Synthesis of conjugates of (a R,7 S)-colchicine with monoterpenoids and investigation of their biological activity

doi:10.1007/s11172-023-3730-4

. 2023;72(1):248-262.

doi: 10.1007/s11172-023-3730-4. Epub 2023 Feb 14.

Synthesis of conjugates of (a R,7 S)-colchicine with monoterpenoids and investigation of their biological activity

Affiliations

¹ Lobachevsky State University of Nizhny Novgorod, k. 2, 23 prosp. Gagarina, 603950 Nizhny Novgorod, Russian Federation.
² N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090 Novosibirsk, Russian Federation.
³ State Scientific Center of Virology and Biotechnology "Vector", 630559 Koltsovo, Novosibirsk Region, Russian Federation.
⁴ Novosibirsk State University, 1 ul. Pirogova, 630090 Novosibirsk, Russian Federation.
⁵ Altai State University, 61 Leninsky prosp., 656049 Barnaul, Russian Federation.
⁶ Department of Immunology, M. M. Shemyakin and Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 ul. Miklukho-Maklaya, 117997 Moscow, Russian Federation.

PMID: 36817557
PMCID: PMC9926439
DOI: 10.1007/s11172-023-3730-4

Synthesis of conjugates of (a R,7 S)-colchicine with monoterpenoids and investigation of their biological activity

E S Shchegravina et al. Russ Chem Bull. 2023.

. 2023;72(1):248-262.

doi: 10.1007/s11172-023-3730-4. Epub 2023 Feb 14.

Authors

Affiliations

¹ Lobachevsky State University of Nizhny Novgorod, k. 2, 23 prosp. Gagarina, 603950 Nizhny Novgorod, Russian Federation.
² N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090 Novosibirsk, Russian Federation.
³ State Scientific Center of Virology and Biotechnology "Vector", 630559 Koltsovo, Novosibirsk Region, Russian Federation.
⁴ Novosibirsk State University, 1 ul. Pirogova, 630090 Novosibirsk, Russian Federation.
⁵ Altai State University, 61 Leninsky prosp., 656049 Barnaul, Russian Federation.
⁶ Department of Immunology, M. M. Shemyakin and Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 ul. Miklukho-Maklaya, 117997 Moscow, Russian Federation.

PMID: 36817557
PMCID: PMC9926439
DOI: 10.1007/s11172-023-3730-4

Abstract

Conjugates of the natural alkaloid (aR,7S)-colchicine with bicyclic monoterpenoids and their derivatives were synthesized for the first time. Molecular docking of the synthesized agents in the active site of the main viral protease of the SARS-CoV-2 virus was carried out. The cytotoxic properties of the agents against different cell lines and the ability to inhibit the main viral protease 3CLPro were studied.

Keywords: SARS-Cov-2 3CLPro; antiproliferative activity; colchicine; molecular docking; monoterpenoids.

PubMed Disclaimer

References

1. Beigel J H, Tomashek K M, Dodd L E, Mehta A K, Zingman B S, Kalil A C, Hohmann E, Chu H Y, Luetkemeyer A, Kline S, Lopez de Castilla D, Finberg R W, Dierberg K, Tapson V, Hsieh L, Patterson T F, Paredes R, Sweeney D A, Short W R, Touloumi G, Lye D C, Ohmagari N, Oh M, Ruiz-Palacios G M, Benfield T, Fätkenheuer G, Kortepeter M G, Atmar R L, Creech C B, Lundgren J, Babiker A G, Pett S, Neaton J D, Burgess T H, Bonnett T, Green M, Makowski M, Osinusi A, Nayak S, Lane H C. New Engl. J. Med. 2020;383:1813–1826. doi: 10.1056/NEJMoa2007764. - DOI - PMC - PubMed
1. Jayk Bernal A, Gomes da Silva M M, Musungaie D B, Kovalchuk E, Gonzalez A, Delos Reyes V, Martín-Quirós A, Caraco Y, Williams-Diaz A, Brown M L, Du J, Pedley A, Assaid C, Strizki J, Grobler J A, Shamsuddin H H, Tipping R, Wan H, Paschke A, Butterton J R, Johnson M G, De Anda C. New Engl. J. Med. 2022;386:509–520. doi: 10.1056/NEJMoa2116044. - DOI - PMC - PubMed
1. Abdelnabi R, Foo C S, Jochmans D, Vangeel L, De Jonghe S, Augustijns P, Mols R, Weynand B, Wattanakul T, Hoglund R M, Tarning J, Mowbray C E, Sjö P, Escudié F, Scandale I, Chatelain E, Neyts J. Nat. Commun. 2022;13:719. doi: 10.1038/s41467-022-28354-0. - DOI - PMC - PubMed
1. Dabbous H M, Abd-Elsalam S, El-Sayed M H, Sherief A F, Ebeid F F S, El Ghafar M S A, Soliman S, Elbahnasawy M, Badawi R, Tageldin M A. Arch. Virol. 2021;166:949–954. doi: 10.1007/s00705-021-04956-9. - DOI - PMC - PubMed
1. K. Srinivasan, M. Rao, Ther. Adv. Infect. Dis., 2021, 8; DOI: 10.1177/20499361211063016. - PMC - PubMed

LinkOut - more resources

Full Text Sources
- Europe PubMed Central
- PubMed Central
Research Materials
- NCI CPTC Antibody Characterization Program
Miscellaneous
- NCI CPTAC Assay Portal

