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Volumn 47, Issue 3, 2012, Pages 539-548

Experimental and theoretical NMR determination of isoniazid and sodium p-sulfonatocalix[n]arenes inclusion complexes

Author keywords

Calix n arenes; In vitro evaluation; Isoniazid; NMR; Supramolecular chemistry; Tuberculosis

Indexed keywords

CALIXARENE; HYDRAZIDE DERIVATIVE; ISONIAZID; SODIUM PARA SULFONATOCALIX[N]ARENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84865428482     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.07.015     Document Type: Article
Times cited : (48)

References (38)
  • 1
    • 68649101487 scopus 로고    scopus 로고
    • Proparacaine complexation with beta-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied (1)H-NMR approaches
    • L.M. Arantes, C. Scarelli, A.J. Marsaioli, E. de Paula, and S.A. Fernandes Proparacaine complexation with beta-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied (1)H-NMR approaches Magn. Reson. Chem. 47 2009 757 763
    • (2009) Magn. Reson. Chem. , vol.47 , pp. 757-763
    • Arantes, L.M.1    Scarelli, C.2    Marsaioli, A.J.3    De Paula, E.4    Fernandes, S.A.5
  • 3
    • 51449116084 scopus 로고    scopus 로고
    • Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR
    • L.F. Cabeça, S.A. Fernandes, E. de Paula, and A.J. Marsaioli Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR Magn. Reson. Chem. 46 2008 832 837
    • (2008) Magn. Reson. Chem. , vol.46 , pp. 832-837
    • Cabeça, L.F.1    Fernandes, S.A.2    De Paula, E.3    Marsaioli, A.J.4
  • 4
    • 0031209054 scopus 로고    scopus 로고
    • A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics
    • E. Cances, B. Mennucci, and J. Tomasi A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics J. Chem. Phys. 107 1997 3032 3041
    • (1997) J. Chem. Phys. , vol.107 , pp. 3032-3041
    • Cances, E.1    Mennucci, B.2    Tomasi, J.3
  • 5
    • 60049087880 scopus 로고
    • Measurement of sensitivity of the tuberculous bacillus to antibacillary drugs by the method of proportions. Methodology, resistance criteria, results and interpretation
    • J. Canetti, E. Rist, and R. Grosset Measurement of sensitivity of the tuberculous bacillus to antibacillary drugs by the method of proportions. Methodology, resistance criteria, results and interpretation Revue de tuberculose et de pneumologie 27 1963 217
    • (1963) Revue de Tuberculose et de Pneumologie , vol.27 , pp. 217
    • Canetti, J.1    Rist, E.2    Grosset, R.3
  • 6
    • 4043061514 scopus 로고    scopus 로고
    • Enlarging the size of calix[4]arene-crowns-6 to improve Cs+/K+ selectivity: A theoretical and experimental study
    • A. Casnati, N. Della Ca, F. Sansone, F. Ugozzoli, and R. Ungaro Enlarging the size of calix[4]arene-crowns-6 to improve Cs+/K+ selectivity: a theoretical and experimental study Tetrahedron 60 2004 7869 7876
    • (2004) Tetrahedron , vol.60 , pp. 7869-7876
    • Casnati, A.1    Della Ca, N.2    Sansone, F.3    Ugozzoli, F.4    Ungaro, R.5
  • 11
    • 79952466815 scopus 로고    scopus 로고
    • Computational databases, pathway and cheminformatics tools for tuberculosis drug discovery
    • S. Ekins, J.S. Freundlich, I. Choi, M. Sarker, and C. Talcott Computational databases, pathway and cheminformatics tools for tuberculosis drug discovery Trends Microbiol. 19 2011 65 74
    • (2011) Trends Microbiol. , vol.19 , pp. 65-74
    • Ekins, S.1    Freundlich, J.S.2    Choi, I.3    Sarker, M.4    Talcott, C.5
  • 12
    • 34047115217 scopus 로고    scopus 로고
    • Investigation of tetracaine complexation with beta-cyclodextrins and p-sulphonic acid calix[6]arenes by nOe and PGSE NMR
    • S.A. Fernandes, L.F. Cabeça, A.J. Marsaioli, and E. de Paula Investigation of tetracaine complexation with beta-cyclodextrins and p-sulphonic acid calix[6]arenes by nOe and PGSE NMR J. Incl. Phenom. Macrocycl. Chem. 57 2007 395 401
    • (2007) J. Incl. Phenom. Macrocycl. Chem. , vol.57 , pp. 395-401
    • Fernandes, S.A.1    Cabeça, L.F.2    Marsaioli, A.J.3    De Paula, E.4
  • 13
    • 0034682859 scopus 로고    scopus 로고
    • Determination of association constants (K-A) from solution NMR data
