Cargando…
Synthesis of Thiophene and NO-Curcuminoids for Antiinflammatory and Anti-Cancer Activities
In search of better NSAIDs four novel nitric oxide donating derivatives of curcumin (compounds 9a–d), and four thiophene curcuminoids (compounds 10a–c, 11) have been synthesised. The cytotoxic effects of these compounds along with the lead compound curcumin (7) and their effect on the production of...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2013
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271105/ https://www.ncbi.nlm.nih.gov/pubmed/23353121 http://dx.doi.org/10.3390/molecules18021483 |
_version_ | 1783376851973963776 |
---|---|
author | Ahmed, Mahera M. Khan, M. Akram Rainsford, Kim Drummond |
author_facet | Ahmed, Mahera M. Khan, M. Akram Rainsford, Kim Drummond |
author_sort | Ahmed, Mahera M. |
collection | PubMed |
description | In search of better NSAIDs four novel nitric oxide donating derivatives of curcumin (compounds 9a–d), and four thiophene curcuminoids (compounds 10a–c, 11) have been synthesised. The cytotoxic effects of these compounds along with the lead compound curcumin (7) and their effect on the production of the reactive oxygen species nitric oxide and pro-inflammatory cytokines IL-1β, TNF-α and chemokine CXCL-8 were evaluated using human monocytic THP-1 and colon adenocarcinoma CACO-2 cell lines. All of the nitric oxide donating curcuminoids 9a–d and the thiophene curcuminoids 10a–c and 11 were non-cytotoxic to THP-1 cells over a concentration range of 10-100 μM and compared with curcumin compounds 10b and 10c, were more toxic. In CACO-2 cells, 10b and 11 appeared to be non-toxic at 10 to 50 μM, whereas 10a and 10c were non-cytotoxic at 10 μM only. These results clearly indicate that the introduction of a nitroxybutyl moiety to curcumin and replacement of phenyl rings with thiophene units reduces the cytotoxic effect of the parent curcumin, whereas a methyl substituted thiophene increases the cytotoxic effects. In THP-1 cells, drugs 10a and 11 significantly decreased IL-1-β production at their non-cytotoxic concentrations, whereas, they did not decrease TNF-α production in CACO-2 cells. Compound 11 showed a significant decrease in CXCL-8 production. |
format | Online Article Text |
id | pubmed-6271105 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62711052018-12-14 Synthesis of Thiophene and NO-Curcuminoids for Antiinflammatory and Anti-Cancer Activities Ahmed, Mahera M. Khan, M. Akram Rainsford, Kim Drummond Molecules Article In search of better NSAIDs four novel nitric oxide donating derivatives of curcumin (compounds 9a–d), and four thiophene curcuminoids (compounds 10a–c, 11) have been synthesised. The cytotoxic effects of these compounds along with the lead compound curcumin (7) and their effect on the production of the reactive oxygen species nitric oxide and pro-inflammatory cytokines IL-1β, TNF-α and chemokine CXCL-8 were evaluated using human monocytic THP-1 and colon adenocarcinoma CACO-2 cell lines. All of the nitric oxide donating curcuminoids 9a–d and the thiophene curcuminoids 10a–c and 11 were non-cytotoxic to THP-1 cells over a concentration range of 10-100 μM and compared with curcumin compounds 10b and 10c, were more toxic. In CACO-2 cells, 10b and 11 appeared to be non-toxic at 10 to 50 μM, whereas 10a and 10c were non-cytotoxic at 10 μM only. These results clearly indicate that the introduction of a nitroxybutyl moiety to curcumin and replacement of phenyl rings with thiophene units reduces the cytotoxic effect of the parent curcumin, whereas a methyl substituted thiophene increases the cytotoxic effects. In THP-1 cells, drugs 10a and 11 significantly decreased IL-1-β production at their non-cytotoxic concentrations, whereas, they did not decrease TNF-α production in CACO-2 cells. Compound 11 showed a significant decrease in CXCL-8 production. MDPI 2013-01-25 /pmc/articles/PMC6271105/ /pubmed/23353121 http://dx.doi.org/10.3390/molecules18021483 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Ahmed, Mahera M. Khan, M. Akram Rainsford, Kim Drummond Synthesis of Thiophene and NO-Curcuminoids for Antiinflammatory and Anti-Cancer Activities |
title | Synthesis of Thiophene and NO-Curcuminoids for Antiinflammatory and Anti-Cancer Activities |
title_full | Synthesis of Thiophene and NO-Curcuminoids for Antiinflammatory and Anti-Cancer Activities |
title_fullStr | Synthesis of Thiophene and NO-Curcuminoids for Antiinflammatory and Anti-Cancer Activities |
title_full_unstemmed | Synthesis of Thiophene and NO-Curcuminoids for Antiinflammatory and Anti-Cancer Activities |
title_short | Synthesis of Thiophene and NO-Curcuminoids for Antiinflammatory and Anti-Cancer Activities |
title_sort | synthesis of thiophene and no-curcuminoids for antiinflammatory and anti-cancer activities |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271105/ https://www.ncbi.nlm.nih.gov/pubmed/23353121 http://dx.doi.org/10.3390/molecules18021483 |
work_keys_str_mv | AT ahmedmaheram synthesisofthiopheneandnocurcuminoidsforantiinflammatoryandanticanceractivities AT khanmakram synthesisofthiopheneandnocurcuminoidsforantiinflammatoryandanticanceractivities AT rainsfordkimdrummond synthesisofthiopheneandnocurcuminoidsforantiinflammatoryandanticanceractivities |