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2011 | 9 | 5 | 855-866
Tytuł artykułu

Investigation of 6-fluoroquinolones activity against Mycobacterium tuberculosis using theoretical molecular descriptors: a case study

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A quantitative structure-activity relationship (QSAR) study on a set of 66 structurally-similar 6-fluoroquinolones was performed using a large pool of theoretical molecular descriptors. Ab initio geometry optimizations were carried out to reproduce the geometrical and electronic structure parameters. The resulting molecular structures were confirmed to be minima via harmonic frequency calculations. Obtained atomic charges, HOMO and LUMO energies, orbital electron densities, dipole moment, energy and many other properties served as quantum-chemical descriptors. A multiple linear regression (MLR) technique was applied to generate a linear model for predicting the biological activity, Minimal Inhibitory Concentration (MIC), treated as negative decade logarithm, (pMIC). The heuristic method was used to optimize the model parameters and select the most significant descriptors. The model was tested internally using the CV LOO procedure on the training set and validated against the external validation set. The result (Q 2 ext = 0.7393), which was obtained on an external, previously excluded validation data set, shows the predictive performances of this model (R 2tr = 0.7416, Q 2 tr = 0.6613) in establishing (Q)SAR of 6-fluoroquinolones. This validated model could be proficiently used to design new 6-fluoroquinolones with possible higher activity. [...]
Wydawca

Czasopismo
Rocznik
Tom
9
Numer
5
Strony
855-866
Opis fizyczny
Daty
wydano
2011-10-01
online
2011-07-24
Twórcy
  • Faculty of Chemistry, University of Wrocław, 50-383, Wrocław, Poland
  • National Institute of Chemistry, POB 660, 1001, Ljubljana, Slovenia
  • National Institute of Chemistry, POB 660, 1001, Ljubljana, Slovenia
Bibliografia
  • [1] C. Dye, S. Scheele, P. Dolin, V. Pathania, M.C. Raviglione, J. Am. Med. Assoc. 282, 677 (1999) http://dx.doi.org/10.1001/jama.282.7.677[Crossref]
  • [2] N.V. Bhanu, D. van Soolingen, J.D.A. van Embden, P. Seth, Diagn. Micr. Infec. Dis. 48, 107 (2004) http://dx.doi.org/10.1016/j.diagmicrobio.2003.09.014[Crossref]
  • [3] O. Dussurget, M. Rodriguez, I. Smith, Tubercle. Lung. Dis. 79(2), 99 (1998) http://dx.doi.org/10.1054/tuld.1998.0011[Crossref]
  • [4] S.K. Field, D. Fisher, R.L. Cowie, Chest 126, 566 (2004) http://dx.doi.org/10.1378/chest.126.2.566[Crossref]
  • [5] J.M. Beale, In: J.H. Block, J.M. Beale (Eds.), Whilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry, 11th edition (Lippincott Williams & Wilkins, Baltimore, MD, 2004) 266
  • [6] Y. Zhang, K.P. -Martens, S. Denkin, Drug Discov. Today 11, 21 (2006) http://dx.doi.org/10.1016/S1359-6446(05)03626-3[Crossref]
  • [7] G. Anquetin, J. Greiner, P. Vierling, Curr. Drug Targets: Infect. Disord. 5, 227 (2005) http://dx.doi.org/10.2174/1568005054880172[Crossref]
  • [8] M.J. Suto, J.M. Domagala. G.E. Roland, G.B. Mailloux, M.A. Cohen, J. Med. Chem. 35, 4745 (1992) http://dx.doi.org/10.1021/jm00103a013[Crossref]
  • [9] L.R. Peterson, Clin. Infect. Dis. 33(Suppl. 3), S180 (2001) http://dx.doi.org/10.1086/321846[Crossref]
