Interaction between epoxidised estradiol and fullerene (C₆₀): possible anticancer activity

References

• Gharbi , N. , Pressac , M. , Hadchouel , M. , Szwarc , H. , Wilson , H. and Moussa , F. 2005 . Fullerene is a powerful antioxidant in vivo with no acute or subacute toxicity . Nano Lett. , 5 : 2578 – 2585 .
   PubMed Web of Science ®Google Scholar
• Nielsen , G.D. , Roursgaard , M. , Jensen , K.A. , Poulsen , S.S. and Larsen , S.T. 2008 . In vivo biology and toxicology of fullerenes and their derivatives . J. Compilation: Nordic Pharmacol. Soc. Basic Clin. Pharmacol. Toxicol. , : 1 – 12 .
   Google Scholar
• Andrievsky , G.V. , Bruskov , V.I. , Tykhomyrov , A.A. and Gudkov , S.V. 2009 . Peculiarities of the antioxidant and radioprotective effects of hydrated C60 fullerene nanostuctures in vitro and in vivo . Free Rad. Biol. Med. , 47 : 786 – 793 .
   PubMed Web of Science ®Google Scholar
• Xie , Q. , Perez-Cordero , E. and Echegoyen , L. 1992 . Unusual 1:2 (ligand:metal) complex formation between an anthraquinone cryptand and Li+ . J. Am. Chem. Soc. , 114 : 3978 – 3980 .
   Web of Science ®Google Scholar
• Haddon , R.C. , Brus , L.E. and Raghavachari , K. 1986 . Electronic structure and bonding in icosahedral C60 . Chem. Phys. Lett. , 125 : 459 – 464 .
   Web of Science ®Google Scholar
• Haddon , R.C. 1992 . Electronic structure, conductivity and superconductivity of alkali metal doped (C60) . Acc. Chem. Res. , 25 : 127 – 133 .
   Web of Science ®Google Scholar
• Wudl , F. 1992 . The chemical properties of buckminsterfullerene (C60) and the birth and infancy of fulleroids . Acc. Chem. Res. , 25 : 157 – 161 .
   Web of Science ®Google Scholar
• Krusic , J. , Wasserman , E. , Keizer , P. , Morton , J.R. and Preston , K.F. 1991 . Radical reactions of C60 . Science , 254 : 1183 – 1185 .
   PubMed Web of Science ®Google Scholar
• Sayes , C.M. , Gobin , A.M. , Ausman , K.D. , Mendez , J. , West , J.L. and Colvin , V.L. 2005 . Nano-C-60 cytotoxicity is due to lipid per oxidation . Biomaterials , 26 : 7587 – 7595 .
   PubMed Web of Science ®Google Scholar
• Jensen , A.W. , Wilson , S.R. and Schuster , D.I. 1996 . Biological applications of fullerenes . Bioorgan. Med. Chem. , 4 : 767 – 779 .
   PubMed Web of Science ®Google Scholar
• Ruoff , R.S. , Tse , D.S. , Malhotra , R. and Lorents , D.C. 1993 . J. Solubility of C60 in a variety of solvents . Phys. Chem. , 97 : 3379 – 3383 .
   Web of Science ®Google Scholar
• Scrivens , W.A. , Cassell , A.M. , Kinsey , K.E. and Tour , J.M. 1994 . Single column purification of Gram quantities of C70 . J. Am. Chem. Soc. , 116 : 6939 – 6940 .
   Web of Science ®Google Scholar
• Beck , M.T. , Mándi , G. and Kéki , S. 1996 . The solubility of C60 in organic and inorganic solvents . Proc. Electrochem. Soc. , 96 : 32 – 38 .
   Google Scholar
• Buzaneva , E.V. , Bulavin , L.A. , Pogorelov , V.E. , Yashchuk , V.N. , Priludski , Y.I. , Durofv , S.S. , Nazarenko , A.B. , Astashkin , Y.A. , Ogulchansky , T.Y. and Andrievsky , G.V. 1998 . C60 based molecular and electronic nanostructures . AIP Conf. Proc. , 442 : 172 – 175 .
