메뉴 건너뛰기




Volumn 7, Issue 8, 2010, Pages 587-595

The quantitative structure activity relationships for predicting HIV protease inhibition by substituted fullerenes

Author keywords

HIV protease inhibition; QSAR; Substituted fullerenes

Indexed keywords

FULLERENE DERIVATIVE; PROTEINASE; PROTEINASE INHIBITOR;

EID: 77958495541     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018010792062759     Document Type: Article
Times cited : (10)

References (66)
  • 1
    • 77958465377 scopus 로고    scopus 로고
    • NIAID-Division of AIDS, Oct 14, 2009
    • NIAID-Division of AIDS. HIV/OI Therapeutics Database. http://chemdb2.niaid.nih.gov/struct_search/class/class_search.asp (accessed Oct 14, 2009).
    • HIV/OI Therapeutics Database
  • 2
    • 0028941196 scopus 로고
    • Antiviral therapy for human immunodeficiency virus infections
    • De Clercq, E. Antiviral therapy for human immunodeficiency virus infections. Clin. Microbiol. Rev., 1995, 8, 200-238.
    • (1995) Clin. Microbiol. Rev , vol.8 , pp. 200-238
    • de Clercq, E.1
  • 3
    • 33947644064 scopus 로고    scopus 로고
    • Molecular dynamics and free energy studies on the wild-type and double mutant HIV-1 protease complexed with Amprenavir and two Amprenavir-related inhibitors: Mechanism for binding and drug resistance
    • Hou, T.; Yu, R. Molecular dynamics and free energy studies on the wild-type and double mutant HIV-1 protease complexed with Amprenavir and two Amprenavir-related inhibitors: mechanism for binding and drug resistance. J. Med. Chem., 2007, 50, 1177-1188.
    • (2007) J. Med. Chem , vol.50 , pp. 1177-1188
    • Hou, T.1    Yu, R.2
  • 6
    • 0034615571 scopus 로고    scopus 로고
    • Structural and biochemical studies of retroviral proteases
    • Wlodawer, A.; Gustchina, A. Structural and biochemical studies of retroviral proteases. Biochem. Biophys. Acta, 2000, 1477, 16-34.
    • (2000) Biochem. Biophys. Acta , vol.1477 , pp. 16-34
    • Wlodawer, A.1    Gustchina, A.2
  • 7
    • 0034042866 scopus 로고    scopus 로고
    • Approaches to the design of effective HIV-1 protease inhibitors
    • Lebon, F.; Ledecq, M. Approaches to the design of effective HIV-1 protease inhibitors. Curr. Med. Chem., 2000, 4, 455-477.
    • (2000) Curr. Med. Chem , vol.4 , pp. 455-477
    • Lebon, F.1    Ledecq, M.2
  • 8
    • 0032537482 scopus 로고    scopus 로고
    • Resistance to HIV protease inhibitors: A comparison of enzyme inhibition and antiviral potency
    • Klabe, R.M.; Bacheler, L.T.; Ala, P.J.; Erickson-Viitanen, S.; Meek, J.L. Resistance to HIV protease inhibitors: a comparison of enzyme inhibition and antiviral potency. Biochem., 1998, 37, 8735-8742.
    • (1998) Biochem , vol.37 , pp. 8735-8742
    • Klabe, R.M.1    Bacheler, L.T.2    Ala, P.J.3    Erickson-Viitanen, S.4    Meek, J.L.5
  • 9
    • 0028143193 scopus 로고
    • Inhibitors of HIV-1 proteinase containing 2-heterosubstituted 4-amino-3-hydroxy-5- phenylpentanoic acid: Synthesis, enzyme inhibition, and antiviral activity
    • Scholz, D.; Billich, A.; Charpiot, B.; Ettmayer, P.; Lehr, P.; Rosenwirth, B.; Schreiner, E.; Gstach, H. Inhibitors of HIV-1 proteinase containing 2-heterosubstituted 4-amino-3-hydroxy-5- phenylpentanoic acid: synthesis, enzyme inhibition, and antiviral activity. J. Med. Chem., 1994, 37, 3079-3089.
