Nuclear magnetic resonance studies of cis-syn, trans-syn, and 6-4 photodimers of thymidylyl(3'-5')thymidine monophosphate and cis-syn photodimers of thymidylyl(3'-5')thymidine cyanoethyl phosphotriester

Kan, Lou Sing; Voituriez, L.; Cadet, Jean

doi:10.1021/bi00415a060

Cited by 42 publications

(28 citation statements)

References 28 publications

(48 reference statements)

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“…The cis-syn and trans-syn I cyclobutane dimer together with the (6-4) photoproduct of TpT were obtained by UVC irradiation of the dinucleoside monophosphate followed by HPLC purification as previously reported (31). The (6-4) photoproduct solution was calibrated by measuring its absorbance at 320 nm.…”

Section: Preparation Of Calibrated Solution Of Thymidylyl-(3ј-5ј)-thymentioning

confidence: 99%

Formation of the Main UV-induced Thymine Dimeric Lesions within Isolated and Cellular DNA as Measured by High Performance Liquid Chromatography-Tandem Mass Spectrometry

Douki¹,

Court²,

Sauvaigo³

et al. 2000

Journal of Biological Chemistry

227

194

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UVB radiation-induced formation of dimeric photoproducts at bipyrimidine sites within DNA has been unambiguously associated with the lethal and mutagenic properties of sunlight. The main lesions include the cyclobutane pyrimidine dimers and the pyrimidine (6-4) pyrimidone adducts. The latter compounds have been shown in model systems to be converted into their Dewar valence isomers upon exposure to UVB light. A new direct assay, based on the use of liquid chromatography coupled to tandem mass spectrometry, is now available to simultaneously detect each of the thymine photoproducts. It was applied to the determination of the yields of formation of the thymine lesions within both isolated and cellular DNA exposed to either UVC or UVB radiation. The cis-syn cyclobutane thymine dimer was found to be the major photoproduct within cellular DNA, whereas the related (6-4) adduct was produced in an approximately 8-fold lower yield. Interestingly, the corresponding Dewar valence isomer could not be detected upon exposure of human cells to biologically relevant doses of UVB radiation.Ultraviolet radiation represents the most deleterious part of solar light to cells and has been associated with the occurrence of skin cancer (1). UVB (290 -320 nm) radiation is highly mutagenic (2, 3) and mostly induces mutations at bipyrimidine sites in cellular DNA (4 -7). Interestingly, a similar mutation spectrum was observed in the p53 gene of skin tumors cells (8,9). Altogether, these data outlined the biological role of dimeric photoproducts of pyrimidine DNA bases. In the last four decades, major efforts have been devoted to the isolation and the characterization of bipyrimidine photolesions in model compounds and isolated DNA (for reviews, see Refs. 10 and 11). These include the cis-syn and trans-syn diastereoisomers of cyclobutane dimers and the pyrimidine (6-4) pyrimidone adducts (Fig. 1). The latter lesions have been shown to undergo an efficient photoconversion into their Dewar valence isomers upon exposure to UVB light (12).Information on the rate of formation of each specific photoproduct is still needed. Indeed, most of the assays developed for the detection of UV-induced photoproducts within DNA involve the use of indirect methods that do not allow differentiation, for a given class of photoproduct, of the lesions arising from the different possible bipyrimidinic sequences. Cyclobutane pyrimidine dimers have been extensively detected by using T4 endonuclease V, which exhibits a N-glycosylase activity at the 5Ј-extremity of the lesion (13). This leads to the formation of strand breaks, which can be quantified using electrophoretic techniques. A second DNA repair system, namely the Escherichia coli Uvr ABC complex, has been used in combination with a photolyase for the quantitation of cyclobutane dimers and (6-4) photoproducts (14). Another widely applied biochemical approach involves the use of either polyclonal or monoclonal antibodies able to recognize specific classes of pyrimidine photoproducts (15)(16)(17)(18)(19)(20)(21)...

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Section: Preparation Of Calibrated Solution Of Thymidylyl-(3ј-5ј)-thymentioning

confidence: 99%

Formation of the Main UV-induced Thymine Dimeric Lesions within Isolated and Cellular DNA as Measured by High Performance Liquid Chromatography-Tandem Mass Spectrometry

Douki¹,

Court²,

Sauvaigo³

et al. 2000

Journal of Biological Chemistry

227

194

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“…Formation of the TG lesion is known to cause distortions in DNA local conformation, disrupting base pairingwith the complementary nucleic acid strand (2)(3)(4). In an earlier investigation TG was positioned at a unique site in the single stranded genome of a bacteriophage Ml3mpl9 derivative.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Stereoisomers of 5,6-Dihydro-5,6-Dihydroxythymidine

Vaishnav¹,

Holwitt²,

Swenberg³

et al. 1991

Journal of Biomolecular Structure and Dynamics

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Six products were isolated by reverse phase HPLC from the reaction of thymidine with osmium tetroxide. Four of the products were identified as stereoisomers of 5,6-dihydro-5,6-dihydroxy-thymidine (TG). The absolute configurations of these four compounds (from the shortest to the longest HPLC retention times) were determined by two-dimensional nuclear magnetic resonance spectroscopy to be (-)-trans-5S,6S-, (+)-trans-5R,6R-, (-)-cis-5R,6S-, and (+)-cis-5S,6R-5,6-dihydro-5,6-dihydroxy-thymidine. The other two products were dimers with unknown linking sites. Parameters of the mass and nuclear magnetic resonance spectra are reported and discussed.

