Theoretical Study of Structural Relationships and Electrochemical Properties of Supramolecular [14-MR Macrolides]@C_n Complexes

REFERENCES

• Anderson , M. R. , H. C. Dorn , and S. A. Stevenson . 2000 . Making connections between metallofullerenes and fullerenes: Electrochemical investigations . Carbon 38 : 1663 – 1670 .
   Web of Science ®Google Scholar
• Assaf , N. A. , J. V. Pothuluri , R.-F. Wang , and C. E. Cerniglia . 1999 . Bioassay procedure for erythromycin in sediments . Aquat. Soc. 30 : 137 – 146 .
   Web of Science ®Google Scholar
• Bolboaca , S. D. , and L. Jantschi . 2007 . How good can the characteristic polynomial be for correlations? Int. J. Mol. Sci. 8 : 335 – 345 .
   Web of Science ®Google Scholar
• Chen , M.-L. , and W. L. Chiou . 1983 . Analysis of erythromycin in biological fluids by high-performance liquid chromatography with electrochemical detection . J. Chromatrogr. 278 : 91 – 100 .
   PubMed Web of Science ®Google Scholar
• Cooper , S. R. 1988 . Crown thioether chemistry . Acc. Chem. Res. 21 : 141 .
   Web of Science ®Google Scholar
• Croteau , D. , F. Vallee , M. G. Bergeron , and M. Lebel . 1987 . High-performance liquid chromatographic assay of erythromycin and its esters using electrochemical detection . J. Chromatrogr. 419 : 205 – 212 .
   PubMed Web of Science ®Google Scholar
• Du , Y. P. , Y. Z. Liang , B. Y. Li , and C. J. Xu . 2002. Orthogonalization of block variables by subspace-projection for quantitative structure property relationship (QSPR) research. J. Chem. Inf. Comput. Sci. 42: 1128–1138.
   Google Scholar
• Dubois , M. , D. Fluchard , E. Sior , and P. Delahaut . 2001 . Identification and quantification of five macrolide antibiotics in several tissues, eggs and milk by liquid chromatography-electrospray tandem mass spectrometry . J. Chromtogr. B 753 : 189 – 202 .
   Web of Science ®Google Scholar
• Duthu , G. S. 1984 . Assay of erythromycin from human serum by high performance liquid chromatography with electrochemical detection . J. Liquid. Chromatrogr. 7 : 1023 – 1032 .
   Web of Science ®Google Scholar
• Eguchi , K. , H. Nagase , M. Ozawa , Y. S. Endoh , K. Goto , K. Hirata , K. Miyamoto , and H. Yoshimura . 2004 . Evaluation of antimicrobial agents for veterinary use in the ecotoxicity test using microalgae . Chemosphere 57 : 1733 – 1738 .
   PubMed Web of Science ®Google Scholar
• Gaynor , M. , and A. S. Mankin . 2005 . Macrolide antibiotics: Binding site, mechanism of action, resistance . Front. Medic. Chem. 2 : 21 – 35 .
   Google Scholar
• Gonzalez de la Huebra , M. J. , U. Vincent , G. Bordin , and A. R. Rodriguez . 2004 . Characterization of dirithromycin and spiramycin using hight performance liquid chromatography and direct in fusion mass spectrometry . Anal. Chim. Acta 503 : 247 – 256 .
   Web of Science ®Google Scholar
• Haufler , R. E. , J. Conceicao , L. P. F. Chibante , Y. Chai , N. E. Byrne , et al.. 1990. Efficient production of C60 (buckminsterfullerene). C60H36, and the solvated buckide ion. J. Phys. Chem. 94: 8634–8636.
   Web of Science ®Google Scholar
• Horie , M. , K. Saito , R. Ishii , T. Yoshida , Y. Haramaki , and H. Nakazawa . 1998 . Simultaneous determination of five macrolide antibiotics in meat by high-performance liquid chromatography. J. Chromatogr. A 812 : 295 – 302 .
