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3902-71-4

3902-71-4 | TRIOXSALEN

CAS No: 3902-71-4 Catalog No: AG003V59 MDL No:MFCD00005010

Product Description

Catalog Number:
AG003V59
Chemical Name:
TRIOXSALEN
CAS Number:
3902-71-4
Molecular Formula:
C14H12O3
Molecular Weight:
228.2433
MDL Number:
MFCD00005010
IUPAC Name:
2,5,9-trimethylfuro[3,2-g]chromen-7-one
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
InChI Key:
FMHHVULEAZTJMA-UHFFFAOYSA-N
SMILES:
Cc1cc2c(o1)c(C)c1c(c2)c(C)cc(=O)o1
EC Number:
223-459-0
UNII:
Y6UY8OV51T

Properties

Complexity:
374  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
228.079g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
228.247g/mol
Monoisotopic Mass:
228.079g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
39.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3  

Literature

Title Journal
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Identification of new scavengers for hydroxyl radicals and superoxide dismutase by utilising ultraviolet A photoreaction of 8-methoxypsoralen and a variety of mutants of Escherichia coli: implications on certain diseases of DNA repair deficiency. Journal of photochemistry and photobiology. B, Biology 20121105
Oligoarray comparative genomic hybridization-mediated mapping of suppressor mutations generated in a deletion-biased mutagenesis screen. G3 (Bethesda, Md.) 20120601
The Rac GTP exchange factor TIAM-1 acts with CDC-42 and the guidance receptor UNC-40/DCC in neuronal protrusion and axon guidance. PLoS genetics 20120401
Single/low-copy integration of transgenes in Caenorhabditis elegans using an ultraviolet trimethylpsoralen method. BMC biotechnology 20120101
Effects of furanocoumarins from apiaceous vegetables on the catalytic activity of recombinant human cytochrome P-450 1A2. The protein journal 20111001
Development of a novel furocoumarin derivative inhibiting NF-κB dependent biological functions: design, synthesis and biological effects. European journal of medicinal chemistry 20111001
Synthesis and transformations of di-endo-3-aminobicyclo-[2.2.2]oct-5-ene-2-carboxylic acid derivatives. Molecules (Basel, Switzerland) 20110907
DAF-12 regulates a connected network of genes to ensure robust developmental decisions. PLoS genetics 20110701
Trimethylangelicin reduces IL-8 transcription and potentiates CFTR function. American journal of physiology. Lung cellular and molecular physiology 20110301
Cyclin E and Cdk2 control GLD-1, the mitosis/meiosis decision, and germline stem cells in Caenorhabditis elegans. PLoS genetics 20110301
An introduction to worm lab: from culturing worms to mutagenesis. Journal of visualized experiments : JoVE 20110101
Large-scale, prospective, observational studies in patients with psoriasis and psoriatic arthritis: A systematic and critical review. BMC medical research methodology 20110101
Analysis of active and inactive X chromosome architecture reveals the independent organization of 30 nm and large-scale chromatin structures. Molecular cell 20101112
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
RACK-1 acts with Rac GTPase signaling and UNC-115/abLIM in Caenorhabditis elegans axon pathfinding and cell migration. PLoS genetics 20101101
Conserved genes act as modifiers of invertebrate SMN loss of function defects. PLoS genetics 20101001
Multivesicular body formation requires OSBP-related proteins and cholesterol. PLoS genetics 20100801
A developmental timing switch promotes axon outgrowth independent of known guidance receptors. PLoS genetics 20100801
Rapid sampling of molecules via skin for diagnostic and forensic applications. Pharmaceutical research 20100701
Whole-genome profiling of mutagenesis in Caenorhabditis elegans. Genetics 20100601
Photoallergic contact dermatitis to 8-methoxypsoralen in Ficus carica. Contact dermatitis 20100601
Two very long chain fatty acid acyl-CoA synthetase genes, acs-20 and acs-22, have roles in the cuticle surface barrier in Caenorhabditis elegans. PloS one 20100101
Topical treatment in vitiligo and the potential uses of new drug delivery systems. Indian journal of dermatology, venereology and leprology 20100101
Structural determinants of photoreactivity of triplex forming oligonucleotides conjugated to psoralens. Journal of nucleic acids 20100101
