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Reactivity of [(PNP)Mn(CO)(2)] with Organophosphates

[Image: see text] Organophosphorus nerve agents (OPAs) are a toxic class of synthetic compounds that cause adverse effects with many biological systems. Development of methods for environmental remediation and passivation has been ongoing for years. However, little progress has been made in therapeu...

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Autores principales: Livesay, Brooke N., Schmidt, Jurgen G., Williams, Robert F., Billow, Brennan S., Tondreau, Aaron M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10401673/
https://www.ncbi.nlm.nih.gov/pubmed/37545657
http://dx.doi.org/10.1021/acsorginorgau.3c00003
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author Livesay, Brooke N.
Schmidt, Jurgen G.
Williams, Robert F.
Billow, Brennan S.
Tondreau, Aaron M.
author_facet Livesay, Brooke N.
Schmidt, Jurgen G.
Williams, Robert F.
Billow, Brennan S.
Tondreau, Aaron M.
author_sort Livesay, Brooke N.
collection PubMed
description [Image: see text] Organophosphorus nerve agents (OPAs) are a toxic class of synthetic compounds that cause adverse effects with many biological systems. Development of methods for environmental remediation and passivation has been ongoing for years. However, little progress has been made in therapeutic development for exposure victims. Given the postexposure behavior of OPA materials in enzymes such as acetylcholinesterase (AChE), development of electrophilic compounds as therapeutics may be more beneficial than the currently employed nucleophilic countermeasures. In this report, we present our studies with an electrophilic, 16-electron manganese complex ((iPr)PNP)Mn(CO)(2) (1) and the nucleophilic hydroxide derivative ((iPr)PN(H)P)Mn(CO)(2)(OH) (2). The reactivity of 1 with phosphorus acids and the reactivity of 2 with the P–F bond of diisopropylfluorophosphate (DIPF) were studied. The role of water in both nucleophilic and electrophilic reactivity was investigated with the use of (17)O-labeled water. Promising results arising from reactions of both 1 and 2 with organophosphorus substrates are reported.
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spelling pubmed-104016732023-08-05 Reactivity of [(PNP)Mn(CO)(2)] with Organophosphates Livesay, Brooke N. Schmidt, Jurgen G. Williams, Robert F. Billow, Brennan S. Tondreau, Aaron M. ACS Org Inorg Au [Image: see text] Organophosphorus nerve agents (OPAs) are a toxic class of synthetic compounds that cause adverse effects with many biological systems. Development of methods for environmental remediation and passivation has been ongoing for years. However, little progress has been made in therapeutic development for exposure victims. Given the postexposure behavior of OPA materials in enzymes such as acetylcholinesterase (AChE), development of electrophilic compounds as therapeutics may be more beneficial than the currently employed nucleophilic countermeasures. In this report, we present our studies with an electrophilic, 16-electron manganese complex ((iPr)PNP)Mn(CO)(2) (1) and the nucleophilic hydroxide derivative ((iPr)PN(H)P)Mn(CO)(2)(OH) (2). The reactivity of 1 with phosphorus acids and the reactivity of 2 with the P–F bond of diisopropylfluorophosphate (DIPF) were studied. The role of water in both nucleophilic and electrophilic reactivity was investigated with the use of (17)O-labeled water. Promising results arising from reactions of both 1 and 2 with organophosphorus substrates are reported. American Chemical Society 2023-05-25 /pmc/articles/PMC10401673/ /pubmed/37545657 http://dx.doi.org/10.1021/acsorginorgau.3c00003 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Livesay, Brooke N.
Schmidt, Jurgen G.
Williams, Robert F.
Billow, Brennan S.
Tondreau, Aaron M.
Reactivity of [(PNP)Mn(CO)(2)] with Organophosphates
title Reactivity of [(PNP)Mn(CO)(2)] with Organophosphates
title_full Reactivity of [(PNP)Mn(CO)(2)] with Organophosphates
title_fullStr Reactivity of [(PNP)Mn(CO)(2)] with Organophosphates
title_full_unstemmed Reactivity of [(PNP)Mn(CO)(2)] with Organophosphates
title_short Reactivity of [(PNP)Mn(CO)(2)] with Organophosphates
title_sort reactivity of [(pnp)mn(co)(2)] with organophosphates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10401673/
https://www.ncbi.nlm.nih.gov/pubmed/37545657
http://dx.doi.org/10.1021/acsorginorgau.3c00003
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