Reinvestigation of the structure of monensin A phenylurethane sodium salt based on X-ray crystallographic and spectroscopic studies, and its activity against hospital strains of methicillin-resistant S. epidermidis and S. aureus
Monensin A phenylurethane sodium salt (MON-UR1-Na) crystals were studied by the X-ray, NMR, FT-IR and PM5 semi-empirical methods. The X-ray data show that the compound forms a pseudocyclic structure, stabilized by three intramolecular hydrogen bonds, and the sodium cation coordinated by five oxygen...
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Published in | Journal of antibiotics Vol. 64; no. 3; pp. 249 - 256 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
London
Nature Publishing Group UK
01.03.2011
Japan Antibiotics Research Assoc Nature Publishing Group |
Subjects | |
Online Access | Get full text |
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Summary: | Monensin A phenylurethane sodium salt (MON-UR1-Na) crystals were studied by the X-ray, NMR, FT-IR and PM5 semi-empirical methods. The X-ray data show that the compound forms a pseudocyclic structure, stabilized by three intramolecular hydrogen bonds, and the sodium cation coordinated by five oxygen atoms in the hydrophilic sphere. The NMR and FT-IR data demonstrate that this pseudocyclic structure is also conserved in CH
2
Cl
2
solution. This structure of MON-UR1-Na is significantly different than the ones previously proposed by Westley
et al.
and Tanaka
et al.
The semi-empirical calculations of the MON-UR1-Na structures indicate that the one of the crystal is the most energetically favorable one. Other parameters, such as the size, chemical and biological nature of the urethane substituent, and especially the free carbonyl urethane group, may have a role in the biological activity of MON-UR1-Na. The
in vitro
microbiological tests provide evidence that MON-UR1-Na shows higher antibacterial activity against human pathogenic bacteria, including antibiotic-resistant
Staphylococcus aureus
and
Staphylococcus epidermidis
than the parent unmodified antibiotic—Monensin A. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0021-8820 1881-1469 |
DOI: | 10.1038/ja.2010.167 |