
    • Jung-Hum P, Sungmin K, Hwangseo P. Toward the virtual screening of α-glucosidase inhibitors with the homology-modelled protein structure. Bull Korean Chem Soc 2008;29:921-927.
    • (2008) Bull Korean Chem Soc , vol.29 , pp. 921-927
    • Jung-Hum, P.1    Sungmin, K.2    Hwangseo, P.3
  • 14
    • 44849136842 scopus 로고    scopus 로고
    • Discovery and biological evaluation of novel α-glucosidase inhibitors with in vivo antidiabetic efect
    • Hwangseo P, Kyo YH, Young HK, Kyung HO, Jae YL, Keun K. Discovery and biological evaluation of novel α-glucosidase inhibitors with in vivo antidiabetic efect. Bioorg Med Chem Lett 2008;18:3711-3715
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 3711-3715
    • Hwangseo, P.1    Kyo, Y.H.2    Young, H.K.3    Kyung, H.O.4    Jae, Y.L.5    Keun, K.6
  • 16
    • 42749087181 scopus 로고    scopus 로고
    • Binding mode analyses and pharmacophore model development for sulphonamide chalcone derivatives, a new class of α-glucosidase inhibitors
    • Kavitha B, Nagakumar B, Ki HP, Keun WL. Binding mode analyses and pharmacophore model development for sulphonamide chalcone derivatives, a new class of α-glucosidase inhibitors. J Mol Graph Model 2008;26:1202-1212.
    • (2008) J Mol Graph Model , vol.26 , pp. 1202-1212
    • Kavitha, B.1    Nagakumar, B.2    Ki, H.P.3    Keun, W.L.4
  • 17
    • 22144477181 scopus 로고    scopus 로고
    • Homology modeling and molecular interaction field studies of α-glucosidases as a guide to structure-based design of novel proposed anti-HIV inhibitors
    • DOI 10.1007/s10822-005-1486-6
    • Tomich CH, da Silva P, Ivone C, Taft CA. Homology modelling and molecular interaction feld studies of α-glucosidase as a guide to structure based drug design of novel proposed anti-HIV inhibitors. J Comput Aided Drug Des 2005;19:83-92. (Pubitemid 40974009)
    • (2005) Journal of Computer-Aided Molecular Design , vol.19 , Issue.2 , pp. 83-92
    • Da Silva, C.H.T.1    Da Silva, P.2    Carvalho, I.3    Taft, C.A.4
  • 18
    • 58949091558 scopus 로고    scopus 로고
    • QSAR study of substituted 2-pyridinyl quanidine as selective urokinase-type plasminogen activator (uPA) inhibitors
    • Karthikeyan C, Moorthy NSHN, Trivedi P. QSAR study of substituted 2-pyridinyl quanidine as selective urokinase-type plasminogen activator (uPA) inhibitors. J Enz Inhib Med Chem 2009;24:6-13.
    • (2009) J Enz Inhib Med Chem , vol.24 , pp. 6-13
    • Karthikeyan, C.1    Moorthy, N.S.H.N.2    Trivedi, P.3
  • 19
    • 34247636613 scopus 로고    scopus 로고
    • Synthesis of andrographolide derivatives: A new family of α-glucosidase inhibitors
    • Xu HW, Dai GF, Liu GZ, Wang JF, Liu HM. Synthesis of andrographolide derivatives: A new family of α-glucosidase inhibitors. Bioorg Med Chem 2007;15:4247-4255.
