Monensin

Izvor: Wikipedia
Monensin A
Monensin A.svg
IUPAC ime
Drugi nazivi monenska kiselina
Identifikacija
CAS registarski broj 17090-79-8
MeSH Monensin
ATCvet code QP51AH03
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



Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala

Infobox references

Monensin[2], koji je izolovan iz Streptomyces cinnamonensis[3], poznati je predstavnik prirodnih polietarskih[4][5] antibiotika.[6][7]

Istorija[uredi - уреди]

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]

Mekanizam akcije[uredi - уреди]

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].

Struktura Monensina A natrijum kompleks


Upotreba[uredi - уреди]

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].

Vidi još[uredi - уреди]

Reference[uredi - уреди]

  1. 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. http://books.mcgraw-hill.com/medical/goodmanandgilman/. 
  2. 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. http://www.merckbooks.com/mindex/online.html. 
  3. 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. 
  4. 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. 
  5. 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. 
  6. 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. http://www.lww.com/productTOC/?ISBN=978-0-7817-6879-5. 
  7. 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. http://www.lancet.com/journals/laninf/article/PIIS1473-3099%2810%2970089-X/fulltext. 
  8. Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. str. 185–187. ISBN 3-527-29284-5. 
  9. 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
  10. 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
  11. 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
  12. M. Pinkerton, L. K. Steinrauf, "Molecular structure of monovalent metal cation complexes of monensin", J. Mol. Biol., 1970 49(3), 533-546
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. K. Toko, ”Taste Sensor”, Sensors and Actuators B: Chemical, 64, 2000, 205-215, DOI:10.1016/S0925-4005(99)00508-0

Literatura[uredi - уреди]

  • Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. str. 185–187. ISBN 3-527-29284-5. 

Spoljašnje veze[uredi - уреди]


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