Solvent Effect Studies on the Absorption and Fluorescence Spectra of Adenine, Thymine and Uracil Derivatives

Hammud, Hassan H.; El-Shazly, S. A.; Sonji, Ghassan; Bouhadir, Kamal H.

doi:10.2174/1573411011666150801002350

Cited by 2 publications

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“…It is important to note that limiting the quantity of palladium catalyst and reaction time was important to minimize loss of Fmoc protection from 17 and 20 in the last hydrogenation step. The PNA monomers having ϵ‐extended backbones were synthesized by O ‐( N ‐succinimidyl)‐ N,N,N ′ ,N ′‐tetramethyluronium tetrafluoroborate (TSTU)‐mediated coupling of the known nucleobase propionic acid derivatives ( 22 [17] and 24 [18] in Scheme 3) with the previously synthesized PNA backbone 21 [19] …”

Section: Resultsmentioning

confidence: 99%

Triplex‐Forming Peptide Nucleic Acids with Extended Backbones

2020

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Peptide nucleic acid (PNA) forms a triple helix with doublestranded RNA (dsRNA) stabilized by a hydrogen-bonding zipper formed by PNA's backbone amides (NÀ H) interacting with RNA phosphate oxygens. This hydrogen-bonding pattern is enabled by the matching~5.7 Å spacing (typical for A-form dsRNA) between PNA's backbone amides and RNA phosphate oxygens. We hypothesized that extending the PNA's backbone by one À CH 2 À group might bring the distance between PNA amide groups closer to 7 Å, which is favourable for hydrogen bonding to the B-form dsDNA phosphate oxygens. Extension of the PNA backbone was expected to selectively stabilize PNA-DNA triplexes compared to PNA-RNA. To test this hypothesis, we synthesized triplex-forming PNAs that had the pseudopeptide backbones extended by an additional À CH 2 À group in three different positions. Isothermal titration calorimetry measurements of the binding affinity of these extended PNA analogues for the matched dsDNA and dsRNA showed that, contrary to our structural reasoning, extending the PNA backbone at any position had a strong negative effect on triplex stability. Our results suggest that PNAs might have an inherent preference for A-form-like conformations when binding double-stranded nucleic acids. It appears that the original six-atom-long PNA backbone is an almost perfect fit for binding to A-form nucleic acids.

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Section: Resultsmentioning

confidence: 99%

Triplex‐Forming Peptide Nucleic Acids with Extended Backbones

2020

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“…It is observed that QY 54 and QY 54 A follow the same trend in gas as well as in DMF (see Table , Figure a.). The dyes in DMF show higher value of (α) than gas phase as DMF interacts with the dyes in an excited state by dipole‐dipole interaction and dipole‐induced interaction which stabilize the dyes in the excited state …”

Section: Resultsmentioning

confidence: 99%

NLO‐Phoric Emissive Quinoxaline Analog of Quinoline Yellow 54 and Z‐Scan Studies

Ayare

Rajeshirke

Sreenath³

et al. 2019

ChemistrySelect

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Quinoxaline derivative QY 54 A, an analog of commercially available C.I. (Colour index) Disperse Yellow 54 (quinoline derivative) is synthesized and confirmed by 1 H, 13 C NMR, LC-MS, and CHN analysis. It is emissive (512 nm) with a quantum yield (φ F ) = 0.34. The electrochemical properties of both the dyes were investigated using cyclic voltammetry (CV). The titled dyes are thermally stable (up to 350°C). A comprehensive study of linear and nonlinear optical (NLO) properties of commercial dye (QY 54) and its analog (QY 54 A) are performed by Z-scan and Density functional theory (DFT). The NLO (β o , γ o ) values obtained are compared with the NLO (β o , γ o ) values of urea.Ten different functionals are used to see the effect of %Hartree Fork (HF) exchange on computed NLO properties of both the dyes. The functional M06-HF (100% HF) and ωB97 (0-100% HF) perform better for evaluating NLO properties. The Z-scan and DFT result reveal that QY 54 A and QY54 are excellent NLOphores. The stability and enhancement in NLO properties of QY 54 A are due to electrophilicity index (ω), the Intramolecular charge transfer (ICT) character is confirmed by HOMO-LUMO study (2.19 eV), quinoid character (0.0230 A°) and molecular electrostatic potential (MEP) plots.[a] N. N. Ayare, M. Rajeshirke, Prof. N. Sekar

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Solvent Effect Studies on the Absorption and Fluorescence Spectra of Adenine, Thymine and Uracil Derivatives

Cited by 2 publications

References 0 publications

Triplex‐Forming Peptide Nucleic Acids with Extended Backbones

Triplex‐Forming Peptide Nucleic Acids with Extended Backbones

NLO‐Phoric Emissive Quinoxaline Analog of Quinoline Yellow 54 and Z‐Scan Studies

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