  • [10] A.A. Miles, Bull. World Hlth. Org. 6, 131 (1952)
  • [11] J.M. Beale, In: J.H. Block, J.M. Beale (Eds.), Whilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry, 11th edition (Lippincott Williams & Wilkins, Baltimore, MD, 2004) 247
  • [12] J.J. Champoux, Annu. Rev. Biochem. 70, 369 (2001) http://dx.doi.org/10.1146/annurev.biochem.70.1.369[Crossref]
  • [13] H. Peng, K.J. Marians, J. Biol. Chem. 268, 24481 (1993)
  • [14] R.J. Reece, A. Maxwell, Crit. Rev. Biochem. Mol. 26, 335 (1991) http://dx.doi.org/10.3109/10409239109114072[Crossref]
  • [15] C. Levine, H. Hiasa, K.J. Marians, Biochim. Biophys. Acta 1400, 29 (1998)
  • [16] D.C. Hooper, Drugs 58(suppl. 2), 6 (1999) http://dx.doi.org/10.2165/00003495-199958002-00002[Crossref]
  • [17] M. Oblak, M. Kotnik, T. Solmajer, Curr. Med. Chem. 14, 2033 (2007) http://dx.doi.org/10.2174/092986707781368414[Crossref]
  • [18] N. Minovski, M. Vračko, T. Šolmajer, Mol. Divers. 15(2), 417 (2011) http://dx.doi.org/10.1007/s11030-010-9238-5[Crossref]
  • [19] Clinical Laboratory Standards Institute/NCCLS. Susceptibility Testing of Mycobacteria, Nocardiae, and Other Aerobic Actinomycetes; Approved Standard. CLSI/NCCLS document M24-A (Clinical Laboratory Standards Institute, Wayne PA, 2003)
  • [20] ChemBioOffice Ultra v11.0, Cambridgesoft (Cambridge, England, 2008) http://www.cambridgesoft.com/software/ChemBioOffice
  • [21] R. Todeschini, V. Consonni, A. Mauri, M. Pavan, DRAGON Version 5.4 (Talete srl, Milan, Italy) http://www.talete.mi.it/dragon.htm
  • [22] A.R. Katritzky, V.S. Lobanov, M. Karelson, CODESSA, Training Manual (University of Florida, Gainsville, 1994)
  • [23] A.R. Katritzky, V.S. Lobanov, M. Karelson, CODESSA, Reference Manual (University of Florida, Gainsville, 1994)
  • [24] G. Schaftenaar, J.H. Noordik, J. Comput.-Aided Mol. Des. 14, 123 (2000) http://dx.doi.org/10.1023/A:1008193805436[Crossref]
  • [25] M.J. Frisch et al., Gaussian 03, Revision A.02 (Gaussian, Inc., Wallingford CT, 2004)
  • [26] C.C. J. Roothaan, Rev. Mod. Phys. 23, 69 (1951) http://dx.doi.org/10.1103/RevModPhys.23.69[Crossref]
  • [27] R. Ditchfield, W.J. Hehre, J.A. Pople, J. Chem. Phys. 54, 724 (1971) http://dx.doi.org/10.1063/1.1674902[Crossref]
  • [28] R.S. Mulliken, J. Chem. Phys. 23, 1833 (1955) http://dx.doi.org/10.1063/1.1740588[Crossref]
  • [29] B.H. Besler BH, K.M. Jr. Merz, P.A. Kollman, J. Comp. Chem. 11, 431 (1990) http://dx.doi.org/10.1002/jcc.540110404[Crossref]
  • [30] P. Thanikaivelan, V. Subramanian, J.R. Rao, B.U. Nair, Chem. Phys. Lett. 23, 59 (2000) http://dx.doi.org/10.1016/S0009-2614(00)00488-7[Crossref]
  • [31] N. Minovski, MinoSuite v2.0, Laboratory for Chemometrics (National Institute of Chemistry, Ljubljana, Slovenia, 2009)
  • [32] J. Rebehmed, F. Barbault, C. Teixeira, F. Maurel, J. Comput. Aided. Mol. Des. 22, 831 (2008) http://dx.doi.org/10.1007/s10822-008-9217-4[Crossref]
  • [33] V. Consonni, D. Ballabio, R. Todeschini, J. Chem. Inf. Model. 49, 1669 (2009) http://dx.doi.org/10.1021/ci900115y[Crossref]
  • [34] A.R. Katritzky, O.V. Kulshyn, I. Stoyanova-Slavova, D.A. Dobchev, M. Kuanar, D.C. Fara, M. Karelson, Bioorg. Med. Chem. 14, 2333 (2006) http://dx.doi.org/10.1016/j.bmc.2005.11.015[Crossref]