    • (2007) Bioorg Med Chem , vol.15 , pp. 4247-4255
    • Xu, H.W.1    Dai, G.F.2    Liu, G.Z.3    Wang, J.F.4    Liu, H.M.5
  • 20
    • 3042600821 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship analysis of a series of 2,3-diaryl benzopyran analogues as novel selective cyclooxygenase-2 inhibitors
    • DOI 10.1016/j.bmcl.2004.05.059, PII S0960894X04007103
    • Prasanna S, Manivannan E, Chaturvedi SC. Quantitative structure-activity relationship analysis of a series of 2,3-diaryl benzopyran analogues as novel selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett 2004;14:4005-4011. (Pubitemid 38844414)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.15 , pp. 4005-4011
    • Prasanna, S.1    Manivannan, E.2    Chaturvedi, S.C.3
  • 24
    • 8844285333 scopus 로고    scopus 로고
    • QSAR modelling of HIV-1 reverse transcriptase inhibition by benzoxazinones using a combination of P-VSA and pharmacophore feature descriptors
    • DOI 10.1016/j.bmcl.2004.09.068, PII S0960894X04011916
    • Balaji S, Karthikeyan C, Moorthy NSHN, Trivedi P. QSAR modelling of HIV-1 reverse transcriptase inhibition by benzoxazinones using a combination of P-VSA and pharmacophore feature descriptors. Bioorg Med Chem Lett 2004;14:6089-6094. (Pubitemid 39531278)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.24 , pp. 6089-6094
    • Balaji, S.1    Karthikeyan, C.2    Hari Narayana Moorthy, N.S.3    Trivedi, P.4
  • 25
    • 0343831900 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship (QSAR) study of new fluorovinyloxyacetamides
    • Cho DH, Lee SK, Kim BT, No KT. Quantitative Structure Activity relationship (QSAR) study of new fuorovinyloxyacetamides. Bull Korean Chem Soc 2001;22:388-394. (Pubitemid 32436156)
    • (2001) Bulletin of the Korean Chemical Society , vol.22 , Issue.4 , pp. 388-394
    • Cho, D.H.1    Lee, S.K.2    Kim, B.T.3    No, K.T.4
  • 26
    • 30244459245 scopus 로고
    • Testing for serial correlation in least squares regression II
    • Durbin J, Watson GS. Testing for serial correlation in least squares regression. II. Biometrika 1951;38:159-178.
    • (1951) Biometrika , vol.38 , pp. 159-178
    • Durbin, J.1    Watson, G.S.2
  • 27
    • 0038724207 scopus 로고    scopus 로고
    • The importance of being earnest: Validation is the absolute essential for successful application and interpretation of QSPR models
    • Tropsha A, Gramatica P, Gombar VK. Te importance of earnest, validation is the absolute essential application and interpretation of QSPR models. QSAR Comb Sci 2003;22:69-77. (Pubitemid 36717473)
    • (2003) QSAR and Combinatorial Science , vol.22 , Issue.1 , pp. 69-77
    • Tropsha, A.1    Gramatica, P.2    Gombar, V.K.3
  • 28
    • 0043132440 scopus 로고    scopus 로고
    • Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs
    • Erikkson L, Jaworsha J, Worth AP, Mark TDC, Robert MM, Gramatica P. Methods for reliability and uncertainty assessment and for applicability evaluation of classifcation and regression based QSARs. Environ Health Perspect 2003;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
  • 30
    • 34250628103 scopus 로고    scopus 로고
    • Principles of QSAR models validation: Internal and external
    • DOI 10.1002/qsar.200610151
    • Gramatica P. Principle of QSAR Model validation: internal and external. QSAR Comb Sci 2007;26:694-701. (Pubitemid 46932857)
    • (2007) QSAR and Combinatorial Science , vol.26 , Issue.5 , pp. 694-701
    • Gramatica, P.1
  • 31
    • 84918743166 scopus 로고
    • Infuential observation in linear regression
    • Cook RD. Infuential observation in linear regression. J Am Stat Assoc 1979;74:169-174.
    • (1979) J Am Stat Assoc , vol.74 , pp. 169-174
    • Cook, R.D.1
  • 34
    • 0001509942 scopus 로고    scopus 로고
    • Prediction of physicochemical parameters by atomic contributions
    • Wildman AS, Crippen GM. Prediction of physicochemical parameters by atomic contributions. J Chem Inf Comput Sci 1999;39:868-873.
    • (1999) J Chem Inf Comput Sci , vol.39 , pp. 868-873
    • Wildman, A.S.1    Crippen, G.M.2
  • 35
    • 0034625096 scopus 로고    scopus 로고
    • Molecular felds in quantitative structure-permeation relationships: Te VolSurf approach
    • Cruciania G, Crivorib P, Carruptb P-A, Testa B. Molecular felds in quantitative structure-permeation relationships: Te VolSurf approach. J Mol Struct (Teochem) 2000;503:17-30.
    • (2000) J Mol Struct (Teochem) , vol.503 , pp. 17-30
    • Cruciania, G.1    Crivorib, P.2    Carruptb, P.-A.3    Testa, B.4
  • 36
    • 79851490616 scopus 로고    scopus 로고
    • http://www.moldiscovery.com/docs/volsurf/descriptors.html#AEN669
  • 37
    • 0033800498 scopus 로고    scopus 로고
    • Volsurf: A new tool for the pharmacokinetic optimization of lead compounds
    • Cruciani G, Pastor M, Guba W. Volsurf: a new tool for the pharmacokinetic optimization of lead compounds. Eur J Pharm Sci 2000;11:S29-S39.
