Trioxsalen

Trioxsalen

Names
IUPAC name 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
Identifiers
CAS Number	3902-71-4
ChEBI	CHEBI:28329
ChEMBL	ChEMBL1475
ChemSpider	5383
DrugBank	DB04571
Jmol interactive 3D	Image
KEGG	D01034
PubChem	5585
UNII	Y6UY8OV51T
InChI InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3 Key: FMHHVULEAZTJMA-UHFFFAOYSA-N InChI=1/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3 Key: FMHHVULEAZTJMA-UHFFFAOYAF
SMILES O=C/3Oc2c(c1oc(cc1cc2\C(=C\3)C)C)C
Properties
Chemical formula	C14H12O3
Molar mass	228.24328
Pharmacology
ATC code	D05AD01 D05BA01
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Trioxsalen (trimethylpsoralen, Trioxysalen or Trisoralen) is a furanocoumarin and a psoralen derivative. It is obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo^[1] and hand eczema.^[2] After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage.^[3] The compound is also being explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair.^[4]

References

1. "Trioxsalen - Compound Summary". PubChem.
2. Van Coevorden, AM; Kamphof, WG; Van Sonderen, E; Bruynzeel, DP; Coenraads, PJ (2004). "Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy.". Archives of dermatology 140 (12): 1463–6. doi:10.1001/archderm.140.12.1463. PMID 15611423.
3. Thazhathveetil, AK; Liu, ST; Indig, FE; Seidman, MM (2007). "Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation". Bioconjugate chemistry 18 (2): 431–7. doi:10.1021/bc060309t. PMID 17373769.
4. Higuchi, M; Yamayoshi, A; Kobori, A; Yamaoka, T; Murakami, A (2005). "Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine". Nucleic acids symposium series (2004) 49 (49): 331–2. doi:10.1093/nass/49.1.331. PMID 17150768.