Monensin

Monensin A
Nazivi
IUPAC naziv
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-dioxaspiro[4.5]dec-7-yl]-3-methoxy-2-methyl-pentanoic acid
Drugi nazivi
monenska kiselina
Identifikacija
3D model (Jmol)
ECHA InfoCard 100.037.398
E-brojevi E714 (antibiotici)
MeSH Monensin
Svojstva
C36H62O11
Molarna masa 670,871g/mol
Agregatno stanje čvrsto stanje, beli kristali
Tačka topljenja 104 °C
3x10-6 g/dm3 (20 °C)
Rastvorljivost etanol, aceton, dietil etar, benzol
Srodna jedinjenja
Srodne
antibiotik[1], jonofor
Srodna jedinjenja
 Monensin A metil estar
Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
Reference infokutije

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

Istorija

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]

Mehanizam akcije

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

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

Reference

  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. изд.). New York: McGraw-Hill. ISBN 0071422803. 
  2. ^ Susan Budavari, ур. (2001). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th изд.). Merck Publishing. стр. 6271. ISBN 0911910131. 
  3. ^ Harvey BM; Hong H; Jones MA; et al. (2006). „Evidence that a novel thioesterase is responsible for polyketide chain release during biosynthesis of the polyether ionophore monensin”. Chembiochem. 7 (9): 1435—42. PMID 16897798. doi:10.1002/cbic.200500474. 
  4. ^ Li C, Hazzard C, Florova G, Reynolds KA (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. PMID 19595787. doi:10.1016/j.ymben.2009.06.004. 
  5. ^ Mollenhauer HH, Morré DJ, Rowe LD (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, ур. (2002). Foye's Principles of Medicinal Chemistry (5. изд.). Baltimore: Lippincott Willams & Wilkins. стр. 819—865. ISBN 0781744431. 
  7. ^ Mandel GL, Bannett JE, Dolin R, ур. (2000). Principles and Practise of Infectious Diseases (5 изд.). Philadelphia, PA: Churchill Livingstone. doi:10.1016/S1473-3099(10)70089-X. ISBN 044307593X. 
  8. ^ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. ISBN 978-3-527-29284-4. 
  9. ^ Huczyński, Adam; Ratajczak-Sitarz, Małgorzata; Katrusiak, Andrzej; Brzezinski, Bogumil (2007). „Molecular structure of the 1:1 inclusion complex of monensin a lithium salt with acetonitrile”. Journal of Molecular Structure. 871 (1–3): 92—97. Bibcode:2007JMoSt.871...92H. doi:10.1016/j.molstruc.2006.07.046. 
  10. ^ Huczyński, Adam; Ratajczak-Sitarz, Małgorzata; Katrusiak, Andrzej; Brzezinski, Bogumil (2007). „Molecular structure of the 1:1 inclusion complex of monensin a sodium salt with acetonitrile”. Journal of Molecular Structure. 832 (1–3): 84—89. Bibcode:2007JMoSt.832...84H. doi:10.1016/j.molstruc.2006.07.043. 
  11. ^ Huczyński, Adam; Ratajczak-Sitarz, Małgorzata; Katrusiak, Andrzej; Brzezinski, Bogumil (2008). „Molecular structure of rubidium six-coordinated dihydrate complex with monensin A”. Journal of Molecular Structure. 888 (1–3): 224—229. Bibcode:2008JMoSt.888..224H. 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. ^ Mollenhauer, Hilton H.; James Morré, D.; Rowe, Loyd D. (1990). „Alteration of intracellular traffic by monensin; mechanism, specificity and relationship to toxicity”. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes. 1031 (2): 225—246. PMC 7148783 Слободан приступ. PMID 2160275. doi:10.1016/0304-4157(90)90008-Z. 
  14. ^ Huczyński, Adam; Stefańska, Joanna; Przybylski, Piotr; Brzezinski, Bogumil; Bartl, Franz (2008). „Synthesis and antimicrobial properties of Monensin a esters”. Bioorganic & Medicinal Chemistry Letters. 18 (8): 2585—2589. PMID 18375122. doi:10.1016/j.bmcl.2008.03.038. 
  15. ^ Huczyñski, Adam; Przybylski, Piotr; Brzezinski, Bogumil; Bartl, Franz (2006). „Spectroscopic and Semiempirical Studies of a Proton Channel Formed by the Methyl Ester of Monensin A”. The Journal of Physical Chemistry B. 110 (31): 15615—15623. PMID 16884286. doi:10.1021/jp062160o. 
  16. ^ Huczyński, Adam; Domańska, Agata; Paluch, Izabela; Stefańska, Joanna; Brzezinski, Bogumil; Bartl, Franz (2008). „Synthesis of new semi-synthetic dipodands and tripodands from naturally occurring polyether ionophores”. Tetrahedron Letters. 49 (39): 5572—5575. doi:10.1016/j.tetlet.2008.06.116. 
  17. ^ Matsuoka, T.; Novilla, M.N.; Thomson, T.D.; Donoho, A.L. (1996). „Review of monensin toxicosis in horses”. Journal of Equine Veterinary Science. 16: 8—15. doi:10.1016/S0737-0806(96)80059-1. 
  18. ^ Tohda, Koji; Suzuki, Koji; Kosuge, Nobutaka; Nagashima, Hitoshi; Watanabe, Kazuhiko; Inoue, Hidenari; Shirai, Tsuneo (1990). „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 (2): 227—232. doi:10.2116/analsci.6.227. 
  19. ^ Kim, Namsoo; Park, Kyung-rim; Park, In-Seon; Cho, Yong-Jin; Bae, Young Min (2005). „Application of a taste evaluation system to the monitoring of Kimchi fermentation☆”. Biosensors and Bioelectronics. 20 (11): 2283—2291. PMID 15797327. doi:10.1016/j.bios.2004.10.007. 
  20. ^ Toko, Kiyoshi (2000). „Taste sensor”. Sensors and Actuators B: Chemical. 64 (1–3): 205—215. Bibcode:2000SeAcB..64..205T. doi:10.1016/S0925-4005(99)00508-0. 

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