New antimalarial and cytotoxic 4-nerolidylcatechol derivatives
4-Nerolidylcatechol (1) was isolated from cultivated Pothomorphe peltata root on a multigram scale using straight-forward solvent extraction-column chromatography. New semi-synthetic derivatives of 1 were prepared and tested in vitro against multidrug-resistant Plasmodium falciparum K1 strain. Mono-...
| Autor principal: | Pinto, Ana Cristina da Silva |
|---|---|
| Outros Autores: | Silva, Luis Francisco Rocha, Coelho Cavalcanti, Bruno, Melo, Márcia R.S., Chaves, Francisco Célio Maia, Costa-Lotufo, Leticia Veras, Moraes, Manœl Odorico de, Andrade Neto, Valter Ferreira de, Tadei, Wanderli Pedro, Pessoa, Cláudia do Ó., Vieira, Pedro Paulo Ribeiro, Pohlit, Adrian Martin |
| Grau: | Artigo |
| Idioma: | English |
| Publicado em: |
European Journal of Medicinal Chemistry
2020
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| Acesso em linha: |
https://repositorio.inpa.gov.br/handle/1/18433 |
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oai:repositorio:1-18433 |
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oai:repositorio:1-18433 New antimalarial and cytotoxic 4-nerolidylcatechol derivatives Pinto, Ana Cristina da Silva Silva, Luis Francisco Rocha Coelho Cavalcanti, Bruno Melo, Márcia R.S. Chaves, Francisco Célio Maia Costa-Lotufo, Leticia Veras Moraes, Manœl Odorico de Andrade Neto, Valter Ferreira de Tadei, Wanderli Pedro Pessoa, Cláudia do Ó. Vieira, Pedro Paulo Ribeiro Pohlit, Adrian Martin 1 O Methyl 4 Nerolidylcatechol 2 O Methyl 4 Nerolidylcatechol 4 Nerolidylcatechol Antimalarial Agent Doxorubicin O,o Dibenzoyl 4 Nerolidylcatechol O,o Dibenzyl 4 Nerolidylcatechol Unclassified Drug Column Chromatography Controlled Study Cytotoxicity Drug Isolation Drug Stability Environmental Temperature Human Human Cell Ic 50 Malaria Medicinal Plant Ph Measurement Plasmodium Falciparum Pothomorphe Peltata Solvent Extraction Animal Antimalarials Antineoplastic Agents, Phytogenic Catechols Cell Line, Tumor Cell Proliferation Dose-response Relationship, Drug Drug Resistance Drug Screening Assays, Antitumor Hl-60 Cells Humans Molecular Structure Parasitic Sensitivity Tests Piperaceae Plant Extracts Plant Roots Plasmodium Falciparum Stereoisomerism 4-Nerolidylcatechol (1) was isolated from cultivated Pothomorphe peltata root on a multigram scale using straight-forward solvent extraction-column chromatography. New semi-synthetic derivatives of 1 were prepared and tested in vitro against multidrug-resistant Plasmodium falciparum K1 strain. Mono-O-methyl, mono-O-benzyl, O,O-dibenzyl and O,O-dibenzoyl derivatives 2-8 exhibited IC50 in the 0.67-22.52 μM range. Mono-O-methyl ethers 6 and 7 inhibited the in vitro growth of human tumor cell lines HCT-8 (colon carcinoma), SF-295 (central nervous system), LH-60 (human myeloblastic leukemia) and MDA/MB-435 (melanoma). In general, derivatives 2-8 are more stable to light, air and pH at ambient temperatures than their labile, natural precursor 1. These derivatives provide leads for the development of a novel class of antimalarial drugs with enhanced chemical and pharmacological properties. © 2008 Elsevier Masson SAS. All rights reserved. 2020-06-15T21:54:58Z 2020-06-15T21:54:58Z 2009 Artigo https://repositorio.inpa.gov.br/handle/1/18433 10.1016/j.ejmech.2008.10.025 en Volume 44, Número 6, Pags. 2731-2735 Restrito European Journal of Medicinal Chemistry |
| institution |
Instituto Nacional de Pesquisas da Amazônia - Repositório Institucional |
| collection |
INPA-RI |
| language |
English |
| topic |
1 O Methyl 4 Nerolidylcatechol 2 O Methyl 4 Nerolidylcatechol 4 Nerolidylcatechol Antimalarial Agent Doxorubicin O,o Dibenzoyl 4 Nerolidylcatechol O,o Dibenzyl 4 Nerolidylcatechol Unclassified Drug Column Chromatography Controlled Study Cytotoxicity Drug Isolation Drug Stability Environmental Temperature Human Human Cell Ic 50 Malaria Medicinal Plant Ph Measurement Plasmodium Falciparum Pothomorphe Peltata Solvent Extraction Animal Antimalarials Antineoplastic Agents, Phytogenic Catechols Cell Line, Tumor Cell Proliferation Dose-response Relationship, Drug Drug Resistance Drug Screening Assays, Antitumor Hl-60 Cells Humans Molecular Structure Parasitic Sensitivity Tests Piperaceae Plant Extracts Plant Roots Plasmodium Falciparum Stereoisomerism |
