Effects of novel antituberculosis agents on OmpF channel activity

Biochemical and Biophysical Research Communications

Volumn 376, Issue 1, 2008, Pages 174-179

  Mahdiuni, H ^a   Mobasheri, H ^a   Shafiee, A ^b   Foroumadi, A ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b Tehran University of Medical Science   (Iran)

Author keywords

1,3,4 Thiadiazoles; OmpF; Tuberculosis

Indexed keywords

ALPHA [5 (5 NITRO 2 THIENYL) 1,3,4 THIADIAZOL 2 YLTHIO]ACETATE DERIVATIVE; OUTER MEMBRANE PROTEIN F; PROPYL ALPHA [5 (5 NITRO 2 THIENYL) 1,3,4 THIADIAZOL 2 YLTHIO]ACETATE DERIVATIVE; THIADIAZOLE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL WALL; BILAYER MEMBRANE; DRUG ACTIVITY; DRUG SYNTHESIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; VOLTAGE CLAMP;

ACETATES; ANTITUBERCULAR AGENTS; ESTERS; LIPID BILAYERS; PORINS; THIADIAZOLES;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM TUBERCULOSIS;

EID: 52349088103     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2008.08.113     Document Type: Article

References (38)

1. Benson S.A., Occi J.L., and Sampson B.A. Mutations that alter the pore function of the OmpF porin of Escherichia coli K12. J. Mol. Biol. 203 (1988) 961-970
2. Saint N., Lou K.L., Widmer C., Luckey M., Schirmer T., and Rosenbusch J.P. Structural and functional characterization of OmpF porin mutants selected for larger pore size. II. Functional characterization. J. Biol. Chem. 271 (1996) 20676-20680
3. Phale P.S., Philippsen A., Widmer C., Phale V.P., Rosenbusch J.P., and Schirmer T. Role of charged residues at the OmpF porin channel constriction probed by mutagenesis and simulation. Biochemistry 40 (2001) 6319-6325
4. Pratt L.A., Hsing W., Gibson K.E., and Silhavy T.J. From acids to osmZ: multiple factors influence synthesis of the OmpF and OmpC porins in Escherichia coli. Mol. Microbiol. 20 (1996) 911-917
5. Matsubara M., Kitaoka S.I., Takeda S.I., and Mizuno T. Tuning of the porin expression under anaerobic growth conditions by His-to-Asp cross-phosphorelay through both the EnvZ-osmosensor and ArcB-anaerosensor in Escherichia coli. Genes Cells 5 (2000) 555-569
6. Cowan S.W., Schirmer T., Rummel G., Steiert M., Ghosh R., Pauptit R.A., Jansonius J.N., and Rosenbusch J.P. Crystal structures explain functional properties of two E. coli porins. Nature 358 (1992) 727-733
7. Muller D.J., and Engel A. Voltage- and pH-induced channel closure of porin OmpF visualized by atomic force microscopy. J. Mol. Biol. 285 (1999) 1347-1351
8. Philippsen A., Im W., Engel A., Schirmer T., Roux B., and Muller D.J. Imaging the electrostatic potential of transmembrane channels: atomic probe microscopy of OmpF porin. Biophys. J. 82 (2002) 1667-1676
9. Im W., and Roux B. Ion permeation and selectivity of OmpF porin: a theoretical study based on molecular dynamics, Brownian dynamics, and continuum electrodiffusion theory. J. Mol. Biol. 322 (2002) 851-869
10. Danelon C., Suenaga A., Winterhalter M., and Yamato I. Molecular origin of the cation selectivity in OmpF porin: single channel conductances vs. free energy calculation. Biophys. Chem. 104 (2003) 591-603
11. Delcour A.H. Function and modulation of bacterial porins: insights from electrophysiology. Lett. FEMS Microbiol. 151 (1997) 115-123
12. Baslé A., Iyer R., and Delcour A.H. Subconductance states in OmpF gating. Biochim. Biophys. Acta 1664 (2004) 100-107
13. van Gelder P., Saint N., Phale P., Eppens E.F., Prilipov A., van Boxtel R., Rosenbusch J.P., and Tommassen J. Voltage sensing in the PhoE and OmpF outer membrane porins of Escherichia coli: role of charged residues. J. Mol. Biol. 269 (1997) 468-472
14. Nestorovich E.M., Rostovtseva T.K., and Bezrukov S.M. Residue ionization and ion transport through OpmF channels. Biophys. J. 85 (2003) 3718-3729
15. Iyer R., and Delcour A.H. Complex inhibition of OmpF and OmpC bacterial porins by polyamines. J. Biol. Chem. 272 (1997) 18595-18601
