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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/17 03:45:54」(JST)
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Trioxsalen
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| Names |
| IUPAC name
2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
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| Identifiers |
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CAS Number
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3902-71-4 N |
| ChEBI |
CHEBI:28329 Y |
| ChEMBL |
ChEMBL1475 Y |
| ChemSpider |
5383 Y |
| DrugBank |
DB04571 Y |
| Jmol interactive 3D |
Image |
| KEGG |
D01034 Y |
| PubChem |
5585 |
| UNII |
Y6UY8OV51T Y |
InChI
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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
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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
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SMILES
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O=C/3Oc2c(c1oc(cc1cc2\C(=C\3)C)C)C
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| Properties |
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Chemical formula
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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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| N verify (what is YN ?) |
| Infobox references |
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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
- ^ "Trioxsalen - Compound Summary". PubChem.
- ^ 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.
- ^ 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.
- ^ 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.
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Drugs used for psoriasis (D05)
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| Topical |
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Tars
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Antracens
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Psoralens
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Other
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- Fumaric acid
- vitamin D (Calcipotriol
- Calcipotriol/betamethasone
- Calcitriol
- Tacalcitol)
- Tazarotene
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| Systemic |
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Psoralens
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- Trioxysalen
- Methoxsalen
- Bergapten
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Retinoids
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Index of skin
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| Description |
- Anatomy
- Physiology
- Development
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| Disease |
- Infections
- Vesiculobullous
- Dermatitis and eczema
- Papulosquamous
- Urticaria and erythema
- Radiation-related
- Pigmentation
- Mucinoses
- Keratosis, ulcer, atrophy, and necrobiosis
- Vasculitis
- Fat
- Neutrophilic and eosinophilic
- Congenital
- Neoplasms and cancer
- nevi and melanomas
- epidermis
- dermis
- Symptoms and signs
- Terminology
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| Treatment |
- Procedures
- Drugs
- antibiotics
- disinfectants
- emollients and protectives
- itch
- psoriasis
- other
- Wound and ulcer
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Types of coumarins
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| Aglycones |
- Aesculetin
- Ferujol
- Umbelliferone
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O-Methylated
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- Fraxetin
- Herniarin (7-O-Methylumbelliferone)
- Osthol
- Scopoletin (6-Methoxyumbelliferone)
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| glycosides |
- Aesculin (Esculetin 6-O-glucoside)
- Fraxin (Fraxetin glucoside)
- Skimmin (Umbelliferone 7-O-glucoside)
- Scopolin
- Umbelliferone 7-apiosylglucoside
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| derivatives |
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Furanocoumarins
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Aglycones
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- Angelicin
- Marmesin
- Psoralen
- Vaginol
- Xanthotoxol (8-Hydroxypsoralen)
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O-Methylated
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- Bergapten (5-methoxypsoralen)
- Isopimpinellin (5,8-Dimethoxypsoralene)
- Methoxsalen (8-Methoxypsoralen)
- Trioxsalen (2,5,9-Trimethylpsoralen)
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Furanocoumarin glycosides
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- Apterin (vaginol glucoside)
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Meroterpene furanocoumarin ether
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- Auraptene
- Bergamottin
- Imperatorin
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| Oligomers |
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| Synthetic |
- Acenocoumarol
- Coumatetralyl
- Ensaculin
- Ethyl biscoumacetate
- 4-Hydroxycoumarins
- Hymecromone
- Phenprocoumon
- Warfarin
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UpToDate Contents
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English Journal
- CSB interacts with SNM1A and promotes DNA interstrand crosslink processing.
- Iyama T1, Lee SY2, Berquist BR3, Gileadi O4, Bohr VA1, Seidman MM1, McHugh PJ2, Wilson DM 3rd5.
- Nucleic acids research.Nucleic Acids Res.2015 Jan;43(1):247-58. doi: 10.1093/nar/gku1279. Epub 2014 Dec 10.
- Cockayne syndrome (CS) is a premature aging disorder characterized by photosensitivity, impaired development and multisystem progressive degeneration, and consists of two strict complementation groups, A and B. Using a yeast two-hybrid approach, we identified the 5'-3' exonuclease SNM1A as one of fo
- PMID 25505141
- Detecting RNA-RNA interactions using psoralen derivatives.
- Nilsen TW.
- Cold Spring Harbor protocols.Cold Spring Harb Protoc.2014 Sep 2;2014(9):996-1000. doi: 10.1101/pdb.prot080861.
- Psoralens are tricyclic compounds that intercalate into double-stranded DNA or RNA and, on irradiation with long-wavelength (365-nm) UV light, covalently link pyrimidines on adjacent strands. More rarely, psoralen cross-links can be observed at the ends of helices (i.e., double-stranded-single-stran
- PMID 25183819
- Methods for single/low-copy integration by ultraviolet and trimethylpsoralen treatment in Caenorhabditis elegans.
- Kage-Nakadai E1, Imae R2, Yoshina S3, Mitani S4.
- Methods (San Diego, Calif.).Methods.2014 Aug 1;68(3):397-402. doi: 10.1016/j.ymeth.2014.02.036. Epub 2014 Mar 12.
- Single/low-copy transgene integration is essential for avoiding overexpression, ectopic expression and gene silencing in the germline. Here, we present an overview of a method that uses ultraviolet and trimethylpsoralen (UV/TMP) to generate single/low-copy gene integrations in Caenorhabditis elegans
- PMID 24613935
Japanese Journal
- Crystal Structure of a Potent Pigmentation Agent Trioxsalen
- Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 14(4), 871-872, 1998-08-10
- NAID 10002416874
- Crystal Structure of a Potent Pigmentation Agent Trioxsalen.
- Comparison of the carcinogenic potential of trioxsalen bath PUVA and oral methoxsalen PUVA. A preliminary report
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トリオキシサレン
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