Bodipy-based photosensitizers with long alkyl tails at the meso position: efficient singlet oxygen generation in Cremophor-EL micelles

Abstract

Bodipy dyes with n-decyloxyphenyl-(4, 5) and pentadecyl-(8) meso substituents can easily embed themselves into micellar structures formed from Cremophor-EL. In micelles of approximately 20 nm median size, heavy-atom substituted dyes show remarkable photosensitization properties as evidenced by the rate of reaction with an anthracene-based selective singlet oxygen trap in buffered aqueous solutions. Considering the ease of Bodipy derivatization and the advantages of Cremophor-EL carried therapeutic agents, these photosensitizing agents may offer novel targeting opportunities and enhanced chemical and photophysical stability.

Rational Design of Efficient Organic Phototherapeutic Agents via Perturbation Theory for Enhancing Anticancer Therapeutics

“…C‐4 , C‐3 , C‐2 , and C‐1 showed decreased temperature changes of 23.1, 22.6, 18.2, and 13.4 °C, respectively (Figure c), indicating the positive influence of the heavy atom effect on the photothermal conversion ability of aza‐BODIPY core. The introduction of a heavy atom (Br or I) was an effective method to increase ISC process for efficient singlet oxygen generation, as reported by Eisenberg, Akkaya, and co‐workers . We then explored the singlet oxygen generation capacity of C‐1 – C‐4 by monitoring the photooxidation of 1,3‐diphenylisobenzofuran (DPBF) under laser irradiation at 660 or 730 nm.…”

“…The introductiono fa heavy atom (Br or I) was an effective method to increaseI SC process for efficient singlet oxygen generation, as reported by Eisenberg, Akkaya, and co-workers. [19][20][21][22][23][24] We then explored the singlet oxygen generation capacity of C-1-C-4 by monitoring the photooxidation of 1,3-diphenylisobenzofuran (DPBF) under laser irradiation at 660 or 730 nm. The introductiono fs ulfur and bromine atoms can promote ISC process for enhanced singlet oxygen generation;b romine atoms at positions 2a nd 6o f the aza-BODIPY core led to the best performance (Figure 1d and S2).…”

Photosensitization and controlled photosensitization with BODIPY dyes

“…or inorganic structures like metallic composites [92][93][94]. BODIPY derivatives substituted with n-decyloxyphenyl and pentadecyl groups which can embed themselves into micellar form and BODIPY chemisorbed on NaYF 4 :Er 3+ , Yb 3+ up-conversion nanoparticles absorbing NIR region are both water soluble designs having desirable properties convenient for the biological media [95,96]. The enhanced permeability and retention (EPR) effect can be facilitated by incorporation of active targeting ligands onto the surface of nanostructures so that specific receptors on the cancerous cell membrane can be targeted selectively.…”

An exploration of new avenues regarding deep tissue penetration and highersinglet oxygen efficiencies: novel near-IR photosensitizers for photodynamictherapy

“…1 H NMR and 13 C NMR spectra were recorded on a Bruker DPX-400 (operating at 400 MHz for 1 H NMR and 100 MHz for 13 C NMR) in CDCl 3 with tetramethylsilane as the internal standard. All spectra were recorded at 25°C and the coupling constants (J values) are given in Hz.…”