Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives
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2020
Authors
Pešić, Marko S.
Bugarinović, Jovana P.

Minić, Aleksandra

Novaković, Slađana B.

Bogdanović, Goran A.

Todosijević, Anka
Stevanović, Dragana D.

Damljanović, Ivan S.

Article (Published version)

© 2019 Elsevier B.V.
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The synthesis of a series of methyl 2-alkyl-5-aryl-4-ferrocenoylpyrrolidine-2-carboxylates has been achieved by [3 + 2] dipolar cycloaddition of azomethine ylides to acryloylferrocene. The electrochemical properties of novel products were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. The DNA-binding capacity of all the products was also studied using CV and DPV, and significant interactions between synthesized compounds and nucleic acid, mostly of the electrostatic type, were disclosed. DFT calculations and molecular docking tests were carried out to gain a more exhaustive insight into the interactions of the obtained products with nucleic acid. A detailed characterization of the new compounds was performed by IR, NMR and elemental analyses, followed by single-crystal X-ray diffraction experiments for two representatives. © 2019 Elsevier B.V.
Keywords:
[3+2] dipolar cycloaddition / Ferrocene / Cyclic voltammetry / Differential pulse voltammetry / DNA-bindingSource:
Bioelectrochemistry, 2020, 132, 107412-Funding / projects:
DOI: 10.1016/j.bioelechem.2019.107412
ISSN: 1567-5394
PubMed: 31889632
WoS: 000518670600011
Scopus: 2-s2.0-85077159291
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VinčaTY - JOUR AU - Pešić, Marko S. AU - Bugarinović, Jovana P. AU - Minić, Aleksandra AU - Novaković, Slađana B. AU - Bogdanović, Goran A. AU - Todosijević, Anka AU - Stevanović, Dragana D. AU - Damljanović, Ivan S. PY - 2020 UR - https://vinar.vin.bg.ac.rs/handle/123456789/8784 AB - The synthesis of a series of methyl 2-alkyl-5-aryl-4-ferrocenoylpyrrolidine-2-carboxylates has been achieved by [3 + 2] dipolar cycloaddition of azomethine ylides to acryloylferrocene. The electrochemical properties of novel products were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. The DNA-binding capacity of all the products was also studied using CV and DPV, and significant interactions between synthesized compounds and nucleic acid, mostly of the electrostatic type, were disclosed. DFT calculations and molecular docking tests were carried out to gain a more exhaustive insight into the interactions of the obtained products with nucleic acid. A detailed characterization of the new compounds was performed by IR, NMR and elemental analyses, followed by single-crystal X-ray diffraction experiments for two representatives. © 2019 Elsevier B.V. T2 - Bioelectrochemistry T1 - Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives VL - 132 SP - 107412 DO - 10.1016/j.bioelechem.2019.107412 ER -
@article{ author = "Pešić, Marko S. and Bugarinović, Jovana P. and Minić, Aleksandra and Novaković, Slađana B. and Bogdanović, Goran A. and Todosijević, Anka and Stevanović, Dragana D. and Damljanović, Ivan S.", year = "2020", abstract = "The synthesis of a series of methyl 2-alkyl-5-aryl-4-ferrocenoylpyrrolidine-2-carboxylates has been achieved by [3 + 2] dipolar cycloaddition of azomethine ylides to acryloylferrocene. The electrochemical properties of novel products were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. The DNA-binding capacity of all the products was also studied using CV and DPV, and significant interactions between synthesized compounds and nucleic acid, mostly of the electrostatic type, were disclosed. DFT calculations and molecular docking tests were carried out to gain a more exhaustive insight into the interactions of the obtained products with nucleic acid. A detailed characterization of the new compounds was performed by IR, NMR and elemental analyses, followed by single-crystal X-ray diffraction experiments for two representatives. © 2019 Elsevier B.V.", journal = "Bioelectrochemistry", title = "Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives", volume = "132", pages = "107412", doi = "10.1016/j.bioelechem.2019.107412" }
Pešić, M. S., Bugarinović, J. P., Minić, A., Novaković, S. B., Bogdanović, G. A., Todosijević, A., Stevanović, D. D.,& Damljanović, I. S.. (2020). Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives. in Bioelectrochemistry, 132, 107412. https://doi.org/10.1016/j.bioelechem.2019.107412
Pešić MS, Bugarinović JP, Minić A, Novaković SB, Bogdanović GA, Todosijević A, Stevanović DD, Damljanović IS. Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives. in Bioelectrochemistry. 2020;132:107412. doi:10.1016/j.bioelechem.2019.107412 .
Pešić, Marko S., Bugarinović, Jovana P., Minić, Aleksandra, Novaković, Slađana B., Bogdanović, Goran A., Todosijević, Anka, Stevanović, Dragana D., Damljanović, Ivan S., "Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives" in Bioelectrochemistry, 132 (2020):107412, https://doi.org/10.1016/j.bioelechem.2019.107412 . .