16. delaVega A.L., and Delcour A.H. Cadaverine induces closing of E. coli porins. EMBO J. 14 (1995) 6058-6065
17. Iyer R., Wu Z., Woster P.M., and Delcour A.H. Molecular basis for the polyamine-OmpF porin interactions: inhibitor and mutant studies. J. Mol. Biol. 297 (2000) 933-945
18. Bainbridge G., Gokce I., and Lakey J. Voltage gating is a fundamental feature of porin and toxin β-barrel membrane channels. FEBS Lett. 431 (1998) 305-308
19. Muller D.J., and Engel A. Voltage and pH-induced channel closure of porin OmpF visualized by atomic force microscopy. J. Mol. Biol. 285 (1999) 1347-1351
20. Asandei A., Mereuta L., and Luchian T. Influence of membrane potentials upon reversible protonation of acidic residues from the OmpF eyelet. Biophys. Chem. 135 (2008) 32-40
21. Robertson K.M., and Tieleman D.P. Molecular basis of voltage gating of OmpF porin. Biochem. Cell Biol. 80 (2002) 517-527
22. Robertson K.M., and Tieleman D.P. Orientation and interactions of dipolar molecules during transport through OmpF porin. FEBS Lett. 528 (2002) 53-57
23. Malek K., and Maghari A. Translocation and interactions of l-arabinose in OmpF porin: a molecular dynamics study. Biochem. Biophys. Res. Commun. 352 (2007) 104-110
24. Nestorovich E.M., Danelon C., Winterhalter M., and Bezrukov S.M. Designed to penetrate: time-resolved interaction of single antibiotic molecules with bacterial pores. Proc. Natl. Acad. Sci. USA 99 (2002) 9789-9794
25. Danelon C., Nestorovich E.M., Winterhalter M., Ceccarelli M., and Bezrukov S.M. Interaction of zwitterionic penicillins with the OmpF channel facilitates their translocation. Biophys. J. 90 (2006) 1617-1627
26. Nikaido H. Molecular basis of bacterial outer membrane permeability revisited. Microbiol. Mol. Biol. Rev. 67 (2003) 593-656
27. Levadny V., Aguilella V.M., Aguilella-Arza M., and Belaya M. Interaction of polar molecule with an ion channel. Phys. Rev. E Stat. Nonlin. Soft Matter Phys. 70 (2004) 041912 (Epub)
28. WHO, Global Tuberculosis Control: Surveillance, Planning, Financing, World Health Organization, Geneva, 2004.
29. Zhang Y., and Amzel L.M. Tuberculosis drug targets. Curr. Drug Targets 3 (2002) 131-154
30. Foroumadi A., Kiani Z., and Soltani F. Antituberculosis agents VIII. Synthesis and in vitro antimycobacterial activity of alkyl α-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio] acetates. Farmaco 58 (2003) 1073-1076
31. Ashour F.A., Habib N.S., Taibbi M., Dine S., and Dine A. Synthesis of 1,3,4-thiadiazoles, imidazo [2,1-b] 1,3,4-thiadiazoles and thiadiazolo [3,2-a] pyrimidines derived from benzimidazole as potential antimicrobial agents. Farmaco 45 (1990) 134-139
32. Montal M., and Mueller P. Formation of bimolecular membranes from lipid monolayers and a study of their electrical properties. Proc. Natl. Acad. Sci. USA 69 (1972) 3561-3566
33. Buehler L.K., Kusumoto S., Zhang H., and Rosenbusch J.P. Plasticity of Escherichia coli porin channels. Dependence of their conductance on strain and lipid environment. J. Biol. Chem. 266 (1991) 24446-24450
34. + complex. Z. Naturforsch. [C] 47 (1992) 757-761
35. Wiese A., Reiner J.O., Brandenburg K., Kawahara K., Zahringer U., and Seydel U. Planar asymmetric lipid bilayers of glycosphingolipid or lipopolysaccharide on the one side and phospholipids on the other: membrane potential, porin function, and complement activation. Biophys. J. 70 (1996) 321-329
36. Wiese A., Schorder G., Brandenburg K., Hirsch A., Welte W., and Seydel U. Influence of the lipid matrix on incorporation and function of LPS-free porin from Paracoccus denitrificans. Biochim. Biophys. Acta 1190 (1994) 231-242
37. Bezrukov S.M. Ion channels as molecular coulter counters to probe metabolite transport. J. Membr. Biol. 174 (2000) 1-13
38. Zakharov S.D., Eroukova V.Y., Rokitskaya T.I., Zhalnina M.V., Sharma O., Loll P.J., Zgurskaya H.I., Antonenko Y.N., and Cramer W.A. Colicin occlusion of OmpF and Tolc channels: outer membrane translocons for colicin import. Biophys. J. 87 (2004) 3901-3911