モネンシン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/03 01:15:37」(JST)
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Monensin A
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| Names |
IUPAC name
4-[2-[5-ethyl-5-[5-[6-hydroxy-6-
(hydroxymethyl)-3,5-dimethyl-oxan-2-yl]- 3-methyl-oxolan-2-yl]oxolan-2-yl]- 9-hydroxy-2,8-dimethyl-1,6-dioxasp iro[4.5]dec-7-yl]-3-methoxy-2-methyl-
pentanoic acid |
| Other names
monensic acid
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| Identifiers |
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CAS Number
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17090-79-8 Y |
| ChEBI |
CHEBI:27617 N |
| ChEMBL |
ChEMBL256105 Y |
| ChemSpider |
389937 Y |
InChI
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InChI=1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28-,29+,30-,31+,33-,34-,35+,36-/m0/s1 Y
Key: GAOZTHIDHYLHMS-KEOBGNEYSA-N Y
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InChI=1/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28-,29+,30-,31+,33-,34-,35+,36-/m0/s1
Key: GAOZTHIDHYLHMS-KEOBGNEYBF
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| Jmol interactive 3D |
Image |
| KEGG |
D08228 Y |
| PubChem |
441145 |
SMILES
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O=C(O)[C@@H](C)[C@H](OC)[C@H](C)[C@H]5O[C@]1(O[C@@](C)(CC1)[C@@H]2O[C@@](CC)(CC2)[C@@H]4O[C@@H]([C@H]3O[C@@](O)(CO)[C@@H](C[C@@H]3C)C)C[C@@H]4C)C[C@H](O)[C@H]5C
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| UNII |
906O0YJ6ZP N |
| Properties |
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Chemical formula
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C36H62O11 |
| Molar mass |
670.871 g/mol |
| Appearance |
solid state, white crystals |
| Melting point |
104 °C (219 °F; 377 K) |
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Solubility in water
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3x10−6 g/dm3 (20 °C) |
| Solubility |
ethanol, acetone, diethyl ether, benzene |
| Pharmacology |
| ATCvet code |
QA16QA06
QP51AH03 |
| Related compounds |
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Related
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antibiotics, ionophores |
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Related compounds
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Monensin A methyl ester, |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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Monensin is a polyether antibiotic isolated from Streptomyces cinnamonensis.[1] It is widely used in ruminant animal feeds.[2][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.[3]
Contents
- 1 Mechanism of action
- 2 Uses
- 3 Toxicity
- 4 References
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 Ti+.[4][5] Monensin A is able to transport these cations across lipid membranes of cells in an electroneutral (i.e. non-depolarizing) exchange, playing an important role as an Na+/H+ antiporter. Recent studies have shown that monensin may transport sodium ion through the membrane in both electrogenic and electroneutral manner.[6] This approach explains ionophoric ability and in consequence antibacterial properties of not only parental monensin, but also its derivatives that do not possess carboxylic groups. It blocks intracellular protein transport, and exhibits antibiotic, antimalarial, and other biological activities.[7] The antibacterial properties of monensin and its derivatives are a result of their ability to transport metal cations through cellular and subcellular membranes.[8]
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.[9] Furthermore monensin, but also its derivatives monensin methyl ester (MME), and particularly monensin decyl ester (MDE) are widely used in ion-selective electrodes.[10][11][12]
Toxicity
Monensin has some degree of activity on mammalian cells and thus toxicity is common. This is especially pronounced in horses, where monensin has an LD50 1/100th that of ruminants. Accidental poisoning of equines with monensin is a well-documented occurrence which has resulted in deaths.[13]
References
- ^ a b Daniel Łowicki and Adam Huczyński (2013). "Structure and Antimicrobial Properties of Monensin A and Its Derivatives: Summary of the Achievements". BioMed Research International 2013: 1–14. doi:10.1155/2013/742149.
- ^ 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
- ^ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. pp. 185–187. ISBN 3-527-29284-5.
