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Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety. / Burmistrov, Vladimir; Morisseau, Christophe; Babkov, Denis A. et al.

In: International Journal of Molecular Sciences, Vol. 23, No. 18, 10710, 14.09.2022.

Research output: Contribution to journal › Article › peer-review

Harvard

Burmistrov, V, Morisseau, C, Babkov, DA, Golubeva, T, Pitushkin, D, Sokolova, EV, Vasipov, V, Kuznetsov, Y, Bazhenov, SV, Novoyatlova, US, Bondarev, NA, Manukhov, IV, Osipova, V, Berberova, N, Spasov, AA, Butov, GM & Hammock, BD 2022, 'Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety', International Journal of Molecular Sciences, vol. 23, no. 18, 10710. https://doi.org/10.3390/ijms231810710

APA

Burmistrov, V., Morisseau, C., Babkov, D. A., Golubeva, T., Pitushkin, D., Sokolova, E. V., Vasipov, V., Kuznetsov, Y., Bazhenov, S. V., Novoyatlova, U. S., Bondarev, N. A., Manukhov, I. V., Osipova, V., Berberova, N., Spasov, A. A., Butov, G. M., & Hammock, B. D. (2022). Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety. International Journal of Molecular Sciences, 23(18), [10710]. https://doi.org/10.3390/ijms231810710

Vancouver

Burmistrov V, Morisseau C, Babkov DA, Golubeva T, Pitushkin D, Sokolova EV et al. Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety. International Journal of Molecular Sciences. 2022 Sept 14;23(18):10710. doi: 10.3390/ijms231810710

Author

Burmistrov, Vladimir ; Morisseau, Christophe ; Babkov, Denis A. et al. / Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety. In: International Journal of Molecular Sciences. 2022 ; Vol. 23, No. 18.

BibTeX

@article{692c7ae5708f4e5fa0e53e63ae4664d3,
title = "Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety",
abstract = "The inhibitory potency of the series of inhibitors of the soluble epoxide hydrolase (sEH) based on the selenourea moiety and containing adamantane and aromatic lipophilic groups ranges from 34.3 nM to 1.2 μM. The most active compound 5d possesses aliphatic spacers between the selenourea group and lipophilic fragments. Synthesized compounds were tested against the LPS-induced activation of primary murine macrophages. The most prominent anti-inflammatory activity, defined as a suppression of nitric oxide synthesis by LPS-stimulated macrophages, was demonstrated for compounds 4a and 5b. The cytotoxicity of the obtained substances was studied using human neuroblastoma and fibroblast cell cultures. Using these cell assays, the cytotoxic concentration for 4a was 4.7-18.4 times higher than the effective anti-inflammatory concentration. The genotoxicity and the ability to induce oxidative stress was studied using bacterial lux-biosensors. Substance 4a does not exhibit genotoxic properties, but it can cause oxidative stress at concentrations above 50 µM. Put together, the data showed the efficacy and safety of compound 4a.",
keywords = "adamantane, anti-inflammatory, inhibitor, selenourea, soluble epoxide hydrolase",
author = "Vladimir Burmistrov and Christophe Morisseau and Babkov, {Denis A.} and Tatiana Golubeva and Dmitry Pitushkin and Sokolova, {Elena V.} and Vladimir Vasipov and Yaroslav Kuznetsov and Bazhenov, {Sergey V.} and Novoyatlova, {Uliana S.} and Bondarev, {Nikolay A.} and Manukhov, {Ilya V.} and Victoria Osipova and Nadezhda Berberova and Spasov, {Alexander A.} and Butov, {Gennady M.} and Hammock, {Bruce D.}",
note = "Funding: The synthesis of compounds by V.B., D.P. and G.M.B. was supported by a grant from the Russian Fund for Basic Research, grant number 20-03-00298. Toxicity studies with stress-inducible whole-cell lux-biosensors based on E. coli and B. subtilis, conducted by I.V.M., U.S.N. and S.V.B., were carried out with the financial support of the Russian Science Foundation as a part of scientific project No. 22-14-00124. The work of B. N.A., including experiments with a human neuroblastoma cell line, was funded under agreement No. 075-15-2019-1672 from 31 October 2019 with the Ministry of Science and Higher Education of the Russian Federation. All experiments of T.G. were carried out within the state assignment of the Ministry of Science and Higher Education of the Russian Federation FWNR-2022-0017. Partial support for the work of M.C. and H.B.D. was provided by NIEHS grant no. R35 ES030443.",
year = "2022",
month = sep,
day = "14",
doi = "10.3390/ijms231810710",
language = "English",
volume = "23",
journal = "International Journal of Molecular Sciences",
issn = "1661-6596",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "18",

}

RIS

TY - JOUR

T1 - Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety

AU - Burmistrov, Vladimir

AU - Morisseau, Christophe

AU - Babkov, Denis A.

