• Journal of Photoscience
• /
• v.9 no.2
• /
• pp.178-181
• /
• 2002

Pyropheophorbide and pheophorbide-photosensitizers as chlorin analogues are promising new compounds for PDT because the chlorin analogues are activated with much longer red light at > 670nm and produce less long-term normal tissue phototoxicity than Photofrin. The various chlorin derivatives can be obtained by moditying peripheral substituted group among which meso-H, vinyl group and exocyclic ring are the most active positions. These characteristics prompted us to introduce various groups for constructing modified pyropheophorbide and pheophorbide a compounds. A stereospecific introduction of various double bonds at 3-position was performed to methylpheophorbide a to give a long hydrophobic moiety and cyclic derivatives. Chlorin-C$_{60}$ dyad and chlorin- $C_{60}$-porphyrin triad also were easily prepared by the reaction of terminal aldehyde of methyl pyropheophorbide a. For the reaction on meso $\delta$-position bromination and Vismeier formylation can occur. N,N-dimethylaminoacrolein also reacted on $\delta$-position and was cyclized to isobacteriochlorin, but other modification has not been succeeded. Exocyclic keto function was also modified to give purpurin derivatives, bicyclic and spiro compounds. In this presentation we report a series of modified pyropheophorbide and pheophorbide a derivatives.s.

• Korean Journal of Clinical Laboratory Science
• /
• v.56 no.1
• /
• pp.52-58
• /
• 2024

Photodynamic therapy (PDT) activates intracellular oxygen using a photosensitizer activated by light of a specific wavelength and is a potential means of treating wound infections caused by antibiotic-resistant bacteria. Pseudomonas aeruginosa (P. aeruginosa) is typically non-pathogenic in healthy individuals but can induce severe illnesses like sepsis in the immunocompromised. Antibiotics have been conventionally used to treat P. aeruginosa infections, but increasing antibiotic resistance caused by drug misuse poses a growing challenge to the management of these infections. This study aimed to investigate the ability of PDT using photosensitizers (PhotoMed, Methyl pheophorbide A, or Radachlorin^®) and a diode laser to inhibit P. aeruginosa. Suspensions of P. aeruginosa and a photosensitizer were inoculated into Petri dishes and incubated for 30 minutes. Samples were then irradiated with the laser at 3 J/cm², and after incubation, colony areas were measured. P. aeruginosa killing rates were 79.65% for PhotoMed, 47.36% for Methyl pheophorbide A, and 40.91% for Radachlorin^®. This study shows that PDT using a diode laser and a photosensitizer constitutes an effective practical therapeutic approach for inhibiting P. aeruginosa.

• Journal of the Korean Applied Science and Technology
• /
• v.2 no.2
• /
• pp.1-9
• /
• 1985

• Journal of the Korean Society of Food Science and Nutrition
• /
• v.27 no.6
• /
• pp.1071-1076
• /
• 1998

Threetypes of Korean traditional kimchi were prepared using green onion, leek or godulbaegi as raw materials and stored at 5oC and 20oC for 13 days. Changes in salt and ascorbic acid contents, pH and total acidity as well as the relationship of the decomposition of chlorophylls and the production of their derivatives were investigated. For the all kimchi samples tested, salt content was not significantly changed during storage at both temperatures, whereas pH and total acidity were decreased and increased, respectively. Especially their remarkable changes were shown at the third day of storage. Ascorbic acid content was remained at high level in the leek kimchi for the experimental period at both storage temperatures, meanwhile godulbaegi kimchi retained the least amount of ascorbic acid. Chlorophylls were decomposed to pheophytin and pheophorbide during storage at both storage temperatures, and this phenomenon was apparent at the third day of storage. Reduction of chlorophylls and increasements of its decomposed products such as pheophytin and pheophorbide were the least in leek kimchi and the greatest in godulbaegi kimchi during storage at both temperatures. These results indicate that decomposition of chlorophylls in kimchi and increasements of pheophytin and pheophorbide were closely related to the ascorbic acid content in kimchi.

• Archives of Pharmacal Research
• /
• v.26 no.9
• /
• pp.716-718
• /
• 2003

In the course of our search for Acyl-CoA: cholesterol acyltransferase (ACAT) inhibitors from natural sources, a new type of ACAT inhibitor was isolated from a methanol extract of Diospyros kaki. On the basis of spectral and structural evidence, the compound was identified as pheophorbide A-methyl ester. Pheophorbide A-methyl ester inhibited ACAT activity in a dose dependent manner with an $IC_{50}$ value of 1.85 $\mu$ g/mL.

