SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS
The search of new treatments for leishmaniasis is an active task nowadays, since there is a lack of nontoxic, cheap and non-resistant medication. In the literature several quinolines have shown in vitro activity against agents of cutaneous leishmaniasis, visceral leishmaniasis, African trypanosomias...
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Universidad de Antioquia
2009
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oai:doaj.org-article:07fca273a0614aeaa1e63f3e0f7779c72021-11-19T04:17:14ZSYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS0121-40042145-2660https://doaj.org/article/07fca273a0614aeaa1e63f3e0f7779c72009-02-01T00:00:00Zhttps://revistas.udea.edu.co/index.php/vitae/article/view/798https://doaj.org/toc/0121-4004https://doaj.org/toc/2145-2660The search of new treatments for leishmaniasis is an active task nowadays, since there is a lack of nontoxic, cheap and non-resistant medication. In the literature several quinolines have shown in vitro activity against agents of cutaneous leishmaniasis, visceral leishmaniasis, African trypanosomiasis and Chagas diseases. Six 2-styrylquinolines derived from galipeine were synthesized by Perkin condensation of quinaldine with aromatic aldehydes. Leishmanicidal activity was estimated for Leishmania panamensis at the amastigote form and cytotoxic activity against U-937 cells. All compounds showed activity against both L. panamensis and U-937 cells. (E)-2-(2,5-dimethoxyphenyl)ethenyl)quinoline (1), (E)-2-(2,3- dimethoxyphenyl)ethenyl)quinoline (2) and (E)-N-[4-(2-quinolin-2-yl-ethenyl)phenyl]acetamide (3) were more active against axenic (EC50= 3.7, 4.5 and 19.1μg/mL) and intracellular amastigotes (EC50= 1.4, 1.8 and 1.7μg/ml, respectively), in comparison with hydrogenated derivatives 2-[2-(2,5-dimethoxy phenyl)ethyl]quinoline (1a), 2-[2-(2,3-dimethoxyphenyl)ethyl]quinoline (2a) and N-[4-(2-quinolin- 2-ylethyl)phenyl]acetamide (3a) (CE50= 31.1, 23.6 and 59.3μg/mL, respectively). All compounds were also active against the U-937 cells. Styrylquinolines 1, 2 and 3 showed a LC50 of 3.7, 6.2 and 4.5μg/mL, respectively and the hydrogenated derivatives 1a, 2a and 3a showed a LC50 of 16.0. 12.9 and 20.2μg/mL, respectively. Although hydrogenation reduced the leishmanicidal and cytotoxic activities, the activity showed against Leishmania parasites suggests this compound series has potential as drug candidates for the treatment of leishmaniasis. Ana M. MESAPaula A. MOLANO M.Blandine SEONBruno FIGADERESara M. ROBLEDODiana L. MUÑOZJairo A. SÁEZ V.Universidad de AntioquiaarticleLeishmanicidal activity2-styrylquinolinescytotoxicityaxenic amastigotesintracellularFood processing and manufactureTP368-456Pharmaceutical industryHD9665-9675ENVitae, Vol 15, Iss 2 (2009) |
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| collection |
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| topic |
Leishmanicidal activity 2-styrylquinolines cytotoxicity axenic amastigotes intracellular Food processing and manufacture TP368-456 Pharmaceutical industry HD9665-9675 |
| spellingShingle |
Leishmanicidal activity 2-styrylquinolines cytotoxicity axenic amastigotes intracellular Food processing and manufacture TP368-456 Pharmaceutical industry HD9665-9675 Ana M. MESA Paula A. MOLANO M. Blandine SEON Bruno FIGADERE Sara M. ROBLEDO Diana L. MUÑOZ Jairo A. SÁEZ V. SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS |
| description |
The search of new treatments for leishmaniasis is an active task nowadays, since there is a lack of nontoxic,
cheap and non-resistant medication. In the literature several quinolines have shown in vitro activity
against agents of cutaneous leishmaniasis, visceral leishmaniasis, African trypanosomiasis and Chagas
diseases. Six 2-styrylquinolines derived from galipeine were synthesized by Perkin condensation of
quinaldine with aromatic aldehydes. Leishmanicidal activity was estimated for Leishmania panamensis at the amastigote form and cytotoxic activity against U-937 cells. All compounds showed activity against
both L. panamensis and U-937 cells. (E)-2-(2,5-dimethoxyphenyl)ethenyl)quinoline (1), (E)-2-(2,3-
dimethoxyphenyl)ethenyl)quinoline (2) and (E)-N-[4-(2-quinolin-2-yl-ethenyl)phenyl]acetamide (3)
were more active against axenic (EC50= 3.7, 4.5 and 19.1μg/mL) and intracellular amastigotes (EC50=
1.4, 1.8 and 1.7μg/ml, respectively), in comparison with hydrogenated derivatives 2-[2-(2,5-dimethoxy
phenyl)ethyl]quinoline (1a), 2-[2-(2,3-dimethoxyphenyl)ethyl]quinoline (2a) and N-[4-(2-quinolin-
2-ylethyl)phenyl]acetamide (3a) (CE50= 31.1, 23.6 and 59.3μg/mL, respectively). All compounds were
also active against the U-937 cells. Styrylquinolines 1, 2 and 3 showed a LC50 of 3.7, 6.2 and 4.5μg/mL,
respectively and the hydrogenated derivatives 1a, 2a and 3a showed a LC50 of 16.0. 12.9 and 20.2μg/mL,
respectively. Although hydrogenation reduced the leishmanicidal and cytotoxic activities, the activity
showed against Leishmania parasites suggests this compound series has potential as drug candidates for
the treatment of leishmaniasis.
|
| format |
article |
| author |
Ana M. MESA Paula A. MOLANO M. Blandine SEON Bruno FIGADERE Sara M. ROBLEDO Diana L. MUÑOZ Jairo A. SÁEZ V. |
| author_facet |
Ana M. MESA Paula A. MOLANO M. Blandine SEON Bruno FIGADERE Sara M. ROBLEDO Diana L. MUÑOZ Jairo A. SÁEZ V. |
| author_sort |
Ana M. MESA |
| title |
SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS |
| title_short |
SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS |
| title_full |
SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS |
| title_fullStr |
SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS |
| title_full_unstemmed |
SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS |
| title_sort |
synthesis and in vitro leishmanicidal and cytotoxic activities of 2-styrylquinolines analogs |
| publisher |
Universidad de Antioquia |
| publishDate |
2009 |
| url |
https://doaj.org/article/07fca273a0614aeaa1e63f3e0f7779c7 |
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