   PubMed Web of Science ®Google Scholar
• International Union of Pure and Applied Chemistry (IUPAC). http://goldbook.iupac.org/M03663.html (accessed 2008).
   Google Scholar
• Janda , P. , T. Krieg , and L. Dunsch . 1998 . Nanostructuring of highly ordered C60 films by charge transfer . Adv. Mater. 17 : 1434 – 1438 .
   Web of Science ®Google Scholar
• Jehoulet , C. , Y. O. Obeng , Y. T. Kim , F. Zhou , and A. J. Bard . 1992 . Electrochemistry and Langmuir trough studies of fullerene C60 and C70 films . J. Am. Chem. Soc. 114 : 4237 – 4247 .
   Web of Science ®Google Scholar
• Jerry , M. , and M. D. Zuckerman . 2004 . Macrolides and ketolides: Azithromycin, clarithromycin, telithromycin . Infect. Dis. Clin. N. Am. 18 : 621 – 649 .
   PubMed Web of Science ®Google Scholar
• Kavan , L. , L. Dunsch , and H. Kataura . 2004 . Electrochemical tuning of electronic structure of carbon nanotubes and fullerene peapods . Carbon 42 : 1011 – 1019 .
   Web of Science ®Google Scholar
• Kees , F. , S. Spangler , and M. Wellenhofer . 1998 . Determination of macrolides in biological matrices by high-performance liquid chromatography with electrochemical detection . J. Chromatrogr. A 812 : 287 – 293 .
   PubMed Web of Science ®Google Scholar
• Keicho , N. , and S. Kudoh . 2002 . Diffuse panbronchiolitis: Role of macrolides in therapy . Am. J. Respir. Med. 1 ( 2 ): 119 – 131 .
   PubMedGoogle Scholar
• Knafer , I. , M. F. Skinner , and R. B. Walker . 1998 . Analysis of macrolide antibiotics . J. Chromatrogr. A 812 : 255 – 286 .
   PubMed Web of Science ®Google Scholar
• Kim , Y.-H. , C. J. Cha , and C. E. Cerniglia . 2002 . Purification and characterization of an erythromycin esterase from an erythromycin-resistant Pseudomonas sp . FEMS Micobial. Lett. 210 : 239 – 244 .
   PubMed Web of Science ®Google Scholar
• Kim , Y.-H. , T. M. Heinze , R. Beger , J. V. Pothuluri , and C. E. Cerniglia . 2004 . A kinetic study on the degradation of erythromycin A in aqueous solution . Int. J. Pharm. 271 : 63 – 76 .
   PubMed Web of Science ®Google Scholar
• Kim , Y.-H. , T. M. Heinze , S.-J. Kim , and C. E. Cerniglia . 2004 . Adsorption and clay-catalyzed degradation of erythromycin A on homoionic clays . J. Environ. Qual. 33 : 257 – 264 .
   PubMed Web of Science ®Google Scholar
• Kim , Y.-H. , K. Park , J. V. Pothuluri , and C. E. Cerniglia . 2004 . Mineralization of erythromycin A in aquaculture sediments . FEMS Micobial. Lett. 234 : 169 – 175 .
   PubMed Web of Science ®Google Scholar
• Kim , Y.-H. , J. V. Pothuluri , and C. E. Cerniglia . 2005 . Voltammetric investigation of macrolides by an HPLC-coulometric assay . J. Pharma. Biom. Anal. 38 : 390 – 396 .
   PubMed Web of Science ®Google Scholar
• Kimura , K. , N. Ikeda , Y. Maruyama , T. Okazaki , H. Shinohara , S. Bandow , and S. Iijima . 2003. Evidence for substantial interaction between Gd ion and SWNT in (Gd@C82)n@SWNT peapods revealed by STM studies. Chem. Phys. Lett. 379: 340–344.
   Web of Science ®Google Scholar
• Kroto , H. W. 1987 . The stability of the fullerences C n , with n = 24, 28, 32. 36. 50, 60 and 70 . Nature 329 : 529 .