AU - Golubeva, Tatiana

AU - Pitushkin, Dmitry

AU - Sokolova, Elena V.

AU - Vasipov, Vladimir

AU - Kuznetsov, Yaroslav

AU - Bazhenov, Sergey V.

AU - Novoyatlova, Uliana S.

AU - Bondarev, Nikolay A.

AU - Manukhov, Ilya V.

AU - Osipova, Victoria

AU - Berberova, Nadezhda

AU - Spasov, Alexander A.

AU - Butov, Gennady M.

AU - Hammock, Bruce D.

N1 - Funding: The synthesis of compounds by V.B., D.P. and G.M.B. was supported by a grant from the Russian Fund for Basic Research, grant number 20-03-00298. Toxicity studies with stress-inducible whole-cell lux-biosensors based on E. coli and B. subtilis, conducted by I.V.M., U.S.N. and S.V.B., were carried out with the financial support of the Russian Science Foundation as a part of scientific project No. 22-14-00124. The work of B. N.A., including experiments with a human neuroblastoma cell line, was funded under agreement No. 075-15-2019-1672 from 31 October 2019 with the Ministry of Science and Higher Education of the Russian Federation. All experiments of T.G. were carried out within the state assignment of the Ministry of Science and Higher Education of the Russian Federation FWNR-2022-0017. Partial support for the work of M.C. and H.B.D. was provided by NIEHS grant no. R35 ES030443.

PY - 2022/9/14

Y1 - 2022/9/14

N2 - The inhibitory potency of the series of inhibitors of the soluble epoxide hydrolase (sEH) based on the selenourea moiety and containing adamantane and aromatic lipophilic groups ranges from 34.3 nM to 1.2 μM. The most active compound 5d possesses aliphatic spacers between the selenourea group and lipophilic fragments. Synthesized compounds were tested against the LPS-induced activation of primary murine macrophages. The most prominent anti-inflammatory activity, defined as a suppression of nitric oxide synthesis by LPS-stimulated macrophages, was demonstrated for compounds 4a and 5b. The cytotoxicity of the obtained substances was studied using human neuroblastoma and fibroblast cell cultures. Using these cell assays, the cytotoxic concentration for 4a was 4.7-18.4 times higher than the effective anti-inflammatory concentration. The genotoxicity and the ability to induce oxidative stress was studied using bacterial lux-biosensors. Substance 4a does not exhibit genotoxic properties, but it can cause oxidative stress at concentrations above 50 µM. Put together, the data showed the efficacy and safety of compound 4a.

AB - The inhibitory potency of the series of inhibitors of the soluble epoxide hydrolase (sEH) based on the selenourea moiety and containing adamantane and aromatic lipophilic groups ranges from 34.3 nM to 1.2 μM. The most active compound 5d possesses aliphatic spacers between the selenourea group and lipophilic fragments. Synthesized compounds were tested against the LPS-induced activation of primary murine macrophages. The most prominent anti-inflammatory activity, defined as a suppression of nitric oxide synthesis by LPS-stimulated macrophages, was demonstrated for compounds 4a and 5b. The cytotoxicity of the obtained substances was studied using human neuroblastoma and fibroblast cell cultures. Using these cell assays, the cytotoxic concentration for 4a was 4.7-18.4 times higher than the effective anti-inflammatory concentration. The genotoxicity and the ability to induce oxidative stress was studied using bacterial lux-biosensors. Substance 4a does not exhibit genotoxic properties, but it can cause oxidative stress at concentrations above 50 µM. Put together, the data showed the efficacy and safety of compound 4a.

KW - adamantane

KW - anti-inflammatory

KW - inhibitor

KW - selenourea

KW - soluble epoxide hydrolase

UR - http://www.scopus.com/inward/record.url?scp=85138433442&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/559d523b-6554-3366-8404-12e4feb20893/

U2 - 10.3390/ijms231810710

DO - 10.3390/ijms231810710

M3 - Article

C2 - 36142611

AN - SCOPUS:85138433442

VL - 23

JO - International Journal of Molecular Sciences

JF - International Journal of Molecular Sciences

SN - 1661-6596

IS - 18

M1 - 10710

ER -

ID: 38015779