Ultraviolet absorption, circular dichroism and magnetic circular dichroism studies of sulfur-containing nucleic acid bases and their nucleosides

Igarashi-Yamamoto, Nobuko; Tajiri, Akio; Hatano, Masahiro; Shibuya, Susumu; Ueda, Tohru

doi:10.1016/0005-2787(81)90020-4

Cited by 48 publications

(96 citation statements)

References 41 publications

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“…In the case of 2TU, the computed transition energies at the TDB3LYP/6-311++G(d,p)//B3LYP/6-311++G(d,p) level were found to be in good agreement with the experimental transition energy data of 2TU and 2-thiouridine (2TUrd) [180]. The computed weak * transition in the 5.3-5.4 eV region were also found to be in good agreement with the experimental transition energy in the range of 5.1-5.3 eV which was only observed in the MCD spectra of 2TU and 2TUrd [176]. The computed transition energies of minor tautomers were also found to be in good agreement with the corresponding methyl substituted analog of 2TU.…”

Section: Electronic Excited States Of Thiouracilssupporting

confidence: 79%

“…Contrary to the conclusion drawn from the ref. [176], the first singlet * transition of 2TU and 2TUrd was not reveled to belong to the thiol form of 2TU.…”

Section: Electronic Excited States Of Thiouracilsmentioning

confidence: 88%

“…However, in ethanol solution 4TU has been suggested to occur in minor (thiol or enol) tautomeric form also [175] and this conclusion was based on the ab initio theoretical calculation and the electronic absorption and fluorescence spectra of the compound. On the basis of extensive absorption, circular dichroism (CD) and magnetic circular dichroism (MCD) spectroscopic investigations of 2TU, 4TU, DTU and their substituted analogs (Figure 14-3) in the water and acetonitrile solutions, Igarashi-Yamamoto [176] have indicated the presence of thiol tautomeric form for 2TU and DTU. Further, based on the NMR study of 2TU in deuterated dimethylsulfoxide solution the presence of thiol tautomeric form has been also suggested [177].…”

Section: Electronic Excited States Of Thiouracilsmentioning

confidence: 99%

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Computational Study of UV-Induced Excitations of DNA Fragments

Shukla

Leszczyński

2008

Challenges and Advances in Computational Chemistry and Physics

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The recent experimental and theoretical results in elucidating the structures and properties of ultraviolet (UV)-induced electronic excitations of DNA fragments and related analogs are discussed. Although, the electronic absorption maxima of nucleic acid bases are in the UV region of the energy spectrum, these genetic molecules are highly photostable. The observed photostability is the outcome of the extremely short excited state life-times. This fundamental characteristic of nucleic acid bases on the other hand is attained by the ultrafast nonradiative decay through internal conversion. Recent theoretical investigations unambiguously show that excited state geometries are generally nonplanar, though the amount of nonplanarity depends on the level of theory used in the calculation. It is also evident that conical intersections involving ground and excited state potential energy surfaces are instrumental for such nonradiative deactivation. Though, theory and experiments are complementary to each other, but the experimental progress in studying excited state properties are far ahead compared to the theoretical methods. For example, it is still very challenging for an extensive investigation of excited state properties of systems like nucleic acid bases at multi-configurational theoretical levels and with large basis sets augmented with diffuse functions. The theoretical and computational bottleneck impedes the investigation of effect of stacking interaction, which is of the fundamental importance for DNA, at the reliable theoretical level. However, we hope that with the theoretical and computational advances such investigations will be possible in near future

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Section: Electronic Excited States Of Thiouracilssupporting

confidence: 79%

“…Contrary to the conclusion drawn from the ref. [176], the first singlet * transition of 2TU and 2TUrd was not reveled to belong to the thiol form of 2TU.…”

Section: Electronic Excited States Of Thiouracilsmentioning

confidence: 88%

Section: Electronic Excited States Of Thiouracilsmentioning

confidence: 99%

See 1 more Smart Citation

Computational Study of UV-Induced Excitations of DNA Fragments

Shukla

Leszczyński

2008

Challenges and Advances in Computational Chemistry and Physics

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“…Stock solutions of monomers and oligomers were kept frozen at -80°C. Concentrations were determined spectrophotometrically using calculated extinction coefficients [38]: 260 (T 17 )=140,900 M -1 cm -1 , 332 = 23,000 M -1 cm -1 and 322 =23,100 M -1 cm -1 for s4 U and s6 I, respectively [39,40]. Spectra were recorded at 25°C and ambient pressure using a Milton Roy 3000 diode-array or a Cary 300 Bio Spectrophotometer and thermostatted 1.00 cm Quartz Suprasil cells.…”

Section: Supplies and Reagentsmentioning

confidence: 99%

Kinetics and mechanism for platination of thione-containing nucleotides and oligonucleotides: evaluation of the salt dependence

Kjellström

Elmroth

2003

J Biol Inorg Chem

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Reactions of cis-[PtCl(NH(3))(CyNH(2))(OH(2))](+) (Cy=cyclohexyl) with thione-containing single-stranded oligonucleotides d(T(8)XT(8)) and d(XT(16)) (X=(s6)I or (s4)U) and the mononucleotides 4-thiouridine ((s4)UMP) and 6-mercaptoinosine ((s6)IMP) have been studied in aqueous solution at pH 4.1. The reaction kinetics was followed using HPLC methodology as a function of ionic strength in the interval 5.0 mM

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“…17,24 On the contrary, a notable number of publications report ab initio calculations on the tautomeric ratio of 2tCyt in gas phase, solid phase, and aqueous solution. 25−32 …”

Section: Introductionmentioning

confidence: 99%

Solvatochromic Effects on the Absorption Spectrum of 2-Thiocytosine

et al. 2017

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The solvatochromic effects of six different solvents on the UV absorption spectrum of 2-thiocytosine have been studied by a combination of experimental and theoretical techniques. The steady-state absorption spectra show significant shifts of the absorption bands, where in more polar solvents the first absorption maximum shifts to higher transition energies and the second maximum to lower energies. The observed solvatochromic shifts have been rationalized using three popular solvatochromic scales and with high-level multireference quantum chemistry calculations including implicit and explicit solvent effects. It has been found that the dipole moments of the excited states account for some general shifts in the excitation energies, whereas the explicit solvent interactions explain the differences in the spectra recorded in the different solvents.

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Ultraviolet absorption, circular dichroism and magnetic circular dichroism studies of sulfur-containing nucleic acid bases and their nucleosides

Cited by 48 publications

References 41 publications

Computational Study of UV-Induced Excitations of DNA Fragments

Computational Study of UV-Induced Excitations of DNA Fragments

Kinetics and mechanism for platination of thione-containing nucleotides and oligonucleotides: evaluation of the salt dependence

Solvatochromic Effects on the Absorption Spectrum of 2-Thiocytosine

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