- ^ 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
- ^ M. Pinkerton, L. K. Steinrauf, "Molecular structure of monovalent metal cation complexes of monensin", J. Mol. Biol., 1970 49(3), 533-546
- ^ Huczyński, Adam; Jan Janczak; Daniel Łowicki; Bogumil Brzezinski (2012). "Monensin A acid complexes as a model of electrogenic transport of sodium cation". Biochim. Biophys. Acta 1818: 2108–2119. doi:10.1016/j.bbamem.2012.04.017.
- ^ 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
- ^ 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
- ^ 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
- ^ 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
- ^ 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
- ^ K. Toko, "Taste Sensor", Sensors and Actuators B: Chemical 64, 2000, 205-215, doi:10.1016/S0925-4005(99)00508-0
- ^ http://www.dailymail.co.uk/news/article-2876463/Tainted-feed-blamed-4-horse-deaths-Florida-stable.html
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Nonribosomally synthesized porters (TC 2B)
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- Valinomycin
- Monensin
- Nigericin
- Ionomycin
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English Journal
- Monensin A acid complexes as a model of electrogenic transport of sodium cation.
- Huczyński A, Janczak J, Lowicki D, Brzezinski B.SourceFaculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland.
- Biochimica et biophysica acta.Biochim Biophys Acta.2012 Sep;1818(9):2108-19. Epub 2012 Apr 30.
- New Monensin A acid complexes with water molecule, sodium chloride and sodium perchlorate were obtained and studied by X-ray and (1)H, (13)C NMR and FT-IR methods as well as ab initio calculations. The crystal structure of the complexes indicates the complexation of the water molecule and Na(+) cati
- PMID 22564680
- Intracellular IL-10 detection in T cells by flowcytometry: The use of protein transport inhibitors revisited.
- Muris AH, Damoiseaux J, Smolders J, Cohen Tervaert JW, Hupperts R, Thewissen M.SourceSchool for Mental Health and Neuroscience, Maastricht University Medical Center, Maastricht, The Netherlands; Department of Internal Medicine, Division of Clinical and Experimental Immunology, Maastricht University Medical Center, Maastricht, The Netherlands; Academic MS Center Limburg, Orbis Medical Center, Sittard, The Netherlands.
- Journal of immunological methods.J Immunol Methods.2012 Jul 31;381(1-2):59-65. Epub 2012 Apr 29.
- In the past two decades, interleukin-10 (IL-10) has gained much attention as an important regulatory cytokine involved in self-tolerance. Functional assessment of IL-10 producing immune cells is traditionally done by stimulation and measurement of cytokine production by flowcytometry. Thereby a prot
- PMID 22565155
Japanese Journal
- モネンシン銀塩とヨウ化メチルとの反応 : 強固に水素結合したカルボキシラートの円滑なアルキル化
- Comparative Analysis of the Expression Patterns of UPR-Target Genes Caused by UPR-Inducing Compounds
- SHINJO Satoko,MIZOTANI Yuji,TASHIRO Etsu,IMOTO Masaya
- Bioscience, Biotechnology, and Biochemistry 77(4), 729-735, 2013
- … cluster A (thapsigargin, tunicamycin, 2-deoxyglucose, and dithiothreitol) and cluster B (brefeldin A, monensin, and eeyarestatin I). …
- NAID 130004138071
- Expression Profile of Apoptosis Related Genes and Radio-sensitivity of Prostate Cancer Cells
- HE Zhenhua,ZHANG Ye,MEHTA Satish K. [他],PIERSON Duane L.,WU Honglu,ROHDE Larry H.
- Journal of radiation research 52(6), 743-751, 2011-11-16
- … We also studied the effect of monensin, an apoptosis inducing reagent, in X-ray-induced cell killing. … however, monensin was shown to be effective in inducing apoptosis in LNCaP, but not in PC3 cells. … In addition, the effect of combined treatment of monensin and X-rays in LNCaP cells appeared to be synergistic. …
- NAID 10029652983
Related Links
- Monensin A. IUPAC name. 4-[2-[5-ethyl-5-[5-[6-hydroxy-6-. (hydroxymethyl)-3,5- dimethyl-oxan-2-yl]- 3-methyl-oxolan-2-yl]oxolan-2-yl]- 9-hydroxy-2,8-dimethyl-1, 6-dioxasp iro[4.5]dec-7-yl]-3-methoxy-2-methyl-. pentanoic acid. Other names ...
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