Green synthesis of mono- and di-selenium-N-heterocyclic carbene adducts: Characterizations, crystal structures and pro-apoptotic activities against human colorectal cancer

From mono- and bis-benzimidazolium salts, three new Se-NHC adducts were synthesized using water as a solvent. Single crystals analyses indicated that crystal structures of Se-NHC adducts are stabilized by face-to-face and edge-to-face pi-pi interactions in the absences of any potential hydrogen bonds donor and acceptor. Benzimidazolium salts and respective Se-NHC adducts were preliminarily screened against human colorectal cell line (HCT 116) where the benzyl substituted benzimidazolium salt and respective Se-NHC adduct showed the far best results among the test compounds. The selected compounds were further studied in detail for pro-apoptotic mechanism of action (Hoest 33342 stain and Rhodamine 123 tests). The tested compounds were found to induce apoptosis via mitochondria pathway. (C) 2015 Elsevier B.V. All rights reserved.