   Web of Science ®Google Scholar
• Kroto , H. W. , J. R. Heath , S. C. O'Brien , R. F. Curl , and R. E. Smalley . 1985 . C60: Buckminsterfullerene . Nature 318 : 162 .
   Web of Science ®Google Scholar
• Laasko , S. , M. Scheinin , and M. Anttila . 1990 . J. Chromatrogr. 526 : 475 – 486 .
   PubMed Web of Science ®Google Scholar
• Lopez-Boado , Y. S. , and B. K. Rubin . 2008 . Macrolides as immunomodulatory medications for the therapy of chronic lung diseases . Curr. Opin. Pharmacol. 8 ( 3 ): 286 – 291 .
   PubMed Web of Science ®Google Scholar
• Ma , Z. , and P. A. Nemoto . 2002 . Discovery and development of ketolides as a new generation of macrolide antimicrobial agents . Curr. Med. Chem.–Anti-Infective Agents 1 : 15 – 34 .
   Google Scholar
• Miroshnyk , I. , S. Mirza , P. M. Zorky , J. Heinämäki , J. Yli-Kauhaluomac , and J. Yliruusia . 2008 . A new insight into solid-state conformation of macrolide antibiotics . Bioorg. Med. Chem. 16 : 232 – 239 .
   PubMed Web of Science ®Google Scholar
• Miyake , T. , and S. Saito . 2003 . Electronic structure of C60-encapsulating semiconducting carbon nanotube . Solid State Commun. 125 : 201 .
   Web of Science ®Google Scholar
• Moats , M. A. 2000 . Determination of tetracycline antibiotics in beef and pork tissues using ion-paired liquid chromatography . J. Agric. Food. Chem. 48 : 2244 .
   PubMed Web of Science ®Google Scholar
• Montenez , J. P. , F. Van Bambeke , J. Piret , R. Brasseur , P. M. Tulkens , and M.-P. Mingeot-Leclercq . 1999 . Conformational analysis and studies on acellular and cell culture models . Toxicol. Appl. Pharmacol. 156 : 3 – 15 .
   Web of Science ®Google Scholar
• Nilsson , L. G. , B. Waldorf , and O. Paulson . 1987 . Determination of erythromycin in human plasma, using column liquid chromatography with a polymeric packing material, alkaline mobile phase and amperometric detection . J. Chromatrogr. 423 : 189 – 197 .
   PubMed Web of Science ®Google Scholar
• Pappa-Louisi , A. , A. Papageorgiou , A. Zitrou , S. Sotiropoulos , E. Georgarakis , and F. Zougrou . 2001 . Study on the electrochemical detection of the macrolide antibiotics clarithromycin and roxithromycin in reversed-phase high-performance liquid chromatography . J. Chromatrogr. B 755 : 57 – 64 .
   PubMed Web of Science ®Google Scholar
• Plavšić , D. , S. Nikolić , N. Trinajstić , and Z. Mihalić . 1993 . On the Harary index for the characterization of chemical graphs . J. Math. Chem. 12 : 235 – 250 .
   Web of Science ®Google Scholar
• Pleasance , S. , J. Kelly , M. D. LeBlanc , M. A. Quilliam , R. K. Boyd , D. D. Kites , K. McErlane , M. R. Bailey , and D. H. North . 1992 . Determination of erythromycin A in salmon tissue by liquid chromatography with ion-spray mass spectrometry . Biol. Mass. Spectrom. 21 : 675 – 687 .
   PubMedGoogle Scholar
• Potera , C. 2001 . Antibody product eyed for replacing antibiotic supplements in feed . ASM News 67 : 292 – 293 .
   Google Scholar
• Randić , M. 1975 . Characterization of molecular branching . J. Am. Chem. Soc. 97 : 6609 – 6615 .
   Web of Science ®Google Scholar
• Rehm , D. , and A. Weller . 1970 . Kinetics of fluorescence quenching by electron and H-atom transfer . Isr. J. Chem. 8 : 259 .
