Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities

7-Benzylidenenaltrexone (BNTX) and most of its derivatives showed in vitro antimalarial activities against chloroquine-resistant and -sensitive Plasmodium falciparum strains (K1 and FCR3, respectively). In addition, the time-dependent changes of the addition reactions of the BNTX derivatives with 1-...

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Autores principales: Kutsumura, Noriki, Koyama, Yasuaki, Saitoh, Tsuyoshi, Yamamoto, Naoshi, Nagumo, Yasuyuki, Miyata, Yoshiyuki, Hokari, Rei, Ishiyama, Aki, Iwatsuki, Masato, Otoguro, Kazuhiko, Ōmura, Satoshi, Nagase, Hiroshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7179212/
https://www.ncbi.nlm.nih.gov/pubmed/32131542
http://dx.doi.org/10.3390/molecules25051112
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author Kutsumura, Noriki
Koyama, Yasuaki
Saitoh, Tsuyoshi
Yamamoto, Naoshi
Nagumo, Yasuyuki
Miyata, Yoshiyuki
Hokari, Rei
Ishiyama, Aki
Iwatsuki, Masato
Otoguro, Kazuhiko
Ōmura, Satoshi
Nagase, Hiroshi
author_facet Kutsumura, Noriki
Koyama, Yasuaki
Saitoh, Tsuyoshi
Yamamoto, Naoshi
Nagumo, Yasuyuki
Miyata, Yoshiyuki
Hokari, Rei
Ishiyama, Aki
Iwatsuki, Masato
Otoguro, Kazuhiko
Ōmura, Satoshi
Nagase, Hiroshi
author_sort Kutsumura, Noriki
collection PubMed
description 7-Benzylidenenaltrexone (BNTX) and most of its derivatives showed in vitro antimalarial activities against chloroquine-resistant and -sensitive Plasmodium falciparum strains (K1 and FCR3, respectively). In addition, the time-dependent changes of the addition reactions of the BNTX derivatives with 1-propanethiol were examined by (1)H-NMR experiments to estimate their thiol group-trapping ability. The relative chemical reactivity of the BNTX derivatives to trap the thiol group of 1-propanethiol was correlated highly with the antimalarial activity. Therefore, the measurements of the thiol group-trapping ability of the BNTX derivatives with a Michael acceptor is expected to become an alternative method for in vitro malarial activity and related assays.
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spelling pubmed-71792122020-04-28 Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities Kutsumura, Noriki Koyama, Yasuaki Saitoh, Tsuyoshi Yamamoto, Naoshi Nagumo, Yasuyuki Miyata, Yoshiyuki Hokari, Rei Ishiyama, Aki Iwatsuki, Masato Otoguro, Kazuhiko Ōmura, Satoshi Nagase, Hiroshi Molecules Communication 7-Benzylidenenaltrexone (BNTX) and most of its derivatives showed in vitro antimalarial activities against chloroquine-resistant and -sensitive Plasmodium falciparum strains (K1 and FCR3, respectively). In addition, the time-dependent changes of the addition reactions of the BNTX derivatives with 1-propanethiol were examined by (1)H-NMR experiments to estimate their thiol group-trapping ability. The relative chemical reactivity of the BNTX derivatives to trap the thiol group of 1-propanethiol was correlated highly with the antimalarial activity. Therefore, the measurements of the thiol group-trapping ability of the BNTX derivatives with a Michael acceptor is expected to become an alternative method for in vitro malarial activity and related assays. MDPI 2020-03-02 /pmc/articles/PMC7179212/ /pubmed/32131542 http://dx.doi.org/10.3390/molecules25051112 Text en © 2020 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 (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Kutsumura, Noriki
Koyama, Yasuaki
Saitoh, Tsuyoshi
Yamamoto, Naoshi
Nagumo, Yasuyuki
Miyata, Yoshiyuki
Hokari, Rei
Ishiyama, Aki
Iwatsuki, Masato
Otoguro, Kazuhiko
Ōmura, Satoshi
Nagase, Hiroshi
Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities
title Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities
title_full Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities
title_fullStr Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities
title_full_unstemmed Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities
title_short Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities
title_sort structure-activity relationship between thiol group-trapping ability of morphinan compounds with a michael acceptor and anti-plasmodium falciparum activities
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7179212/
https://www.ncbi.nlm.nih.gov/pubmed/32131542
http://dx.doi.org/10.3390/molecules25051112
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