    • (1994) J. Med. Chem , vol.37 , pp. 3079-3089
    • Scholz, D.1    Billich, A.2    Charpiot, B.3    Ettmayer, P.4    Lehr, P.5    Rosenwirth, B.6    Schreiner, E.7    Gstach, H.8
  • 14
    • 22844449003 scopus 로고    scopus 로고
    • Hydrophobicity in the design of P2/P2' tetrahydropyrimidinone HIV protease inhibitors
    • Garg, R.; Patel D. Hydrophobicity in the design of P2/P2' tetrahydropyrimidinone HIV protease inhibitors. Bioorg. Med. Chem. Lett., 2005, 15, 3767-3770.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 3767-3770
    • Garg, R.1    Patel, D.2
  • 15
    • 30344477669 scopus 로고    scopus 로고
    • QSAR by LFER of HIV protease inhibitor mannitol derivatives using FA-MLR, PCRA, and PLS techniques
    • Leonard, J. T.; Roy, K. QSAR by LFER of HIV protease inhibitor mannitol derivatives using FA-MLR, PCRA, and PLS techniques. Bioorg. Med. Chem., 2006, 14, 1039-1046.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 1039-1046
    • Leonard, J.T.1    Roy, K.2
  • 16
  • 17
    • 54949153723 scopus 로고    scopus 로고
    • QSAR study of cyclic urea type HIV-1 PR inhibitors using ab initio MO calculation of their complex structures with HIV-1 PR
    • Yoshida, T.; Yamagishi, K.; Chuman, H. QSAR study of cyclic urea type HIV-1 PR inhibitors using ab initio MO calculation of their complex structures with HIV-1 PR. QSAR Comb. Sci., 2008, 27, 694-703.
    • (2008) QSAR Comb. Sci , vol.27 , pp. 694-703
    • Yoshida, T.1    Yamagishi, K.2    Chuman, H.3
  • 18
    • 0027244713 scopus 로고
    • Inhibition of the HIV-1 protease by fullerene derivatives: Model building studies and experimental verification
    • Friedman, S.H.; DeCamp, D.L.; Sijbesma, R.P.; Srdanov, G.; Wudl, F.; Kenyon, G.L. Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification. J. Am. Chem. Soc., 1993, 115, 6506-6509.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 6506-6509
    • Friedman, S.H.1    Decamp, D.L.2    Sijbesma, R.P.3    Srdanov, G.4    Wudl, F.5    Kenyon, G.L.6
  • 19
    • 39149122408 scopus 로고    scopus 로고
    • Solubility of fullerenes C60 and C70 in water
    • Heymann, D. Solubility of fullerenes C60 and C70 in water. Lunar Planet Sci., 1996, 27, 542-543.
    • (1996) Lunar Planet Sci , vol.27 , pp. 542-543
    • Heymann, D.1
  • 22
    • 1542503371 scopus 로고    scopus 로고
    • Singlet oxygen production from fullerene derivatives: Effect of sequential functionalization of the fullerene core
    • Hamano, T.; Okuda, K.; Mashino, T.; Hirobe, M.; Arakane, K.; Ryu, A.; Mashiko, S.; Nagano, T. Singlet oxygen production from fullerene derivatives: effect of sequential functionalization of the fullerene core. Chem. Commun., 1997, 21-22.
    • (1997) Chem. Commun , pp. 21-22
    • Hamano, T.1    Okuda, K.2    Mashino, T.3    Hirobe, M.4    Arakane, K.5    Ryu, A.6    Mashiko, S.7    Nagano, T.8
  • 23
    • 0027255192 scopus 로고
    • Synthesis and virucidal activity of a water-soluble, configurationally stable, derivatized C60 fullerene
    • Schinazi, R.F.; Sijbesma, R.; Srdanov, G.; Hill, C.L.; Wudl, F. Synthesis and virucidal activity of a water-soluble, configurationally stable, derivatized C60 fullerene. Antimicrob. Agents Chemother., 1993, 37, 1707-1710.