   Web of Science ®Google Scholar
• Riedel , K.-D. , A. Wildfeuer , H. Laufen , and T. Zimmerman . 1992 . Equivalence of a high-performance liquid chromatographic assay and a bioassay of azithromycin in human serum samples . J. Chromatogr. 576 : 358 – 362 .
   PubMed Web of Science ®Google Scholar
• Roets , E. , X. Lepoudre , V. Van Rompaey , G. Velghe , L. Liu , and J. Hoogmartens . Chromatography of josamycin propionateon poly (styrene-divinyl benzene) . J. Chromatrogr. A 812 : 303 – 308 .
   Web of Science ®Google Scholar
• Schultz , M. J. 2004 . Macrolide activities beyond their antimicrobial effects: Macrolides in diffuse panbronchiolitis and cystic fibrosis . J. Antimicrob. Chemother. 54 ( 1 ): 21 – 28 .
   PubMed Web of Science ®Google Scholar
• Shen , H. 2007 . The compressive mechanical properties of Cn (n = 20, 60, 80, 180) and endohedral M@C60(M = Na, Al, Fe) fullerene molecules . Mol. Phys. 105 ( 17–18 ): 2405 – 2409 .
   Web of Science ®Google Scholar
• Shepard , R. M. , G. S. Duthu , R. A. Ferraina , and M. A. Mullins . 1991. High-performance liquid chromatographic assay with electrochemical detection for azithromycin in serum and tissues. J. Chromatrogr. 565: 321–337.
   PubMed Web of Science ®Google Scholar
• Sherigara , B. S. , W. Kutner , and F. D'Souza . 2003 . Electrocatalytic properties and sensor applications of fullerenes and carbon nanotubes . Electroanalysis 15 : 753 – 72 .
   Web of Science ®Google Scholar
• Slanina , Z. , M.-C. Chao , S.-L. Lee , and I. Gutman . 1997 . On applicability of the Wiener index to estimate relative stabilities of the higher-fullerene IPR isomers . J. Serb. Chem. Soc. 62 ( 3 ): 211 – 217 .
   Google Scholar
• Slanina , Z. , F. Uhlik , S. L. Lee , and E. Osawa . 2001 . Geometrical and thermodynamic approaches to the relative stabilities of fullerene isomers . MATCH Commun. Math. Comput. Chem. 44 : 335 – 348 .
   Google Scholar
• Smith , B. W. , M. Monthioux , and D. E. Luzzi . 1998 . Encapsulated C60 in carbon nanotubes . Nature 396 : 3239 .
   Web of Science ®Google Scholar
• Suzuki , T. , K. Kikuchi , F. Oguri , Y. Nakao , S. Suzuki , Y. Achiba , K. Yamamoto , H. Funasaka , and T. Takahashi . 1996 . Electrochemical properties of fullerenolanthanides . Tetrahedron 52 ( 14 ): 4973 – 4982 .
   Web of Science ®Google Scholar
• Taherpour , A. A. 2007a . Structural relationship between degree of unsaturation with polarizability of (5.5) armchair single-wall carbon nanotubes . Fullerenes, Nanotubes, Carbon Nanostruct. 15 : 279 – 289 .
   Web of Science ®Google Scholar
• Taherpour , A. A. 2007b . Quantitative structural relationship study of cis-unsaturated thiocrown ethers and their supramolecular [X-UT-Y][C60] and [X-UT-Y][La@C82] complexes . Fullerenes, Nanotubes, Carbon Nanostruct. 15 : 405 – 415 .
   Web of Science ®Google Scholar
• Taherpour , A. A. 2008 . Quantitative relationship study of mechanical structure properties of empty fullerenes . Fullerenes, Nanotubes, Carbon Nanostruct. 16 : 196 – 205 .
   Web of Science ®Google Scholar
• Taherpour , A. A. 2009a . Structural relationship study of electrochemical properties of the nano structures of cis-unsaturated thiocrown ethers and their supramolecular complexes [X-UTY][La@C72(C6H3C12)] non-IPR carbon cage . Fullerenes, Nanotubes, Carbon Nanostruct. 17 ( 2 ): 171 – 186 .
