Structure and Antimicrobial Properties of Monensin A and Its Derivatives: Summary of the Achievements

In this paper structural and microbiological studies on the ionophorous antibiotic monensin A and its derivatives have been collected. Monensin A is an ionophore which selectively complexes and transports sodium cation across lipid membranes, and therefore it shows a variety of biological properties. This antibiotic is commonly used as coccidiostat and nonhormonal growth promoter. The paper focuses on both the latest and earlier achievements concerning monensin A antimicrobial activity. The activities of monensin derivatives, including modifications of hydroxyl groups and carboxyl group, are also presented.

[1]  B. Brzeziński,et al.  Structure of 1:1 complex of 1-naphthylmethyl ester of monensin A with sodium perchlorate studied by X-ray, FT-IR and ab initio methods , 2012 .

[2]  B. Brzeziński,et al.  Monensin A acid complexes as a model of electrogenic transport of sodium cation. , 2012, Biochimica et biophysica acta.

[3]  A. Katrusiak,et al.  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. , 2011 .

[4]  A. Katrusiak,et al.  Structural investigation of a new complex of N-allylamide of Monensin A with strontium perchlorate using X-ray, FT-IR, ESI MS and semiempirical methods , 2011 .

[5]  B. Brzeziński,et al.  1H, 13C NMR, FT-IR, ESI MS and PM5 studies of a new 3,6,9-trioxadecylamide of monensin A and its complexes with Li+, Na+ and K+ cations , 2011 .

[6]  B. Brzeziński,et al.  Spectroscopic, semi-empirical and antimicrobial studies of a new amide of monensin A with 4-aminobenzo-15-crown-5 and its complexes with Na⁺ cation at 1:1 and 1:2 ratios , 2011 .

[7]  B. Brzeziński,et al.  Crystal structure and FT-IR study of aqualithium 1-naphthylmethyl ester of monensin A perchlorate , 2011 .

[8]  B. Brzeziński,et al.  Structural characterization and antibacterial activity against clinical isolates of Staphylococcus of N-phenylamide of monensin A and its 1:1 complexes with monovalent cations. , 2010, European journal of medicinal chemistry.

[9]  M. Mitewa,et al.  Crystal structures and spectral properties of new Cd(II) and Hg(II) complexes of monensic acid with different coordination modes of the ligand , 2010 .

[10]  M. Mitewa,et al.  Nickel(II) and zinc(II) dimonensinates: Single crystal X-ray structure, spectral properties and bactericidal activity , 2010 .

[11]  M. Mitewa,et al.  First solid state alkaline-earth complexes of monensic acid A (MonH): crystal structure of [M(Mon)2(H2O)2] (M = Mg, Ca), spectral properties and cytotoxicity against aerobic Gram-positive bacteria , 2010, BioMetals.

[12]  V. Atanasov,et al.  Crystal structure and properties of the copper(II) complex of sodium monensin A. , 2009, Journal of inorganic biochemistry.

[13]  B. Brzeziński,et al.  Syntheses, structural and antimicrobial studies of a new N-allylamide of monensin A and its complexes with monovalent metal cations , 2009 .

[14]  A. Katrusiak,et al.  Structural and antimicrobial studies of a new N-phenylamide of monensin A complex with sodium chloride , 2009 .

[15]  B. Brzeziński,et al.  Structure of 1-naphthylmethyl ester of monensin A complexes with monovalent metal cations , 2009 .

[16]  A. Katrusiak,et al.  Molecular structure of rubidium six-coordinated dihydrate complex with monensin A , 2008 .

[17]  B. Brzeziński,et al.  Synthesis of new semi-synthetic dipodands and tripodands from naturally occurring polyether ionophores , 2008 .

[18]  B. Brzeziński,et al.  Structures of complexes of benzyl and allyl esters of monensin A with Mg2+, Ca2+, Sr2+, Ba2+ cations studied by ESI-MS and PM5 methods , 2008 .

[19]  Iris M. Oppel,et al.  First divalent metal complexes of the polyether ionophore Monensin A: X-Ray structures of [Co(Mon)2(H2O)2] and [Mn(Mon)2(H2O)2] and their bactericidal properties. , 2008, Current drug discovery technologies.

[20]  B. Brzeziński,et al.  Spectroscopic, mass spectrometry, and semiempirical investigations of a new 2-(2-methoxyethoxy)ethyl ester of Monensin A and its complexes with monovalent cations , 2008 .