Trioxsalen derivatives with lipoxygenase inhibitory activity. Journal of enzyme inhibition and medicinal chemistry 20091201
Role of tacrolimus (FK506) 0.1% ointment WW in vitiligo in children and imperatives of combine therapy with Trioxsalen and Silymarin suspension in progressive vitiligo. Journal of the European Academy of Dermatology and Venereology : JEADV 20091001
Cancer risk in hospitalised psoriasis patients: a follow-up study in Sweden. British journal of cancer 20090505
Nematode homologue of PQBP1, a mental retardation causative gene, is involved in lipid metabolism. PloS one 20090101
Electron microscopy methods for studying in vivo DNA replication intermediates. Methods in molecular biology (Clifton, N.J.) 20090101
The germinal center kinase GCK-1 is a negative regulator of MAP kinase activation and apoptosis in the C. elegans germline. PloS one 20090101
The HLH-6 transcription factor regulates C. elegans pharyngeal gland development and function. PLoS genetics 20081001
3-Methyladenine DNA glycosylase is important for cellular resistance to psoralen interstrand cross-links. DNA repair 20080802
Application of TILLING and EcoTILLING as Reverse Genetic Approaches to Elucidate the Function of Genes in Plants and Animals. Current genomics 20080601
DNA interstrand crosslinks repair in mammalian cells. Zeitschrift fur Naturforschung. C, Journal of biosciences 20080101
An unexpectedly high degree of specialization and a widespread involvement in sterol metabolism among the C. elegans putative aminophospholipid translocases. BMC developmental biology 20080101
BINOL-amino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents. Journal of medicinal chemistry 20071227
In vivo footprint of a picornavirus internal ribosome entry site reveals differences in accessibility to specific RNA structural elements. The Journal of general virology 20071101
Food deprivation attenuates seizures through CaMKII and EAG K+ channels. PLoS genetics 20070901
German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version). Archives of dermatological research 20070601
Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjugate chemistry 20070101
Regulation of Caenorhabditis elegans body size and male tail development by the novel gene lon-8. BMC developmental biology 20070101
Specific apoptosis induction in human papillomavirus-positive cervical carcinoma cells by photodynamic antisense regulation. Oligonucleotides 20070101
Counting mutagenized genomes and optimizing genetic screens in Caenorhabditis elegans. PloS one 20070101
Synthesis and biological in vitro evaluation of novel PEG-psoralen conjugates. Biomacromolecules 20061201
Permeability of psoralen derivatives in lipid membranes. Biophysical journal 20061001
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Enhanced repair of DNA interstrand crosslinks in S phase. FEBS letters 20060306
Psoralen and coumarin photochemistry in HSA complexes and DMPC vesicles. Photochemistry and photobiology 20060101
Occupational allergic contact dermatitis disseminated from multifunctional acrylates in ultraviolet-cured lacquers. International journal of occupational medicine and environmental health 20060101
TILLING is an effective reverse genetics technique for Caenorhabditis elegans. BMC genomics 20060101
Properties of novel antisense oligonucleotides containing 2'-O-modified adenosine with a photo-reactive group. Nucleic acids symposium series (2004) 20060101
Inhibition of interferon-gamma signaling by a mercurio-substituted dihydropsoralen in murine keratinocytes. Biochemical pharmacology 20051205
Repair of DNA interstrand crosslinks may take place at the nuclear matrix. Journal of cellular biochemistry 20050901
Psoralen photocrosslinking, a tool to study the chromatin structure of RNA polymerase I--transcribed ribosomal genes. Biochemistry and cell biology = Biochimie et biologie cellulaire 20050801
Spectral study of interactions of 4,8,4'-trimethylpsoralen and 4,4'-dimethylangelicin dyes with DNA. Biochemistry. Biokhimiia 20050701
Disappearance of nucleosome positioning in mitotic chromatin in vivo. The Journal of biological chemistry 20050415
Interplay between human high mobility group protein 1 and replication protein A on psoralen-cross-linked DNA. Biochemistry 20050322
