Enzymes, Reacting with Organophosphorus Compounds as Detoxifiers: Diversity and Functions

Lyagin, Ilya; Ефременко, Елена

doi:10.3390/ijms22041761

Cited by 27 publications

(25 citation statements)

References 117 publications

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“…In order to avoid cyclization reaction to a stable 6-membered ring, 1,6-dibromohexane was used as the substrate, experimenting with the synthesis of diethyl 6-bromohexylphosphonate (1). Moreover, to promote mono-substitution reaction, triethyl phosphite was added dropwise in 30 minutes [44].…”

Section: Resultsmentioning

confidence: 99%

“…Phosphonic acid (PA) functionalization of organic compounds is of great interest in various scientific areas. Several pharmacologically active compounds bearing a PA group (or the corresponding phosphonate salt) have been developed over the years [1,2]. Organic phosphonic acid derivatives, such as phosphonoformic or phosphonoacetic acids and many others, resulted in promising antiviral drugs [3,4] and, recently, the aromatic analogue, phosphonobenzoic acid, has been object of a theoretical study on Covid-SARS [5].…”

Section: Introductionmentioning

confidence: 99%

“…The silyl ester was converted to the corresponding acid by hydrolysis with 30 mL of methanol, under magnetic stirring, within an hour. Phosphonic acid, in form of a purple precipitate, was isolated by vacuum filtration, washed with diethyl ether and characterized by1 H and 31 P NMR in DMSO-d 6 , IR and HRMS (see Supplementary Materials).1-[4-(Dihydroxyphosphonyl)butyl]KuQuinone (7). Purple powder (44.83 mg, 0.097 mmol, 97% yield) mp > 250 • C. 1 H NMR (DMSO-d 6 , 400 MHz): δ 1.493-1.617 (m, 6H), δ 7.529-7.697 (m, 4H), δ 7.891-8.035 (m, 4H).…”

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confidence: 99%

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A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

et al. 2021

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Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

et al. 2021

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“…That is, from the toxicological point of view, the consequences of such interaction are not positive, but exclusively negative, and to change it for better it is necessary to seek for modulators of the binding activity of albumin, which could weaken the interaction of OPs with Sudlow site I. In this case, OPs molecules would remain in the bloodstream for a longer time and could really be detoxified stoichiometrically or catalytically by other blood plasma esterases [ 52 ].…”

Section: Discussionmentioning

confidence: 99%

Esterase Activity of Serum Albumin Studied by 1H NMR Spectroscopy and Molecular Modelling

Belinskaia

Voronina

Vovk

et al. 2021

IJMS

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Serum albumin possesses esterase and pseudo-esterase activities towards a number of endogenous and exogenous substrates, but the mechanism of interaction of various esters and other compounds with albumin is still unclear. In the present study, proton nuclear magnetic resonance (1H NMR) has been applied to the study of true esterase activity of albumin, using the example of bovine serum albumin (BSA) and p-nitrophenyl acetate (NPA). The site of BSA esterase activity was then determined using molecular modelling methods. According to the data obtained, the accumulation of acetate in the presence of BSA in the reaction mixture is much more intense as compared with the spontaneous hydrolysis of NPA, which indicates true esterase activity of albumin towards NPA. Similar results were obtained for p-nitophenyl propionate (NPP) as substrate. The rate of acetate and propionate release confirms the assumption that there is a site of true esterase activity in the albumin molecule, which is different from the site of the pseudo-esterase activity Sudlow II. The results of molecular modelling of BSA and NPA interaction make it possible to postulate that Sudlow site I is the site of true esterase activity of albumin.

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“…Среди них наиболее эффективны биосенсоры, использующие ферменты в качестве биочувствительных элементов [6, 7] (рисунок 1). ФОС способны по-разному взаимодействовать с ферментами и могут быть как ингибиторами, так и субстратами для них [2,9]. Для гарантированного внедрения в практику такие биосенсоры должны обеспечивать экспрессность анализа, его селективность и эффективность, то есть быть пригодными для количественного определения ФОС.…”

Section: Enzymes and Their Forms Used In Detection Of Organophosphorus Compoundsunclassified

Enzymes and Their Forms Used in Detection of Organophosphorus Compounds

2021

Journal of NBC Protection Corps

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Еnzymes are able to effectively interact with various organophosphorus compounds (OPC), entering into (bio)chemical reactions with them. Changes in the initial activity of enzymes as a result of their inhibition by OPC, the formation of OPC degradation products under the action of hydrolytic enzymes, etc. can be determined using different physical and chemical methods and used in bioanalytic systems to determine the concentrations of OPC. The purpose of the review is to analyze the main scientific results achieved over the past 10 years in the development of analytical systems based on enzymes intended for the determination of OPC. It is shown in the article, that the requirements for the sensitivity of biosensors are based on the norms of the content of the analyzed substances detected in/at the objects of mandatory control. The cholinesterases compose a basis for the development of the largest number of ultra-sensitive biosensors, although other enzymes can be successfully used as a biosensitive element. The most technologically advanced solution that is close to the practical implementation seems to be bioanalytical systems using immobilized enzymes. Improving the detection limits of the OPC can be achieved by using nanoobjects together with modern methods of signal transducers, for example, with nanomechanical detectors and signal converters. This combination of technical solutions ensures the sensitivity of the OPC analysis up to pg/l. At present, «reagentless» systems have received significant development, which have become the basis for the production of a large number of commercially available strips for the express determination of OPC. Modern demands stimulate the rapid development of portable and, especially, wearable biosensors that can be attached to various surfaces, including a clothing. The progress in the development of affine amino acid sequences, in the future, will allow the creation of enzyme biosensors on any surface.

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Enzymes, Reacting with Organophosphorus Compounds as Detoxifiers: Diversity and Functions

Cited by 27 publications

References 117 publications

A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

Esterase Activity of Serum Albumin Studied by 1H NMR Spectroscopy and Molecular Modelling

Enzymes and Their Forms Used in Detection of Organophosphorus Compounds

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