    • (1993) Antimicrob. Agents Chemother , vol.37 , pp. 1707-1710
    • Schinazi, R.F.1    Sijbesma, R.2    Srdanov, G.3    Hill, C.L.4    Wudl, F.5
  • 25
    • 0029809466 scopus 로고    scopus 로고
    • Biological activity of water-soluble fullerenes. Structural dependence of DNA cleavage, cytotoxicity, and enzyme inhibitory activities including HIV-protease inhibition
    • Nakamura, E.; Tokuyama, H.; Yamago, S.; Shiraki, T.; Sugiura, Y. Biological activity of water-soluble fullerenes. Structural dependence of DNA cleavage, cytotoxicity, and enzyme inhibitory activities including HIV-protease inhibition. Bull. Chem. Soc. Jpn., 1996, 69, 2143-2151.
    • (1996) Bull. Chem. Soc. Jpn , vol.69 , pp. 2143-2151
    • Nakamura, E.1    Tokuyama, H.2    Yamago, S.3    Shiraki, T.4    Sugiura, Y.5
  • 26
    • 0029931172 scopus 로고    scopus 로고
    • Anti-human immunodeficiency virus activity and cytotoxicity of derivatized buckminsterfullerenes
    • Schuster, D.I.; Wilson, S.R.; Schinazi, R.F. Anti-human immunodeficiency virus activity and cytotoxicity of derivatized buckminsterfullerenes. Bioorg. Med. Chem. Lett., 1996, 11, 1253-1256.
    • (1996) Bioorg. Med. Chem. Lett , vol.11 , pp. 1253-1256
    • Schuster, D.I.1    Wilson, S.R.2    Schinazi, R.F.3
  • 28
    • 0032543623 scopus 로고    scopus 로고
    • Optimizing the binding of fullerene inhibitors of the HIV-1 protease through predicted increases in hydrophobic desolvation
    • Friedman, S.H.; Ganapathi, P.S.; Rubin, Y.; Kenyon, G.L. Optimizing the binding of fullerene inhibitors of the HIV-1 protease through predicted increases in hydrophobic desolvation. J. Med. Chem., 1998, 41, 2424-2429.
    • (1998) J. Med. Chem , vol.41 , pp. 2424-2429
    • Friedman, S.H.1    Ganapathi, P.S.2    Rubin, Y.3    Kenyon, G.L.4
  • 29
    • 0344495996 scopus 로고    scopus 로고
    • Synthesis and anti-HIV properties of new water-soluble bisfunctionalized[ 60]fullerene derivatives
    • Bosi, S.; Da Ros, T.; Spalluto, G.; Balzarini, J.; Prato, M. Synthesis and anti-HIV properties of new water-soluble bisfunctionalized[ 60]fullerene derivatives. Bioorg. Med. Chem. Lett., 2003, 13, 4437-4440.
    • (2003) Bioorg. Med. Chem. Lett , vol.13 , pp. 4437-4440
    • Bosi, S.1    da Ros, T.2    Spalluto, G.3    Balzarini, J.4    Prato, M.5
  • 32
    • 16244403943 scopus 로고    scopus 로고
    • Human immunodeficiency virus-reverse transcriptase inhibition and hepatitis C virus RNA-dependent RNA polymerase inhibition activities of fullerene derivatives
    • Mashino, T.; Shimotohno, K.; Ikegami, N.; Nishikawa, D.; Okuda, K.; Takahashi, K.; Nakamura, S.; Mochizuki, M. Human immunodeficiency virus-reverse transcriptase inhibition and hepatitis C virus RNA-dependent RNA polymerase inhibition activities of fullerene derivatives. Bioorg. Med. Chem. Lett., 2005, 15, 1107-1109.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 1107-1109
    • Mashino, T.1    Shimotohno, K.2    Ikegami, N.3    Nishikawa, D.4    Okuda, K.5    Takahashi, K.6    Nakamura, S.7    Mochizuki, M.8
  • 33
    • 34547888000 scopus 로고    scopus 로고
    • Chlorofullerene C60Cl6: A precursor for straightforward preparation of highly water-soluble polycarboxylic fullerene derivatives active against HIV
    • Troshina, O.A.; Troshin, P.A.; Peregudov, A.S.; Kozlovskiy, V.I.; Balzarini, J.; Lyubovskaya, R.N. Chlorofullerene C60Cl6: a precursor for straightforward preparation of highly water-soluble polycarboxylic fullerene derivatives active against HIV. Org. Biomol. Chem., 2007, 5, 2783-2791.