| spellingShingle |
1 O Methyl 4 Nerolidylcatechol 2 O Methyl 4 Nerolidylcatechol 4 Nerolidylcatechol Antimalarial Agent Doxorubicin O,o Dibenzoyl 4 Nerolidylcatechol O,o Dibenzyl 4 Nerolidylcatechol Unclassified Drug Column Chromatography Controlled Study Cytotoxicity Drug Isolation Drug Stability Environmental Temperature Human Human Cell Ic 50 Malaria Medicinal Plant Ph Measurement Plasmodium Falciparum Pothomorphe Peltata Solvent Extraction Animal Antimalarials Antineoplastic Agents, Phytogenic Catechols Cell Line, Tumor Cell Proliferation Dose-response Relationship, Drug Drug Resistance Drug Screening Assays, Antitumor Hl-60 Cells Humans Molecular Structure Parasitic Sensitivity Tests Piperaceae Plant Extracts Plant Roots Plasmodium Falciparum Stereoisomerism Pinto, Ana Cristina da Silva New antimalarial and cytotoxic 4-nerolidylcatechol derivatives |
| topic_facet |
1 O Methyl 4 Nerolidylcatechol 2 O Methyl 4 Nerolidylcatechol 4 Nerolidylcatechol Antimalarial Agent Doxorubicin O,o Dibenzoyl 4 Nerolidylcatechol O,o Dibenzyl 4 Nerolidylcatechol Unclassified Drug Column Chromatography Controlled Study Cytotoxicity Drug Isolation Drug Stability Environmental Temperature Human Human Cell Ic 50 Malaria Medicinal Plant Ph Measurement Plasmodium Falciparum Pothomorphe Peltata Solvent Extraction Animal Antimalarials Antineoplastic Agents, Phytogenic Catechols Cell Line, Tumor Cell Proliferation Dose-response Relationship, Drug Drug Resistance Drug Screening Assays, Antitumor Hl-60 Cells Humans Molecular Structure Parasitic Sensitivity Tests Piperaceae Plant Extracts Plant Roots Plasmodium Falciparum Stereoisomerism |
| description |
4-Nerolidylcatechol (1) was isolated from cultivated Pothomorphe peltata root on a multigram scale using straight-forward solvent extraction-column chromatography. New semi-synthetic derivatives of 1 were prepared and tested in vitro against multidrug-resistant Plasmodium falciparum K1 strain. Mono-O-methyl, mono-O-benzyl, O,O-dibenzyl and O,O-dibenzoyl derivatives 2-8 exhibited IC50 in the 0.67-22.52 μM range. Mono-O-methyl ethers 6 and 7 inhibited the in vitro growth of human tumor cell lines HCT-8 (colon carcinoma), SF-295 (central nervous system), LH-60 (human myeloblastic leukemia) and MDA/MB-435 (melanoma). In general, derivatives 2-8 are more stable to light, air and pH at ambient temperatures than their labile, natural precursor 1. These derivatives provide leads for the development of a novel class of antimalarial drugs with enhanced chemical and pharmacological properties. © 2008 Elsevier Masson SAS. All rights reserved. |
| format |
Artigo |
| author |
Pinto, Ana Cristina da Silva |
| author2 |
Silva, Luis Francisco Rocha Coelho Cavalcanti, Bruno Melo, Márcia R.S. Chaves, Francisco Célio Maia Costa-Lotufo, Leticia Veras Moraes, Manœl Odorico de Andrade Neto, Valter Ferreira de Tadei, Wanderli Pedro Pessoa, Cláudia do Ó. Vieira, Pedro Paulo Ribeiro Pohlit, Adrian Martin |
| author2Str |
Silva, Luis Francisco Rocha Coelho Cavalcanti, Bruno Melo, Márcia R.S. Chaves, Francisco Célio Maia Costa-Lotufo, Leticia Veras Moraes, Manœl Odorico de Andrade Neto, Valter Ferreira de Tadei, Wanderli Pedro Pessoa, Cláudia do Ó. Vieira, Pedro Paulo Ribeiro Pohlit, Adrian Martin |
| title |
New antimalarial and cytotoxic 4-nerolidylcatechol derivatives |
| title_short |
New antimalarial and cytotoxic 4-nerolidylcatechol derivatives |
| title_full |
New antimalarial and cytotoxic 4-nerolidylcatechol derivatives |
| title_fullStr |
New antimalarial and cytotoxic 4-nerolidylcatechol derivatives |
| title_full_unstemmed |
New antimalarial and cytotoxic 4-nerolidylcatechol derivatives |
| title_sort |
new antimalarial and cytotoxic 4-nerolidylcatechol derivatives |
| publisher |
European Journal of Medicinal Chemistry |
| publishDate |
2020 |
| url |
https://repositorio.inpa.gov.br/handle/1/18433 |
| _version_ |
1787141152902742016 |
| score |
11.755432 |