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Mar. Drugs 2018, 16(6), 206; https://doi.org/10.3390/md16060206

Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells

1
Department of Pharmacy, University of Naples Federico II, 80131 Napoli, Italy
2
Laboratory of Pre-Clinical and Translational Research, IRCCS—Referral Cancer Center of Basilicata (CROB), 85028 Rionero in Vulture, Italy
3
Department of Chemical Sciences, University of Naples Federico II, via Cintia 4, 80126 Naples, Italy
These authors contribute equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 29 May 2018 / Revised: 5 June 2018 / Accepted: 10 June 2018 / Published: 13 June 2018
(This article belongs to the Special Issue Synthetic and Biosynthetic Approaches to Marine Natural Products)
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Abstract

Smenamides are an intriguing class of peptide/polyketide molecules of marine origin showing antiproliferative activity against lung cancer Calu-1 cells at nanomolar concentrations through a clear pro-apoptotic mechanism. To probe the role of the activity-determining structural features, the 16-epi-analogue of smenamide A and eight simplified analogues in the 16-epi series were prepared using a flexible synthetic route. The synthetic analogues were tested on multiple myeloma (MM) cell lines showing that the configuration at C-16 slightly affects the activity, since the 16-epi-derivative is still active at nanomolar concentrations. Interestingly, it was found that the truncated compound 8, mainly composed of the pyrrolinone terminus, was not active, while compound 13, essentially lacking the pyrrolinone moiety, was 1000-fold less active than the intact substance and was the most active among all the synthesized compounds. View Full-Text
Keywords: smenamides; marine natural products; peptide/polyketide molecules; synthetic analogues; functional-analogues; antiproliferative activity; MM cell line smenamides; marine natural products; peptide/polyketide molecules; synthetic analogues; functional-analogues; antiproliferative activity; MM cell line
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Caso, A.; Laurenzana, I.; Lamorte, D.; Trino, S.; Esposito, G.; Piccialli, V.; Costantino, V. Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells. Mar. Drugs 2018, 16, 206.

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