Monensin


Monensin
Monensin A
Identifiers
CAS number 17090-79-8 YesY
PubChem 441145
ChemSpider 389937 YesY
UNII 906O0YJ6ZP N
KEGG D08228 YesY
ChEBI CHEBI:27617 N
ChEMBL CHEMBL256105 YesY
ATCvet code QP51AH03
Jmol-3D images Image 1
Properties
Molecular formula C36H62O11
Molar mass 670.871g/mol
Appearance solid state, white crystals
Melting point

104°C

Solubility in water 3x10-6 g/dm3 (20 °C)
Solubility ethanol, acetone, diethyl ether, benzene
Related compounds
Related antibiotics, ionophores
Related compounds Monensin A methyl ester,
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Monensin is a polyether antibiotic isolated from Streptomyces cinnamonensis. It is widely used in animal feeds.[1]

The structure of monensin was first described by Agtarap et al. in 1967, and was the first polyether antibiotic to have its structure elucidated in this way. The first total synthesis of monensin was reported in 1979 by Kishi et al.[2]

Mechanism of action

Monensin A is an ionophore related to the crown ethers with a preference to form complexes with monovalent cations such as: Li+, Na+, K+, Rb+, Ag+, and Tl+.[3][4] Monensin A is able to transport these cations across lipid membranes of cells, playing an important role as an Na+/H+ antiporter. It blocks intracellular protein transport, and exhibits antibiotic, antimalarial, and other biological activities.[5] The antibacterial properties of monensin and its derivatives are a result of their ability to transport metal cations through cellular and subcellular membranes.[6]

The structure of the sodium (Na+) complex of monensin A.

Uses

Monensin is used extensively in the beef and dairy industries to prevent coccidiosis, increase the production of propionic acid and prevent bloat.[7]. Furthermore monensin, but also its derivatives monensin methyl ester (MME), and particularly monensin decyl ester (MDE) are widely used in ion selective electrodes.[8][9][10]

References

  1. ^ Patrick Butaye, Luc A. Devriese, Freddy Haesebrouck "Antimicrobial Growth Promoters Used in Animal Feed: Effects of Less Well Known Antibiotics on Gram-Positive Bacteria" Clinical Microbiology Reviews, 2003, p. 175-188, Vol. 16. doi:10.1128/CMR.16.2.175-188.2003
  2. ^ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. pp. 185–187. ISBN 3-527-29284-5. 
  3. ^ 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., 2007, 871, 92-97, doi:10.1016/j.molstruc.2006.07.046
  4. ^ M. Pinkerton, L. K. Steinrauf, "Molecular structure of monovalent metal cation complexes of monensin", J. Mol. Biol., 1970 49(3), 533-546
  5. ^ H. H. Mollenhauer, D. J. Morre, L. D. Rowe, ”Alteration of intracellular traffic by monensin; mechanism, specificity and relationship to toxicity”, Biochim. Biophys. Acta, 1990, 1031(2), 225-246, doi:10.1016/0304-4157(90)90008-Z
  6. ^ A. Huczyński, J. Stefańska, P. Przybylski, B. Brzezinski and F. Bartl, "Synthesis and antimicrobial properties of Monensin A esters", Bioorg. Med. Chem. Lett., 2008, 18, 2585-2589, doi:10.1016/j.bmcl.2008.03.038
  7. ^ T. Matsuoka, M.N. Novilla, T.D. Thomson and A.L. Donoho, "Review of monensin toxicosis in horses", Journal of Equine Veterinary Science 16, 1996, 8-15, doi:10.1016/S0737-0806(96)80059-1
  8. ^ K. Tohda, K. Suzuki, N. Kosuge, H. Nagashima, H. Inoue K. Watanabe, ”A Sodium Ion Selective Electrode Based on a Highly Lipophilic Monensin Derivative and Its Application to the Measurement of Sodium Ion Concentrations in Serum”, Anal. Sci. 6, 1990, 227-232, doi:10.2116/analsci.6.227
  9. ^ N. Kim, K. Park, I. Park, Y. Cho, Y. Bae, ”Application of a taste evaluation system to the monitoring of Kimchi fermentation”, Biosensors and Bioelectronics 20, 2005, 2283-2291,doi:10.1016/j.bios.2004.10.007
  10. ^ K. Toko, ”Taste Sensor”, Sensors and Actuators B: Chemical 64, 2000, 205-215, doi:10.1016/S0925-4005(99)00508-0

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Look at other dictionaries:

  • monensin — A sodium ionophore (671D) from Streptomyces cinnamonensis. Has antibiotic properties, and is used as a feed additive in chickens. Also used in ion selective electrodes …   Dictionary of molecular biology

  • monensin — /moh nen sin/, n. Biochem. a complex derivative of butyric acid, C36H62O11, produced by the bacterium Streptomyces cinnamonensis and used as an antibiotic in animals. [1967; < NL (cinna)monens(is) specific epithet of the bacterium (see CINNAMON,… …   Universalium

  • monensin — noun An antibiotic obtained from Streptomyces cinnamonensis …   Wiktionary

  • monensin — mo·nen·sin mō nen sən n an antibiotic C36H62O11 obtained from a bacterium of the genus Streptomyces (S. cinnamonensis) and used as an antiprotozoal, antibacterial, and antifungal agent and as an additive to cattle feed * * * mo·nen·sin (mo… …   Medical dictionary

  • monensin — /moh nen sin/, n. Biochem. a complex derivative of butyric acid, C36H62O11, produced by the bacterium Streptomyces cinnamonensis and used as an antibiotic in animals. [1967; < NL (cinna)monens(is) specific epithet of the bacterium (see… …   Useful english dictionary

  • monensin sodium — [USP] the sodium salt of monensin, having the same uses as the base …   Medical dictionary

  • MON — monensin; Mongolian [gerbil] …   Medical dictionary

  • MON — • monensin; • Mongolian [gerbil] …   Dictionary of medical acronyms & abbreviations

  • Ionophore — An ionophore is a lipid soluble molecule usually synthesized by microorganisms to transport ions across the lipid bilayer of the cell membrane. There are two broad classifications of ionophores. # Small molecules (mobile ion carriers) that bind… …   Wikipedia

  • Nigericin — IUPAC name (2R) 2 [(2R,3S,6R) 6 [[(2S,4R,5R,7R,9R,10R) 2 [(2R,5S) 5 [(2R,3S,5R) 5 [(2S,3S,5R,6R) 6 hydroxy 6 (hydroxymethyl) 3,5 dimethyl 2 …   Wikipedia


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