   Google Scholar
• Scrivens , W.A. , Tour , J.M. , Creek , K.E. and Pirisi , L. 1994 . Synthesis of 14C-labeled C60, its suspension in water, and its uptake by human keratinocytes . J. Am. Chem. Soc. , 116 : 4517 – 4518 .
   Web of Science ®Google Scholar
• Creek , K.E. , Geslani , G. , Batova , A. and Pirisi , L. 1995 . Progressive lost of sensitivity to growth control by retinoic acid and transforming growth factor-beta at late stages of human papilloma virus type 16-initiated transformation of human keratinocytes . Adv. Exp. Med. Biol. , 375 : 117 – 135 .
   PubMedGoogle Scholar
• Bosi , S. , Da Ros , T. , Spalluto , G. and Prato , M. 2003 . Fullerene derivatives: an attractive tool for biological applications . Eur. J. Med. Chem. , 38 : 913 – 923 .
   PubMed Web of Science ®Google Scholar
• Kroto , H.M. , Heath , J.R. , O'Brien , S.C. , Curl , R.F. and Smalley , R.E. 1985 . C60: buckminsterfullerene . Nature , 318 : 162 – 163 .
   Web of Science ®Google Scholar
• Schinazi , R.F. , Sijbesma , R. , Srdanov , G. , Hill , C.G. and Wudl , F. 1993 . Synthesis and virucidal activity of a water-soluble, configurationally stable, derivatized C60 fullerene . Antimicrob. Agents Chemother. , 37 : 1707 – 1710 .
   PubMed Web of Science ®Google Scholar
• Marcorin , G.L. , Ros , T.D. , Castellano , S. , Stefancich , G. , Bonin , I. , Miertus , S. and Prato , M. 2000 . Design and synthesis of novel [60]fullerene derivatives as potential HIV aspartic protease inhibitors . Org. Lett. , 2 : 3955 – 3958 .
   PubMed Web of Science ®Google Scholar
• Tabata , Y. , Murakami , Y. and Ikada , Y. 1997 . Photodynamic effect of polyethylene glycol-modified fullerene on tumor . Jpn J. Cancer Res. , 88 : 1108 – 1116 .
   PubMedGoogle Scholar
• Tabata , Y. and Ikada , Y. 1999 . Biological functions of fullerene . Pure Appl. Chem. , 71 : 2047 – 2053 .
   Web of Science ®Google Scholar
• Chen , C. , Xing , G. , Wang , J. , Zhao , Y. , Li , B. , Tang , J. , Jia , G. , Wang , T. , Sun , J. , Xing , L. , Yuan , H. , Gao , Y. , Meng , H. , Chen , Z. , Zhao , F. , Chai , Z. and Fang , X. 2005 . Multihydroxylated [Gd@C82(OH)22]n nanoparticles: antineoplastic activity of high efficiency and low toxicity . Nano Lett. , 5 : 2050 – 2057 .
   PubMed Web of Science ®Google Scholar
• Grodin , J.M. , Siiteri , P.K. and MacDonald , P.C. 1973 . Source of estrogenproduction in postmenopausal women . J. Clin. Endocrinol. Metab. , 36 : 207 – 214 .
   PubMed Web of Science ®Google Scholar
• Henderson , B.E. , Ross , R. and Bernstein , L. 1998 . Estrogens as a cause of human cancer: the Richard and Linda Rosenthal Foundation award lecture . Cancer Res. , 48 : 246 – 253 .
