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Volume 25
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Open AccessCommunication

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

by
Noriki Kutsumura
1,2,
Yasuaki Koyama
2,
Tsuyoshi Saitoh
1,
Naoshi Yamamoto
1,
Yasuyuki Nagumo
1,
Yoshiyuki Miyata
3,
Rei Hokari
4,
Aki Ishiyama
4,
Masato Iwatsuki
4,
Kazuhiko Otoguro
4,
Satoshi Ōmura
4 and
Hiroshi Nagase
1,2,*
1
International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan
2
Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
3
School of Medicine, Keio University, 35, Shinanomachi, Shinjuku, Tokyo 160-8582, Japan
4
Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
*
Author to whom correspondence should be addressed.
Academic Editors: Mariana Spetea and Helmut Schmidhammer
Molecules 2020, 25(5), 1112; https://doi.org/10.3390/molecules25051112
Received: 24 January 2020 / Revised: 28 February 2020 / Accepted: 28 February 2020 / Published: 2 March 2020
(This article belongs to the Special Issue Opioids and Their Receptors: Present and Emerging Concepts in Opioid Drug Discovery)
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Abstract

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 1H-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. View Full-Text
Keywords: morphinan; BNTX; δ opioid receptor antagonist; 1H-NMR experiments; mechanism elucidation morphinan; BNTX; δ opioid receptor antagonist; 1H-NMR experiments; mechanism elucidation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited

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MDPI and ACS Style

Kutsumura, N.; Koyama, Y.; Saitoh, T.; Yamamoto, N.; Nagumo, Y.; Miyata, Y.; Hokari, R.; Ishiyama, A.; Iwatsuki, M.; Otoguro, K.; Ōmura, S.; Nagase, H. Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities. Molecules 2020, 25, 1112. https://doi.org/10.3390/molecules25051112

AMA Style

Kutsumura N, Koyama Y, Saitoh T, Yamamoto N, Nagumo Y, Miyata Y, Hokari R, Ishiyama A, Iwatsuki M, Otoguro K, Ōmura S, Nagase H. Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities. Molecules. 2020; 25(5):1112. https://doi.org/10.3390/molecules25051112

Chicago/Turabian Style

Kutsumura, Noriki; Koyama, Yasuaki; Saitoh, Tsuyoshi; Yamamoto, Naoshi; Nagumo, Yasuyuki; Miyata, Yoshiyuki; Hokari, Rei; Ishiyama, Aki; Iwatsuki, Masato; Otoguro, Kazuhiko; Ōmura, Satoshi; Nagase, Hiroshi. 2020. "Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities" Molecules 25, no. 5: 1112. https://doi.org/10.3390/molecules25051112

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