Monensin a acid complexes as a model of electrogenic transport of sodium cation

Biochimica et Biophysica Acta - Biomembranes

Volumn 1818, Issue 9, 2012, Pages 2108-2119

  Huczyński, Adam ^a   Janczak, Jan ^b   Łowicki, Daniel ^a   Brzezinski, Bogumil ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b INSTITUTE OF LOW TEMPERATURE AND STRUCTURE RESEARCH   (Poland)

Author keywords

Ab initio calculation; Cation transport; Crystal structure; Hydrogen bond; Ionophore; Molecular electrostatic potential

Indexed keywords

DICHLOROMETHANE; MONENSIN; MONENSIN A ACID; SODIUM CHLORIDE; SODIUM PERCHLORATE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATION TRANSPORT; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG STRUCTURE; ELECTRON TRANSPORT; HYDROGEN BOND; INFRARED SPECTROSCOPY; IONIC STRENGTH; MOLECULAR STABILITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; X RAY DIFFRACTION;

BIOPHYSICS; CATIONS; ELECTROCHEMISTRY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; METHYLENE CHLORIDE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MONENSIN; PROTEIN BINDING; SODIUM; SPECTROPHOTOMETRY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STATIC ELECTRICITY; WATER; X-RAYS;

EID: 84861741129     PISSN: 00052736     EISSN: 18792642     Source Type: Journal    
DOI: 10.1016/j.bbamem.2012.04.017     Document Type: Article

References (44)

