Ultraviolet Absorption Spectra of Purines, Pyrimidines and Triazolopyrimidines<sup>1</sup>

Cavalieri, Liebe F.; Bendich, Adrianne; Tinker, John F.; Brown, George Bosworth

doi:10.1021/ja01191a102

Cited by 97 publications

(29 citation statements)

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“…8-Hydroxyguanine was purchased from Aldrich. 8-Hydroxyadenine and 2,6-diamino-4-hydroxy-5-formamidopyrimidine (FAPy guanine) were synthesized (courtesy of Dr. H. Kaur, Kings College, London) by, respectively, treatment of 8-bromoadenine with concentrated formic acid (95%) at 150°C for 45 min with purification by crystallization with water, as described in ref 25, and treatment of 2,5,6-triamino-4-hydroxypyrimidine with concentrated formic acid with purification by crystallization from water, as described in ref 26. Thymine glycol was synthesized by reaction of 5-methyl-1 Abbreviations: GC-MS, gas chromatography-mass spectrometry; FAPy adenine, 4,6-diamino-5-formamidopyrimidine; FAPy guanine, 2,6-diamino-4-hydroxy-5-formamidopyrimidine; 8-OH guanine, 8-hydroxyguanine; 2-OH adenine, 2-hydroxyadenine; 8-OH adenine, 8-hydroxyadenine; 5-(OH,Me) uracil, 5-(hydroxymethyl)uracil; 5-(OH,Me)-hydantoin, 5-(hydroxymethyl)hydantoin; 5-OH hydantoin, 5-hydroxyhydantoin; 5-Cl uracil, 5-chlorouracil; 5-OH uracil, 5-hydroxyuracil; 5-OH cytosine, 5-hydroxycytosine; TCMS, trimethylchorosilane; TMS, trimethylsilyl.…”

Section: Methodsmentioning

confidence: 99%

Hypochlorous Acid-Induced Base Modifications in Isolated Calf Thymus DNA

Whiteman

Jenner

Halliwell

1997

Chem. Res. Toxicol.

158

105

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Exposure of calf thymus DNA to hypochlorous acid/hypochlorite leads to extensive DNA base modification. Large concentration-dependent increases in pyrimidine oxidation products [thymine glycol (cis/trans), 5-hydroxycytosine, 5-hydroxyuracil, 5-hydroxyhydantoin] but not purine oxidation products (8-hydroxyguanine, 2- and 8-hydroxyadenine, FAPy guanine, FAPy adenine) were observed at pH 7.4. In addition, large increases in 5-chlorouracil (probably formed from 5-chlorocytosine during sample preparation), a novel chlorinated base, were observed. Addition of HOCl to DNA already damaged by .OH generated by a mixture of ascorbate, copper(II) chloride, and hydrogen peroxide showed that hypochlorous acid led to a loss of 8-hydroxyguanine, 2- and 8-hydroxyadenine, FAPy guanine, FAPy adenine, and 5-hydroxycytosine in a concentration- and pH-dependent manner. Nevertheless, time course studies suggested that the formation of purine oxidation products in isolated DNA by hypochlorous acid was not a major oxidation pathway. If this pattern of damage, especially the production of 5-chlorocytosine, is unique to hypochlorous acid, it might act as a "fingerprint" of damage to DNA by HOCl.

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Section: Methodsmentioning

confidence: 99%

Hypochlorous Acid-Induced Base Modifications in Isolated Calf Thymus DNA

Whiteman

Jenner

Halliwell

1997

Chem. Res. Toxicol.

158

105

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“…: (monomer)l + (monomer) ( 8 ) It is probable, however, that other factors connected with the total potential energy of the several structures are equally or more important.…”

Section: (Polymer)mentioning

confidence: 99%

Base pairing equilibria between polynucleotides and complementary monomers

Davies

Davidson

1971

Biopolymers

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SynopsisI*:qitilibrium dialysis meawremeiits and optical nieltitig ciirve data have been used to study the formation atid stability of a number of complexes betweeti polyttucleotides atid complementary monomers. The cooperativity parameter, (dO/d 111 c )~ = 0.5, where O is the fraction of U or C residues complexed, atid c is the ooticeiitratiori of free monomer has beeri measured as 1.4 for the 2: I poly U:d-adetiositie complex, arid 2.0, for the 2: 1 poly C:d-guanosine complex a t pH 7. The variittioti of Y',,, with c for several complexes has beeri used to calculate their partial molar etith:tlpies of formatioil at the midpoint of the transition: in 1.0 M Na+ a t pH 7, for the 2: 1 complex of poly-U with 2-amino-adenirie, this is -18.7 kcal/mole of 2-amirio-aderiirie, for poly-U with adenosine it is -18.7 kcall mole; for poly-C with dG, it is -16.8 kcal/mole. These resulk do not agree very well wit,h calorimetric integral heats of reaction reported in the literature.33 Complexes with random copolymers were also studied. The ratidom copolymer, poly-UC, can form a mixed complex with dG and either dA or 2-aniiiitradeiiositie; the binding of dG is enhanced by an adenine derivative arid vicr vi'rsu. Similarly, poly AC can form a mixed complex with d(; alid 3-met.hyl-xatithitie. 111 each case, it appears that the ideal composition is a 2 : 1 hydrogen-bonded complex, blit the ac*tual stoichiometry is stich that each bwe oti the random polytiuc*leotide binds Icss t,hail oiie-half of a molecule of its complementary tnoiiomer. Poly UG call bind dG and dA, but in a less cooperative atid specific way.

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“…Herein, we report the important development of an assay allowing, for the first time, simultaneous measurement of two key lesions of oxidative DNA damage (8-oxodG and 8-oxodA) by high performance liquid chromatography combined with tandem mass spectrometry in multiple reaction monitoring (MRM) mode. [23]). Dilutions into HPLC buffer were performed giving concentrations appropriate for mass spectral analysis and generation of calibration curves.…”

mentioning

confidence: 99%