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Review
, 2013, 742149

Structure and Antimicrobial Properties of Monensin A and Its Derivatives: Summary of the Achievements

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Review

Structure and Antimicrobial Properties of Monensin A and Its Derivatives: Summary of the Achievements

Daniel Aowicki et al. Biomed Res Int.

Abstract

In this paper structural and microbiological studies on the ionophorous antibiotic monensin A and its derivatives have been collected. Monensin A is an ionophore which selectively complexes and transports sodium cation across lipid membranes, and therefore it shows a variety of biological properties. This antibiotic is commonly used as coccidiostat and nonhormonal growth promoter. The paper focuses on both the latest and earlier achievements concerning monensin A antimicrobial activity. The activities of monensin derivatives, including modifications of hydroxyl groups and carboxyl group, are also presented.

Figures

Scheme 1
Scheme 1
The formula and atom numbering of monensinA and its homologs.
Figure 1
Figure 1
Structure of MONA monohydrate: (a) schematic representation [5], (b) complete crystal structure [6].
Figure 2
Figure 2
Crystal structures of monensin salts with (a) Ag+ dihydrate [14], (b and c) Li+ [7], and Na+ [8] inclusion complexes with ACN molecule, respectively, (d) Na+ [9], (e) K+ [11], and (f) Rb+ [12] dihydrates.
Figure 3
Figure 3
Crystal structures of monensin A free acid complexes with (a) NaCl, (b) NaClO4, and (c) NaBr [6, 29].
Figure 4
Figure 4
Crystal structures of (a) Ca(Mon)2(H2O)2, (b) Co(MonNa+)2Cl2, and (c) HgMon-H2O (protons are omitted for clarity).
Figure 5
Figure 5
Different models of ion transport by monensin: (a) electroneutral, (b) mixed electroneutral and electrogenic.
Figure 6
Figure 6
Structures of selected monensin A urethanes (a) [41]; crystal structure of monensin sodium urethane (b) [42].
Figure 7
Figure 7
Monensin A derivatives modified at C(26) atom.
Figure 8
Figure 8
Monensin A derivatives with O(IV)H group modified.
Figure 9
Figure 9
Structures of monensin amides.
Figure 10
Figure 10
Crystal structures of monensin A amide complexes: (a) [5a—NaCl], (b) [5b—Sr(ClO4)2-CH3CN].
Figure 11
Figure 11
Structures of monensylamino acid lactones.
Figure 12
Figure 12
Structures of monensin A esters.
Figure 13
Figure 13
Crystal structures of (a) [8m—LiClO4-H2O] and (b) [8m—NaClO4] complexes.
Figure 14
Figure 14
Ball and stick projection of the proton channel structure made up of eight (8a + 3H2O) species calculated by the PM5 method.

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References

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