   Google Scholar
• Pasqualini , J.R. , Chetrite , G. , Nguyen , B.L. , Maloche , C. , Delalonde , L. , Talbi , M. , Feinstein , M.C. , Blacke , C. , Botella , J. and Paris , J. 1995 . Estronesulfate-sulfatase and 17 beta-hydroxysteroid dehydrogenaseactivities: a hypothesis for their role in the evolution of human breast cancer from hormone-dependence to hormoneindependence . Steroid Biochem. Mol. Biol. , 53 : 407 – 4012 .
   PubMed Web of Science ®Google Scholar
• Picazo , A. and Salcedo , R. 2003 . Carcinogenic activity in estrone and its derivatives: a theoretical study . J. Mol. Struct.: THEOCHEM , 624 : 29 – 36 .
   Web of Science ®Google Scholar
• Becke , A.D. 1988 . Density-functional exchange-energy approximation with correct asymptotic behaviour . Phys. Rev. A , 38 : 3098 – 3100 .
   PubMed Web of Science ®Google Scholar
• Perdew , J.P. and Wang , Y. 1992 . Accurate and simple analytic representation of the electron-gas correlation energy . Phys. Rev. B , 45 : 13244 – 13249 .
   PubMed Web of Science ®Google Scholar
• Frisch , M.J. , Trucks , G.W. , Schlegel , H.B. , Scuseria , G.E. , Robb , M.A. , Cheeseman , J.R. , Zakrzewski , V.G. , Montgomery , J.A. Jr. , Stratmann , R.E. , Burant , J.C. , Dapprich , S. , Millarn , J.M. , Daniels , A.D. , Kudin , K.N. , Strain , M.C. , Farkas , O. , Tomasi , J. , Barone , V. , Cossi , M. , Cammi , R. , Mennucci , B. , Pomelli , C. , Adamo , C. , Clifford , S. , Ochterski , J. , Petersson , G.A. , Ayala , P.Y. , Cui , Q. , Morokuma , K. , Malick , D.K. , Rabuck , A.D. , Raghavachari , K. , Foresman , J.B. , Cioslovski , J. , Ortiz , J.V. , Stefanov , B.B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Gomperts , R. , Martin , R.L. , Fox , D.J. , Keith , T. , Al-Laham , M.A. , Peng , C.Y. , Nanayakkara , A. , Gonzalez , C. , Challacombe , M. , Gill , P.M.W. , Johnson , B.G. , Chen , W. , Wong , M.W. , Andres , J.L. , Head-Gordon , M. , Replogle , E.S. and Pople , J.A. 2004 . Gaussian 03 , Wallingford, CT : Gaussian Inc. .
   Google Scholar
• Zhao , Y. and Truhlar , D.G. 2004 . Development and assessment of a new hybrid density functional model for thermochemical kinetics . J. Phys. Chem. A , 108 : 2715 – 2719 .
   Web of Science ®Google Scholar
• Frisch , M.J. , Trucks , G.W. , Schlegel , H.B. , Scuseria , G.E. , Robb , M.A. , Cheeseman , J.R. , Scalmani , G. , Barone , V. , Mennucci , B. , Petersson , G.A. , Nakatsuji , H. , Caricato , M. , Li , X. , Hratchian , H.P. , Izmaylov , A.F. , Bloino , J. , Zheng , G. , Sonnenberg , J.L. , Hada , M. , Ehara , M. , Toyota , K. , Fukuda , R. , Hasegawa , J. , Ishida , M. , Nakajima , T. , Honda , Y. , Kitao , O. , Nakai , H. , Vreven , T. , Montgomery , J.A. Jr. , Peralta , J.E. , Ogliaro , F. , Bearpark , M. , Heyd , J.J. , Brothers , E. , Kudin , K.N. , Staroverov , V.N. , Kobayashi , R. , Normand , J. , Raghavachari , K. , Rendell , A. , Burant , J.C. , Iyengar , S.S. , Tomasi , J. , Cossi , M. , Rega , N. , Millam , N.J. , Klene , M. , Knox , J.E. , Cross , J.B. , Bakken , V. , Adamo , C. , Jaramillo , J. , Gomperts , R. , Stratmann , R.E. , Yazyev , O. , Austin , A.J. , Cammi , R. , Pomelli , C. , Ochterski , J.W. , Martin , R.L. , Morokuma , K. , Zakrzewski , V.G. , Voth , G.A. , Salvador , P. , Dannenberg , J.J. , Dapprich , S. , Daniels , A.D. , Farkas , Ö. , Foresman , J.B. , Ortiz , J.V. , Cioslowski , J. and Fox , D.J. 2009 . Gaussian 09, Revision A.1 , Wallingford, CT : Gaussian, Inc. .
