Jump to content

Trioxsalen: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
Undid revision 727505657 by 217.214.145.29 (talk)
m →top: clean up, replaced: Wormboo → WormBoo (2)
 
(10 intermediate revisions by 7 users not shown)
Line 4: Line 4:
| verifiedrevid = 470616373
| verifiedrevid = 470616373
| ImageFile=Trioxsalen.png
| ImageFile=Trioxsalen.png
| IUPACName=2,5,9-trimethyl-7''H''-furo[3,2-''g'']chromen-7-one
| PIN=2,5,9-Trimethyl-7''H''-furo[3,2-''g''][1]benzopyran-7-one
| OtherNames=
| OtherNames=
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
Line 28: Line 28:
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28329
| ChEBI = 28329
| SMILES = O=C/3Oc2c(c1oc(cc1cc2\C(=C\3)C)C)C
| SMILES = Cc1cc2c(o1)c(C)c1c(c2)c(C)cc(=O)o1
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
Line 51: Line 51:
}}
}}


'''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 [[topical]]ly or [[mouth|oral]]ly in conjunction with [[UV-A]] (the least damaging form of [[ultraviolet]] light) for [[phototherapy]] treatment of [[vitiligo]]<ref>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5585|title=Trioxsalen - Compound Summary |work=PubChem}}</ref> and hand [[eczema]].<ref>{{cite journal |pmid=15611423 |year=2004 |last1=Van Coevorden |first1=AM |last2=Kamphof |first2=WG |last3=Van Sonderen |first3=E |last4=Bruynzeel |first4=DP |last5=Coenraads |first5=PJ |title=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. |volume=140 |issue=12 |pages=1463–6 |doi=10.1001/archderm.140.12.1463 |journal=Archives of Dermatology}}</ref> After [[photoactivation]] it creates [[Crosslinking of DNA|interstrand cross-link]]s 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.<ref>{{cite journal |pmid=17373769 |year=2007 |last1=Thazhathveetil |first1=AK |last2=Liu |first2=ST |last3=Indig |first3=FE |last4=Seidman |first4=MM |title=Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation |volume=18 |issue=2 |pages=431–7 |doi=10.1021/bc060309t |journal=Bioconjugate Chemistry}}</ref> The compound is also being explored for development of [[antisense]] [[oligonucleotide]]s that can be cross-linked specifically to a mutant [[mRNA]] sequence without affecting normal transcripts differing at even a single base pair.<ref>{{cite journal |pmid=17150768 |year=2005 |last1=Higuchi |first1=M |last2=Yamayoshi |first2=A |last3=Kobori |first3=A |last4=Yamaoka |first4=T |last5=Murakami |first5=A |title=Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine |issue=49 |pages=331–2 |doi=10.1093/nass/49.1.331 |journal=Nucleic acids symposium series (2004) |volume=49}}</ref>
'''Trioxsalen''' ('''trimethylpsoralen (TMP)''', '''trioxysalen''' ([[International nonproprietary name|INN]]) 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 [[topical]]ly or [[mouth|oral]]ly in conjunction with [[UV-A]] (the least damaging form of [[ultraviolet]] light) for [[phototherapy]] treatment of [[vitiligo]]<ref>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5585|title=Trioxsalen - Compound Summary |work=PubChem}}</ref> and hand [[eczema]].<ref>{{cite journal |pmid=15611423 |year=2004 |last1=Van Coevorden |first1=AM |last2=Kamphof |first2=WG |last3=Van Sonderen |first3=E |last4=Bruynzeel |first4=DP |last5=Coenraads |first5=PJ |title=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. |volume=140 |issue=12 |pages=1463–6 |doi=10.1001/archderm.140.12.1463 |journal=Archives of Dermatology|doi-access=free }}</ref> After [[photoactivation]] it creates [[Crosslinking of DNA|interstrand cross-link]]s 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.<ref>{{cite journal |pmid=17373769 |year=2007 |last1=Thazhathveetil |first1=AK |last2=Liu |first2=ST |last3=Indig |first3=FE |last4=Seidman |first4=MM |title=Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation |volume=18 |issue=2 |pages=431–7 |doi=10.1021/bc060309t |journal=Bioconjugate Chemistry}}</ref> The compound is also being explored for development of [[antisense]] [[oligonucleotide]]s that can be cross-linked specifically to a mutant [[mRNA]] sequence without affecting normal transcripts differing at even a single base pair.<ref>{{cite journal |pmid=17150768 |year=2005 |last1=Higuchi |first1=M |last2=Yamayoshi |first2=A |last3=Kobori |first3=A |last4=Yamaoka |first4=T |last5=Murakami |first5=A |title=Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine |issue=49 |pages=331–2 |doi=10.1093/nass/49.1.331 |journal=Nucleic Acids Symposium Series |volume=49|doi-access=free }}</ref>

Trioxsalen (abbreviated as TMP) activated by UV-A exposure is commonly used in [[genetics]] research as an experimental [[mutagen]]. UV/TMP generates small deletions (~1-3 Kbp), but all base transitions and transversions can also be obtained.<ref>{{cite journal |last1=Kutscher |first1=Lena M. |last2=Shaham |first2=Shai |title=Forward and reverse mutagenesis in C. elegans |journal=WormBook: The Online Review of C. Elegans Biology |year=2014 |pages=1–26 |url=http://www.wormbook.org/chapters/www_frmutagenesis/frmutagenesis.html |doi=10.1895/wormbook.1.167.1 |pmid=24449699 |pmc=4078664 |access-date=18 June 2021}}</ref>


== References ==
== References ==
Line 61: Line 63:


[[Category:Furanocoumarins]]
[[Category:Furanocoumarins]]
[[Category:O-Methylated coumarins]]
[[Category:O-methylated coumarins]]

Latest revision as of 19:13, 7 April 2022

Trioxsalen
Names
Preferred IUPAC name
2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.021.327 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: FMHHVULEAZTJMA-UHFFFAOYSA-N checkY
  • 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
  • Cc1cc2c(o1)c(C)c1c(c2)c(C)cc(=O)o1
Properties
C14H12O3
Molar mass 228.24328
Pharmacology
D05AD01 (WHO) D05BA01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Trioxsalen (trimethylpsoralen (TMP), trioxysalen (INN) 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]

Trioxsalen (abbreviated as TMP) activated by UV-A exposure is commonly used in genetics research as an experimental mutagen. UV/TMP generates small deletions (~1-3 Kbp), but all base transitions and transversions can also be obtained.[5]

References

[edit]
  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. 49 (49): 331–2. doi:10.1093/nass/49.1.331. PMID 17150768.
  5. ^ Kutscher, Lena M.; Shaham, Shai (2014). "Forward and reverse mutagenesis in C. elegans". WormBook: The Online Review of C. Elegans Biology: 1–26. doi:10.1895/wormbook.1.167.1. PMC 4078664. PMID 24449699. Retrieved 18 June 2021.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Trioxsalen&oldid=1081494963"