Psoralen

Description

Psoralen is a kind of naturally occurring furocoumarin. It is naturally occurred in the seeds of Psoralea corylifolia as well as in the common fig, celery, parsley, West Indian Satinwood and all citrus fruits. It is capable of binding to DNA via single- and double-strand cross-linking upon photoactivation with UV radiation. It can intercalate with DNA, blocking its synthesis and cell division. For this reason, it is an important mutagen and can be used in related molecular biology studies. It also exhibits anti- proliferative, anti-allergenic and anti-histamine functions. It can also be used in PUVA treatment for skin diseases such as psoriasis, eczema and vitiligo. It is also effective tanning activator in sunscreens. Some of its derivatives, e.g. amino-psoralen, amotosalen HCl, can even inactivate pathogens in blood products.

References

https://en.wikipedia.org/wiki/Psoralen
https://pubchem.ncbi.nlm.nih.gov/compound/Psoralen#section=Top

Chemical Properties

Crystalline Solid

Uses

Use as photochemical probe in biological systems

Uses

Psoralens are phytoalexins; they are used by plants in a defensive response to attacks by fungi and insects. They have also shown photosensitizing and phototoxic effects in animals and humans and have been used in photochemotherapy for management of vitiligo, psoriasis, and mycosis fungoides. Used as photochemical probe in biological systems.

Uses

As photochemical probe in biological systems: P.-S. Song, C.-N. Ou, Ann. N.Y. Acad. Sci. 346, 355 (1980).

Definition

ChEBI: The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 6735, 1984 DOI: 10.1021/ja00334a044
Synthetic Communications, 37, p. 63, 2007 DOI: 10.1080/00397910600978093

Biochem/physiol Actions

Psoralen belongs to the linear type furanocoumarins. It intercalates and induces interstrand cross-links in DNA. On UV exposure psoralen is excited leading to irreversible intercalation with DNA by covalent bond formation. This property of psoralen ultraviolet A light (PUVA) is exploited in treating skin diseases and cutaneous T-cell lymphoma. However, usage psoralen also leads to hepatotoxicity and cytotoxicity by the generation of psoralen photoproducts (POPs). It may be useful in treating osteoporosis