   Google Scholar
• Peng , C. , Ayala , P.Y. and Schlegel , H.B. 1996 . Using redundant internal coordinates to optimize equilibrium geometries and transition states . J. Comput. Chem. , 17 : 49 – 56 .
   Web of Science ®Google Scholar
• Mohajeri , A. and Jenabi,Singlet , M.J. 2007 . triplet potential energy surfaces of C3H2 . J. Mol. Struct.: THEOCHEM , 820 : 65 – 73 .
   Web of Science ®Google Scholar
• Ziegler , B.E. and McMAhon , T.B. 2010 . Energetics and structural elucidation of mechanisms for gas phase H/D exchange of protonated peptides . J. Phys. Chem. A , 114 : 11953 – 11963 .
   PubMed Web of Science ®Google Scholar
• Zhang , J.C. , Sen , Z. , Yang , Z.Y. and Cao , W.L. 2005 . A theoretical study on the reaction mechanism of epoxidation reaction of the [4-(bromomethyl)bicyclo[4.4.1]undeca-1,3,5,7,9-pentaen-3-yl]methanol . Chin. J. Chem. Phys. , 18 : 167 – 173 .
   Web of Science ®Google Scholar
• Wang , P. , Wesdemiotis , C. , Kapota , C. and Ohanessian , G. 2007 . The sodium ion affinities of simple di, tri, and tetrapeptides . J. Am. Soc. Mass Spectrom. , 18 : 541 – 552 .
   PubMed Web of Science ®Google Scholar
• Car , R. and Parrinello , M. 1985 . Unified approach for molecular dynamics and density-functional theory . Phys. Rev. Lett. , 55 : 2471 – 2474 .
   PubMed Web of Science ®Google Scholar
• dos Santos , M.V.P. , Teixeira , E.S. and Longo , R.L. 2009 . A direct dynamics study of protonated alcohol dehydration and the Diels-Alder reaction . J. Braz. Chem. Soc. , 20 : 652 – 662 .
   Web of Science ®Google Scholar
• Marenich , A.V. , Cramer , C.J. and Truhlar , D.G. 2009 . Universal solvation model based on solute electron density and a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions . J. Phys. Chem. B , 113 : 6378 – 6396 .
   PubMed Web of Science ®Google Scholar
• Wilson , S.R. , Schuster , D.I. , Nuber , B. , Meier , M.S. , Maggini , M. , Prato , M. and Taylor , R. 2000 . “ Organic chemistry of fullerenes ” . In Fullerenes: Chemistry, Physics, and Technology Edited by: Kadish , K. M. and Ruoff , R. S. 91 – 176 . John Wiley and Sons, New York
   Google Scholar
• Cioslowski , J. 1995 . Electronic Structure Calculations on Fullerene and their Derivatives , Oxford : Oxford University Press .
   Google Scholar
• Sijbesma , R. , Srdanov , G. , Wudl , F. , Castoro , J.A. , Wilkins , C. , Friedman , S.H. , DeCamp , D.L. and Kenyon , G.L. 1993 . Synthesis of a fullerene derivative for the inhibition of HIV enzymes . J. Am. Chem. Soc. , 115 : 6510 – 6512 .
