title: Synthesis and cell imaging applications of fluorescent mono/di/tri-heterocyclyl-2,6-dicyanoanilines.
abstract: Synthesis of 3,4,5-triheterocyclyl-2,6-dicyanoanilines, starting from heterocyclic aldehydes and 1,2-diheterocycle-substituted ethanones, is described. 2,6-Dicyanoanilines with one or two heterocyclic substituents have also been synthesized. It was found that some of these molecules have selective cell-staining properties useful for cell imaging applications. The compounds 1g, 10f and 11 were found to stain cytoplasm of the cells in contact but not the nucleus while the compound 12 showed affinity to apoptotic cells resulting in blue fluorescence. The cell imaging results with compound 12 were similar to Annexin V-FITC, a known reagent containing recombinant Annexin V conjugated to green-fluorescent FITC dye, used for detection of apoptotic cells. These compounds were found to be non-cytotoxic and have potential application as cell imaging agents.
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India.
authors.forename: Mahesh M
authors.initials: MM
authors.lastname: Pisal
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India.
authors.forename: Ritesh A
authors.initials: RA
authors.lastname: Annadate
authors.affiliation: Combichem Bio-resource Centre, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India.
authors.forename: Meghana C
authors.initials: MC
authors.lastname: Athalye
authors.affiliation: Physical Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India.
authors.forename: Deepak
authors.initials: D
authors.lastname: Kumar
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India.
authors.forename: Subhash P
authors.initials: SP
authors.lastname: Chavan
authors.affiliation: Combichem Bio-resource Centre, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India.
authors.forename: Dhiman
authors.initials: D
authors.lastname: Sarkar
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411 008, India. Electronic address: hb.borate@ncl.res.in.
authors.forename: Hanumant B
authors.initials: HB
authors.lastname: Borate
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D017209:Apoptosis; D002460:Cell Line; D005456:Fluorescent Dyes / Q000737:chemistry*; D006801:Humans; D057054:Molecular Imaging
chemical_list: D000814:Aniline Compounds; D005456:Fluorescent Dyes
keywords: Cell imaging; Dicyanoanilines; Fluorescence; Heterocyclic