1. J.W. Westley, Polyether Antibiotics, Naturally Occurring Acid Ionophores, Vol. 1, Marcel Dekker Inc., New York, 1982.
2. J.W. Westley, Polyether Antibiotics, Naturally Occurring Acid Ionophores, Vol. 2, Marcel Dekker Inc., New York, 1983.
3. D.A. Kevin, D.A.F. Meujo, M.T. Hamann, Polyether ionophores: broad-spectrum and promising biologically active molecules for the control of drug-resistant bacteria and parasites, Expert Opin. Drug Discov. 4 (2009) 109-146.
4. Y. Wang, Effects of salinomycin on cancer stem cell in human lung adenocarcinoma A549 cells, Med. Chem. 7 (2011) 106-111.
5. C. Naujokat, D. Fuchs, G. Opelz, Salinomycin in cancer: a new mission for an old agent, Mol. Med. Rep. 3 (2010) 555-559.
6. A. Kart, A. Bilgili, Ionophore antibiotics: toxicity, mode of action and neurotoxic aspect of carboxylic ionophores, J. Anim. Vet. Adv. 7 (2008) 748-751.
7. B.C. Pressman, Antibiotics and their complexes, Vol. 1, Marcel Dekker Inc., New York, 1985.
8. M. Mimouni, M. Hebrant, G. Dauphin, J. Juillard, Monovalent cation salts of the bacterial ionophore monensin in methanol. Structural aspects from NMR experiments, J. Chem. Res. 6 (1996) 278-279. (Pubitemid 126458795)
9. C. Nebbia, L. Ceppa, M. Dacasto, C. Nachtmann, M. Carletti, Oxidative monensin metabolism and cytochrome P450 3A content and functions in liver microsomes from horses, pigs, broiler chicks, cattle and rats, J. Vet. Pharmacol. Ther. 24 (2001) 399-403. (Pubitemid 34092307)
10. H.H. Mollenhauer, D.J. Morre, L.D. Rowe, Alteration of intracellular traffic by monensin; mechanism, specificity and relationship to toxicity, Biochim. Biophys. Acta 1031 (1990) 225-246.
11. A. Huczyński, J. Stefańska, P. Przybylski, B. Brzezinski, F. Bartl, Synthesis and antimicrobial properties of monensin A esters, Bioorg.Med. Chem. Lett. 18 (2008) 2585-2589. (Pubitemid 351506519)
12. A. Huczyński, M. Ratajczak-Sitarz, J. Stefańska, A. Kartusiak, B. Brzezinski, F. Bartl, Reinvestigation of the structure of monensin A phenylurethane sodium salt based on X-ray crystallographic and spectroscopic studies, and its activity against hospital strains of methicillin-resistant S. epidermidis and S. aureus, J. Antibiot. 64 (2011) 249-256.
13. M. Inabayashi, S. Miyauchi, N. Kamo, T. Jin, Conductance change in phospholipid bilayer membrane by an electroneutral ionophore, monensin, Biochemistry 34 (1995) 3455-3460.
14. B.C. Pressman, Biological applications of ionophores, Annu. Rev. Biochem. 45 (1976) 501-530.
15. 23Na-NMR spectroscopy, Biochim. Biophys. Acta - Biomembranes 17 (1985) 313-317.
16. B.C. Pressman, Ionophorous antibiotics as models for biological transport, Fed. Proc. 27 (1968) 1283-1288.
17. J.B. Russell, A.J. Houlihan, Ionophore resistance of ruminal bacteria and its potential impact on human health, FEMS Microbiol. Rev. 27 (2003) 65-74. (Pubitemid 36412187)
18. N. Ben-Tal, D. Sitkoff, S. Bransburg-Zabary, E. Nachliel, M. Gutman, Theoretical calculations of the permeability of monensin-cation complexes in model biomembranes, Biochim. Biophys. Acta - Biomembranes 1466 (2000) 221-233.
19. F.G. Riddell, Structure, conformation, and mechanism in the membrane transport of alkali metal ions by ionophoric antibiotics, Chirality 14 (2002) 121-125. (Pubitemid 34113142)
20. + complexes with monensin anion in dipolar aprotic solvents, Monatsh. Chem. Chem. Mon. 125 (1994) 801-809.
21. B.G. Cox, N. Van Truong, J. Rzeszotarska, H. Schneider, Rates and equilibria of alkali metal and silver ion complex formation with monensin in ethanol, J. Am. Chem. Soc. 106 (1984) 5965-5969. (Pubitemid 14641987)
22. J.G. Hoogerheide, A.I. Popov, Study of monensin complexes with monovalent metal ions in anhydrous methanol solutions, J. Solut. Chem. 7 (1978) 357-372.
23. W.L. Duax, G.D. Smith, P.D. Strong, Complexation of metal ions by monensin. Crystal and molecular structure of hydrated and anhydrous crystal forms of sodium Monensin, J. Am. Chem. Soc. 102 (1980) 6725-6729.
24. -, Acta Crystallogr. B B34 (1978) 110-115.
25. M. Pinkerton, L.K. Steinrauf, Molecular structure of monovalent metal cation complexes of monensin, J. Mol. Biol. 49 (1970) 533-546.
26. W. Pangborn, W. Duax, D. Langs, The hydrated potassium complex of the ionophore monensin A, J. Am. Chem. Soc. 109 (1987) 2163-2165. (Pubitemid 17043737)
27. A. Huczyński, M. Ratajczak-Sitarz, A. Katrusiak, B. Brzezinski, Molecular structure of the 1:1 inclusion complex of monensin A sodium salt with acetonitrile, J. Mol. Struct. 832 (2007) 84-89. (Pubitemid 46367043)
28. A. Huczyński, M. Ratajczak-Sitarz, A. Katrusiak, B. Brzezinski, Molecular structure of the 1:1 inclusion complex of monensin A lithium salt with acetonitrile, J. Mol. Struct. 871 (2007) 92-97. (Pubitemid 350060915)
29. A. Huczyński, M. Ratajczak-Sitarz, A. Katrusiak, B. Brzezinski, Molecular structure of rubidium six-coordinated dihydrate complex with monensin A, J. Mol. Struct. 888 (2008) 224-229.
30. P. Dorkov, I.N. Pantcheva, W.S. Sheldrick, H. Mayer-Figge, R. Petrova, M. Mitewa, Synthesis, structure and antimicrobial activity of manganese(II) and cobalt(II) complexes of the polyether ionophore antibiotic sodium monensin A, J. Inorg. Biochem. 102 (2008) 26-32. (Pubitemid 350235044)
31. T. Martinek, F.G. Riddell, C. Wilson, C.T. Weller, The conformations of monensin-A metal complexes in solution determined by NMR spectroscopy, J. Chem. Soc. Perkin Trans. 2 (2001) 35-41. (Pubitemid 35166653)
32. K. Nakazato, Y. Hatano, Monensin-mediated antiport of Na+ and H+ across liposome membrane, Biochim. Biophys. Acta - Biomembranes 1064 (1991) 103-110.
33. J.G. Hoogerheide, A.I. Popov, A study of metal complexes of a naturally occurring macrocyclic ionophore-monensin, J. Solut. Chem. 8 (1979) 83-95.
34. P.G. Gertenbach, A.I. Popov, Solution chemistry of monensin and its alkali metal ion complexes. Potentiometric and spectroscopic studies, J. Am. Chem. Soc. 97 (1975) 4738-4744.
35. CrysAlis CCD and CrysAlis Red, Version 171.32.8, Oxford Diffraction Poland, Wrocław, Poland, 2006.
36. G.M. Sheldrick, SHELXS97, SHELXL97, Programs for Crystal Stuctures Solution and Refinement, University of Göttingen, Göttingen, Germany, 1997.
37. K. Brandenburg, H. Putz, DIAMOND Version 3.0, Crystal Impact GbR, Bonn, Germany, 2006.
38. J.M. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cislowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, W.M. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, B.B. Stewart, M. Head-Gordon, C. Gonzales, J.A. Pople, Gaussian98, Revision A.3, Gaussian, Inc., Pittsburgh, PA, 1998.
39. A.D. Becke, Density-functional thermochemistry. IV. A new dynamical correlation functional and implications for exact-exchange mixing, J. Chem. Phys. 104 (1996) 1040-1046. (Pubitemid 126747264)
40. C. Lee, W. Yang, R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B37 (1988) 785-789.
41. C.A. Hunter, Quantifying intermolecular interactions: guidelines for the molecular recognition toolbox, Angew. Chem. Int. Ed. 43 (2004) 5310-5324. (Pubitemid 39433908)
42. P. Politzer, J.S. Murray, Molecular electrostatic potentials, Computational Medicinal Chemistry for Drug Discovery, Mracel Dekker Inc., New York, 2004, pp. 213-234.
43. A.L. Cashin, E. James Petersson, H.A. Lester, D.A. Dougherty, Using physical chemistry to differentiate nicotinic from cholinergic agonists at the nicotinic acetylcholine receptor, J. Am. Chem. Soc. 127 (2005) 350-356. (Pubitemid 40094396)
44. H.D. Lutz, Bonding and structure of water molecules in solid hydrates. Correlation of spectroscopic and structural data, Struct. Bond. 69 (1988) 97-125.