    • (2007) Org. Biomol. Chem , vol.5 , pp. 2783-2791
    • Troshina, O.A.1    Troshin, P.A.2    Peregudov, A.S.3    Kozlovskiy, V.I.4    Balzarini, J.5    Lyubovskaya, R.N.6
  • 34
    • 0034649734 scopus 로고    scopus 로고
    • Design and synthesis of novel [60]fullerene derivatives as potential HIV aspartic protease inhibitors
    • Marcorin, G.L.; Da Ros, T.; Castellano, S.; Stefancich, G.; Bonin, I.; Miertus, S.; Prato, M. Design and synthesis of novel [60]fullerene derivatives as potential HIV aspartic protease inhibitors. Org. Lett., 2000, 25, 3955-3958.
    • (2000) Org. Lett , vol.25 , pp. 3955-3958
    • Marcorin, G.L.1    da Ros, T.2    Castellano, S.3    Stefancich, G.4    Bonin, I.5    Miertus, S.6    Prato, M.7
  • 35
    • 34548256207 scopus 로고    scopus 로고
    • Structural analysis of lead fullerene-based inhibitor bound to human immunodeficiency virus type 1 protease in solution from molecular dynamics simulations
    • Lee, V.S.; Nimmanpipug, P.; Aruksakunwong, O.; Promsri, S.; Sompornpisut, P.; Hannongbua, S. Structural analysis of lead fullerene-based inhibitor bound to human immunodeficiency virus type 1 protease in solution from molecular dynamics simulations. J. Mol. Graph. Modell., 2007, 26, 558-570.
    • (2007) J. Mol. Graph. Modell , vol.26 , pp. 558-570
    • Lee, V.S.1    Nimmanpipug, P.2    Aruksakunwong, O.3    Promsri, S.4    Sompornpisut, P.5    Hannongbua, S.6
  • 36
    • 55749100817 scopus 로고    scopus 로고
    • Computational design of novel analogues as potential HIV-1 PR inhibitors: Analysis of the binding interactions between fullerene inhibitors and HIV-1 PR residues using 3D QSAR, molecular docking and molecular dynamic simulations
    • Durdagi, S.; Mavromoustakos, T.; Chronakis, N.; Papadopoulos, M.G. Computational design of novel analogues as potential HIV-1 PR inhibitors: Analysis of the binding interactions between fullerene inhibitors and HIV-1 PR residues using 3D QSAR, molecular docking and molecular dynamic simulations. Bioorg. Med. Chem., 2008, 16, 9957-9974.
    • (2008) Bioorg. Med. Chem , vol.16 , pp. 9957-9974
    • Durdagi, S.1    Mavromoustakos, T.2    Chronakis, N.3    Papadopoulos, M.G.4
  • 37
    • 55549144296 scopus 로고    scopus 로고
    • 3D QSAR CoMFA/CoMSIA, molecular docking and molecular dynamics studies of fullerene-based HIV-1 PR inhibitors
    • Durdagi, S.; Mavromoustakos, T.; Papadopoulos, M.G. 3D QSAR CoMFA/CoMSIA, molecular docking and molecular dynamics studies of fullerene-based HIV-1 PR inhibitors. Bioorg. Med. Chem. Lett., 2008, 18, 6283-6289.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 6283-6289
    • Durdagi, S.1    Mavromoustakos, T.2    Papadopoulos, M.G.3
  • 45
    • 0034668386 scopus 로고    scopus 로고
    • Polyhydroxylated C60, fullerenols, as glutamate receptor antagonists and neuroprotecive agents
    • Jin, H.; Chem, W.Q.; Tang, X.W.; Chiang, L.Y.; Yang, C.Y.; Schloss, J.V. Polyhydroxylated C60, fullerenols, as glutamate receptor antagonists and neuroprotecive agents. J. Neurosci. Res., 2000, 62, 600-607.