• Journal of Photoscience
• /
• v.8 no.1
• /
• pp.23-25
• /
• 2001

The methyl pheophorbide-a (MP-a) and methyl pyropheophorbide-a (MPP-a) were modified by reaction of exocyclic ketone in E-ring with nucleophilic reagent and several chlorin derivatives were synthesized. The change of the structure in E-ring served an expanding conjugation region and introduction of electron-withdrawing group, which strongly influenced the visible spectra. The Qy bands of synthesized compounds were affected by the substituents on the Qy axis(N$\sub$21/-N$\sub$23/).

• Journal of Microbiology and Biotechnology
• /
• v.24 no.3
• /
• pp.346-353
• /
• 2014

The chlorophyll-related compound pheophorbide a (Pa) was successively purified from an edible red seaweed, Grateloupia elliptica, using silica, octadecyl silica column chromatography and reversed phase-high-performance liquid chromatography, as well as the cell cycle inhibitory and apoptotic effects of Pa being investigated in U87MG glioblastoma cells. The Pa exhibited strong anticancer effects in the absence of direct photo-irradiation against various cancer cell lines, including U87MG, SK-OV-3, and HeLa cells. Among the cancer cells, the strongest anticancer activity of Pa exhibited on U87MG cells with $IC_{50}$ values of 2.8 ${\mu}g/ml$. In addition, Pa specifically had cytostatic activity on glioblastoma cells rather than human umbilical vein endothelial cells. Analysis of the cell cycle distribution showed that Pa induced G0/G1 arrest of U87 MG cells. In addition, arrested cells induced late apoptosis and DNA degradation under dark condition. These results suggest that Pa isolated from G. elliptica is a potential glioblastoma-specific anticancer agent without side effects on normal cells.

• Proceedings of the Korean Society of Sericultural Science Conference
• /
• 2002.10a
• /
• pp.25-26
• /
• 2002

No Abstract, See Full Text

• Bulletin of the Korean Chemical Society
• /
• v.32 no.spc8
• /
• pp.2981-2987
• /
• 2011

A comparative study of the photodynamic and antioxidant activities of methyl pheophorbide-a (MPa, 1) and its transition metal(II) complexes (2-5) is described. Four transition metal complexes (palladium(II): 2, zinc(II): 3, cobalt(II): 4 and copper(II): 5) of MPa were prepared by reaction between the corresponding transition metal and 1, respectively, and were characterized by $^1H$-NMR and UV-vis spectroscopic and mass spectrometric analyses. In vitro results show a photodynamic therapy (PDT) efficacy with A549 cells might be attributed to a heavy atom effect of the transition metal complexes of MPa. Among them, 4 and 5 showed higher photodynamic activity than that of 1 at the concentration of 5 ${\mu}M$ at 24 h incubation after photoirradiation. The images of morphological change for 2-5 show evidence for the PDT effect with A549 cells. And the all transition metal complexes of MPa showed higher antioxidant activity than that of MPa, in which 4 showed the highest antioxidant activity.

• Journal of Food Hygiene and Safety
• /
• v.20 no.3
• /
• pp.141-146
• /
• 2005

A simple and sensitive analysis method based on reverse phase (RP) HPLC with UV detector was developed for simultaneous determination of chlorophyll a and b, pheophorbide a and $\beta-Carotene$ in Chlorella and Spirulina products. For added concentration $(50\;\mug/ml)$ of chlorophyll a and b, pheophorbide a and $\beta-Carotene$, recoveries of those were 70.3, 71.6, 60.1 and $90.5\%$, respectively, with relative standard deviations of 2.8,6.0, 10.6 and $10.4\%$. Limit of detection and quantification had ranges of $0.1\sim1.0\;\mug/ml$ and $0.2\sim2.0\;\mug/ml$, respectively. Calibration curve was linear with correlation coefficient of 0.995 for chlorophyll a and b, pheophorbide a and $\beta-Carotene$. Results of simultaneous determination in Chlorella and Spirulina products were showed ranges of $121.g\sim543.0\;\mug/ml$ for chlorophyll a,$0.6\sim160.0\;\mug/ml$ for chlorophyll b, $19.2\sim60.3\;\mug/ml$ for pheophorbide a and $383.6\sim1713.7\;\mug/ml$ for $\beta-Carotene$, respectively. Chlorophyll b contents in Chlorella products were detected above 30 times level to those in Spirulina products. $\beta-Carotene$ contents in Spirulina products were detected 2.7 times level to those in Chlorella products.