CAS 3902-71-4|trioxsalen|2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one|trioxysalen|trisoralen|Trioxsalen|trimethylpsoralen|Trioxsalen|2,5,9-三甲基呋[3,2-g]苯并吡喃-7-酮|三甲沙林|三甲补骨脂内酯|4,5′,8-...

基本信息

化学结构

分子式

C₁₄H₁₂O₃

分子量

228.24328

精确质量

228.07864424

电荷

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

InChIKey

FMHHVULEAZTJMA-UHFFFAOYSA-N

Canonic Smiles

Cc1cc2c(o1)c(C)c1c(c2)c(C)cc(=O)o1

Isomeric Smiles

Cc1cc(=O)oc2c1cc1cc(oc1c2C)C

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

2.9548604

LogD (pH = 7.4)

2.9548604

Log P

2.9548604

摩尔折射率

64.8626

极化性

25.444344

极化表面积

39.44

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

3.26

LOG S

-3.56

溶解度

6.27e-02 g/l

数据来源

名称和标识

IUPAC传统名

trioxsalen 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

IUPAC标准名

2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

别名

trioxysalentrisoralenTrioxsalentrimethylpsoralenTrioxsalen2,5,9-三甲基呋[3,2-g]苯并吡喃-7-酮三甲沙林三甲补骨脂内酯4,5′,8-三甲基补骨脂素TMPTrioxsalen2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one4,5',8-TRIMETHYLPSORALEN4,5′,8-Trimethylpsoralen2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-oneLevrison4,5',8-TrimethylpsoralenDermetrixTrioxysalenTripsos

名称和标识

数据登录号

EC号

MDL号

CAS号

Beilstein号

PubChem SID

2488964424900351160967571

PubChem CID

DrugBank ID

ATC码

Chemspider ID

CHEBI ID

CHEMBL

维基百科标题

美国药典/FDA物质标识码

KEGG ID

数据登录号

化合物性质

安全信息

-20°C

Room Temperature (15-30°C), Protect from light

S:26-27/28-36/37/39-46-64

理化性质

229-231 °C(lit.)

233-235 °C

229 - 231°C

λex 321 nm; λem 445 nm (bound to DNA in Tris, pH 8.1)

λex 269 nm; λem 445 nm in methanol

λex 321 nm; λem 445 nm in 10 mM Tris; 1 mM EDTA; pH 8.0; DNA

药理学性质

Action depends on the presence of functional melanocytes and their proliferation by photoactivated drug

Exact mechanism with epidermal melanocytes and keratinocytes unknown.

Conjugates and forms covalent-bonds with DNA which leads to the formation of both monofunctional and bifunctional adducts upon photoactivation

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

Selleck Chemicals

S2022

Research Area: Immunology
Biological Activity:
Trioxsalen(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 and hand eczema. 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. 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. [1]

MP Biomedicals

02154157

Potent photosensitizing agent; rapid and sensitive assay for interstrand DNA cross links: Biochemistry, 20: 143, (1981).

DrugBank

DB04571

Drug Groups

approved

Description

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.

Indication

Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.

Pharmacology

Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.

References

• van Coevorden AM, Kamphof WG, van Sonderen E, Bruynzeel DP, Coenraads PJ: 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. Arch Dermatol. 2004 Dec;140(12):1463-6. [Pubmed]

• Thazhathveetil AK, Liu ST, Indig FE, Seidman MM: Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7. [Pubmed]

• Higuchi M, Yamayoshi A, Kobori A, Yamaoka T, Murakami A: Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. Nucleic Acids Symp Ser (Oxf). 2005;(49):331-2. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

Wikipedia

Trioxsalen

Sigma Aldrich

T6137

包装
1 g in glass bottle
100, 500 mg in glass bottle
Biochem/physiol Actions
DNA 的光化学交联剂，可作为探针用于核酸结构和功能研究。三甲沙林也用于使 DNA 在云母表面交联。

861391

Biochem/physiol Actions
DNA 的光化学交联剂，可作为探针用于核酸结构和功能研究。三甲沙林也用于使 DNA 在云母表面交联。

92895

Biochem/physiol Actions
DNA 的光化学交联剂，可作为探针用于核酸结构和功能研究。三甲沙林也用于使 DNA 在云母表面交联。

描述信息

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Trioxsalen

• Thompson, H.J. et al., J. Chromatogr., 1984, 314, 323, (hplc)

• Hassan, M.A., Anal. Profiles Drug Subst., 1981, 10, 705, (rev)

• Elgamal, M.H.A. et al., Phytochemistry, 1979, 18, 139, (cmr)

• Gencheva, M. et al., J. Biol. Chem., 1996, 271, 2608, (pharmacol)

• Caporale, G. et al., Experientia, 1967, 23, 985, (pharmacol)

• Bender, D.R. et al., J.O.C., 1979, 44, 2176, (synth)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1098

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 684C, (ir)

• Dimitrova, D. et al., Nucleic Acids Res., 1993, 21, 5554, (pharmacol)

• Scheel, L.D. et al., Biochemistry, 1963, 2, 1127, (isol)

• Taskineu, J. et al., Biomed. Mass Spectrom., 1980, 7, 556, (ms)

• Russev, G. et al., J. Mol. Biol., 1982, 161, 77, (pharmacol)

• Nivsarkar, M. et al., Biochem. Mol. Biol. Int., 1996, 38, 625, (pharmacol)

• Kaufman, K.D., J.O.C., 1961, 26, 117; 1980, 45, 738, (synth, uv)

• IARC Monog., 1986, 40, 357; Suppl. 7, 366; Suppl. 6, 541, (rev, tox)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC传统名

trioxsalen 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

IUPAC标准名

2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

别名

数据登录号

EC号

MDL号

CAS号

Beilstein号

PubChem SID

2488964424900351160967571

PubChem CID

DrugBank ID

ATC码

Chemspider ID

CHEBI ID

CHEMBL

维基百科标题

美国药典/FDA物质标识码

KEGG ID

描述信息

S2022

Potent photosensitizing agent; rapid and sensitive assay for interstrand DNA cross links: Biochemistry, 20: 143, (1981).

DrugBank

DB04571

Drug Groups

approved

Description

Indication

Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.

Pharmacology

Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.

References

External Links

• [Wikipedia]

• [Drugs.com]

Wikipedia

Trioxsalen

Sigma Aldrich

T6137

861391

Biochem/physiol Actions
DNA 的光化学交联剂，可作为探针用于核酸结构和功能研究。三甲沙林也用于使 DNA 在云母表面交联。

92895

Biochem/physiol Actions
DNA 的光化学交联剂，可作为探针用于核酸结构和功能研究。三甲沙林也用于使 DNA 在云母表面交联。