• Title/Summary/Keyword: 8-Methoxypsoralen

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Isolation and Identification of Two Psoralen Derivatives as Antioxidative Compounds from the Aerial Parts of Angelica keiskei (신선초에 함유된 항산화활성물질 Psoralen 유도체들의 단리 및 동정)

  • Kim, So-Joong;Cho, Jeong-Yong;Wee, Ji-Hyang;Jang, Mi-Young;Rim, Yo-Sup;Kim, Cheol;Shin, Soo-Cheol;Moon, Jae-Hak;Park, Keun-Hyung
    • Korean Journal of Food Science and Technology
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    • v.37 no.4
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    • pp.656-659
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    • 2005
  • Hot water extracts of Angelica keiskei aerial parts were solvent-fractionated with ethyl acetate (EtOAc) and buffers (5% $NaHCO_3$, pH 8.0; 1.0 N HCl, pH 3.0) to obtain EtOAc-soluble acidic and neutral fractions. EtOAc-soluble neutral fraction was purified by Sephadex LH-20 column chromatography and reverse phase HPLC. Assay for purification of antioxidative compounds was performed by spraying DPPH solution on thin layer chromatography. Two isolated substances were identified as pseudoisopsoralen and 8-methoxypsoralen(xanthotoxin) by FAB-MS and NMR analyses.

Validation of Photo-comet Assay as a Model for the Prediction of Photocarcinogenicity

  • Kim, Ji-Young;Koh, Woo-Suk;Lee, Mi-Chael
    • Toxicological Research
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    • v.22 no.4
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    • pp.423-429
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    • 2006
  • Recent reports on the photocarcinogenicity and photogerotoxicity of many compounds led to an increasing awareness for the need of a standard approach to test for photogenotoxicity. The comet assay has been recently validated as a sensitive and specific test system for the quantification of DNA damage. Thus, the objectives of this study are to investigate the utility of photo-comet assay for detecting photo-mutagens, and to evaluate its ability to predict rodent photo-carcinogenicity. Photo-comet assays were performed using L5178Y $Tk^{+/-}$ mouse lymphoma cells on five test substances (8-methoxypsoralen, chlorpromazine, lomefloxacin, anthracene and retinoic acid) that demonstrated positive results in photocarcinogenicity tests. For the best discrimination between the test substance-mediated DNA damage and the undesirable DNA damage caused by direct UV absorption, a UV dose-response of the cells in the absence of the test substances was firstly fnalized. Out of 5 test substances, positive comet results were obtained for chlorpromazine, lomefloxacin, anthracene and retinoic acid while 8-methoxypsoralen found negative. An investigation into the predictive value of this photo-comet assay for determining the photocarcinogenicity showed that photo-comet assay has relatively high sensitivity. Therefore, the photo-comet assay with mammalian cells seems to be a good and sensitive predictor of the photocarcinogenic potential of new substances.

Comparison of Photophysical and Photochemical Properties of Khellin and 8-Methoxypsoralen

  • Ho Kwon Kang;Eun Ju Shin;Sang Chul Shim
    • Bulletin of the Korean Chemical Society
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    • v.12 no.5
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    • pp.554-559
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    • 1991
  • The photophysical and photochemical properties of khellin were compared with those of 8-methoxypsoralen (8-MOP). Quantum yields of fluorescence and triplet formation decreases as solvent polarity increases, which is opposite to 8-MOP, and photocycloadditivity of khellin to olefins is much lower than that of 8-MOP. Electron ejection from khellin by laser flash was not observed, but observed from 8-MOP. As models of 4',5'-monoadducts of khellin or 8-MOP with thymine base, khellin<>dimethylfumarate 4',5'-monoadduct (KDF) was also compared with 8-MOP<>thymidine 4',5'-monoadduct (F-2) in those properties to give some insight on the second-step biadduct formation resulting in cross-links of DNA duplex. KDF and F-2 were very similar to khellin and 8-MOP in photophysical properties, respectively. However, KDF did not form adducts with various olefins, and thus it is thought that 2,3-double bond of chromone moiety in khellin is hardly reactive in contrast with 3,4-double bond of coumarin moiety in 8-MOP. These results indicate that khellin is fairly photostable compound, a poor type Ⅰ photodynamic sensitizer and producer of ${O_2}^{-}$ which is some cause of phototoxic erythemal reactions and undesirable side effects. Therefore khellin is safer to use than 8-MOP in photochemotherapy of some skin diseases. Although khellin is much less reactive than 8-MOP, khellin must be also a monofunctional drug. Since khellin is, however, as effective as 8-MOP in photochemotherapy of some skin diseases, it is suggested that khellin may be different from 8-MOP in the action mechanism.

