FarFaR - Pharmacy Repository
University of Belgrade, Faculty of Pharmacy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   FarFaR
  • Pharmacy
  • Radovi istraživača / Researchers’ publications
  • View Item
  •   FarFaR
  • Pharmacy
  • Radovi istraživača / Researchers’ publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

An electrochemical study of 9-chloroacridine redox behavior and its interaction with double-stranded DNA

Authorized Users Only
2020
Authors
Rupar, Jelena
Aleksić, Mara
Dobričić, Vladimir
Brborić, Jasmina
Čudina, Olivera
Article (Published version)
Metadata
Show full item record
Abstract
The electrochemical behavior of 9-chloroacridine (9Cl-A), a precursor molecule for synthesis of acridine derivatives with cytostatic activity, is a complex, pH-dependent, diffusion-controlled irreversible process. Oxidation of 9Cl-A initiates with the formation of a cation radical monomer, continues via the formation of a dimer subsequent oxidation to new cation radical. Reduction of 9Cl-A produces radical monomers which are stabilized by dimer formation. The investigation was performed using cyclic, differential pulse and square wave voltammetry at a glassy carbon electrode. The interaction between 9Cl-A and double-stranded DNA (dsDNA) was investigated using a multilayer dsDNA-electrochemical biosensor and 9Cl-A solutions from 1.0×10-7M (the lowest 9Cl-A concentration whose interaction with DNA was possible to detect) up to 1×10-4M. These allowed the binding constant, K=3.45×105M-1 and change in Gibbs free energy of the formed adsorbed complex to be calculated. Complex formation was a... spontaneous process proceeding via 9Cl-A intercalation into dsDNA inducing structural changes. The intercalation of 9Cl-A into dsDNA was supported by molecular docking analysis. The combination of simple methodology and the use of biosensors to investigate DNA interactions is a powerful tool to offer insight into aspects of drug design during pharmaceutical development.

Keywords:
9-Chloroacridine redox mechanism / dsDNA-electrochemical biosensor / Interaction / Molecular docking / Square wave voltammetry
Source:
Bioelectrochemistry, 2020, 135
Publisher:
  • Elsevier B.V.
Funding / projects:
  • Synthesis, Quantitative Structure and Activity Relationship, Physico-Chemical Characterisation and Analysis of Pharmacologically Active Substances (RS-172033)
  • Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-172041)

DOI: 10.1016/j.bioelechem.2020.107579

ISSN: 1567-5394

WoS: 000579730600005

Scopus: 2-s2.0-85086144465
[ Google Scholar ]
13
2
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/3611
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Rupar, Jelena
AU  - Aleksić, Mara
AU  - Dobričić, Vladimir
AU  - Brborić, Jasmina
AU  - Čudina, Olivera
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3611
AB  - The electrochemical behavior of 9-chloroacridine (9Cl-A), a precursor molecule for synthesis of acridine derivatives with cytostatic activity, is a complex, pH-dependent, diffusion-controlled irreversible process. Oxidation of 9Cl-A initiates with the formation of a cation radical monomer, continues via the formation of a dimer subsequent oxidation to new cation radical. Reduction of 9Cl-A produces radical monomers which are stabilized by dimer formation. The investigation was performed using cyclic, differential pulse and square wave voltammetry at a glassy carbon electrode. The interaction between 9Cl-A and double-stranded DNA (dsDNA) was investigated using a multilayer dsDNA-electrochemical biosensor and 9Cl-A solutions from 1.0×10-7M (the lowest 9Cl-A concentration whose interaction with DNA was possible to detect) up to 1×10-4M. These allowed the binding constant, K=3.45×105M-1 and change in Gibbs free energy of the formed adsorbed complex to be calculated. Complex formation was a spontaneous process proceeding via 9Cl-A intercalation into dsDNA inducing structural changes. The intercalation of 9Cl-A into dsDNA was supported by molecular docking analysis. The combination of simple methodology and the use of biosensors to investigate DNA interactions is a powerful tool to offer insight into aspects of drug design during pharmaceutical development.
PB  - Elsevier B.V.
T2  - Bioelectrochemistry
T1  - An electrochemical study of 9-chloroacridine redox behavior and its interaction with double-stranded DNA
VL  - 135
DO  - 10.1016/j.bioelechem.2020.107579
ER  - 
@article{
author = "Rupar, Jelena and Aleksić, Mara and Dobričić, Vladimir and Brborić, Jasmina and Čudina, Olivera",
year = "2020",
abstract = "The electrochemical behavior of 9-chloroacridine (9Cl-A), a precursor molecule for synthesis of acridine derivatives with cytostatic activity, is a complex, pH-dependent, diffusion-controlled irreversible process. Oxidation of 9Cl-A initiates with the formation of a cation radical monomer, continues via the formation of a dimer subsequent oxidation to new cation radical. Reduction of 9Cl-A produces radical monomers which are stabilized by dimer formation. The investigation was performed using cyclic, differential pulse and square wave voltammetry at a glassy carbon electrode. The interaction between 9Cl-A and double-stranded DNA (dsDNA) was investigated using a multilayer dsDNA-electrochemical biosensor and 9Cl-A solutions from 1.0×10-7M (the lowest 9Cl-A concentration whose interaction with DNA was possible to detect) up to 1×10-4M. These allowed the binding constant, K=3.45×105M-1 and change in Gibbs free energy of the formed adsorbed complex to be calculated. Complex formation was a spontaneous process proceeding via 9Cl-A intercalation into dsDNA inducing structural changes. The intercalation of 9Cl-A into dsDNA was supported by molecular docking analysis. The combination of simple methodology and the use of biosensors to investigate DNA interactions is a powerful tool to offer insight into aspects of drug design during pharmaceutical development.",
publisher = "Elsevier B.V.",
journal = "Bioelectrochemistry",
title = "An electrochemical study of 9-chloroacridine redox behavior and its interaction with double-stranded DNA",
volume = "135",
doi = "10.1016/j.bioelechem.2020.107579"
}
Rupar, J., Aleksić, M., Dobričić, V., Brborić, J.,& Čudina, O.. (2020). An electrochemical study of 9-chloroacridine redox behavior and its interaction with double-stranded DNA. in Bioelectrochemistry
Elsevier B.V.., 135.
https://doi.org/10.1016/j.bioelechem.2020.107579
Rupar J, Aleksić M, Dobričić V, Brborić J, Čudina O. An electrochemical study of 9-chloroacridine redox behavior and its interaction with double-stranded DNA. in Bioelectrochemistry. 2020;135.
doi:10.1016/j.bioelechem.2020.107579 .
Rupar, Jelena, Aleksić, Mara, Dobričić, Vladimir, Brborić, Jasmina, Čudina, Olivera, "An electrochemical study of 9-chloroacridine redox behavior and its interaction with double-stranded DNA" in Bioelectrochemistry, 135 (2020),
https://doi.org/10.1016/j.bioelechem.2020.107579 . .

DSpace software copyright © 2002-2015  DuraSpace
About FarFaR - Pharmacy Repository | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceCommunitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About FarFaR - Pharmacy Repository | Send Feedback

OpenAIRERCUB