Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity

Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim...

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Autores principales:	Damian Pawelski, Alicja Walewska, Sylwia Ksiezak, Dariusz Sredzinski, Piotr Radziwon, Marcin Moniuszko, Ramesh Gandusekar, Andrzej Eljaszewicz, Ryszard Lazny, Krzysztof Brzezinski, Marta E. Plonska-Brzezinska
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	curcumin pseudopelletierine granatanone granatane anti-inflammatory property cytotoxicity Biology (General) QH301-705.5 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/5414efc6a9bb4919bf8d0cdde9e999cc
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spelling	oai:doaj.org-article:5414efc6a9bb4919bf8d0cdde9e999cc2021-11-11T16:51:41ZMonocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity10.3390/ijms2221113841422-00671661-6596https://doaj.org/article/5414efc6a9bb4919bf8d0cdde9e999cc2021-10-01T00:00:00Zhttps://www.mdpi.com/1422-0067/22/21/11384https://doaj.org/toc/1661-6596https://doaj.org/toc/1422-0067Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim of this work is to synthesize monocarbonyl analogs of CUR based on the 9-methyl-9-azabicyclo[3.2.1]nonan-3-one (pseudopelletierine, granatanone) scaffold to improve its bioavailability. Granatane is a homologue of tropane, whose structure is present in numerous naturally occurring alkaloids, e.g., <span style="font-variant: small-caps;">l</span>-cocaine and <span style="font-variant: small-caps;">l</span>-scopolamine. In this study, ten new pseudopelletierine-derived monocarbonyl analogs of CUR were successfully synthesized and characterized by spectral methods and X-ray crystallography. Additionally, in vitro test of the cytotoxicity and anti-inflammatory properties of the synthesized compounds were performed.Damian PawelskiAlicja WalewskaSylwia KsiezakDariusz SredzinskiPiotr RadziwonMarcin MoniuszkoRamesh GandusekarAndrzej EljaszewiczRyszard LaznyKrzysztof BrzezinskiMarta E. Plonska-BrzezinskaMDPI AGarticlecurcuminpseudopelletierinegranatanonegranataneanti-inflammatory propertycytotoxicityBiology (General)QH301-705.5ChemistryQD1-999ENInternational Journal of Molecular Sciences, Vol 22, Iss 11384, p 11384 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	curcumin pseudopelletierine granatanone granatane anti-inflammatory property cytotoxicity Biology (General) QH301-705.5 Chemistry QD1-999
spellingShingle	curcumin pseudopelletierine granatanone granatane anti-inflammatory property cytotoxicity Biology (General) QH301-705.5 Chemistry QD1-999 Damian Pawelski Alicja Walewska Sylwia Ksiezak Dariusz Sredzinski Piotr Radziwon Marcin Moniuszko Ramesh Gandusekar Andrzej Eljaszewicz Ryszard Lazny Krzysztof Brzezinski Marta E. Plonska-Brzezinska Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity
description	Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim of this work is to synthesize monocarbonyl analogs of CUR based on the 9-methyl-9-azabicyclo[3.2.1]nonan-3-one (pseudopelletierine, granatanone) scaffold to improve its bioavailability. Granatane is a homologue of tropane, whose structure is present in numerous naturally occurring alkaloids, e.g., <span style="font-variant: small-caps;">l</span>-cocaine and <span style="font-variant: small-caps;">l</span>-scopolamine. In this study, ten new pseudopelletierine-derived monocarbonyl analogs of CUR were successfully synthesized and characterized by spectral methods and X-ray crystallography. Additionally, in vitro test of the cytotoxicity and anti-inflammatory properties of the synthesized compounds were performed.
format	article
author	Damian Pawelski Alicja Walewska Sylwia Ksiezak Dariusz Sredzinski Piotr Radziwon Marcin Moniuszko Ramesh Gandusekar Andrzej Eljaszewicz Ryszard Lazny Krzysztof Brzezinski Marta E. Plonska-Brzezinska
author_facet	Damian Pawelski Alicja Walewska Sylwia Ksiezak Dariusz Sredzinski Piotr Radziwon Marcin Moniuszko Ramesh Gandusekar Andrzej Eljaszewicz Ryszard Lazny Krzysztof Brzezinski Marta E. Plonska-Brzezinska
author_sort	Damian Pawelski
title	Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity
title_short	Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity
title_full	Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity
title_fullStr	Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity
title_full_unstemmed	Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity
title_sort	monocarbonyl analogs of curcumin based on the pseudopelletierine scaffold: synthesis and anti-inflammatory activity
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/5414efc6a9bb4919bf8d0cdde9e999cc
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Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity

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