    • L. Fielding Determination of association constants (K-a) from solution NMR data Tetrahedron 56 2000 6151 6170
    • (2000) Tetrahedron , vol.56 , pp. 6151-6170
    • Fielding, L.1
  • 15
    • 11244282931 scopus 로고    scopus 로고
    • Gaussian, Inc.; Wallingford, CT
    • Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Calabrese, J.R.; Montgomery, Jr.; J.A.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Oldham, H.N.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Choi, J.H.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Van Der Molen, M.K.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Bakken, V.; Macera, C.A.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Aquino, A.J.A.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Lee, K.M.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Li, S.D.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Han, D.K.M.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Zakrzewski, J.V.O.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; R.L.M.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; A.N.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; W.C.; Wong, M.W.; Gonzalez, C.; Pople, J.A. 2004. Gaussian 03, Revision D.01. Gaussian, Inc.; Wallingford, CT.
    • (2004) Gaussian 03, Revision D.01
    • Frisch, M.J.1    Trucks, G.W.2    Schlegel, H.B.3    Scuseria, G.E.4
  • 17
    • 0003909854 scopus 로고
    • 2nd ed. John Wiley & Sons Chichester
    • H. Gunther NMR Spectroscopy 2nd ed. 1994 John Wiley & Sons Chichester
    • (1994) NMR Spectroscopy
    • Gunther, H.1
  • 18
    • 0000873890 scopus 로고
    • Calixarenes.13. The conformational properties of calix[4]arenes, calix[6]arenes, calix[8]arenes, and oxacalixarenes
    • C.D. Gutsche, and L.J. Bauer Calixarenes.13. the conformational properties of calix[4]arenes, calix[6]arenes, calix[8]arenes, and oxacalixarenes J. Am. Chem. Soc. 107 1985 6052 6059
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 6052-6059
    • Gutsche, C.D.1    Bauer, L.J.2
  • 19
    • 33748545144 scopus 로고
    • Influence of polarization functions on molecular-orbital hydrogenation energies
    • P.C. Hariharan, and J.A. Pople Influence of polarization functions on molecular-orbital hydrogenation energies Theor. Chim. Acta 28 1973 213 222
    • (1973) Theor. Chim. Acta , vol.28 , pp. 213-222
    • Hariharan, P.C.1    Pople, J.A.2
  • 20
    • 0347170005 scopus 로고
    • Self - Consistent molecular orbital methods XII. Further extensions of Gaussian - Type basis sets for use in molecular orbital studies of organic molecules
    • W.J. Hehre, R. Ditchfield, and J.A. Pople Self - consistent molecular orbital methods XII. Further extensions of Gaussian - type basis sets for use in molecular orbital studies of organic molecules J. Chem. Phys. 56 1972 2257 2261
    • (1972) J. Chem. Phys. , vol.56 , pp. 2257-2261
    • Hehre, W.J.1    Ditchfield, R.2    Pople, J.A.3
  • 21
    • 84874553913 scopus 로고    scopus 로고
    • World Health Organization. (accessed 04.02.12)
    • World Health Organization. < http://www.who.int/research/en/ > (accessed 04.02.12).
  • 23
    • 0001470568 scopus 로고    scopus 로고
    • Drugs, in cyclodextrins, in liposomes: A novel approach to the chemical stability of drugs sensitive to hydrolysis
    • Y.L. Loukas, V. Vraka, and G. Gregoriadis Drugs, in cyclodextrins, in liposomes: a novel approach to the chemical stability of drugs sensitive to hydrolysis Int. J. Pharm. 162 1998 137 142
    • (1998) Int. J. Pharm. , vol.162 , pp. 137-142
    • Loukas, Y.L.1    Vraka, V.2    Gregoriadis, G.3
  • 24
    • 0007630831 scopus 로고
    • Hydrazine derivatives of pyridine-carboxylic acids
    • H. Meyer, and J. Mally Hydrazine derivatives of pyridine-carboxylic acids Monatsh 33 1912 393 414
    • (1912) Monatsh , vol.33 , pp. 393-414
    • Meyer, H.1    Mally, J.2
  • 25
    • 34548665052 scopus 로고    scopus 로고
    • Preparação e caracterização físico-química de complexos de inclusão entre anestésicos locais e hidroxipropil-β-ciclodextrina
    • C.M. Moraes, P. Abrami, M.M. Gonçalves, N.A. Filho, S.A. Fernandes, E. Paula, and L.F. Fraceto Preparação e caracterização físico-química de complexos de inclusão entre anestésicos locais e hidroxipropil-β- ciclodextrina Quím. Nova 30 2007 777 784
