Trioxsalen

Trioxsalen
IUPAC name 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
Identifiers
CAS number	3902-71-4 N
PubChem	5585
ChemSpider	5383 Y
UNII	Y6UY8OV51T Y
DrugBank	DB04571
KEGG	D01034 Y
ChEBI	CHEBI:28329 Y
ChEMBL	CHEMBL1475 Y
ATC code	D05AD01,D05BA01
Jmol-3D images	Image 1
SMILES O=C/3Oc2c(c1oc(cc1cc2\C(=C\3)C)C)C
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 Y Key: FMHHVULEAZTJMA-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C14H12O3
Molar mass	228.24328
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.