5-Methoxypsoralen, an ingredient in several suntan preparations, has lethal, mutagenic and clastogenic properties

@article{AshwoodSmith19805MethoxypsoralenAI,
  title={5-Methoxypsoralen, an ingredient in several suntan preparations, has lethal, mutagenic and clastogenic properties},
  author={M. J. Ashwood‐Smith and Gerald Arthur Poulton and Mg Barker and Maria Mildenberger},
  journal={Nature},
  year={1980},
  volume={285},
  pages={407-409}
}
Many furocoumarins found in several species of plant1,2 are potent photosensitizing agents known to cause lethal and mutagenic effects in a wide range of organisms, from viruses to man2. Their role in the aetiology of cancer is debatable3–8, but work has focused on the PUVA (psoralen-UVA) treatment of psoriasis with 8-methoxypsoralen (8-MOP) and near UV radiation9–18. Bergaptene (5-methoxypsoralen, 5-MOP) is a major constituent of oil of bergamot1,19, and might be expected to have qualitatively… 
Genotoxicity of 5-methoxypsoralen and near ultraviolet light in repair-deficient strains of Escherichia coli WP2.
  • B. Pool, R. Klein, R. Deutsch-Wenzel
  • Biology, Medicine
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association
  • 1982
TLDR
The lethal effects of 5-MOP and near ultraviolet light (NUV) on repair-deficient Escherichia coli strains was considerably reduced and strain WP100 UVRA- recA- was more sensitive than strain WP2 UVRA-.
Application of the equivalency factor concept to the phototoxicity and -genotoxicity of furocoumarin mixtures.
  • N. Raquet, D. Schrenk
  • Chemistry, Medicine
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association
  • 2014
TLDR
Analysis of FC properties in V79 cells suggests that FCs can differ widely in their photo-toxic and photo-genotoxic properties but show relatively strict additivity with respect to their on target-effects when occurring as complex mixtures.
Relative photomutagenicity of furocoumarins and limettin in the hypoxanthine phosphoribosyl transferase assay in V79 cells.
TLDR
A new concept for the description of the relative photomutagenic potency of coumarins and furocoumarins is provided and it is indicated that, in V79 cells, 8-MOP is less photomUTagenic and limettin and angelicin are much lessPhototoxic than 5-Mop.
Phototumorigenesis studies of 5-methoxypsoralen in bergamot oil: evaluation and modification of risk of human use in an albino mouse skin model.
TLDR
The skin of the female hairless albino mouse was used to study the enhancement of solar simulated radiation (SSR) tumorigenesis by 5-methoxypsoralen (5-MOP) in model perfumes that contain bergamot oil, indicating that 5-Mop has phototumorigenic potential even at 5 ppm.
Fate of photosensitizing furanocoumarins in tolerant and sensitive insects
TLDR
The fate of [14C]xanthotoxin was studied in larvae of insect species that are tolerant or sensitive to the phototoxic effects of photosensitizing psoralens to indicate that psoralen tolerance inP.
Genotoxicity of bergapten and bergamot oil in Saccharomyces cerevisiae.
TLDR
Experiments on suction blister fluids taken from patients after topical treatment with BO containing 5-MOP indicate that in comparison with water the bioavailability and thus the genotoxic effects of the compounds are decreased.
Genotoxic effects and DNA photoadducts induced in Chinese hamster V79 cells by 5-methoxypsoralen and 8-methoxypsoralen.
The induction of lethal effects and 6-thioguanine-resistant (6-TGr) mutants were studied in Chinese hamster V79 cells after treatment with the two bifunctional furocoumarins 5- and 8-methoxypsoralens
Photobiological studies with dictamnine, a furoquinoline alkaloid.
TLDR
The concept of 'unit dose' relating the observable photoinduced damage by the photosensitizer and the total irradiation appears to apply reasonably well to the actions of dictamnine in killing bacterial and mammalian cells, in the formation of sister-chromatid exchanges, but not to the induction of bacterial mutations.
The clastogenic effect of 5-methoxypsoralen plus UV-A in human lymphocytes in vitro and its modification by the anticlastogen β-aminoethylisothiouronium
TLDR
The treatment of human lymphocytes in vitro with 5-methoxypsoralen plus UV-A induces a dose-dependent increase in the SCE rate and in structural chromosome aberrations and the occurrence of a protective effect proved to be dependent upon the conditions of treatment.
Phototoxic properties of perfumes containing bergamot oil on human skin: photoprotective effect of UVA and UVB sunscreens.
TLDR
Despite their promising protective effect in vitro, UVB and UVA sunscreens at low concentration (0.5%-1%) in perfumes cannot suppress the phototoxicity of bergamot oil on human skin.
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Structural specificity in the lethal and mutagenic activity of furocoumarins in yeast cells
TLDR
The frequency of cytoplasmic “petite” mutations per survivors decreases during dark repair conditions more efficiently after Angelicin than after Psoralen plus 365 nm light treatment.
Mutagenicity of 8-methoxypsoralen and long-wave ultraviolet irradiation in V-79 Chinese hamster cells. A first approach to a risk estimate in photochemotherapy.
The effect of 8-methoxypsoralen (8-MOP) and long-wave ultraviolet irradiation (UVA) on cell killing and mutation induction was studied in V-79 Chinese hamster cells. No effect was observed after
Mutagenicity of 8-methoxypsoralen and long-wave ultraviolet irradiation in diploid human skin fibroblasts: an improved risk estimate in photochemotherapy.
TLDR
Cell killing and the induction of mutation were studied in dividing and non-dividing human skin fibroblasts as a result of treatment by 8-MOP and long-wave UV irradiation and the significance of absence in patients of SCE induction by photochemotherapy is discussed.
Frameshift mutagenesis in bacteria by 8-methoxypsoralen (methoxalen) in the dark.
We confirm that 8-methoxypsoralen (8-MOP) in the dark induces frameshift mutations in both Escherichia coli and Salmonella typhimurium when present in adequate concentration under growth conditions.
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In vitro and in vivo assays demonstrate that 8-methoxypsoralen, in the presence of ultraviolet light (8MOP-UV), induces phenotypic alterations in certain mammalian cells. Transformation for certain
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TLDR
Under the conditions of this test, enhanced photocarcinogenesis is not a necessary consequence of prolonged contact with the phototoxic agent anthracene.
Studies on the reactivation of bacteria photodamaged by an angular furocoumarin: Angelicin
TLDR
It is concluded that the damage produced directly by the shorter wavelength radiations (formation of pyrimidine dimers) is greater than the small repair produced under the authors' experimental conditions.
Chromosome damage in Chinese hamster cells sensitized to near-ultraviolet light by psoralen and angelicin.
TLDR
It is noteworthy that extensive chromosomal damage is induced in mammalian cells by the combination of psoralen and near-UV, a treatment which is currently widely used in the therapy of psoriasis.
Mutagenesis in Escherichia coli. IV. Photosensitization to near ultraviolet light by 8-methoxypsoralen.
TLDR
8-MOP may represent a new type of antimutagen for suppressor mutations arising from potentially excisable damage in Escherichia coli WP2, similar to that for far ultraviolet light alone although there are some differences.
Psoralen monoadducts and interstrand cross-links in DNA.
  • R. S. Cole
  • Chemistry, Medicine
    Biochimica et biophysica acta
  • 1971
TLDR
Psoralen cross-links may be an important DNA defect contributing to the sensitizing action of this class of drugs, suggesting a mechanism for the formation of psoralen adducts to DNA.
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