Binding studies of erythromycin a and its analogues using molecular docking technique

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Date
2006
Authors
Kamarulzaman, Ezatul Ezleen
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Abstract
Erythromycin A is a macrolide antibiotic that binds to the 50S bacterial ribosome and can be used to combat bacteria by inhibiting the elongation of the nascent peptide chain during the bacterial protein synthesis. However, the success of erythromycin A as an antibiotic is limited due to it's sensitivity to acidic environment and short half-life. This limitation leads to the design of the semi synthetic and also ketolide analogues of erythromycin A. The research aims to investigate the molecular interactions of various erythromycin A analogues with the ribosomes as well as to predict the binding mode and affinities of the analogues in the ribosome complex. The interactions of twelve analogues with the 50S ribosomal subunit from Deinococcus radiodurans were studied using molecular docking technique employing the AutoDock 3.0.5. The results showed that all active analogues bound at the same binding sites as erythromycin A and scored lower free energy of binding than erythromycin A. In contrast, the inactive analogues showed comparable free energy of binding to erythromycin A but they were found to bind at a location slightly further away from the binding site of erythromycin A. In addition, erythromycin A anhydride did not bind to the ribosome and showed higher free energy of binding than erythromycin A. The interaction of erythromycins A, 8 and C, clarithromycin, roxithromycin, azithromycin, cethromycin and telithromycin with the ribosomal complex showed consistency to the X-ray data from the perspectives of hydrogen bonding and hydrophobic interactions. The results also showed that all sugars play a major role in the formation of hydrogen bonding and hydrophobic interactions with the ribosomal target. Thus, these results provide useful information for the designing of a new erythromycin A analogue.
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Keywords
Erythromycin , Molecular docking
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