   Web of Science ®Google Scholar
• Friedman , S.H. , DeCamp , D.L. , Sijbesma , R. , Srdanov , G. , Wudl , F. and Kenyon , G.L. 1993 . Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification . J. Am. Chem. Soc. , 115 : 6506 – 6509 .
   Web of Science ®Google Scholar
• Schinazi , R.F. , Sijbesma , R. , Srdanov , G. , Hill , C.L. and Wudl , F. 1993 . Synthesis and virucidal activity of a water-soluble, configurationally stable, derivatized C60 fullerene . Antimicrob, Agents Chemother. , 37 : 1707 – 1710 .
   PubMed Web of Science ®Google Scholar
• Zhu , Z. , Schuster , D.I. and Tuckerman , M.E. 2003 . Molecular dynamics investigation of the connection between flap-closing and binding of fullerene-based inhibitors of the HIV-1 protease . Biochemistry , 42 : 1326 – 1333 .
   PubMed Web of Science ®Google Scholar
• Da Ros , T. , Spalluto , G. and Prato , M. 2001 . Biological applications of fullerene derivatives: a brief overview . Croat. Chem. Acta , 74 : 743 – 755 .
   Web of Science ®Google Scholar
• Mashino , T. , Shimotohno , K. , Ikegami , N. , Nishikawa , D. , Okuda , K. , Takahashi , K. , Nakamura , S. and Mochizuki , M. 2005 . An immunodeficiency virus-reverse transcriptase inhibition and hepatitis C virus RNA-dependent RNA polymerase inhibition activities of fullerene derivative . Bioorg. Med. Chem. Lett. , 15 : 1107 – 1109 .
   PubMed Web of Science ®Google Scholar
• Tsao , N. , Luh , T.Y. , Chou , C.K. , Chang , T.Y. , Wu , J.J. , Liu , C.C. and Lei , H.Y. 2002 . In vitroaction of carboxyfullerene . J. Antimicrob. Chemother. , 49 : 641 – 649 .
   PubMedGoogle Scholar
• Bosi , S. , Da Ros , T. , Castellano , S. , Banfi , E. and Prato , M. 2000 . Antimycobacterial activity of ionic fullerene derivatives . Bioorg. Med. Chem. Lett. , 10 : 1043 – 1045 .
   PubMed Web of Science ®Google Scholar
• Bosi , S. , Feruglio , L. , Da Ros , T. , Spalluto , G. , Gregoretti , B. , Terdoslavich , M. , Decorti , G. , Passamonti , S. , Moro , S. and Prato , M. 2004 . Hemolytic effects of water-soluble fullerene derivatives . J. Med. Chem. , 47 : 6711 – 6715 .
   PubMed Web of Science ®Google Scholar
• Dugan , L.L. , Turetsky , D.M. , Du , C. , Lobner , D. , Wheeler , M. , Almli , C.R. , Shen , C.K.-F. , Luh , T.-Y. , Choi , D.W. and Lin , T.-S. 1997 . Carboxyfullerenes as neuroprotective agents . Proc. Natl. Acad. Sci. USA , 94 : 9434 – 9439 .
   PubMed Web of Science ®Google Scholar
• Huang , Y.L. , Shen , C.K. , Luh , T.Y. , Yang , H.C. , Hwang , K.C. and Chou , C.K. 1998 . Blockage of apoptotic signaling of transforming growth factor-β in human hepatoma cells by carboxyfullerene . Eur. J. Biochem. , 254 : 38 – 43 .
   PubMedGoogle Scholar
• Tuktarov , A.R. , Khuzina , L.L. and Dzhemilev , U.M. 2011 . Covalent binding of fullerene C60 to pharmacologically important compounds . Russ. Chem. Bull., Int. Ed. , 60 : 662 – 666 .
   Google Scholar
• LeQuesne , P.W. , Durga , A.V. , Subramanian , V. , Soloway , A.H. , Hart , R.H. and Purdy , R.H. 1980 . Biomimetic synthesis of catechol estrogens: potentially mutagenic arene oxide intermediates in estrogen metabolism . J. Med. Chem. , 23 : 239 – 240 .
