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Design, synthesis and phototoxicity studies of novel iodinated amphiphilic porphyrins
- Source :
- Photodiagnosis and Photodynamic Therapy, Photodiagnosis and Photodynamic Therapy, Elsevier, 2017, 17, pp.A61. ⟨10.1016/j.pdpdt.2017.01.137⟩, Photodiagnosis and Photodynamic Therapy, 2017, 17, pp.A61. ⟨10.1016/j.pdpdt.2017.01.137⟩
- Publication Year :
- 2017
- Publisher :
- Elsevier BV, 2017.
-
Abstract
- International audience; In this study, we focus on is the enhancement of singlet oxygen generation, which can be promoted by the introduction of heavy atoms on the photosensitizer. Metalation of tetrapyrrole core by heavy atoms such as platinum or palladium is another option but these metals tend to aggravate the aggregation tendency of the macrocycle. Halogenation proved to be much more successful on photosensitizing phthalocyanine [1] and BOPDIPY [2]. Besides, our recent systematic study on monohalogenated trihydroxylated porphyrins [3] demonstrated that the effect of iodination on photoproperties is extremely positive, without significantly modifying the amphiphilicity of the molecules, another important parameter that directly affects cellular uptake. On another hand, we recently designed and demonstrated the efficiency of the amphiphilic porphyrin 1 which exhibited excellent phototoxicity [4]. To further enhance the PDT efficiency, we decided to introduce three iodine atoms on the structure of 1. The relevance of the design of resultant porphyrin 2 (Fig. 1) was assessed by determining its photoproperties and its in vitro phototoxicity [5].
- Subjects :
- [CHIM.ORGA]Chemical Sciences/Organic chemistry
010405 organic chemistry
Singlet oxygen
Metalation
Biophysics
Halogenation
[CHIM.CATA]Chemical Sciences/Catalysis
[CHIM.MATE]Chemical Sciences/Material chemistry
Dermatology
[CHIM.INOR]Chemical Sciences/Inorganic chemistry
010402 general chemistry
01 natural sciences
Combinatorial chemistry
Porphyrin
Tetrapyrrole
0104 chemical sciences
chemistry.chemical_compound
Oncology
chemistry
Phthalocyanine
Pharmacology (medical)
Photosensitizer
Phototoxicity
Subjects
Details
- ISSN :
- 15721000
- Volume :
- 17
- Database :
- OpenAIRE
- Journal :
- Photodiagnosis and Photodynamic Therapy
- Accession number :
- edsair.doi.dedup.....9ea25dc0f25a663be6495f78e1cd17ce