Synthesis of novel long wavelength cationic chlorins via stereoselective aldol-like condensation

Using stereoselective aldol-like condensation as a key methodology, a series of chlorophyll a-based long wavelength cationic chlorins were synthesized using methyl pyropheophorbide a (MPPa) and purpurin-18-N-methoxylimide methyl ester as starting materials. Such long wavelength cationic chlorins pos...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2012-03, Vol.22 (5), p.1846-1849
Main Authors: Li, Jia Zhu, Wang, Jin Jun, Yoon, Il, Cui, Bing Cun, Shim, Young Key
Format: Article
Language:English
Subjects:
absorption
Aldol-like condensation
Biological and medical sciences
Cell Survival - drug effects
Chlorin
chlorins
chlorophyll
Chlorophyll - chemical synthesis
Chlorophyll - chemistry
Chlorophyll a
condensation
General pharmacology
HeLa Cells
Humans
Long wavelength cationic photosensitizer
Medical sciences
Neoplasms - drug therapy
Pharmaceutical technology. Pharmaceutical industry
Pharmacology. Drug treatments
Photochemotherapy
Photodynamic therapy
photosensitizing agents
Photosensitizing Agents - chemical synthesis
Photosensitizing Agents - chemistry
Photosensitizing Agents - pharmacology
phototoxicity
Porphyrins - chemical synthesis
Porphyrins - chemistry
Porphyrins - pharmacology
Stereoisomerism
therapeutics
wavelengths
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Summary:Using stereoselective aldol-like condensation as a key methodology, a series of chlorophyll a-based long wavelength cationic chlorins were synthesized using methyl pyropheophorbide a (MPPa) and purpurin-18-N-methoxylimide methyl ester as starting materials. Such long wavelength cationic chlorins possess covalently linked cationic moieties (pyridinium or quinolinium) on the peripheral of their tetrapyrrole macrocycles. It was found that all long wavelength cationic chlorins showed their longest absorption maxima in the range of 712–763nm, making them potential photosensitizers in photodynamic therapy. The results of preliminary experiments probing in vitro photodynamic effects showed that the purpurinimide derivatives exhibit relatively high phototoxicity in HeLa cells as compared to MPPa derivatives.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.01.088