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“…However, proton NMR shows also (see the experimental section) that even the hydroxyi groups are involved in the self-association process, indicating that the self-association scheme for d(CpC) in DMSO is more complicated than for cytidine (16). The carbon-13 chemical shifts of d(CpC), d(TpT), and (ApA) are close to those for the corresponding monomers (9,17). It is worth noting that in d(TpT) the chemical shifts for the C3' and C5' carbons adjacent to the phosphate group are very similar to those of d(CpC) and d(ApA), suggesting that the geometry of the sugar-phosphate backbone of the three homo dimers is nearly the same.…”

Section: Resultsmentioning

confidence: 55%

“…The carbon-13 chemical shifts of d(TpT) in water have already been reported (17,22) and are larger than those in DMSO, given in Table 4. Since the major differences are found for the carbons of the bases, this is probably due to the effect of the stacking interactions existing in H20.…”

Section: Protonation Of Thymidylyl-(3'5')-thymidinementioning

confidence: 83%

¹⁵N and ¹³C nuclear magnetic resonance of deoxydinucleotide monophosphates. II. Protonation of the homo dimers deoxycytidylyl-(3′,5′)-deoxycytidine, thymidylyl-(3′,5′)-thymidine, and deoxyadenylyl-(3′,5′)-deoxyadenosine in dimethyl sulfoxide

Barbarella¹,

Capobianco²,

Tondelli³

et al. 1990

Can. J. Chem.

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GIOVANNA BARBARELLA, MASSIMO LUIGI CAPOBIANCO, LUISA TONDELLI, and VITALIANO TUGNOLI. Can. J. Chem. 68, 2033 (1990).The preferential protonation sites of the homo dimers deoxycytidylyl-(3',5')-deoxycytidine, thymidylyl-(3',5')-thymidine, and deoxyadenylyl-(3',5')-deoxyadenosine were established by nitrogen-15 and carbon-13 NMR in dimethyl sulfoxide, in the presence of varying amounts of CF3COOH. The nitrogen-15 NMR data show that in d(CpC) the capability of the two N3 nitrogens to accept the proton is slightly different. In d(TpT) and d(ApA) the protonation of the phosphate group leads to significant variations of the chemical shift of the carbons adjacent to phosphorus.

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Nuclear magnetic resonance studies of cis-syn, trans-syn, and 6-4 photodimers of thymidylyl(3'-5')thymidine monophosphate and cis-syn photodimers of thymidylyl(3'-5')thymidine cyanoethyl phosphotriester

Cited by 42 publications

References 28 publications

Formation of the Main UV-induced Thymine Dimeric Lesions within Isolated and Cellular DNA as Measured by High Performance Liquid Chromatography-Tandem Mass Spectrometry

Formation of the Main UV-induced Thymine Dimeric Lesions within Isolated and Cellular DNA as Measured by High Performance Liquid Chromatography-Tandem Mass Spectrometry

Synthesis and Characterization of Stereoisomers of 5,6-Dihydro-5,6-Dihydroxythymidine

¹⁵N and ¹³C nuclear magnetic resonance of deoxydinucleotide monophosphates. II. Protonation of the homo dimers deoxycytidylyl-(3′,5′)-deoxycytidine, thymidylyl-(3′,5′)-thymidine, and deoxyadenylyl-(3′,5′)-deoxyadenosine in dimethyl sulfoxide

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Nuclear magnetic resonance studies of cis-syn, trans-syn, and 6-4 photodimers of thymidylyl(3'-5')thymidine monophosphate and cis-syn photodimers of thymidylyl(3'-5')thymidine cyanoethyl phosphotriester

Cited by 42 publications

References 28 publications

Formation of the Main UV-induced Thymine Dimeric Lesions within Isolated and Cellular DNA as Measured by High Performance Liquid Chromatography-Tandem Mass Spectrometry

Formation of the Main UV-induced Thymine Dimeric Lesions within Isolated and Cellular DNA as Measured by High Performance Liquid Chromatography-Tandem Mass Spectrometry

Synthesis and Characterization of Stereoisomers of 5,6-Dihydro-5,6-Dihydroxythymidine

15N and 13C nuclear magnetic resonance of deoxydinucleotide monophosphates. II. Protonation of the homo dimers deoxycytidylyl-(3′,5′)-deoxycytidine, thymidylyl-(3′,5′)-thymidine, and deoxyadenylyl-(3′,5′)-deoxyadenosine in dimethyl sulfoxide

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¹⁵N and ¹³C nuclear magnetic resonance of deoxydinucleotide monophosphates. II. Protonation of the homo dimers deoxycytidylyl-(3′,5′)-deoxycytidine, thymidylyl-(3′,5′)-thymidine, and deoxyadenylyl-(3′,5′)-deoxyadenosine in dimethyl sulfoxide