Pyrido[1,2-a]pyrimidinium ions – a novel bridgehead nitrogen heterocycles: synthesis, characterisation, and elucidation of DNA binding and cell imaging properties

Susanta Kumar Manna; Arabinda Mandal; Suresh Kumar Mondal; Arup Kr Adak; Akash Jana; Somnath Das; Sourav Chattopadhyay; Somenath Roy; Shyamal Kr Ghorai; Shubhankar Samanta; Maidul Hossain; Mahiuddin Baidya

doi:10.1039/C5OB01082A

Pyrido[1,2-a]pyrimidinium ions – a novel bridgehead nitrogen heterocycles: synthesis, characterisation, and elucidation of DNA binding and cell imaging properties†

Susanta Kumar Manna,*^a Arabinda Mandal,^a Suresh Kumar Mondal,^a Arup Kr Adak,^a Akash Jana,^a Somnath Das,^b Sourav Chattopadhyay,^c Somenath Roy,^c Shyamal Kr Ghorai,^d Shubhankar Samanta,*^a Maidul Hossain*^b and Mahiuddin Baidya*^e

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^a Department of Chemistry, Haldia Government College, Haldia 721657, India
E-mail: smanna19@gmail.com, mbaidya@iitm.ac.in, hossainm@mail.vidyasagar.ac.in

^b Department of Chemistry and Chemical Technology, Vidyasagar University, Midnapore 721102, India

^c Department of Human Physiology with Community Health, Vidyasagar University, Midnapore 721102, India

^d Department of Chemistry and Biochemistry, Presidency University, 86/1, College Street, Kolkata 700073, India

^e Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India

Abstract

A novel class of bridgehead nitrogen heterocycles, pyrido[1,2-a]pyrimidinium ions, has been readily synthesized by a two-step one-pot reaction in high yields (up to 93%). These ionic compounds are bench stable and moisture tolerant and have highly fluorescent properties (quantum yield up to 0.65). A characteristic bright bluish fluorescence was observed in polar solvents such as acetonitrile and fluorescent intensity gradually diminishes with decreasing the polarity of the medium, which becomes almost negligible in toluene. These compounds also show interesting bioactivity. DNA interaction, imaging, and viability experiments with human leukemic Jurkat and KG-1A cells revealed that they are potential candidates for cancer diagnosis.

Organic & Biomolecular Chemistry

Pyrido[1,2-a]pyrimidinium ions – a novel bridgehead nitrogen heterocycles: synthesis, characterisation, and elucidation of DNA binding and cell imaging properties†

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Pyrido[1,2-a]pyrimidinium ions – a novel bridgehead nitrogen heterocycles: synthesis, characterisation, and elucidation of DNA binding and cell imaging properties

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