Photohysical Properties of New Psoralen Derivatives:Psoralens Linked to Adenine through Polymethylene Chains

  • Yoo, Dong-Jin;Park, Hyung-Du;Kim, Ae-Rhan;Rho, Young S.;Shim, Sang-Chul
    • Bulletin of the Korean Chemical Society
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    • v.23 no.9
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    • pp.1315-1327
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    • 2002
  • The model compounds, 8-methoxypsoralen-CH2O(CH2)n-adenine (MOPCH2OCnAd, n=2, 3, 5, 6, 8, and 10) in which 5 position of 8-methoxypsoralen (8-MOP) is linked by various lengths of polymethylene bridge to N9 of adenine. UV absorption spectra are identical with the sum of MOPCH2OC3 and adenine absorption spectra. Solvent effects on the UV absorption and fluorescence emission spectra indicate that the lowest excited singlet state is the $(\pi${\rightarrow}$\pi*)$ state. The spectral characteristics of the fluorescence of MOPCH2OCnAd are strongly dependent upon the nature of the solvents. The fluorescence emission spectra in aprotic solvents are broad and structureless due to the excimer formation through the folded conformation accelerated by hydrophobic ${\pi}-{\pi}$ stacking interaction. Increasing polarity of the protic solvents leads to higher population of unfolded conformation stabilized through favorable solvation and H-bonding, and consequently to an increase in the fluorescence intensity, fluorescence lifetime, and a shift of fluorescence maximum to longer wavelengths. The decay characteristics of the fluorescence in polar protic solvents shows two exponential decays with the lifetimes of 0.6-0.8 and 1.6-1.9 ns in 5% ethanol/water, while MOPCH2OC3 shows 0.5 and 1.7 ns fluorescence lifetimes. The long-lived component of fluorescence can be attributed to the relaxed species (i.e., the species for which the solvent reorientation (or relaxation) has occurred), while the short-lived components can be associated with the unrelaxed, or only partially relaxed, species.

In Vitro Alternative Phototoxicity Test for Various Cosmetic Natural Extracts and Chemicals (수종의 화장품용 천연물과 화합물의 In Vitro 광독성 대체 시험)

  • Cho, Wan-Goo;Park, Jee-Eun;Park, Mun-Euek;Lee, Sang-Min
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.35 no.3
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    • pp.193-202
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    • 2009
  • This study was done to assess an alternative method as a replacement of in vivo phototoxicity test. The human fibroblasts were exposed to several phototoxic chemicals (promethazine, chlorpromazine chlortetracycline, 8-methoxypsoralen, neutral red, bithionol) and non-phototoxic materials (cinnamic aldehyde, p-aminobenzoic acid, sodium lauryl sulfate, L-cysteine). The cell viability was measured by neutral red uptake (NRU) assay. The results of the NRU phototoxicity (PT) assay showed a close agreement with in vivo test except bithionol. We also have tested the cosmetic ingredients including $Medimin^{(R)}$ A, $Medimin^{(R)}$ D, $LG^{(R)}$ 106W, $Phytoclear^{(R)}$ EL-1, Carex humilis L. extract, Canna indica L. extract, Salvia miltiorrhira Bunge extract, $Parsol^{(R)}$ MCX and $Parsol^{(R)}$ 1789. Most materials except Salvia miltiorrhira Bunge extract did not show any phototoxicity.

PHOTOCHEMISTRY AND PHOTOBIOLOGY OF PSORALENS

  • Shim, Sang-Chul;Jeon, Young Hee;Kim, DongWon;Han, GyuSeok;Yoo, Dong Jin
    • Journal of Photoscience
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    • v.2 no.1
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    • pp.37-45
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    • 1995
  • INTRODUCTION : Psoralens are planar tricyclic furocoumarins present in numerous plants and fungi found throughout the world.' Naturally occurring and synthesized psoralen derivatives(see Figure 1) are photosensitizers of UVA especially from 320 nm to 400 nm, a range at which cellular nucleic acids and proteins are weakly absorbing if any at all. Because of their skinphotosensitizing properties, these compounds have been used in the photochemotherapy of psoriasis and vitiligo. However, undesirable side effects such as carcinoma development in hairless mice as well as possible liver damage from the use of 8-methoxypsoralen(8-MOP) have been reported. The other photobiological effects include inactivation of DNA viruses, killing and mutagenesis of bacteria, inhibition of tumor transmitting capacity of various cells, and hyperpigmentation on human and guinea pig skin. PUVA(psoralen+UVA) photochemotherapy is in fact thousands of years old, having been used in Egypt and India since B.C. 1200-2000. Photochemotherapy for a common disfiguring disease, vitiligo, was practiced in the ancient world by physicians and herbalists who used boiled extracts of the fruits of certain umbelliferous plants, e.g. Ammi majus Linnaeus in Egypt or the leguminous plants, Psoralea corylifolia L. in India. It was first described by Kuske in 19388 that photosensitization of skin by plants was related to the presence of psoralen. He identified natural psoralens in plants as photosensitizers and isolated bergapten(5methoxypsoralen) from the oil of bergamot. The scientific interest in photosensitizing psoralens, however, has grown considerably after the introduction into clinics of the psoralen photochemotherapy for the treatment of psoriasis and of other skin (abbreviation)