[21]  B. Brzeziński,et al.  Synthesis and antimicrobial properties of monensin A esters. , 2008, Bioorganic & medicinal chemistry letters.

[22]  B. Brzeziński,et al.  Spectroscopic, mass spectrometry and semiempirical investigation of a new 2-methoxyethyl ester of monensin A and its complexes with Li + , Na + and K + cations , 2008 .

[23]  V. McKee,et al.  Rubidium(I) monensinate dihydrate , 2007, Acta crystallographica. Section E, Structure reports online.

[24]  B. Brzeziński,et al.  NMR, FTIR, ESI-MS and semiempirical study of a new 2-(2-hydroxyethoxy)ethyl ester of monensin A and its complexes with alkali metal cations , 2007 .

[25]  A. Katrusiak,et al.  Molecular structure of the 1:1 inclusion complex of monensin A lithium salt with acetonitrile , 2007 .

[26]  G. Schroeder,et al.  Investigation of complex structures of a new 2-hydroxyethyl ester of Monensin A with Mg2+, Ca2+, Sr2+, Ba2+ cations using electrospray ionization mass spectrometry and semiempirical PM5 methods , 2007 .

[27]  B. Brzeziński,et al.  Spectroscopic, mass spectrometry and semiempirical investigation of a new Monensin A allyl ester and its complexes with Li+, Na+ and K+cations , 2007 .

[28]  B. Brzeziński,et al.  The structures of monensin A derivatives and its complexes with some monovalent cations studied by the AM1d, PM3 as well as PM5 semiempirical methods , 2007 .

[29]  B. Brzeziński,et al.  Monensin A benzyl ester and its complexes with monovalent metal cations studied by spectroscopic, mass spectrometry and semiempirical methods , 2006 .

[30]  B. Brzeziński,et al.  Spectroscopic, mass spectrometry, and semiempirical investigation of a new ester of Monensin A with ethylene glycol and its complexes with monovalent metal cations , 2006, Biopolymers.

[31]  B. Brzeziński,et al.  Spectroscopic and semiempirical studies of a proton channel formed by the methyl ester of monensin A. , 2006, The journal of physical chemistry. B.

[32]  B. Brzeziński,et al.  Complexes of monensin A methyl ester with Mg2+, Ca2+, Sr2+, Ba2+ cations studied by electrospray ionization mass spectrometry and PM5 semiempirical method , 2006 .

[33]  B. Brzeziński,et al.  Monensin A methyl ester complexes with Li+, Na+, and K+ cations studied by ESI‐MS, 1H‐ and 13C‐NMR, FTIR, as well as PM5 semiempirical method , 2006, Biopolymers.

[34]  J. Klinowski,et al.  Sodium monensin dihydrate , 2003 .

[35]  Joon-Oh Park,et al.  Monensin inhibits the growth of renal cell carcinoma cells via cell cycle arrest or apoptosis. , 2003, International journal of oncology.

[36]  T. Fukuyama,et al.  SYNTHETIC STUDIES ON POLYETHER ANTIBIOTICS. 4. TOTAL SYNTHESIS OF MONENSIN. 1. STEREOCONTROLLED SYNTHESIS OF THE LEFT HALF OF MONENSIN , 2002 .

[37]  W. C. Still,et al.  SYNTHESIS OF THE POLYETHER ANTIBIOTIC MONENSIN. 3. COUPLING OF PRECURSORS AND D TRANSFORMATION TO MONENSIN , 2002 .

[38]  T. Fukuyama,et al.  SYNTHETIC STUDIES ON POLYETHER ANTIBIOTICS. 6. TOTAL SYNTHESIS OF MONENSIN. 3. STEREOCONTROLLED TOTAL SYNTHESIS OF MONENSIN , 2002 .

[39]  Kevin Barraclough,et al.  I and i , 2001, BMJ : British Medical Journal.

[40]  A. Nagatsu,et al.  Studies on chemical modification of monensin IX. Synthesis of 26-substituted monensins and their Na+ ion transport activity. , 2001, Chemical & pharmaceutical bulletin.

[41]  A. Nagatsu,et al.  Studies on chemical modification of monensin VIII. Synthesis of 7- O -substituted-25-carboxymonensins and their Ca 2+ ion transport activity , 2001 .

[42]  S. Touzain,et al.  Thermodynamics of complexation of monovalent metal cations by the ionophore monensin free acid in acetonitrile , 1997 .

[43]  J. Schrével,et al.  Carboxylic ionophores in malaria chemotherapy: the effects of monensin and nigericin on Plasmodium falciparum in vitro and Plasmodium vinckei petteri in vivo. , 1996, Life sciences.

