A two-photon responsive naphthyl tagged p-hydroxyphenacyl based drug delivery system: uncaging of anti-cancer drug in the phototherapeutic window with real-time monitoring

Abstract

We report a two-photon responsive drug delivery system (DDS) namely, p-hydroxyphenacyl-naphthalene-chlorambucil (pHP-Naph-Cbl) having two-photon absorption (TPA) cross-section of ≥ 20 GM in the phototherapeutic window (700 nm). Our DDS exhibited...

Mitochondria-Targeted Photoactivatable Real-Time Monitoring of a Controlled Drug Delivery Platform

“…Among these, light-triggered drug delivery systems (DDSs) are more superior since the release of drug can be modulated by simply adjusting the wavelength, intensity, or time of exposure of light to attain high-precision spatiotemporal control over the process . To date, different light-responsive DDSs have been developed using well-known photocleavable groups such as o -nitrobenzyl, ,, coumarinyl, ,, anthracenyl, quinolinyl, , p -hydroxyphenacyl, , and o -hydroxycinnamate. , Within these, coumarinyl-, , p -hydroxyphenacyl-, and o -hydroxycinnamate-based systems have gained more traction due to their two-photon phototriggering capability. In the past few years, researchers have demonstrated o -hydroxycinnamate platforms for the uncaging of alcohols with real-time monitoring using one- and two-photon irradiation. ,, The groups of Zhang and Wang have reported an o -hydroxycinnamate-based theranostic prodrug system for tumor selected controlled release of anticancer drugs triggered by hypoxia (internal stimuli) and UV-light (external stimuli) .…”

DNA Interaction, DNA Photocleavage, Photocytotoxicity In Vitro, and Molecular Docking of Naphthyl-Appended Ruthenium Complexes

“…Thus, singlet oxygen quantum yield is not only factor that affects PDT activities of ruthenium complexes. Combined with previous reports [11][12][13][14][15][16][17], DNA affinity is also an important factor for PDT activity, since DNA is the target for PDT agents. [Ru(bpy) 3 ] 2+ displayed high singlet oxygen quantum yield, but exhibited low PI, since it has weak DNA affinity [20].…”

“…Photofrin ® is the first PDT clinical drug based on porphyrin compound, which showed excellent photocytotoxicity against solid tumors [10]. Ruthenium-based compounds usually exhibit high singlet oxygen quantum yields [11][12][13][14][15][16][17]. Most of them have been reported as efficient photodynamic therapy (PDT) and photochemotherapy (PCT) agents and display remarkable antitumor activities, which provokes interests of more and more scientists [11][12][13][14][15][16][17].…”

“…Naphthyl moiety has shown its importance in developing chemosensors and drugs with chemotherapeutic activities [12,13]. Naphthyl unit is a typical fluorophore, which improves the emission properties of organic molecules and their biological activities, such as DNA topoisomerase inhibition, antitumor agents, and antibacterial activities [10][11][12][13][14][15][16][17][18][19]. Naphthyl moiety is also introduced into the ligand on metal complexes, which exhibits excellent biological properties [14][15][16][17].…”

Targeted Cancer Therapy Using Compounds Activated by Light

“…Without irradiation, the cell viability remained above 90% for different PPGchlorambucil concentrations; however, ≥410 nm irradiation efficiently restored the activity of the parent drug. To address tissue penetration issues, a p-hydroxyphenacyl-based twophoton (TP) responsive system for caging chlorambucil [59] was also designed. The novel PPG system showed ESIPT and aggregation-induced emission (AIE) phenomenon.…”