    • (2000) J. Neurosci. Res , vol.62 , pp. 600-607
    • Jin, H.1    Chem, W.Q.2    Tang, X.W.3    Chiang, L.Y.4    Yang, C.Y.5    Schloss, J.V.6
  • 46
    • 77958456107 scopus 로고    scopus 로고
    • Agent for inhibition of human immunodeficiency virus (HIV) and cytomegalovirus (CMV) infections and method of their inhibition
    • January 20
    • Miller, G.G.; Kushch, A.A.; Romanova, V.S. Agent for inhibition of human immunodeficiency virus (HIV) and cytomegalovirus (CMV) infections and method of their inhibition. Russia Patent 2,196,602, January 20, 2003.
    • (2003) Russia Patent , vol.2 , Issue.196 , pp. 602
    • Miller, G.G.1    Kushch, A.A.2    Romanova, V.S.3
  • 47
    • 77958514538 scopus 로고    scopus 로고
    • Chemical
    • NIAID Home, Oct 14
    • NIAID Home. Chemical. Therapeutical Class Search. http://chemdb.niaid.nih.gov/struct_search/class/class_many.asp?class=FULLERENES (accessed Oct 14, 2009).
    • (2009) Therapeutical Class Search
  • 48
    • 37449022029 scopus 로고    scopus 로고
    • Docking mode of delvardine and its analogues into the p66 domain of HIV-1 reverse transcriptase: Screening using molecular mechanics-generalized born/surface area and absorption, distribution, metabolism and excretion properties
    • Sengupta, D.; Verma, D.; Naik, P.K. Docking mode of delvardine and its analogues into the p66 domain of HIV-1 reverse transcriptase: screening using molecular mechanics-generalized born/surface area and absorption, distribution, metabolism and excretion properties. J. Biosci., 2007, 32(7), 1307-1316.
    • (2007) J. Biosci , vol.32 , Issue.7 , pp. 1307-1316
    • Sengupta, D.1    Verma, D.2    Naik, P.K.3
  • 50
    • 0029912748 scopus 로고    scopus 로고
    • Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids
    • Jorgensen, W.L.; Maxwell, D.S.; Tirado-Rives, J. Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J. Am. Chem. Soc., 1996, 118, 11225-11236.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 11225-11236
    • Jorgensen, W.L.1    Maxwell, D.S.2    Tirado-Rives, J.3
  • 51
    • 0842341771 scopus 로고
    • The development and use of quantum-mechanical molecular-models.76. AM1 - a new general-purpose quantum-mechanical molecularmodel
    • Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. The development and use of quantum-mechanical molecular-models.76. AM1 - a new general-purpose quantum-mechanical molecularmodel. J. Am. Chem. Soc., 1985, 107, 3902-3909.
    • (1985) J. Am. Chem. Soc , vol.107 , pp. 3902-3909
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4
  • 52
    • 0025390935 scopus 로고
    • MOPAC: A semiempirical molecular orbital program
    • Stewart, J.J.P. MOPAC: a semiempirical molecular orbital program. J. Comput.-Aided. Mol. Des., 1990, 4, 1-103.
    • (1990) J. Comput.-Aided. Mol. Des , vol.4 , pp. 1-103
    • Stewart, J.J.P.1
  • 53
    • 77958457504 scopus 로고    scopus 로고
    • QSAR Model, Molcode, Ltd., Tartu
    • QSAR Model, Molcode, Ltd., Tartu, 2008.
