Ionisation potential and electron affinity of free 5′,8-cyclopurine-2′-deoxynucleosides. DFT study in gaseous and aqueous phase

• Authors: Boleslaw Karwowski
• Languages of publication: EN

Abstracts

EN

Oxidatively generated damage to DNA frequently appears in the human genome as an effect of aerobic metabolism or as the result of exposure to exogenous oxidizing agents. Due to these facts it was decided to present, for the first time, the electron affinity, ionization potential of 5′,8-cyclo-2′-deoxyadenosine/guanosine (cdA, cdG) in their 5′R and 5′S diastereomeric forms. For all points of quantum mechanics studies presented, the density functional theory (DFT) with B3LYP parameters on 6-311++G** basis set level was used. The zero-point vibrational corrected adiabatic electron affinity (AEA) and adiabatic ionization potential (AIP) were calculated. Additionally the vertical electron affinity (VEA), vertical detachment energy (VDE) and vertical ionization potential were taken into consideration. AEA in eV (gaseous/aqueous phase) are as follows: 0.3/1.81 (5′R)cdA, 0.13/1.76 (5′S)cdA, 0.17/1.49 (5′R)cdG, 0.14/1.53 (5′S)cdG and AIP followed the order 7.43/5.59(5′S)cdG, 7.49/5.60(5′R)cdG, 7.77/5.97(5′R)cdA, 7.84/5.93(5′S)cdA. The obtained AIPs were found to be lower than that for corresponding natural nucleosides. Therefore, even though the 5′,8-cyclopurine-2′-deoxynucleoside level in a cell was judged as low, they can play an important role in the stability, replication and transcription of genes. [...]

Keywords

EN

DNA damage; cyclopurine-2′-deoxynucleosides; DFT; adiabatic ionization potential; adiabatic electron affinity

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 1
• Pages: 70-76

Dates

published

1 - 2 - 2010

online

16 - 2 - 2010

Contributors

author

Boleslaw Karwowski

• Department of Biopharmacy, Medical University of Lodz, 90-151, Łodz, Poland

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Identifiers

DOI

10.2478/s11532-009-0105-0