DNA fluorescence probes based on N-[5-(11-functionalised-undecylamino)- 9H-benzo[a]phenoxazin-9-ylidene]propan-1-aminium chlorides

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ECSOC-13 | Bioorganic Chemistry and Natural Products

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13th Int. Electron. Conf. Synth. Org. Chem. 2009, c018:1-6

Communication

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DNA fluorescence probes based on N-[5-(11-functionalised-undecylamino)- 9H-benzo[a]phenoxazin-9-ylidene]propan-1-aminium chlorides

Sarala Naik ¹, M. Sameiro Gonçalves ¹ and Paulo Coutinho ²^,*

1 Centro de Química, Universidade do Minho, Gualtar, 4710-057 Braga, Portugal; 2 Centro de Física, Universidade do Minho, Gualtar, 4710-057 Braga, Portugal; * Author to whom correspondence should be addressed.

(This article belongs to the section C. Bioorganic Chemistry and Natural Products)

Cite this paper as: Naik, S.; Gonçalves, M.; Coutinho, P. DNA fluorescence probes based on N-[5-(11-functionalised-undecylamino)- 9H-benzo[a]phenoxazin-9-ylidene]propan-1-aminium chlorides. In Proceedings of the 13th Int. Electron. Conf. Synth. Org. Chem., 1-30 November 2009; Sciforum Electronic Conferences Series, 2009, c018:1-6.

Abstract: Several fluorescent benzo[a]phenoxazinium chlorides possessing undecylamino chains with non-functionalised (methyl group) or functionalised terminals (hydroxyl, carboxylic acid and the ester group) as substituents at the 5-position of the heterocycles were used in photophysical studies with DNA. It was found that the functionalised terminal has a dramatic influence on the type of interaction with the hydroxyl group promoting intercalation, while the ester group promotes groove binding.

Keywords: Benzo[a]phenoxazinium dyes; Nile Blue; DNA probes; Near-Infrared fluorophores

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