[1] Beigel J H, Tomashek K M, Dodd L E, Mehta A K, Zingman B S, Kalil A C, Hohmann E, Chu H Y, Luetkemeyer A, Kline S, Lopez de Castilla D, Finberg R W, Dierberg K, Tapson V, Hsieh L, Patterson T F, Paredes R, Sweeney D A, Short W R, Touloumi G, Lye D C, Ohmagari N, Oh M, Ruiz-Palacios G M, Benfield T, Fätkenheuer G, Kortepeter M G, Atmar R L, Creech C B, Lundgren J, Babiker A G, Pett S, Neaton J D, Burgess T H, Bonnett T, Green M, Makowski M, Osinusi A, Nayak S, Lane H C. New Engl. J. Med. 2020;383:1813–1826. doi: 10.1056/NEJMoa2007764. - DOI - PMC - PubMed

[2] Beigel J H, Tomashek K M, Dodd L E, Mehta A K, Zingman B S, Kalil A C, Hohmann E, Chu H Y, Luetkemeyer A, Kline S, Lopez de Castilla D, Finberg R W, Dierberg K, Tapson V, Hsieh L, Patterson T F, Paredes R, Sweeney D A, Short W R, Touloumi G, Lye D C, Ohmagari N, Oh M, Ruiz-Palacios G M, Benfield T, Fätkenheuer G, Kortepeter M G, Atmar R L, Creech C B, Lundgren J, Babiker A G, Pett S, Neaton J D, Burgess T H, Bonnett T, Green M, Makowski M, Osinusi A, Nayak S, Lane H C. New Engl. J. Med. 2020;383:1813–1826. doi: 10.1056/NEJMoa2007764. - DOI - PMC - PubMed

[3] Jayk Bernal A, Gomes da Silva M M, Musungaie D B, Kovalchuk E, Gonzalez A, Delos Reyes V, Martín-Quirós A, Caraco Y, Williams-Diaz A, Brown M L, Du J, Pedley A, Assaid C, Strizki J, Grobler J A, Shamsuddin H H, Tipping R, Wan H, Paschke A, Butterton J R, Johnson M G, De Anda C. New Engl. J. Med. 2022;386:509–520. doi: 10.1056/NEJMoa2116044. - DOI - PMC - PubMed

[4] Jayk Bernal A, Gomes da Silva M M, Musungaie D B, Kovalchuk E, Gonzalez A, Delos Reyes V, Martín-Quirós A, Caraco Y, Williams-Diaz A, Brown M L, Du J, Pedley A, Assaid C, Strizki J, Grobler J A, Shamsuddin H H, Tipping R, Wan H, Paschke A, Butterton J R, Johnson M G, De Anda C. New Engl. J. Med. 2022;386:509–520. doi: 10.1056/NEJMoa2116044. - DOI - PMC - PubMed

[5] Abdelnabi R, Foo C S, Jochmans D, Vangeel L, De Jonghe S, Augustijns P, Mols R, Weynand B, Wattanakul T, Hoglund R M, Tarning J, Mowbray C E, Sjö P, Escudié F, Scandale I, Chatelain E, Neyts J. Nat. Commun. 2022;13:719. doi: 10.1038/s41467-022-28354-0. - DOI - PMC - PubMed

[6] Abdelnabi R, Foo C S, Jochmans D, Vangeel L, De Jonghe S, Augustijns P, Mols R, Weynand B, Wattanakul T, Hoglund R M, Tarning J, Mowbray C E, Sjö P, Escudié F, Scandale I, Chatelain E, Neyts J. Nat. Commun. 2022;13:719. doi: 10.1038/s41467-022-28354-0. - DOI - PMC - PubMed

[7] Dabbous H M, Abd-Elsalam S, El-Sayed M H, Sherief A F, Ebeid F F S, El Ghafar M S A, Soliman S, Elbahnasawy M, Badawi R, Tageldin M A. Arch. Virol. 2021;166:949–954. doi: 10.1007/s00705-021-04956-9. - DOI - PMC - PubMed

[8] Dabbous H M, Abd-Elsalam S, El-Sayed M H, Sherief A F, Ebeid F F S, El Ghafar M S A, Soliman S, Elbahnasawy M, Badawi R, Tageldin M A. Arch. Virol. 2021;166:949–954. doi: 10.1007/s00705-021-04956-9. - DOI - PMC - PubMed

[9] K. Srinivasan, M. Rao, Ther. Adv. Infect. Dis., 2021, 8; DOI: 10.1177/20499361211063016. - PMC - PubMed

[10] K. Srinivasan, M. Rao, Ther. Adv. Infect. Dis., 2021, 8; DOI: 10.1177/20499361211063016. - PMC - PubMed

Save citation to file

Email citation

Add to Collections

Add to My Bibliography

Your saved search

Create a file for external citation management software

Your RSS Feed

Synthesis of conjugates of (a R,7 S)-colchicine with monoterpenoids and investigation of their biological activity

Affiliations

Synthesis of conjugates of (a R,7 S)-colchicine with monoterpenoids and investigation of their biological activity

Authors

Affiliations

Abstract

Similar articles

References

LinkOut - more resources

Full Text Sources

Research Materials

Miscellaneous

Abstract

Similar articles

References

Related information

LinkOut - more resources

Full Text Sources

Research Materials

Miscellaneous