   Web of Science ®Google Scholar
• Taherpour , A. A. 2009b . Structural relationship between degree of unsaturation with fermi energy, chemical hardness, and the HOMO-LUMO Gap of (5.5) Armchair single-walled carbon nanotubes . Fullerenes, Nanotubes, Carbon Nanostruct. 17 ( 1 ): 26 – 37 .
   Web of Science ®Google Scholar
• Taherpour , A. A. 2009c . Quantitative structural relationship and theoretical study of electrochemical properties of C60@[SWCN(5.5)-Armchair-C n H20] complexes . Chem. Phys. Lett. 469 : 135 – 139 .
   Web of Science ®Google Scholar
• Taherpour , A. A. 2009d . Theoretical and quantitative structural relationship study of the electrochemical properties of [M-2@C-x]@[SWCNT(5.5)-armchair-C n H20] (M = Er and Sc, x = 82 and 84, and n = 20–300) complexes . J. Phys. Chem. C 113 : 5402 – 5408 .
   Web of Science ®Google Scholar
• Taherpour , A. A. , and F. Shafiei . 2005 . The structural relationship between Randić indices, adjacency matrixes, distance matrixes and maximum wave length of linear simple conjugated polyene compounds . J. Mol. Struct. THEOCHEM 726 : 183 – 188 .
   Web of Science ®Google Scholar
• Touzik , A. , H. Hermann , P. Janda , L. Dunsch , and K. Wetzig . 2002 . Nanostructuring of potassium fulleride layers . Europhys. Lett. 60 : 411 – 417 .
   Google Scholar
• Tserng , K. , and J. G. Wagner . 1976 . Fluorometric determination of erythromycin propionate in whole blood or plasma and correlation of results with microbiological assay . Anal. Chem. 48 : 348 – 353 .
   PubMed Web of Science ®Google Scholar
• Tsuchiya , T. , H. Kurihara , K. Sato , T. Wakahara , T. Akasaka , T. Shimizu , N. Kamigata , N. Mizorogi , and S. Nagase . 2006 . Supramolecular complexes of La@C82 with unsaturated thiacrown ethers . Chem. Commun. 20 : 3585 – 3587 .
   Web of Science ®Google Scholar
• Tsuchiya , T. , T. Shimizu , and N. Kamigata . 2001 . Unsaturated thiacrown ethers: Synthesis. physical properties, and formation of silver complexes . J. Am. Chem. Soc. 123 : 11534 – 11538 .
   PubMed Web of Science ®Google Scholar
• Tsuji , K. 1978. Fluorimetric determination of erythromycin and erythromycin ethylsuccinate in serum by a high-performance liquid chromatographic post-column, on-stream derivatization and extraction method. J. Chromatogr. 158: 337–348.
   PubMed Web of Science ®Google Scholar
• Tsuji , K. , and J. F. Groetz . 1978 . High performance liquid chromatographic determination of erythromycin . J. Chromatogr. 147 : 359 – 367 .
   PubMed Web of Science ®Google Scholar
• Volmer , D. A. , and J. P. M. Hui . 1992 . Rapid determination of corticosteroids in urine by combined solid-phase microextraction/liquid chromatography mass spectrometry . Rapid Commun. Mass Spectrom. Anal. 21 : 123 – 129 .
   Google Scholar
• Wikipedia. http://en.wikipedia.org/wiki/Macrolide (accessed 2008 ).
   Google Scholar
• Xie , Q. , E. Perez-Codero , and L. Echegoyen . 1992 . Electrochemical detection of and : Enhanced stability of fullerides in solution . J. Am. Chem. Soc. 114 : 3978 – 3980 .
   Web of Science ®Google Scholar
• Zhang , M. , M. Yudasaka , S. Bandow , and S. Iijima . 2003 . Thermogravimetric analysis for the array of C60 molecules formed in single-wall carbon nanotube . Chem. Phys. Lett. 369 : 680 .
   Web of Science ®Google Scholar