  • [35] A.R. Katritzky, L.M. Pacureanu, D.A. Dobchev, D.C. Fara, P.R. Duchowicz, M. Karelson, Bioorg. Med. Chem. 14, 4987 (2006) http://dx.doi.org/10.1016/j.bmc.2006.03.009[Crossref]
  • [36] A.R. Katritzky, D.A. Dobchev, I. Tulp, M. Karelson, D.A. Carlson, Bioorg. Med. Chem. Lett. 16, 2306 (2006) http://dx.doi.org/10.1016/j.bmcl.2005.11.113[Crossref]
  • [37] A.R. Katritzky, D.A. Dobchev, E. Hur, D. Fara, M. Karelson, Bioorg. Med. Chem. 13, 1623 (2005) http://dx.doi.org/10.1016/j.bmc.2004.12.015[Crossref]
  • [38] G. Schüürmann, E. Ralf-Uwe, J. Chen, B. Wang, R. Kühne, J. Chem. Inf. Model. 48(11), 2140 (2008) http://dx.doi.org/10.1021/ci800253u[Crossref]
  • [39] Guidance Document on the Validation of (Quantitative) Structure-Activity Relationships [(Q)SAR] Models (Head of Publication Service, OECD, Paris, France, 2007) http://www.oecd.org/dataoecd/55/35/38130292.pdf
  • [40] J. Jaworska, N. Nikolova-Jeliazkova, T. Aldenberg, Altern. Lab. Anim. 33, 445 (2005)
  • [41] J. Jaworska, M. Comber, C.V. Leewen, C. Auer, Environ. Health Perspect. 11, 1358 (2003) http://dx.doi.org/10.1289/ehp.5757[Crossref]
  • [42] H. Liu, E. Papa, P. Gramatica, Chem. Res. Toxicol. 19, 1540 (2006) http://dx.doi.org/10.1021/tx0601509[Crossref]
  • [43] T.I. Netzeva et al., Altern. Lab. Anim. 33, 155 (2005)
  • [44] L. Eriksson et al., Environ. Health Perspect. 11, 1361 (2003) http://dx.doi.org/10.1289/ehp.5758[Crossref]
  • [45] E. Papa, S. Kovarich, P. Gramatica, QSAR Comb. Sci. 28(8), 790 (2009) http://dx.doi.org/10.1002/qsar.200860183[Crossref]
  • [46] L.A. Mitscher, Chem. Rev. 105, 559 (2005) http://dx.doi.org/10.1021/cr030101q[Crossref]
  • [47] L.A. Mitscher, Z. K. Ma, In: A.R. Ronald, D.E. Low(Eds.), Fluoroquinolone Antibiotics (Birkhaeuser, Basel, 2003) 11
  • [48] M.R. Jacobs, Curr. Pharm. Des. 10, 3213 (2004) http://dx.doi.org/10.2174/1381612043383296[Crossref]
  • [49] L.R. Peterson, Clin. Infect. Dis. 33, S180 (2001) http://dx.doi.org/10.1086/321846[Crossref]
  • [50] B. Ledoussal et. al, Curr. Med. Chem.: Agents 2, 13 (2003) http://dx.doi.org/10.2174/1568012033354531[Crossref]
  • [51] M.C. Bagchi, D. Mills, S.C. Basak, J. Mol. Model. 13, 111 (2007) http://dx.doi.org/10.1007/s00894-006-0133-z[Crossref]
  • [52] M. Randić, J. Chem. Inf. Comput. Sci. 41, 639 (2001) [Crossref]
  • [53] J.G. Topliss, R.P. Edwards, J. Med. Chem. 22, 1238 (1979) http://dx.doi.org/10.1021/jm00196a017[Crossref]
  • [54] J.G. Heddle et al., Nucleosides, Nucleotides Nucleic Acids 19, 1249 (2000) http://dx.doi.org/10.1080/15257770008033048[Crossref]
  • [55] I. Laponogov et al., Nat. Struct. Mol. Biol. 16,6, 667 (2009) http://dx.doi.org/10.1038/nsmb.1604[Crossref]
  • [56] I. Laponogov et al., Plos one 5,6, e11338 (2010) http://dx.doi.org/10.1371/journal.pone.0011338[Crossref]
  • [57] J. Piton et al., Plos one 5, 8, e12245 (2010) http://dx.doi.org/10.1371/journal.pone.0012245[Crossref]
  • [58] J.T. Smith, Eur. J. Clin. Microbiol. 3, 347 (1984) http://dx.doi.org/10.1007/BF01977492[Crossref]
  • [59] P. Gramatica, QSAR Comb. Sci. 26, 694 (2007) http://dx.doi.org/10.1002/qsar.200610151[Crossref]
  • [60] T. Yamamoto et al., Toxicol. In Vitro 15, 721 (2001) http://dx.doi.org/10.1016/S0887-2333(01)00089-3[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-011-0071-1
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