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

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-a...
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Autor*in:	Alessia Caso [verfasserIn] Ilaria Laurenzana [verfasserIn] Daniela Lamorte [verfasserIn] Stefania Trino [verfasserIn] Germana Esposito [verfasserIn] Vincenzo Piccialli [verfasserIn] Valeria Costantino [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	smenamides marine natural products peptide/polyketide molecules synthetic analogues functional-analogues antiproliferative activity MM cell line

Übergeordnetes Werk:	In: Marine Drugs - MDPI AG, 2005, 16(2018), 6, p 206
Übergeordnetes Werk:	volume:16 ; year:2018 ; number:6, p 206

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/md16060206

Katalog-ID:	DOAJ078707145

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spelling	10.3390/md16060206 doi (DE-627)DOAJ078707145 (DE-599)DOAJ9ef13e5b8f844aa98c1d35ce79ef662c DE-627 ger DE-627 rakwb eng QH301-705.5 Alessia Caso verfasserin aut Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. smenamides marine natural products peptide/polyketide molecules synthetic analogues functional-analogues antiproliferative activity MM cell line Biology (General) Ilaria Laurenzana verfasserin aut Daniela Lamorte verfasserin aut Stefania Trino verfasserin aut Germana Esposito verfasserin aut Vincenzo Piccialli verfasserin aut Valeria Costantino verfasserin aut In Marine Drugs MDPI AG, 2005 16(2018), 6, p 206 (DE-627)477992420 (DE-600)2175190-0 16603397 nnns volume:16 year:2018 number:6, p 206 https://doi.org/10.3390/md16060206 kostenfrei https://doaj.org/article/9ef13e5b8f844aa98c1d35ce79ef662c kostenfrei http://www.mdpi.com/1660-3397/16/6/206 kostenfrei https://doaj.org/toc/1660-3397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_381 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 16 2018 6, p 206
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source	In Marine Drugs 16(2018), 6, p 206 volume:16 year:2018 number:6, p 206
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callnumber-first	Q - Science
author	Alessia Caso
spellingShingle	Alessia Caso misc QH301-705.5 misc smenamides misc marine natural products misc peptide/polyketide molecules misc synthetic analogues misc functional-analogues misc antiproliferative activity misc MM cell line misc Biology (General) Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells
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topic_title	QH301-705.5 Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells smenamides marine natural products peptide/polyketide molecules synthetic analogues functional-analogues antiproliferative activity MM cell line
topic	misc QH301-705.5 misc smenamides misc marine natural products misc peptide/polyketide molecules misc synthetic analogues misc functional-analogues misc antiproliferative activity misc MM cell line misc Biology (General)
topic_unstemmed	misc QH301-705.5 misc smenamides misc marine natural products misc peptide/polyketide molecules misc synthetic analogues misc functional-analogues misc antiproliferative activity misc MM cell line misc Biology (General)
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title	Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells
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title_full	Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells
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title_sort	smenamide a analogues. synthesis and biological activity on multiple myeloma cells
callnumber	QH301-705.5
title_auth	Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells
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.
abstractGer	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.
abstract_unstemmed	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.
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title_short	Smenamide A Analogues. Synthesis and Biological Activity on Multiple Myeloma Cells
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