Monensin
Monensin A | |||
---|---|---|---|
IUPAC ime |
| ||
Drugi nazivi | monenska kiselina | ||
Identifikacija | |||
CAS registarski broj | 17090-79-8 | ||
MeSH | |||
ATCvet code | QP51 | ||
Jmol-3D slike | Slika 1 | ||
Svojstva | |||
Molekulska formula | C36H62O11 | ||
Molarna masa | 670.871g/mol | ||
Agregatno stanje | čvrsto stanje, beli kristali | ||
Tačka topljenja |
104 °C | ||
Rastvorljivost u vodi | 3x10-6 g/dm3 (20 °C) | ||
Rastvorljivost | etanol, aceton, dietil etar, benzol | ||
Srodna jedinjenja | |||
Srodna | antibiotik[1], jonofor | ||
Srodna jedinjenja | Monensin A metil estar | ||
| |||
Infobox references |
Monensin[2], koji je izolovan iz Streptomyces cinnamonensis[3], poznati je predstavnik prirodnih polietarskih[4][5] antibiotika.[6][7]
Hemijska struktura monensina je prvo opisana 1967. godine (Agtarp et al.). To je bio prvi polietarski antibiotik. Prvi izveštaj o totalnoj sintezi monensina je objavljen 1979. godine.[8]
Monensin A manifestuje naklonost ka formiranju kompleksa sa monovalentnim katjonima kao što su Li+, Na+, K+, Rb+, Ag+ and Tl+ [9][10][11][12]. Monensin A ima sposobnot transportovanja tih katjona kroz lipidne membrane ćelija, što mu daje značajnu ulogu Na+/H+ antitransportera. On blokira intraćelijski proteinski transport, i poseduje antibiotička, antimalarijska, i druga biološka svojstva.[13]. Antibakteriske osobine Monensina i njegovih derivata su rezultat njihove sposobnosti da transportuju metalne katjone kroz ćeliske i intraćeliske membrane.[14][15][16].
Monenin je u širokoj upotrebi u industriji prerade mleka i mesa kao stredstvo za sprečavanje cocodiosisa, intenzivnog oslobađanja propionske kiselene.[17]. Monensin, monensin metil estar (MME), i posebno monensin decil estar (MDE) se široko koriste kao sastojak selectivnih elektroda.[18][19][20].
- ↑ Keith Parker; Laurence Brunton; Goodman, Louis Sanford; Lazo, John S.; Gilman, Alfred (2006). „Chapter 42. General principles of antimicrobial therapy”. Goodman & Gilman's The Pharmacological Basis of Therapeutics (11 izd.). New York: McGraw-Hill. ISBN 0-07-142280-3.
- ↑ Susan Budavari, ur. (2001). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th izd.). Merck Publishing. str. 6271. ISBN 0-911910-13-1.
- ↑ Harvey BM, Hong H, Jones MA, et al. (September 2006). „Evidence that a novel thioesterase is responsible for polyketide chain release during biosynthesis of the polyether ionophore monensin”. Chembiochem 7 (9): 1435–42. DOI:10.1002/cbic.200500474. PMID 16897798.
- ↑ Li C, Hazzard C, Florova G, Reynolds KA (November 2009). „High titer production of tetracenomycins by heterologous expression of the pathway in a Streptomyces cinnamonensis industrial monensin producer strain”. Metab. Eng. 11 (6): 319–27. DOI:10.1016/j.ymben.2009.06.004. PMID 19595787.
- ↑ Mollenhauer HH, Morré DJ, Rowe LD (May 1990). „Alteration of intracellular traffic by monensin; mechanism, specificity and relationship to toxicity”. Biochim. Biophys. Acta 1031 (2): 225–46. PMID 2160275.
- ↑ Thomas L. Lemke, David A. Williams, ur. (2002). Foye's Principles of Medicinal Chemistry (5 izd.). Baltimore: Lippincott Willams & Wilkins. str. 819-865. ISBN 0-7817-4443-1.
- ↑ Mandel GL, Bannett JE, Dolin R, ur. (2000). Principles and Practise of Infectious Diseases (5 izd.). Philadelphia, PA: Churchill Livingstone. DOI:10.1016/S1473-3099(10)70089-X. ISBN 0-443-07593-X.
- ↑ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. str. 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
- ↑ 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., 2007, 832, 84-89, DOI:10.1016/j.molstruc.2006.07.043
- ↑ A. Huczyński, M. Ratajczak-Sitarz, A. Katrusiak, B. Brzezinski, "Molecular structure of rubidium six-coordinated dihydrate complex with monensin A", J. Mol. Struct.DOI:10.1016/j.molstruc.2007.12.005
- ↑ M. Pinkerton, L. K. Steinrauf, "Molecular structure of monovalent metal cation complexes of monensin", J. Mol. Biol., 1970 49(3), 533-546
- ↑ 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", Bioorganic & Medicinal Chemistry Letters, 2008, 18, 2585-2589, DOI:10.1016/j.bmcl.2008.03.038
- ↑ A. Huczyński, P. Przybylski, B. Brzezinski, F. Bartl, ”Spectroscopic and semiempirical studies of a proton channel formed by the methyl ester of Monensin A”, J. Phys. Chem. B, 2006, 110, 15615-15623, DOI:10.1021/jp062160o
- ↑ A. Huczyński, A. Domańska, I. Paluch, J. Stefańska, B. Brzezinski, F. Bartl, "Synthesis of new semi-synthetic dipodands and tripodands from naturally occurring polyether ionophores", Tetrahedron Letters, 2008, 49(39), 5572-5575 DOI:10.1016/j.tetlet.2008.06.116
- ↑ T. Matsuoka, M.N. Novilla, T.D. Thomson and A.L. Donoho, "Review of monensin toxicosis in horses", J. 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”, Analytical Sciences, 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
- Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. str. 185–187. ISBN 3-527-29284-5.
- BioNet škola Arhivirano 2012-07-02 na Wayback Machine-u