Fluorescent cyclic phosphoramide mustard (cas 10159-53-2)s and their cytotoxicity against cancer and cancer stem cells

Add time:07/17/2019    Source:sciencedirect.com

Two fluorescent cyclic phosphoramides, 1,3-dihydronaphtho[1,8-cd][1,2,6]phosphdiazine-2-oxide-(2-bis(2-chloroethyl)amide) (1) and 2,3-dihydro-2-oxo-1H-anthra[1,2-d][1,3,2]diazaphosphole-6,11-dione-2[N,N-bis(2-chloroethyl)]amide (2) were synthesized and characterized using standard analytical techniques. The single crystal X-ray diffraction studies of 1 showed that it crystallizes in triclinic space group P1¯. The comparison of the bond distances and angles data of the single crystal structure of 1 with the theoretical value obtained from DFT calculations show that they are well commensurate with each other. 1H and 31P NMR studies reveal that 1 is more stable than 2 towards hydrolysis and formation of the active phosphoramide. 1 showed no dissociation in 48 h but 25% dissociation of 2 was observed using DMSO-phosphate buffer pH 7.4 (8:2 v/v). Compound 1 and 2 exhibit blue (λem = 375 nm) and orange fluorescence (λem = 585 nm) respectively. However, the ligand of 2 daq exhibits red fluorescence (λem = 635 nm) in its free form. 1 and 2 showed cytotoxicity to cancer cells (MCF-7, A549, HepG2 and HeLaWT) and the toxicity enhanced in vitro, in presence of the cellular reducing agent ascorbic acid. The fluorescent imaging study of 2 showed that the intact compound enters organelles like mitochondria within 1 h of treatment. The compound localizes in other organelles too and upon 10 h incubation red emissions from endoplasmic reticulum, mitochondria and lysozome suggests that the ligand daq dissociated from 2. Compound 2 depolarises the mitochondria. Both 1 and 2 are efficient in killing the slow growing cancer stem cells (CSCs), known to cause cancer relapse. 1 and 2 also exhibit excellent anti cell migratory activity at IC10 dosage even after 48 h of removal of the compounds and causes cell death by apoptosis.

We also recommend Trading Suppliers and Manufacturers of phosphoramide mustard (cas 10159-53-2). Pls Click Website Link as below: cas 10159-53-2 suppliers

Prev:Some new associated (phenylethynyl)metallic and octynylmetallic compounds
Next:phosphoramide mustard (cas 10159-53-2) induces autophagy markers and mTOR inhibition prevents follicle loss due to phosphoramide mustard (cas 10159-53-2) exposure)