title: Benzo[a]acridinylmethyl esters as pH sensitive fluorescent photoactive precursors: synthesis, photophysical, photochemical and biological applications.
abstract: A newsworthy class of carboxylate esters based on the (benzo[a]acridin-12-yl)methyl (BAM) chromophore has been shown to perform dual functions as a "pH sensitive fluorescent probe" and a "phototrigger" for acids. The photophysical properties of all the BAM ester conjugates were investigated and found to be highly sensitive to solvent polarity, H-bonding capability and pH of the environment. On irradiation using UV light (≥410 nm), BAM ester conjugates underwent heterolytic cleavage of C-O bonds resulting in efficient release of carboxylic and amino acids. Interestingly, the newly synthesized BAM chromophore was also explored for the construction of a drug delivery system (DDS). In the current DDS, the BAM chromophore plays two important roles: (i) a "fluorophore" for cell imaging and (ii) a "phototrigger" for the drug release. In vitro biological studies revealed that the newly developed BAM based DDS has a good biocompatibility, cellular uptake properties and efficient photoregulated anticancer drug release ability.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur-721302, India. ndpradeep@yahoo.co.in.
authors.forename: Mohammed
authors.initials: M
authors.lastname: Ikbal
authors.forename: Biswajit
authors.initials: B
authors.lastname: Saha
authors.forename: Shrabani
authors.initials: S
authors.lastname: Barman
authors.forename: Sanghamitra
authors.initials: S
authors.lastname: Atta
authors.forename: Deb Ranjan
authors.initials: DR
authors.lastname: Banerjee
authors.forename: Sudip Kumar
authors.initials: SK
authors.lastname: Ghosh
authors.forename: N D Pradeep
authors.initials: ND
authors.lastname: Singh
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000494:pharmacology; D016923:Cell Death / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002699:Chlorambucil / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016503:Drug Delivery Systems; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D006860:Hydrogen Bonding / Q000187:drug effects; D006863:Hydrogen-Ion Concentration; D008027:Light; D062105:Molecular Docking Simulation; D057054:Molecular Imaging; D055668:Photochemical Processes; D010782:Photolysis / Q000187:drug effects; D066244:Proton Magnetic Resonance Spectroscopy; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013997:Time Factors
chemical_list: D000166:Acridines; D000970:Antineoplastic Agents; D004952:Esters; D005456:Fluorescent Dyes; D002699:Chlorambucil