[44]  H. Vial,et al.  Ionophore properties of monensin derivatives studied on human erythrocytes by 23Na NMR and K+ and H+ potentiometry: relationship with antimicrobial and antimalarial activities. , 1996, Journal of medicinal chemistry.

[45]  D. Turner.  The conformation of the monensin-A-sodium complex in solution determined from self-consistent NOE distance constraints. , 1995, Journal of magnetic resonance. Series B.

[46]  N. Kamo,et al.  Conductance change in phospholipid bilayer membrane by an electroneutral ionophore, monensin. , 1995, Biochemistry.

[47]  N. Murakami,et al.  Studies on chemical modification of monensin. V. Synthesis, sodium ion permeability, antibacterial activity, and crystal structure of 7-O-(4-substituted benzyl)monensins. , 1994, Chemical & pharmaceutical bulletin.

[48]  A. Nakamura,et al.  Studies on the chemical modification of monensin. IV. Synthesis, sodium ion permeability, and biological activity of 7-O-acyl- and 7-O-alkylmonensins. , 1992, Chemical & pharmaceutical bulletin.

[49]  A. Nakamura,et al.  Studies on the chemical modification of monensin. III. Synthesis and sodium ion transport activity of macrocyclic monensylamino acid-1,29-lactones. , 1991, Chemical & pharmaceutical bulletin.

[50]  Y. Hatano,et al.  Monensin-mediated antiport of Na+ and H+ across liposome membrane. , 1991, Biochimica et biophysica acta.

[51]  H. Mollenhauer,et al.  Alteration of intracellular traffic by monensin; mechanism, specificity and relationship to toxicity , 1990, Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes.

[52]  T. Ishida,et al.  Studies on the chemical modification of monensin. I. Synthesis and crystal structures of NaBr complexes of monensylamino acids. , 1988, Chemical & pharmaceutical bulletin.

[53]  J. Russell.  A proposed mechanism of monensin action in inhibiting ruminal bacterial growth: effects on ion flux and protonmotive force. , 1987, Journal of animal science.

[54]  W. Pangborn,et al.  The hydrated potassium complex of the ionophore monensin A , 1987 .

[55]  F. Riddell,et al.  The monensin-mediated transport of sodium ions through phospholipid bilayers studied by 23Na-NMR spectroscopy. , 1985, Biochimica et biophysica acta.

[56]  B. Cox,et al.  Rates and equilibria of alkali metal and silver ion complex formation with monensin in ethanol , 1984 .

[57]  A. Donoho.  Biochemical studies on the fate of monensin in animals and in the environment. , 1984, Journal of animal science.

[58]  E. Potter,et al.  Monensin toxicity in cattle. , 1984, Journal of animal science.

[59]  R. D. Goodrich,et al.  Influence of monensin on the performance of cattle. , 1984, Journal of animal science.

[60]  J. Westley,et al.  Preparation, properties and biological activity of natural and semisynthetic urethanes of monensin. , 1983, The Journal of antibiotics.

[61]  W. Sly,et al.  The role of intermediate vesicles in the adsorptive endocytosis and transport of ligand to lysosomes by human fibroblasts , 1983, The Journal of cell biology.

[62]  P. Spear,et al.  Monensin inhibits the processing of herpes simplex virus glycoproteins, their transport to the cell surface, and the egress of virions from infected cells , 1982, Journal of virology.

[63]  A. Helenius,et al.  Monensin inhibits Semliki Forest virus penetration into culture cells. , 1982, Proceedings of the National Academy of Sciences of the United States of America.

[64]  I. Pastan,et al.  Monensin blocks endocytosis of vesicular stomatitis virus. , 1981, Biochemical and biophysical research communications.

[65]  M. Tanzer,et al.  Immunocytochemical localization of procollagen and fibronectin in human fibroblasts: effects of the monovalent ionophore, monensin , 1980, The Journal of cell biology.

[66]  W. Duax,et al.  Complexation of metal ions by monensin. Crystal and molecular structure of hydrated and anhydrous crystal forms of sodium monensin , 1980 .

[67]  W. C. Still,et al.  Synthesis of the polyether antibiotic monensin. 3. Coupling of precursors and transformation to monensin , 1980 .

[68]  W. C. Still,et al.  Synthesis of the polyether antibiotic monensin. 1. Strategy and degradations , 1980 .

[69]  W. C. Still,et al.  Synthesis of the polyether antibiotic monensin. 2. Preparation of intermediates , 1980 .