   PubMed Web of Science ®Google Scholar
• Cavallieri , E. , Frenkel , K. , Liehr , J.G. , Rogan , E. and Roy , D. 2000 . Estrogen as endogenous genotoxic agents—DNA adducts and mutations . J. Natl. Cancer Inst. Mon. , 27 : 75 – 93 .
   PubMedGoogle Scholar
• Slaga , T.J. , Bracken , W.J. , Gleason , C. , Lewin , W. , Yagi , H. , Jerina , D.M. and Conney , A.H. 1979 . Marked differences in the skin tumor-initiating activities of the optical enantiomers of the diasteromericbenzo(a)pyrene 7,8-diol-9,10-epoxides . Cancer Res. , 39 : 67 – 71 .
   PubMed Web of Science ®Google Scholar
• Huetz , P. and Poux , V. 2006 . Carcinogenicity of benzo[a]pyrene diol epoxide stereoisomers: a linear free energy relationship study . J. Mol. Struct.: THEOCHEM , 764 : 167 – 176 .
   Web of Science ®Google Scholar
• Woodward , R.B. and Hoffmann , R. 1970 . The Conservation of Orbital Symmetry , New York : Academic Press .
   Google Scholar
• Mikie , T. , Asahara , H. , Nagao , K. , Ikuma , N. , okubo , K. and Oshima , T. 2011 . Thermal [2+2] cycloaddition of morpholinoenamines with C60 via a single electron transfer . Org. Lett. , 13 : 4244 – 4247 .
   PubMed Web of Science ®Google Scholar
• Martín , N. , Altable , M. , Filippone , S. , Domenech , A.M. , Güell , M. and Solà , M. 2006 . Thermal [2+2] Intramolecular cycloadditions of fuller-1,6-enynes . Angew. Chem. Int. Ed. Eng. , 45 : 1439 – 1442 .
   PubMed Web of Science ®Google Scholar
• Mehta , G. and Vishwanath , M.B. 1995 . Novel bicyclo[2.2.0]hexane-fused [60]fullerene derivatives via cycloaddition with a cyclobutadiene diester . Tetrahedron Lett. , 36 : 5631 – 5632 .
   Web of Science ®Google Scholar
• Iyengar , S.S. , Schleger , H.B. , Millian , J.M. , Voth , G.A. , Scuseria , G.E. and Frisch , M.J. 2002 . Ab initio molecular dynamics: propagating the density matrix with Gaussian orbitals. III. Comparison with Born–Oppenheimer dynamics . J. Chem. Phys. , 117 : 8694 – 8704 .
   Web of Science ®Google Scholar
• Banás , P. , Rulisek , L. , Hánosová , V. , Svozil , D. , Walter , N.G. , Sponer , J. and Otyepka , M. 2008 . General base catalysis for cleavage by the active-site of the hepatitis delta virus ribozyme: QM/MM calculations establish chemical feasibility . J. Phys. Chem. B , 112 : 11177 – 11187 .
   PubMed Web of Science ®Google Scholar
• Díaz , N. , Suárez , D. and Sordo , T.L. 2000 . Theoretical study of the water-assisted aminolysis of β-lactams: implications for the reaction between human serum albuminum and penicillins . J. Am. Chem. Soc. , 122 : 6710 – 6719 .
   Web of Science ®Google Scholar
• Martín , N. , Altable , M. , Filippone , S. and Martín-Domenech , A. 2007 . New Reactions in fullerene chemistry . Synlett , 20 : 3077 – 3095 .
   Web of Science ®Google Scholar
• Xu , L. , Doubleday , C.E. and Houk , K.N. 2011 . Dynamics of carbine cycloadditions . J. Am. Chem. Soc. , 133 : 17848 – 17854 .
   PubMed Web of Science ®Google Scholar