    • (2000) Eur J Pharm Sci , vol.11
    • Cruciani, G.1    Pastor, M.2    Guba, W.3
  • 38
    • 17644388125 scopus 로고    scopus 로고
    • Quantitative structure activity relationship studies of diaryl thiophen derivatives as selective COX-2 inhibitors
    • Shahapurkar S, Kawathekar N, Chaturvedi SC. Quantitative structure activity relationship studies of diaryl thiophen derivatives as selective COX-2 inhibitors. Pharmazie 2005;60:254-258. (Pubitemid 40571186)
    • (2005) Pharmazie , vol.60 , Issue.4 , pp. 254-258
    • Shahapurkar, S.1    Kawathekar, N.2    Chaturvedi, S.C.3
  • 39
    • 0000697995 scopus 로고
    • Applications of the radius-diameter diagram to the classifcation of topological and geometrical shapes of chemical compounds
    • Petitjean M. Applications of the radius-diameter diagram to the classifcation of topological and geometrical shapes of chemical compounds. J Chem Inf Comput Sci 1992;32:331-337.
    • (1992) J Chem Inf Comput Sci , vol.32 , pp. 331-337
    • Petitjean, M.1
  • 40
    • 0041683426 scopus 로고
    • Topological statistics on a large structural fle
    • Petitjean M, Dubois JE. Topological statistics on a large structural fle. J Chem Inf Comput Sci 1990;30:332-343.
    • (1990) J Chem Inf Comput Sci , vol.30 , pp. 332-343
    • Petitjean, M.1    Dubois, J.E.2
  • 41
    • 33749680786 scopus 로고    scopus 로고
    • Quantitative structure-activity-activity and quantitative structure-activity investigations of human and rodent toxicity
    • Iglika L, Andrew PW, Tatiana IN, John CD, Mark TDC Quantitative structure-activity-activity and quantitative structure-activity investigations of human and rodent toxicity. Chemosphere 2006;65:1878-1887.
    • (2006) Chemosphere , vol.65 , pp. 1878-1887
    • Iglika, L.1    Andrew, P.W.2    Tatiana, I.N.3    John, C.D.4    Mark, T.D.C.5
  • 42
    • 34248359982 scopus 로고    scopus 로고
    • QSAR studies of 4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridines as potent angiotensin II receptor antagonists by MLR and NLR analysis
    • Balasubramanian N, Avinash D, Vishnukant M. QSAR studies of 4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridines as potent angiotensin II receptor antagonists by MLR and NLR analysis. ARKIVOC 2007;i:189-1204.
    • (2007) ARKIVOC , vol.1 , pp. 189-1204
    • Balasubramanian, N.1    Avinash, D.2    Vishnukant, M.3
  • 43
    • 33947314923 scopus 로고    scopus 로고
    • A DFT-based QSARs study of acetazolamide/sulfanilamide derivatives with carbonic anhydrase (CA-II) isozyme inhibitory activity
    • Erol E, Hasan T, Semra G, Selami P, Oral O. A DFT-based QSARs study of acetazolamide/sulfanilamide derivatives with carbonic anhydrase (CA-II) isozyme inhibitory activity. Int J Mol Sci 2007;8:145-155.
    • (2007) Int J Mol Sci , vol.8 , pp. 145-155
    • Erol, E.1    Hasan, T.2    Semra, G.3    Selami, P.4    Oral, O.5
  • 44
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity\a rapid access to atomic charges
    • Gasteiger J, Marsili M. Iterative partial equalization of orbital electronegativity\a rapid access to atomic charges. Tetrahedron 1980;36:3219-3228.
    • (1980) Tetrahedron , vol.36 , pp. 3219-3228
    • Gasteiger, J.1    Marsili, M.2
  • 45
    • 0343626600 scopus 로고
    • A new electroafnity scale; Together with data on valence states and on valence ionization potentials and electron afnities
    • Mulliken RS. A new electroafnity scale; Together with data on valence states and on valence ionization potentials and electron afnities. J Chem Phys 1934;2:782-793.
    • (1934) J Chem Phys , vol.2 , pp. 782-793
    • Mulliken, R.S.1
  • 46
    • 0002954125 scopus 로고
    • Robust estimate, residuals and outlier detection with multipurpose data
    • Gnanadesikan R, Kettenring JR. Robust estimate, residuals and outlier detection with multipurpose data. Biometrics 1972;28:81-124.
    • (1972) Biometrics , vol.28 , pp. 81-124
    • Gnanadesikan, R.1    Kettenring, J.R.2


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