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Treatment Result of Photochemotherapy for Systemic Psoriasis Patients (전신성 건선환자의 광선치료 후의 임상적 특성에 대한 고찰)

  • Cho, Eun-Jung;Yi, Chung-Hwi
    • Physical Therapy Korea
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    • v.3 no.1
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    • pp.73-79
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    • 1996
  • Photochemotherapy(UVA with 8-methoxypsoralen) was given to 30 patients with systemic psoriasis. The results of clearing and long-term(6-month) interval maintenance were reported. Clearing requirements were in general similar to these reported by Melski and Burger. The skin of the 14 patients (46.6%) recovered good skin condition by a once weekly maintenance dose. This result was better than that reported by other authors. 1. During initial treatment period, average number of treatment was 27.3 and average duration treatment was 24.8 weeks. 2. The factors to quit treatment were motion decrease, moving to the remote area, complications, etc. 3. Number of patient who received maintenance treatment was 14. 4. The complications reported from the patients were hyperpigmentation, nausea, headache, pruritis, vomiting, gastritis.

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BIOLOGICAL HUMAN MONITORING OF CARCINOGEN EXPOSURE: A NEW STRATEGY IN CANCER PREVENTION

  • Lee, Byung-Mu
    • Toxicological Research
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    • v.6 no.1
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    • pp.63-73
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    • 1990
  • Human exposure to environmental carcinogens can be detected by a number of methods including immunoassay, $^{32}P-postlabeling$ assay, and fluorescence technique. These assays have been applied to measure biological markers of carcinogen-adducts formed with macromolecules such as DNA, RNA and protein. In an attempt to investigate causal relationships between carcinogen exposure and tumor formation, specific carcinogen-adducts have been quantitated from human tissues and body fluids of cancer patients, occupational workers heavily exposed to certain carcinogens, smokers and controls. Carcinogens studied for biological human monitoring include benzo(a)pyrene, aflatoxin B1, UV light, ethylene oxide, 8-methoxypsoralen, 4-aminobiphenyl, vinyl choride, N-nitrosamine, cisplatin and other chemotherapeutic agents. Relevance of human monitoring for cancer research, progress in this field, methods to detect carcinogen-adducts are reviewed here. It is hoped that these approaches will be used for the risk assessment of carcinogen exposure, cancer etiology study and cancer prevention in humans.

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BIOLOGICAL HUMAN MONITORING OF CARCINOGEN EXPOSURE: A NEW STRATEGY IN CANCER PREVENTION

  • Lee, Byung-Mu
    • Toxicological Research
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    • v.6 no.1
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    • pp.61-61
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    • 1990
  • Human exposure to environmental carcinogens can be detected by a number of methods including immunoassay, $^{32}P$-postlabeling assay, and fluorescence technique. These assays have been applied to measure biological markers of carcinogen-adducts formed with macromolecules such as DNA, RNA and protein. In an attempt to investigate causal relation ships between carcinogen exposure and tumor formation, specific carcinogen-adducts have been quantitated from human tissues and body fluids of cancer patients, occupational workers heavily exposed to certain carcinogens, smokers and controls. Carcinogens studied for biological human monitoring include benzo(a)pyrene, aflatoxin B1, UV light, ethylene oxide, 8-methoxypsoralen, 4-aminobiphenyl, vinyl chloride, N-nitrosamine, cisplatin and other chemotherapeutic agents. Relevance of human monitoring for cancer research, progress in this field, methods to detect carcinogen-adducts are reviewed here. It is hoped that these approaches will be used for the risk assessment of carcinogen exposure, cancer etiology study and cancer prevention in humans.