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

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.

SUBMITTER: Kutsumura N

PROVIDER: S-EPMC7179212 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Kutsumura Noriki N Koyama Yasuaki Y Saitoh Tsuyoshi T Yamamoto Naoshi N Nagumo Yasuyuki Y Miyata Yoshiyuki Y Hokari Rei R Ishiyama Aki A Iwatsuki Masato M Otoguro Kazuhiko K Ōmura Satoshi S Nagase Hiroshi H

Molecules (Basel, Switzerland) 20200302 5

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 ...[more]

PMID: 32131542

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Project description:Step-growth thiol-Michael photopolymerizable resins, constituting an alternative chemistry to the current methacrylate-based chain-growth polymerizations, were developed and evaluated for use as dental restorative materials. The beneficial features inherent to anion-mediated thiol-Michael polymerizations were explored, such as rapid photocuring, low stress generation, ester content tunability, and improved mechanical performance in a moist environment. An ester-free tetrafunctional thiol and a ultraviolet-sensitive photobase generator were implemented to facilitate thiol-Michael photopolymerization. Thiol-Michael resins of varied ester content were fabricated under suitable light activation. Polymerization kinetics and shrinkage stress were determined with Fourier-transform infrared spectroscopy coupled with tensometery measurements. Thermomechanical properties of new materials were evaluated by dynamic mechanical analysis and in 3-point bending stress-strain experiments. Photopolymerization kinetics, polymerization shrinkage stress, glass transition temperature, flexural modulus, flexural toughness, and water sorption/solubility were compared between different thiol-Michael systems and the BisGMA/TEGDMA control. Furthermore, the mechanical performance of 2 thiol-Michael composites and a control composite were compared before and after extensive conditioning in water. All photobase-catalyzed thiol-Michael polymerization matrices achieved >90% conversion with a dramatic reduction in shrinkage stress as compared with the unfilled dimethacrylate control. One prototype of ester-free thiol-Michael formulations had significantly better water uptake properties than the BisGMA/TEGDMA control system. Although exhibiting relatively lower Young's modulus and glass transition temperatures, highly uniform thiol-Michael materials achieved much higher toughness than the BisGMA/TEGDMA control. Moreover, low-ester thiol-Michael composite systems show stable mechanical performance even after extensive water treatment. Although further resin/curing methodology optimization is required, the photopolymerized thiol-Michael prototype resins can now be recognized as promising candidates for implementation in composite dental restorative materials.

Dataset Information

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

Publications

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

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