[70]  D. L. Ward,et al.  The crystal and molecular structure of the sodium bromide complex of monensin, C36H62O11.Na+Br− , 1978 .

[71]  A. I. Popov,et al.  Solution chemistry of monensin and its alkali metal ion complexes. Potentiometric and spectroscopic studies , 1975 .

[72]  C. Sheu,et al.  Inhibitory Effects of Lipophilic Acids and Related Compounds on Bacteria and Mammalian Cells , 1975, Antimicrobial Agents and Chemotherapy.

[73]  W. Gärtner,et al.  Cation complexation by valinomycin- and nigericin-type inophores registered by the fluorescence signal of Tl+. , 1974, Biochemistry.

[74]  M. Gorman,et al.  Biosynthesis of Monensin , 1973, Antimicrobial Agents and Chemotherapy.

[75]  F. Winkler,et al.  Crystal structure of the antibiotic monensin similarities and differences betweeen free acid and metal complex. , 1971, Helvetica chimica acta.

[76]  L. Steinrauf,et al.  Molecular structure of monovalent metal cation complexes of monensin. , 1970, Journal of molecular biology.

[77]  Pressman Bc.  Ionophorous antibiotics as models for biological transport. , 1968 .

[78]  J. Dunitz,et al.  Structure of the K+ complex with nonactin, a macrotetrolide antibiotic possessing highly specific K+ transport properties. , 1967, Journal of molecular biology.

[79]  J. H. Johnson,et al.  Antibiotic-mediated transport of alkali ions across lipid barriers. , 1967, Proceedings of the National Academy of Sciences of the United States of America.

[80]  L. Steinrauf,et al.  The structure of monensic acid, a new biologically active compound. , 1967, Journal of the American Chemical Society.

[81]  R. Mandrou,et al.  Synthèses , 1954, Annales. Histoire, Sciences Sociales.

[82]  W. Marsden.  I and J , 2012 .

[83]  T. Řezanka,et al.  Fatty acids ofStreptomyces cinnamonensis, producer of monensin , 2008, Folia Microbiologica.

[84]  M. Mitewa,et al.  Synthesis, structure and antimicrobial activity of manganese(II) and cobalt(II) complexes of the polyether ionophore antibiotic Sodium Monensin A. , 2008, Journal of inorganic biochemistry.

[85]  Z. Vaněk,et al.  Improving the production of monensin byStreptomyces cinnamonensis , 2008, Folia Microbiologica.

[86]  J. Russeu,et al.  A PROPOSED MECHANISM OF MONENSIN ACTION IN INHIBITING RUMINAL BACTERIAL GROWTH : EFFECTS ON ION FLUX AND PROTONMOTIVE FORCE , 2007 .

[87]  A. Iacoangeli,et al.  The ionophore monensin inhibits mouse polyomavirus DNA replication and destabilizes viral early mRNAs. , 2000, Biochimie.

[88]  B. Cox,et al.  Stability constants of complexes of monensin and lasalocid with alkali-metal and alkaline-earth-metal ions in protic and polar aprotic solvents , 1984 .

[89]  A. I. Popov,et al.  A study of metal complexes of a naturally occurring macrocyclic ionophore-monensin , 1979 .

[90]  G. Schmid,et al.  Synthetic studies on polyether antibiotics. 5. Total synthesis of monensin. 2. Stereocontrolled synthesis of the right half of monensin , 1979 .

[91]  R. Williams,et al.  Journal of American Chemical Society , 1979 .

[92]  W. Simon,et al.  [Alkali-cation specificity and carrier qualities of the antibiotics nigericin and monensin]. , 1970, Helvetica Chimica Acta.

[93]  W. Lutz,et al.  Alkalikationen‐Spezifität und Träger‐Eigenschaften der Antibiotica Nigericin und Monensin , 1970 .

[94]  B. Pressman,et al.  Ionophorous antibiotics as models for biological transport. , 1968, Federation proceedings.

[95]  M. Callender,et al.  Monensin, a new biologically active compound. VI. Anticoccidial activity. , 1967, Antimicrobial agents and chemotherapy.

[96]  M. Hoehn,et al.  Monensin, a new biologically active compound. I. Discovery and isolation. , 1967, Antimicrobial agents and chemotherapy.

[97]  Shumard Rf,et al.  Monensin, a new biologically active compound. VI. Anticoccidial activity , 1967 .

[98]  I. Miyazaki,et al.  AND T , 2022 .