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Synthesis and Characterization of Novel Purpurinimides as Photosensitizers for Photodynamic Therapy
Cui, Bing Cun,Yoon, Il,Li, Jia Zhu,Lee, Woo Kyoung,Shim, Young Key Molecular Diversity Preservation International (MD 2014 INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES Vol.15 No.5
<P>A series of novel purpurinimides with long wavelength absorption were designed and synthesized to develop novel and potential photosensitizers. These compounds were investigated through reduction, oxidation, rearrangement reaction and amidation reactions of methyl pheophorbide <I>a</I>. They demonstrated a considerable bathochromic shift of the major absorption band in the red region of the optical spectrum (695–704 nm). Newly synthesized purpurinimides were screened for their antitumor activities, and showed higher photodynamic efficiency against A549 cell lines as compared to purpurin-18 methyl ester. The results revealed the novel purpurinimides could be potential photosensitizers.</P>
Efficient Synthesis and in vitro PDT Effect of Purpurin-18-N-Aminoimides
Bing Cun Cui,Min Uk Cha,Jia Zhu Li,Ho Sung Park,윤일,Young Key Shim 대한화학회 2010 Bulletin of the Korean Chemical Society Vol.31 No.11
A simple and efficient synthetic route for making purpurin-18-N-aminoimides is described. The purpurin-18-Naminoimides are obtained by treatment of purpurin-18 methyl ester with various amines. These new compounds have long wavelength absorptions in the range of 706 - 711 nm. In preliminary screening, the purpurin-18-N-aminoimides have shown promising photosensitizing activity for the cancer cell by in vitro study in photodynamic therapy.
Efficient Synthesis and in vitro PDT Effect of Purpurin-18-N-Aminoimides
Cui, Bing Cun,Cha, Min-Uk,Li, Jia Zhu,Park, Ho-Sung,Yoon, Il,Shim, Young-Key Korean Chemical Society 2010 Bulletin of the Korean Chemical Society Vol.31 No.11
A simple and efficient synthetic route for making purpurin-18-N-aminoimides is described. The purpurin-18-Naminoimides are obtained by treatment of purpurin-18 methyl ester with various amines. These new compounds have long wavelength absorptions in the range of 706 - 711 nm. In preliminary screening, the purpurin-18-N-aminoimides have shown promising photosensitizing activity for the cancer cell by in vitro study in photodynamic therapy.
윤일,Ho Sung Park,Bing Cun Cui,Jung Hwa Kim,Young Key Shim 대한화학회 2011 Bulletin of the Korean Chemical Society Vol.32 No.1
The synthesis of new pyrazolyl and cyclopropyl derivatives of purpurin-18 methyl ester and purpurin-18-N-butylimide 1a, 1b, 2a, 2b and 8 is described. The new compounds were characterized by NMR, UV-vis spectroscopy and mass spectrometry. UV-vis spectra of the new compounds showed long wavelength absorption of ranges 692 - 708 nm (λmax). Photodynamic effects of the chlorin derivatives 1a, 1b, 2a and 2b were investigated by WST-1 assay in A549 cells,and showed good photodynamic activities with high photocytotoxicity and low cytotoxicity in the dark. In comparison between pyrazolyl and cyclopropyl derivatives, purpurin-18 methyl ester compounds 1a and 1b showed comparable photocytotoxicity result of the cell viabilities, otherwise, pyrazolyl derivative of purpurin-18-N-butylimide 2a showed better cell viabilities than those of cyclopropyl derivative 2b. And cyclopropyl derivative of purpurin-18-N-butylimide 2b showed higher dark cytotoxicity than that of others.
Binding Affinities of Carbohydrate-Conjugated Chlorins for Galectin-3
Park, Young K.,Bold, Bayarmaa,Cui, Bing Cun,Bai, Jin Quan,Lee, Woo-Kyoung,Shim, Young-Key Korean Chemical Society 2008 Bulletin of the Korean Chemical Society Vol.29 No.1
Carbohydrate-conjugated chlorins were synthesized for use as biosensors for the detection of the galectin-3 cancer marker. We used ELISA, SDS-gel electrophoresis, and Bradford assays to examine the binding of galectins to d-(+)-galactose- and b-lactose-conjugated chlorins. The binding affinities of these conjugated chlorins for galectin-3 were quantified using fluorescence spectroscopy. The fluorescence emission of the carbohydrate-conjugated chlorins decreased as the amount of galectin-3 in the binding reaction increased over a limited concentration range, indicating that carbohydrate-conjugated chlorins are potentially useful fluorescence biosensors for the galectin-3 cancer marker.
Il Yoon,Ho Sung Park,Bing Cun Cui,Jia Zhu Li,Jung Hwa Kim,Byambajav Lkhagvadulam,Young Key Shim 대한화학회 2011 Bulletin of the Korean Chemical Society Vol.32 No.8
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 μM 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.
Binding Affinities of Carbohydrate-Conjugated Chlorins for Galectin-3
Young K. Park,이우경,심영기,Bayarmaa Bold,Bing Cun Cui,Jin Quan Bai 대한화학회 2008 Bulletin of the Korean Chemical Society Vol.29 No.1
Carbohydrate-conjugated chlorins were synthesized for use as biosensors for the detection of the galectin-3 cancer marker. We used ELISA, SDS-gel electrophoresis, and Bradford assays to examine the binding of galectins to d-(+)-galactose- and b-lactose-conjugated chlorins. The binding affinities of these conjugated chlorins for galectin-3 were quantified using fluorescence spectroscopy. The fluorescence emission of the carbohydrate-conjugated chlorins decreased as the amount of galectin-3 in the binding reaction increased over a limited concentration range, indicating that carbohydrate-conjugated chlorins are potentially useful fluorescence biosensors for the galectin-3 cancer marker.
Yoon, Il,Park, Ho-Sung,Cui, Bing Cun,Li, Jia Zhu,Kim, Jung-Hwa,Lkhagvadulam, Byambajav,Shim, Young-Key Korean Chemical Society 2011 Bulletin of the Korean Chemical Society Vol.32 No.suppl8
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.