Photodynamic therapy and two-photon bio-imaging applications of hydrophobic chromophores through amphiphilic polymer delivery

• Published in: Photochemical & photobiological sciences 2011-07, Vol.10 (7), p.1216-1225
• Main Authors: Gallavardin, Thibault, Maurin, Mathieu, Marotte, Sophie, Simon, Timea, Gabudean, Ana-Maria, Bretonnière, Yann, Lindgren, Mikael, Lerouge, Frédéric, Baldeck, Patrick L., Stéphan, Olivier, Leverrier, Yann, Marvel, Jacqueline, Parola, Stéphane, Maury, Olivier, Andraud, Chantal
• Format: Article
• Language: English
• Subjects: Alkynes - chemistry; Alkynes - pharmacology; Alkynes - therapeutic use; Aniline Compounds - chemistry; Aniline Compounds - pharmacology; Aniline Compounds - therapeutic use; Animals; Anthracenes - chemistry; Anthracenes - pharmacology; Anthracenes - therapeutic use; Apoptosis; Biochemistry; Biomaterials; Bromobenzenes - chemistry; Bromobenzenes - pharmacology; Bromobenzenes - therapeutic use; Cell Line, Tumor; Chemical Sciences; Chemistry; Fluorescent Dyes - chemistry; Hydrophobic and Hydrophilic Interactions; Material chemistry; Microscopy, Fluorescence; Nanoparticles - chemistry; Neoplasms - drug therapy; Organic chemistry; Photochemotherapy; Photons; Photosensitizing Agents - chemistry; Photosensitizing Agents - pharmacology; Photosensitizing Agents - therapeutic use; Physical Chemistry; Plant Sciences; Poloxamer - chemistry; Polymers - chemistry; Quantum Theory; Rats; Singlet Oxygen - metabolism
• ISSN: 1474-905X; 1474-9092
• DOI: 10.1039/c0pp00381f

The synthesis and photophysical properties of two lipophilic quadrupolar chromophores featuring anthracenyl ( 1 ) or dibromobenzene ( 2 ) were described. These two chromophores combined significant two-photon absorption cross-sections with high fluorescence quantum yield for 1 and improved singlet oxygen generation efficiency for 2 , in organic solvents. The use of Pluronic nanoparticles allowed a simple and straightforward introduction of these lipophilic chromophores into biological cell media. Their internal distribution in various cell lines was studied using fluorescence microscopy and flow-cytometry following a successful staining that was achieved upon 2 h of incubation. Finally, multiphoton excitation microscopy and photodynamic therapy capability of the chromophores were demonstrated by cell exposure to a 820 nm fs laser and cell death upon one photon resonant irradiation at 436 ± 10 nm, respectively.