EventsThe 13th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-13-00218
This submission belongs to the session c. Bioorganic Chemistry and Natural Products of the event The 13th International Electronic Conference on Synthetic Organic Chemistry
Published date
01 Nov, 2009
Citation
Paulo J. G. Coutinho, M. Sameiro T. Gonçalves, Sarala Naik, 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 International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2009, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-13-00218
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DNA fluorescence probes based on N-[5-(11-functionalised-undecylamino)- 9H-benzo[a]phenoxazin-9-ylidene]propan-1-aminium chlorides

Paulo J. G. Coutinho 1
M. Sameiro T. Gonçalves 2
Sarala Naik 2
1. Centro de Física, Universidade do Minho, Gualtar, 4710-057 Braga, Portugal
2. Centro de Química, Universidade do Minho, Gualtar, 4710-057 Braga, Portugal
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
Near-Infrared fluorophores based on N-(di)icosyl-substituted benzo[a]phenoxazinium chlorides as biomembrane probes
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