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Concept
Psoralen
Summary
Psoralen (also called psoralene) is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. It is structurally related to coumarin by the addition of a fused furan ring, and may be considered as a derivative of umbelliferone. Psoralen occurs naturally in the seeds of Psoralea corylifolia, as well as in the common fig, celery, parsley, West Indian satinwood, and in all citrus fruits. It is widely used in PUVA (psoralen + UVA) treatment for psoriasis, eczema, vitiligo, and cutaneous T-cell lymphoma; these applications are typically through the use of medications such as Methoxsalen. Many furanocoumarins are extremely toxic to fish, and some are deposited in streams in Indonesia to catch fish.
Psoralen is a mutagen, and is used for this purpose in molecular biology research. Psoralen intercalates into DNA and on exposure to ultraviolet (UVA) radiation can form monoadducts and covalent interstrand cross-links (ICL) with thymines, preferentially at 5'-TpA sites in the genome, inducing apoptosis. Psoralen plus UVA (PUVA) therapy can be used to treat hyperproliferative skin disorders like psoriasis and certain kinds of skin cancer. Unfortunately, PUVA treatment itself leads to a higher risk of skin cancer.
An important use of psoralen is in PUVA treatment for skin problems such as psoriasis and, to a lesser extent, eczema and vitiligo. This takes advantage of the high UV absorbance of psoralen. The psoralen is applied first to sensitise the skin, then UVA light is applied to clean up the skin problem. Psoralens are also used in photopheresis, where they are mixed with the extracted leukocytes before UV radiation is applied.
Despite the photocarcinogenic properties of psoralen, it was used as a tanning activator in sunscreens until 1996. Psoralens are used in tanning accelerators, because psoralen increases the skin's sensitivity to light. Some patients have had severe skin loss after sunbathing with psoralen-containing tanning activators.
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Related publications (5)
Biobased Composites from Eugenol- and Coumarin-Derived Methacrylic Latex and Hemp Nanocellulose: Cross-Linking via [2+2] Photocycloaddition and Barrier Properties
Yves Leterrier, Sara Dalle Vacche
A novel-biobased latex was synthesized by redox-initiated emulsion copolymerization of ethoxy dihydroeugenyl methacrylate with 5 wt % of a photosensitive methacrylate containing a coumarin group. A stable copolymer latex having 16 wt % solids content and a ...
Amer Chemical Soc2024Effect of furan pi-spacer and triethylene oxide methyl ether substituents on performance of phenothiazine sensitizers in dye-sensitized solar cells
Conjugated pi-spacers are used to improve the light harvesting properties of sensitizers for dye-sensitized solar cells. In several recent works, furan has outperformed other popular pi-spacers such as thiophene and phenyl. One of the best performing pheno ...
ROYAL SOC CHEMISTRY2019Related concepts (9)
Sunburn
Sunburn is a form of radiation burn that affects living tissue, such as skin, that results from an overexposure to ultraviolet (UV) radiation, usually from the sun. Common symptoms in humans and other animals include red or reddish skin that is hot to the touch or painful, general fatigue, and mild dizziness. Other symptoms include blistering, peeling skin, swelling, itching, and nausea. Excessive UV radiation is the leading cause of (primarily) non-malignant skin tumors, which in extreme cases can be life-threatening.
Homologous recombination
Homologous recombination is a type of genetic recombination in which genetic information is exchanged between two similar or identical molecules of double-stranded or single-stranded nucleic acids (usually DNA as in cellular organisms but may be also RNA in viruses). Homologous recombination is widely used by cells to accurately repair harmful DNA breaks that occur on both strands of DNA, known as double-strand breaks (DSB), in a process called homologous recombinational repair (HRR).
Phototoxicity
Phototoxicity, also called photoirritation, is a chemically induced skin irritation, requiring light, that does not involve the immune system. It is a type of photosensitivity. The skin response resembles an exaggerated sunburn. The involved chemical may enter into the skin by topical administration, or it may reach the skin via systemic circulation following ingestion or parenteral administration. The chemical needs to be "photoactive," which means that when it absorbs light, the absorbed energy produces molecular changes that cause toxicity.