In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues
[Display omitted] •Imines resveratrol analogues are less cytotoxicity than thioimines and hydrazones.•The imines are more effective than resveratrol on DPPH scavenger.•The imines reduce pro-inflammatory mediators production in vitro.•The imines decrease lymphocyte proliferation and costimulatory mol...
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Published in | Bioorganic & medicinal chemistry Vol. 26; no. 17; pp. 4898 - 4906 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
England
Elsevier Ltd
15.09.2018
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Subjects | |
Online Access | Get full text |
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Abstract | [Display omitted]
•Imines resveratrol analogues are less cytotoxicity than thioimines and hydrazones.•The imines are more effective than resveratrol on DPPH scavenger.•The imines reduce pro-inflammatory mediators production in vitro.•The imines decrease lymphocyte proliferation and costimulatory molecules.•The imines control edema formation, cytokines and myeloperoxidase production in vivo.
Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important anti-inflammatory/immunomodulatory molecule. However, its bioavailability problems have limited its use encouraging the search for new alternatives agents. Thus, in this study, we synthetize 12 resveratrol analogues (6 imines, 1 thioimine and 5 hydrazones) and investigated its cytotoxicity, antioxidant activity and in vitro anti-inflammatory/immunomodulatory properties. The most promising compounds were also evaluated in vivo. The results showed that imines presented less cytotoxicity, were more effective than resveratrol on DPPH scavenger and exhibited an anti-inflammatory profile. Among them, the imines with a radical in the para position, on the ring B, not engaged in an intramolecular hydrogen-interaction, showed more prominent anti-inflammatory activity modulating, in vivo, the edema formation, the inflammatory infiltration and cytokine levels. An immunomodulatory activity also was observed in these molecules. Thus, our results suggest that imines with these characteristics presents potential to control inflammatory disorders. |
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AbstractList | [Display omitted]
•Imines resveratrol analogues are less cytotoxicity than thioimines and hydrazones.•The imines are more effective than resveratrol on DPPH scavenger.•The imines reduce pro-inflammatory mediators production in vitro.•The imines decrease lymphocyte proliferation and costimulatory molecules.•The imines control edema formation, cytokines and myeloperoxidase production in vivo.
Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important anti-inflammatory/immunomodulatory molecule. However, its bioavailability problems have limited its use encouraging the search for new alternatives agents. Thus, in this study, we synthetize 12 resveratrol analogues (6 imines, 1 thioimine and 5 hydrazones) and investigated its cytotoxicity, antioxidant activity and in vitro anti-inflammatory/immunomodulatory properties. The most promising compounds were also evaluated in vivo. The results showed that imines presented less cytotoxicity, were more effective than resveratrol on DPPH scavenger and exhibited an anti-inflammatory profile. Among them, the imines with a radical in the para position, on the ring B, not engaged in an intramolecular hydrogen-interaction, showed more prominent anti-inflammatory activity modulating, in vivo, the edema formation, the inflammatory infiltration and cytokine levels. An immunomodulatory activity also was observed in these molecules. Thus, our results suggest that imines with these characteristics presents potential to control inflammatory disorders. Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important anti-inflammatory/immunomodulatory molecule. However, its bioavailability problems have limited its use encouraging the search for new alternatives agents. Thus, in this study, we synthetize 12 resveratrol analogues (6 imines, 1 thioimine and 5 hydrazones) and investigated its cytotoxicity, antioxidant activity and in vitro anti-inflammatory/immunomodulatory properties. The most promising compounds were also evaluated in vivo. The results showed that imines presented less cytotoxicity, were more effective than resveratrol on DPPH scavenger and exhibited an anti-inflammatory profile. Among them, the imines with a radical in the para position, on the ring B, not engaged in an intramolecular hydrogen-interaction, showed more prominent anti-inflammatory activity modulating, in vivo, the edema formation, the inflammatory infiltration and cytokine levels. An immunomodulatory activity also was observed in these molecules. Thus, our results suggest that imines with these characteristics presents potential to control inflammatory disorders. |
Author | Souza, Isabela de Oliveira Macedo, Gilson Costa Lacerda, Leticia Moroni da Silva, Adilson David Pinto, Nícolas de Castro Campos Scio, Elita Zimmermann-Franco, Danielle Cristina Santos, Juliana Alves dos Esteves, Bruna |
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Keywords | NO MCP-1 OPD DMSO MHC HTAB MTT AP-1 MPO LPS BSA NF-κB SD IFN-γ OD Resveratrol iNOS IC Immunomodulatory v/v 5-LOX CCL-2 CD IL DPPH Analogues 1H NMR Imine 13C NMR EDTA COX AR TH TNF-α PMSF TMS HE Anti-inflammatory ELISA |
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•Imines resveratrol analogues are less cytotoxicity than thioimines and hydrazones.•The imines are more effective than resveratrol on DPPH... Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important anti-inflammatory/immunomodulatory molecule. However,... |
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SubjectTerms | Adjuvants, Immunologic - pharmacology Analogues Animals Anti-inflammatory Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacokinetics Anti-Inflammatory Agents - pharmacology Antioxidants - pharmacology Biological Availability Biphenyl Compounds - metabolism Cell Proliferation - drug effects Cytokines - antagonists & inhibitors Cytokines - biosynthesis Down-Regulation - drug effects Imine Imines - chemistry Immunomodulatory Inflammation - prevention & control Inflammation Mediators - antagonists & inhibitors Inflammation Mediators - metabolism Lymphocytes - cytology Lymphocytes - drug effects Major Histocompatibility Complex - drug effects Mice Mice, Inbred C57BL Peroxidase - biosynthesis Picrates - metabolism RAW 264.7 Cells Resveratrol Resveratrol - analogs & derivatives |
Title | In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues |
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