    • (2007) Quím. Nova , vol.30 , pp. 777-784
    • Moraes, C.M.1    Abrami, P.2    Gonçalves, M.M.3    Filho, N.A.4    Fernandes, S.A.5    Paula, E.6    Fraceto, L.F.7
  • 28
    • 5944261746 scopus 로고
    • Density-functional approximation for the correlation energy of the inhomogeneous electron gas
    • J. Perdew Density-functional approximation for the correlation energy of the inhomogeneous electron gas P. Phys. Rev. B 33 1986 8822 8824
    • (1986) P. Phys. Rev. B , vol.33 , pp. 8822-8824
    • Perdew, J.1
  • 29
    • 4243943295 scopus 로고    scopus 로고
    • Generalized gradient approximation made simple
    • J.P. Perdew, K. Burke, and M. Ernzerhof Generalized gradient approximation made simple Phys. Rev. Lett. 77 1996 3865 3868
    • (1996) Phys. Rev. Lett. , vol.77 , pp. 3865-3868
    • Perdew, J.P.1    Burke, K.2    Ernzerhof, M.3
  • 30
    • 2442551918 scopus 로고    scopus 로고
    • Comparison of flow cytometric and alamar blue tests with the proportional method for testing susceptibility of Mycobacterium tuberculosis to rifampin and isoniazid
    • R.S. Reis, I. Neves, S.L.S. Lourenco, L.S. Fonseca, and M.C.S. Lourenco Comparison of flow cytometric and alamar blue tests with the proportional method for testing susceptibility of Mycobacterium tuberculosis to rifampin and isoniazid J. Clin. Microbiol. 42 2004 2247 2248
    • (2004) J. Clin. Microbiol. , vol.42 , pp. 2247-2248
    • Reis, R.S.1    Neves, I.2    Lourenco, S.L.S.3    Fonseca, L.S.4    Lourenco, M.C.S.5
  • 31
    • 85027944841 scopus 로고    scopus 로고
    • Computational analysis and physico-chemical characterization of an inclusion compound between praziquantel and methyl-beta-cyclodextrin for use as an alternative in the treatment of schistosomiasis
    • S.G. Rodrigues, I.D. Chaves, N.F.S. de Melo, M.B. de Jesus, L.F. Fraceto, S.A. Fernandes, E. de Paula, M.P. de Freitas, and L.D.A. Pinto Computational analysis and physico-chemical characterization of an inclusion compound between praziquantel and methyl-beta-cyclodextrin for use as an alternative in the treatment of schistosomiasis J. Incl. Phenom. Macrocycl. Chem. 70 2011 19 28
    • (2011) J. Incl. Phenom. Macrocycl. Chem. , vol.70 , pp. 19-28
    • Rodrigues, S.G.1    Chaves, I.D.2    De Melo, N.F.S.3    De Jesus, M.B.4    Fraceto, L.F.5    Fernandes, S.A.6    De Paula, E.7    De Freitas, M.P.8    Pinto, L.D.A.9
  • 32
    • 3242749733 scopus 로고    scopus 로고
    • Recent application of ab initio calculations on calixarenes and calixarene complexes
    • J. Schatz Recent application of ab initio calculations on calixarenes and calixarene complexes A Rev. Collect. Czech. Chem. Commun. 69 2004 1169 1194
    • (2004) A Rev. Collect. Czech. Chem. Commun. , vol.69 , pp. 1169-1194
    • Schatz, J.1
  • 35
    • 77649173585 scopus 로고    scopus 로고
    • Thermodynamics of inclusion complexes between cyclodextrins and isoniazid
    • I.V. Terekhova, and R.S. Kumeev Thermodynamics of inclusion complexes between cyclodextrins and isoniazid Russ. J. Phys. Chem. A 84 2010 1 6
    • (2010) Russ. J. Phys. Chem. A , vol.84 , pp. 1-6
    • Terekhova, I.V.1    Kumeev, R.S.2
  • 36
    • 3042756206 scopus 로고    scopus 로고
    • Evaluation of microplate Alamar blue assay for drug susceptibility testing of Mycobacterium avium complex isolates
    • J.D. Vanitha, and C.N. Paramasivan Evaluation of microplate Alamar blue assay for drug susceptibility testing of Mycobacterium avium complex isolates Diagn. Microbiol. Infect. Dis. 49 2004 179 182
    • (2004) Diagn. Microbiol. Infect. Dis. , vol.49 , pp. 179-182
    • Vanitha, J.D.1    Paramasivan, C.N.2
  • 38
    • 11744305193 scopus 로고
    • Efficient implementation of the gauge-independent atomic orbital method for nmr chemical-shift calculations
    • K. Wolinski, J.F. Hinton, and P. Pulay Efficient implementation of the gauge-independent atomic orbital method for nmr chemical-shift calculations J. Am. Chem. Soc. 112 1990 8251 8260
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8251-8260
    • Wolinski, K.1    Hinton, J.F.2    Pulay, P.3


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