    • (2008)
  • 55
    • 77958458199 scopus 로고    scopus 로고
    • Virtual Computational Chemistry Laboratory, Oct 14 2009
    • Virtual Computational Chemistry Laboratory. http://vcclab.org/lab/alogps/ (accessed Oct 14 2009)
  • 58
    • 0043228681 scopus 로고    scopus 로고
    • On the use of cross-validation to assess performance in multivariate prediction
    • Jonathan, P.; Krzanowski, W. J.; McCarthy W. V. On the use of cross-validation to assess performance in multivariate prediction. Stat. Comput., 2000, 10, 209-229.
    • (2000) Stat. Comput , vol.10 , pp. 209-229
    • Jonathan, P.1    Krzanowski, W.J.2    McCarthy, W.V.3
  • 59
    • 77958513898 scopus 로고    scopus 로고
    • note
    • 2=0.41. This low correlation indicates that the docking calculations do not fully explain the interactions between the substituted fullerenes and the HIV protease and alternative calculation methods should be tried for better explaining the inhibitory power of the substituted fullerenes towards HIV protease.
  • 60
    • 18144404059 scopus 로고    scopus 로고
    • Correlation of boiling points with molecular structure. 1. A training set of 298 diverse organics and a test set of 9 simple inorganics
    • Katritzky, A.R.; Mu, L.; Lobanov, V.S.; Karelson, M. Correlation of boiling points with molecular structure. 1. A training set of 298 diverse organics and a test set of 9 simple inorganics. J. Phys. Chem., 1996, 100, 10400-10407.
    • (1996) J. Phys. Chem , vol.100 , pp. 10400-10407
    • Katritzky, A.R.1    Mu, L.2    Lobanov, V.S.3    Karelson, M.4
  • 61
    • 0013602932 scopus 로고
    • Activation hardness: New index for describing the orientation of electrophilic aromatic substitution
    • Zhou, Z.; Parr, R.G. Activation hardness: new index for describing the orientation of electrophilic aromatic substitution. J. Am. Chem. Soc., 1990, 112, 5720-5724.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 5720-5724
    • Zhou, Z.1    Parr, R.G.2
  • 62
    • 0000356254 scopus 로고
    • Calculation schemes for atomic electronegativities in molecular graphs within the framework of Snderson's principle
    • Zefirov, N.S.; Kirpichenov, M.A.; Izmailov, F.F.; Trofimov, M.I. Calculation schemes for atomic electronegativities in molecular graphs within the framework of Snderson's principle. Dokl Akad Nauk SSSR, 1987, 96, 883-887.
    • (1987) Dokl Akad Nauk SSSR , vol.96 , pp. 883-887
    • Zefirov, N.S.1    Kirpichenov, M.A.2    Izmailov, F.F.3    Trofimov, M.I.4
  • 63
    • 0000115399 scopus 로고    scopus 로고
    • A QSPR study of the solubility of gases and vapors in water
    • Katritzky, A.R.; Mu, L.; Karelson, M. A QSPR study of the solubility of gases and vapors in water. J. Chem. Inf. Comput. Sci., 1996, 36, 1162-1168.
    • (1996) J. Chem. Inf. Comput. Sci , vol.36 , pp. 1162-1168
    • Katritzky, A.R.1    Mu, L.2    Karelson, M.3
  • 64
    • 11644266970 scopus 로고
    • Electronic population analysis on LCAO-MO molecular wave functions
    • Mulliken, R.S. Electronic population analysis on LCAO-MO molecular wave functions. J. Chem. Phys., 1955, 23, 1833-1840.
    • (1955) J. Chem. Phys , vol.23 , pp. 1833-1840
    • Mulliken, R.S.1
  • 65
    • 10344253046 scopus 로고
    • Development and use of charged partial surface-area structural descriptors in computer-assisted quantitative structure property relationship studies
    • Stanton, D.T.; Jurs, P.C. Development and use of charged partial surface-area structural descriptors in computer-assisted quantitative structure property relationship studies. Anal. Chem., 1990, 62, 2323-2329.
    • (1990) Anal. Chem , vol.62 , pp. 2323-2329
    • Stanton, D.T.1    Jurs, P.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.