Sugar-dependent aggregation of glycoconjugated chlorins and its effect on photocytotoxicity in HeLa cells
| Autor: | Chikara Ohtsuki, Shigenobu Yano, Shinichi Ogata, Makoto Obata, Kazumi Kajiwara, Masao Tanihara, Shiho Hirohara |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
Glycosylation
Porphyrins Photochemistry Stereochemistry Carbohydrates Biophysics Uterine Cervical Neoplasms HeLa chemistry.chemical_compound Tetraphenylporphyrin polycyclic compounds Humans Radiology Nuclear Medicine and imaging Hexose Cytotoxicity chemistry.chemical_classification Microscopy Confocal Photosensitizing Agents Radiation Dose-Response Relationship Drug Molecular Structure Radiological and Ultrasound Technology biology Chemistry Spectrum Analysis Water Biological Transport biology.organism_classification Fluorescence In vitro Solutions Photochemotherapy Cytoplasm Chlorin Female Glycoconjugates HeLa Cells |
| Zdroj: | Journal of Photochemistry and Photobiology B: Biology. 84:56-63 |
| ISSN: | 1011-1344 |
| DOI: | 10.1016/j.jphotobiol.2006.01.011 |
| Popis: | In order to explore the influence of the sugar moieties of glycoconjugated chlorins on the photocytotoxicity, we studied the photochemical properties of four glycoconjugated chlorins in aqueous media such as cytoplasm and the concentration dependence of photocytotoxicity in HeLa cells. In phosphate-buffered saline, the fluorescence intensities of 5,10,15,20-tetrakis[3-(β- d -glucopyranosyloxy)phenyl]chlorin ( m - 1a ) and 5,10,15,20-tetrakis[3-(β- d -galactopyranosyloxy)phenyl]chlorin ( m - 1b ), i.e., chlorins having hexose groups, were about 2-fold greater than those of 5,10,15,20-tetrakis[3-(β- d -xylopyranosyloxy)phenyl]chlorin ( m - 1c ) and 5,10,15,20-tetrakis[3-(β- d -arabinopyranosyloxy)phenyl]chlorin ( m - 1d ), i.e., chlorins having pentose groups, owing to a sugar-dependent difference of aggregation behavior. While no cytotoxicity was found in the dark, the highest photocytotoxicity was shown by m - 1a (82% inhibition) in HeLa cells. This was higher than those of m - 1b , m - 1c , m - 1d and tetraphenylporphyrin tetrasulfonic acid. The glycoconjugated chlorins except for m - 1b appeared to be distributed diffusely throughout the cytoplasm. Among the four photosensitizers, m - 1a showed the highest intensity in confocal fluorescence images, in agreement with the in vitro photocytotoxicity results. For m - 1c , no photocytotoxicity was found at drug concentrations from 0.2 to 0.04 μM. Hence, sugar-dependent aggregation is not the major reason for the unexpected lack of efficacy of m - 1c , which is uptaken efficiently by HeLa cells. For the glycoconjugated chlorins, these results suggest the biological aspects of sugar moiety play much crucial role rather than chemical aspects. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect