Photoproducts of the Photodynamic Therapy Agent Verteporfin Identified via Laser Interfaced Mass Spectrometry

Abstract

Verteporfin, a free base benzoporphyrin derivative monoacid ring A, is a photosensitizing drug for photodynamic therapy (PDT) used in the treatment of the wet form of macular degeneration and activated by red light of 689 nm. Here, we present the first direct study of its photofragmentation channels in the gas phase, conducted using a laser interfaced mass spectrometer across a broad photoexcitation range from 250 to 790 nm. The photofragmentation channels are compared with the collision-induced dissociation (CID) products revealing similar dissociation pathways characterized by the loss of the carboxyl and ester groups. Complementary solution-phase photolysis experiments indicate that photobleaching occurs in verteporfin in acetonitrile; a notable conclusion, as photoinduced activity in Verteporfin was not thought to occur in homogenous solvent conditions. These results provide unique new information on the thermal break-down products and photoproducts of this light-triggered drug.

Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

“…Nonetheless, the combination of on-line solution-phase photolysis coupled with gas-phase photolysis of the mass-selected species of interest clearly allows a rapid and straightforward link to be established between the gas-phase measurement and the “real world” environment of the solution photochemistry. This approach has potential for widespread application across photochemical systems of interest, including photopharmaceuticals [ 35 ] and sunscreens [ 23 , 36 , 37 ].…”

Progress of cell membrane-derived biomimetic nanovesicles for cancer phototherapy

“…268 Verteporfin is a photodynamic agent approved by the FDA for eradicating abnormal blood vessels in eyes. 269,270 Despite having a similar capacity for increasing a nanoparticle's systemic circulation, the platelet membrane-coated nanoparticle (NP-Ver@P) exhibits even better tumor absorption when injected iv than its RBCMcoated counterpart (NP-Ver@R). 271 NP-Ver@P outperforms NP-Ver@R when exposed to sunlight in the 680 nm-730 nm range at an output energy density of just 0.05 W cm −2 , enabling useful therapeutic results without harming skin tissue at the tumor location.…”

Anti-Inflammatory and Antithrombotic Potential of Metal-Based Complexes and Porphyrins

“…Verteporfin is a free-base benzoporphyrin (BPD-MA) derivative monoacid ring A and, furthermore, is a photosensitizing drug for photodynamic therapy (PDT) (Figure 11) [61]. When activated in the presence of oxygen, reactive oxygen radicals are generated and cause local damage to the vascular endothelium.…”