NDLI: UV-induced formation of the thymine-thymine pyrimidine (6-4) pyrimidone photoproduct--a DFT study of the oxetane intermediate ring opening.

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The solvent effect and identification of a weakly emissive state in nonradiative dynamics of guanine nucleosides and nucleotides--a combined femtosecond broadband time-resolved fluorescence and transient absorption study.

Electronic coupling between photo-excited stacked bases in DNA and RNA strands with emphasis on the bright states initially populated.

Sensitized photochemistry of di(4-tetrazolouracil) dinucleoside monophosphate as a route to dicytosine cyclobutane photoproduct precursors.

The variety of UV-induced pyrimidine dimeric photoproducts in DNA as shown by chromatographic quantification methods.

A joint experimental/theoretical study of the ultrafast excited state deactivation of deoxyadenosine and 9-methyladenine in water and acetonitrile.

Photochemistry and photophysics of the amino and imino tautomers of 1-methylcytosine: tautomerisation as a side product of the radiationless decay.

The photoinduced transformation of fluorescent DNA base analogue tC triggers DNA melting

Strong impact of the solvent on the photokinetics of a 2(1H)-pyrimidinone.

Electronic excited states of guanine-cytosine hairpins and duplexes studied by fluorescence spectroscopy.

Electronic excitation and structural relaxation of the adenine dinucleotide in gas phase and solution.

Photophysical properties of 5-substituted 2-thiopyrimidines.

Ultrafast electronic deactivation dynamics of the inosine dimer--a model case for H-bonded purine bases.

Accumulation of the cyclobutane thymine dimer in defined sequences of free and nucleosomal DNA.

The relative roles of DNA damage induced by UVA irradiation in human cells.

The effect of dimerization on the excited state behavior of methylated xanthine derivatives: a computational study.

UV-induced formation of the thymine-thymine pyrimidine (6-4) pyrimidone photoproduct--a DFT study of the oxetane intermediate ring opening.

Role of intercalation and redox potential in DNA photosensitization by ruthenium(II) polypyridyl complexes: assessment using DNA repair protein tests.

The interplay between neutral exciton and charge transfer states in single-strand polyadenine: a quantum dynamical investigation.

Interaction of UV radiation with DNA.

Cytosine containing dipyrimidine sites can be hotspots of cyclobutane pyrimidine dimer formation after UVB exposure.

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UV-induced formation of the thymine-thymine pyrimidine (6-4) pyrimidone photoproduct--a DFT study of the oxetane intermediate ring opening.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Labet, Vanessa Jorge, Nelly Morell, Christophe Douki, Thierry Grand, André Cadet, Jean Eriksson, Leif A.
Description	Country affiliation: France Author Affiliation: Labet V ( UPMC Univ Paris 06, UMR 7075, LADIR, F-75005, Paris, France. vanessa.labet@upmc.fr)
Abstract	The mechanism by which the hypothetical oxetane/azetidine intermediate formed during the photochemical process leading to pyrimidine (6-4) pyrimidone photoproducts when DNA is submitted to UV radiation opens is investigated computationally by DFT using a 5'-TT-3' dinucleoside monophosphate as a structural model. First, the feasibility of an intramolecular mechanism involving one proton transfer inducing opening of the oxetane ring is examined. It results in a very high Gibbs energy of activation (+166 kJ mol(-1)) and quite a low Gibbs energy of reaction (-35 kJ mol(-1)). The protonation state of the phosphate group is shown to have little effect while the bulk effect of an aqueous environment modeled by the Polarizable Continuum Model method lowers slightly the activation barrier (by about 10-20 kJ mol(-1)), not enough to explain the fact that the oxetane intermediate is not observed experimentally. Then the catalytic effect of water molecules on the reaction pathway is studied by including either 1 or 2 assisting water molecules in the chemical system. The resulting activation barrier is considerably lowered and in the most favorable situation - a phosphate group deprotonated and 2 assisting water molecules - the Gibbs energy activation is as low as +44 kJ mol(-1) and the Gibbs energy of reaction is quite favorable: -79 kJ mol(-1), suggesting that in biological systems the oxetane ring opening process proceeds with explicit intervention of water molecules from the environment.
File Format	HTM / HTML
ISSN	1474905X
Issue Number	8
Volume Number	12
e-ISSN	14749092
Journal	Photochemical & Photobiological Sciences
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2013-08-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Chemistry Discipline Biology Dna Chemistry Ethers, Cyclic Pyrimidines Pyrimidinones Thymine Models, Molecular Protons Thermodynamics Ultraviolet Rays Water Journal Article Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry

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UV-induced formation of the thymine-thymine pyrimidine (6-4) pyrimidone photoproduct - a DFT study of the oxetane intermediate ring opening

Structural determination of the ultraviolet light-induced thymine-cytosine pyrimidine-pyrimidone (6-4) photoproduct.

Mutagenicity of a Unique Thymine-Thymine Dimer or Thymine-Thymine Pyrimidine Pyrimidone (6–4) Photoproduct in Mammalian Cells

The thymine-thymine pyrimidine-pyrimidone(6-4) ultraviolet light photoproduct is highly mutagenic and specifically induces 3' thymine-to-cytosine transitions in Escherichia coli.

The thymine-thymine pyrimidine-pyrimidone(6-4) ultraviolet light photoproduct is highly mutagenic and specifically induces 3' thymine-to-cytosine transitions in Escherichia coli.

All You Need Is Light. Photorepair of UV-Induced Pyrimidine Dimers

Mutagenicity of a unique thymine-thymine dimer or thymine-thymine pyrimidine pyrimidone (6-4) photoproduct in mammalian cells.

Structural basis of pyrimidine-pyrimidone (6–4) photoproduct recognition by UV-DDB in the nucleosome

Mutagenic and Nonmutagenic Bypass of DNA Lesions byDrosophila DNA Polymerases dpolη and dpolι

UV-induced formation of the thymine-thymine pyrimidine (6-4) pyrimidone photoproduct--a DFT study of the oxetane intermediate ring opening.

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