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Solar UV Radiation-Induced DNA Bipyrimidine Photoproducts: Formation and Mechanistic Insights

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Photoinduced Phenomena in Nucleic Acids II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 356))

Abstract

This review chapter presents a critical survey of the main available information on the UVB and UVA bipyrimidine photoproducts which constitute the predominant recipient classes of photo-induced DNA damage. Evidence is provided that UVB irradiation of isolated DNA in aqueous solutions and in cells gives rise to the predominant generation of cis-syn cyclobutane pyrimidine dimers (CPDs) and, to a lesser extent, of pyrimidine (6-4) pyrimidone photoproducts (6-4PPs), the importance of which is strongly primary sequence dependent. A notable change in the photoproduct distribution is observed when DNA either in the dry or in desiccated microorganisms is exposed to UVC or UVB photons with an overwhelming formation of 5-(α-thymidyl)-5,6-dihydrothymidine, also called spore photoproduct (dSP), at the expense of CPDs and 6-4PPs. UVA irradiation of isolated and cellular DNA gives rise predominantly to bipyrimidine photoproducts with the overwhelming formation of thymine-containing cyclobutane pyrimidine dimers at the exclusion of 6-4PPs. UVA photons have been shown to modulate the distribution of UVB dimeric pyrimidine photoproducts by triggering isomerization of the 6-4PPs into related Dewar valence isomers. Mechanistic aspects of the formation of bipyrimidine photoproducts are discussed in the light of recent photophysical and theoretical studies.

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Abbreviations

●OH:

Hydroxyl radical

6-4PPs:

Pyrimidine (6-4) pyrimidone photoproducts

8-oxodGuo:

8-Oxo-7,8-dihydro-2′-deoxyguanosine

8-oxoGua:

8-Oxo-7,8-dihydroguanine

BCCs:

Basal cell carcinoma

CMMs:

Cutaneous malignant melanoma

CPDs:

Cyclobutane pyrimidine dimers

DEW:

Dewar valence isomer

DFT:

Density functional theory

DNA-PF:

DNA protection factor

dSP:

5-(α-Thymidyl)-5,6-dihydrothymidine or “spore photoproduct”

HPLC-ESI-MS/MS:

High performance coupled to electrospray ionization – tandem mass spectrometry

LM-PCR:

Ligation-mediated polymerase chain reaction

mC:

5-Methylcytosine

MED:

Minimal erythemal dose

SASP:

Small, acid-soluble spore protein

SCCs:

Squamous cell carcinoma (SCCs

SPF:

Sun protection factor

TD-DFT:

Time-dependent density functional theory

Th:

Thymidine

TTET:

Triple-triplet energy transfer

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Authors and Affiliations

  1. Institut Nanosciences et Cryogénie/DSM, CEA-Grenoble, 17 avenue des Martyrs, 38054, Grenoble Cedex 9, France

    Jean Cadet

  2. Département de Médecine Nucléaire et Radiobiologie, Faculté de Médecine, Université de Sherbrooke, Québec, Canada

    Jean Cadet

  3. Universidad Autonoma de Chile, Carlos Antunez, 1920, Providencia, Santiago, Chile

    André Grand

  4. Laboratoire Lésions des Acides Nucléiques, INac/SCIB UMR-E3 CEA-UJF, CEA-Grenoble, CEA-Grenoble, 17 avenue des Martyrs, 38054, Grenoble Cedex 9, France

    André Grand

  5. Laboratoire Lésions des Acides Nucléiques, INac/SCIB UMR-E3 CEA-UJF, CEA-Grenoble, 17 avenue des Martyrs, 38054, Grenoble Cedex 9, France

    Thierry Douki

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  1. Jean Cadet
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  2. André Grand
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  3. Thierry Douki
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Correspondence to Jean Cadet .

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  1. Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany

    Mario Barbatti

  2. Institute of Chemistry, University of São Paulo, São Paulo, Brazil

    Antonio Carlos Borin

  3. Department of Physics and Astronomy, The University of Georgia, Athens, Georgia, USA

    Susanne Ullrich

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Cadet, J., Grand, A., Douki, T. (2014). Solar UV Radiation-Induced DNA Bipyrimidine Photoproducts: Formation and Mechanistic Insights. In: Barbatti, M., Borin, A., Ullrich, S. (eds) Photoinduced Phenomena in Nucleic Acids II. Topics in Current Chemistry, vol 356. Springer, Cham. https://doi.org/10.1007/128_2014_553

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