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Prototropic interactions of pyrimidine nucleic acid bases with acridine: a spectroscopic investigation.
J Phys Chem B. 2012 Aug 30; 116(34):10275-82.JP

Abstract

In this article, we have investigated the interactions of three pyrimidine nucleic acid bases, cytosine (C), thymine (T), and uracil (U) with acridine (Acr), an N-heterocyclic DNA intercalator, through the changes in photophysics of Acr inside SDS micelles. Fluorescence of AcrH(+)* at 478 nm and its lifetime are quenched on addition of C, T, and U, while a concomitant increment of Acr* is observed only with C. However, the relative amplitude of Acr* increases with a simultaneous decrease in AcrH(+)* only with C. The fluorescence quenching of AcrH(+)* is explained by photoinduced electron transfer (PET), while changes in the relative contributions of Acr* and AcrH(+)* with C are due to associated excited-state proton transfer (ESPT). The rate of electron transfer (kET) is maximum for T, followed by U and C. The associated ESPT from AcrH(+)* is the reason behind the reduced efficiency of PET with C. The lack of proton transfer with T and U as well as the higher kET for T compared to U are explained by keto-enol tautomerization and subtle changes in the structure and geometry of the pyrimidine bases.

Authors+Show Affiliations

Chemical Sciences Division, Saha Institute of Nuclear Physics , 1/AF, Bidhannagar, Kolkata 700064, India.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22816664

Citation

Sarangi, Manas Kumar, et al. "Prototropic Interactions of Pyrimidine Nucleic Acid Bases With Acridine: a Spectroscopic Investigation." The Journal of Physical Chemistry. B, vol. 116, no. 34, 2012, pp. 10275-82.
Sarangi MK, Mitra A, Basu S. Prototropic interactions of pyrimidine nucleic acid bases with acridine: a spectroscopic investigation. J Phys Chem B. 2012;116(34):10275-82.
Sarangi, M. K., Mitra, A., & Basu, S. (2012). Prototropic interactions of pyrimidine nucleic acid bases with acridine: a spectroscopic investigation. The Journal of Physical Chemistry. B, 116(34), 10275-82. https://doi.org/10.1021/jp305352b
Sarangi MK, Mitra A, Basu S. Prototropic Interactions of Pyrimidine Nucleic Acid Bases With Acridine: a Spectroscopic Investigation. J Phys Chem B. 2012 Aug 30;116(34):10275-82. PubMed PMID: 22816664.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Prototropic interactions of pyrimidine nucleic acid bases with acridine: a spectroscopic investigation. AU - Sarangi,Manas Kumar, AU - Mitra,Ankita, AU - Basu,Samita, Y1 - 2012/08/17/ PY - 2012/7/24/entrez PY - 2012/7/24/pubmed PY - 2014/9/24/medline SP - 10275 EP - 82 JF - The journal of physical chemistry. B JO - J Phys Chem B VL - 116 IS - 34 N2 - In this article, we have investigated the interactions of three pyrimidine nucleic acid bases, cytosine (C), thymine (T), and uracil (U) with acridine (Acr), an N-heterocyclic DNA intercalator, through the changes in photophysics of Acr inside SDS micelles. Fluorescence of AcrH(+)* at 478 nm and its lifetime are quenched on addition of C, T, and U, while a concomitant increment of Acr* is observed only with C. However, the relative amplitude of Acr* increases with a simultaneous decrease in AcrH(+)* only with C. The fluorescence quenching of AcrH(+)* is explained by photoinduced electron transfer (PET), while changes in the relative contributions of Acr* and AcrH(+)* with C are due to associated excited-state proton transfer (ESPT). The rate of electron transfer (kET) is maximum for T, followed by U and C. The associated ESPT from AcrH(+)* is the reason behind the reduced efficiency of PET with C. The lack of proton transfer with T and U as well as the higher kET for T compared to U are explained by keto-enol tautomerization and subtle changes in the structure and geometry of the pyrimidine bases. SN - 1520-5207 UR - https://www.unboundmedicine.com/medline/citation/22816664/Prototropic_interactions_of_pyrimidine_nucleic_acid_bases_with_acridine:_a_spectroscopic_investigation L2 - https://dx.doi.org/10.1021/jp305352b DB - PRIME DP - Unbound Medicine ER -