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Pawelski D, Walewska A, Ksiezak S, et al. Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity. Int J Mol Sci. 2021;22(21)doi: 10.3390/ijms222111384.
Pawelski, D., Walewska, A., Ksiezak, S., Sredzinski, D., Radziwon, P., Moniuszko, M., Gandusekar, R., Eljaszewicz, A., Lazny, R., Brzezinski, K., & Plonska-Brzezinska, M. E. (2021). Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity. International journal of molecular sciences, 22(21), . https://doi.org/10.3390/ijms222111384
Pawelski, Damian, et al. "Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity." International journal of molecular sciences vol. 22,21 (2021). doi: https://doi.org/10.3390/ijms222111384
Pawelski D, Walewska A, Ksiezak S, Sredzinski D, Radziwon P, Moniuszko M, Gandusekar R, Eljaszewicz A, Lazny R, Brzezinski K, Plonska-Brzezinska ME. Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity. Int J Mol Sci. 2021 Oct 21;22(21). doi: 10.3390/ijms222111384. PMID: 34768818; PMCID: PMC8583854.
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Int J Mol Sci. 2021 Oct 21;22(21). doi: 10.3390/ijms222111384.

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

International journal of molecular sciences

Damian Pawelski, Alicja Walewska, Sylwia Ksiezak, Dariusz Sredzinski, Piotr Radziwon, Marcin Moniuszko, Ramesh Gandusekar, Andrzej Eljaszewicz, Ryszard Lazny, Krzysztof Brzezinski, Marta E Plonska-Brzezinska

Affiliations

  1. Department of Organic Chemistry, Faculty of Pharmacy with the Division of Laboratory Medicine, Medical University of Bialystok, Mickiewicza 2A, 15-222 Bialystok, Poland.
  2. Department of Regenerative Medicine and Immune Regulation, Medical University of Bialystok, Waszyngtona 13, 15-269 Bialystok, Poland.
  3. Regional Blood Donation and Blood Treatment Center in Bialystok, M. Sklodowskiej-Curie 23, 15-950 Bialystok, Poland.
  4. Department of Hematology, Medical University of Bialystok, M. Sklodowskiej-Curie 24A, 15-276 Bialystok, Poland.
  5. Department of Allergology and Internal Medicine, Medical University of Bialystok, M. Sklodowskiej-Curie 24A, 15-276 Bialystok, Poland.
  6. Faculty of Chemistry, University of Bialystok, Ciolkowskiego 1K, 15-245 Bialystok, Poland.
  7. Department of Structural Biology of Prokaryotic Organisms, Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-074 Poznan, Poland.

PMID: 34768818 PMCID: PMC8583854 DOI: 10.3390/ijms222111384

Abstract

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., l-cocaine and l-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.

Keywords: anti-inflammatory property; curcumin; cytokines; cytotoxicity; granatane; granatanone; pseudopelletierine

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