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Semisynthetic Latrunculin B Analogs: Studies of Actin Docking Support a Proposed Mechanism for Latrunculin Bioactivity

Semisynthetic Latrunculin B Analogs: Studies of Actin Docking Support a Proposed Mechanism for Latrunculin Bioactivity

Sucheta Kudrimoti, Safwat A Ahmed, Pankaj R Daga, Amir E Wahba, Sherief I Khalifa, Robert J Doerksen, Mark T Hamann

Bioorg Med Chem. 2009 Nov 1;17(21):7517-22.

PMID: 19800245

Abstract:

Latrunculins are unique macrolides containing a thiazolidinone moiety. Latrunculins A, B and T and 16-epi-latrunculin B were isolated from the Red Sea sponge Negombata magnifica. N-Alkylated, O-methylated analogs of latrunculin B were synthesized and biological evaluation was performed for antifungal and antiprotozoal activity. The natural latrunculins showed significant bioactivity, while the semisynthetic analogs did not. Docking studies of these analogs into the X-ray crystal structure of G-actin showed that, in comparison with latrunculins A and B, N-alkylated latrunculins did not dock satisfactorily. This suggests that the analogs do not fit well into the active site of G-actin due to steric clashes and provides an explanation for the absence of bioactivity.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP76343947	Latrunculin B from Latruncula magnifica		76343-94-7	Price

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