5-(3-Phenylpropoxy)psoralen and 5-(4-phenylbutoxy)psoralen: mechanistic studies on phototoxicity. Die Pharmazie 20050301
Identification of ciliated sensory neuron-expressed genes in Caenorhabditis elegans using targeted pull-down of poly(A) tails. Genome biology 20050101
Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models. Photochemistry and photobiology 20050101
Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. Nucleic acids symposium series (2004) 20050101
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 20041201
Tandem mass spectrometry for the determination of the sites of DNA interstrand cross-link. Journal of the American Society for Mass Spectrometry 20041101
Psoralen derivatives and longwave ultraviolet irradiation are active in vitro against human melanoma cell line. Journal of photochemistry and photobiology. B, Biology 20041025
Identification of chaperonin CCT gamma subunit as a determinant of retinotectal development by whole-genome subtraction cloning from zebrafish no tectal neuron mutant. Development (Cambridge, England) 20040501
Defining the function of xeroderma pigmentosum group F protein in psoralen interstrand cross-link-mediated DNA repair and mutagenesis. The Biochemical journal 20040401
Shower PUVA: a novel variant of photochemotherapy. Distribution of photosensitivity and accumulation of trioxsalen in the skin. Skin pharmacology and physiology 20040101
Randomized half-side comparison of narrowband UVB and trimethylpsoralen bath plus UVA treatments for psoriasis. Acta dermato-venereologica 20040101
Nucleosome positioning in the human c-Fos promoter analyzed by in vivo footprinting with psoralen and ionizing radiation. Biochemistry 20031230
Determination of 8-methoxypsoralen in human plasma, and microdialysates using liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20031225
Structure elucidation of DNA interstrand cross-link by a combination of nuclease P1 digestion with mass spectrometry. Analytical chemistry 20031115
Representational difference analysis, high-resolution physical mapping, and transcript identification of the zebrafish genomic region for a motor behavior. Genomics 20030801
An intraindividual comparative study of psoralen-UVA erythema induced by bath 8-methoxypsoralen and 4, 5', 8-trimethylpsoralen. Journal of the American Academy of Dermatology 20030701
Characterization of trimethylpsoralen as a mutagen for mouse embryonic stem cells. Mutation research 20030409
Isolation of null alleles of the Caenorhabditis elegans gly-12, gly-13 and gly-14 genes, all of which encode UDP-GlcNAc: alpha-3-D-mannoside beta1,2-N-acetylglucosaminyltransferase I activity. Biochimie 20030101
UDP-N-acetylglucosamine:alpha-3-D-mannoside beta-1,2-N-acetylglucosaminyltransferase I and UDP-N-acetylglucosamine:alpha-6-D-mannoside beta-1,2-N-acetylglucosaminyltransferase II in Caenorhabditis elegans. Biochimica et biophysica acta 20021219
Binding affinities of commonly employed sensitizers of viral inactivation. Photochemistry and photobiology 20020601
Amino acids in SRS1 and SRS6 are critical for furanocoumarin metabolism by CYP6B1v1, a cytochrome P450 monooxygenase. Insect molecular biology 20020401
Cell-impermeant pyridinium derivatives of psoralens as inhibitors of keratinocyte growth. Biochemical pharmacology 20020101
Trioxsalen in the presence of UVA is able to induce nuclear factor kappa B binding activity in HaCaT keratinocytes. Skin pharmacology and applied skin physiology 20020101
[Application of gauze with metallic inclusions for the treatment of purulent wounds]. Klinichna khirurhiia 20020101
The 4N cell cycle delay in Fanconi anemia reflects growth arrest in late S phase. Molecular genetics and metabolism 20011201
The crystal structures of psoralen cross-linked DNAs: drug-dependent formation of Holliday junctions. Journal of molecular biology 20010420
Mapping psoralen cross-links at the nucleotide level in mammalian cells: suppression of cross-linking at transcription factor- or nucleosome-binding sites. Biochemistry 20010403
Photodynamic antisense regulation of human cervical carcinoma cell growth using psoralen-conjugated oligo(nucleoside phosphorothioate). European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20010401
Concentration-dependent phototoxicity in trimethylpsoralen bath psoralen ultraviolet A. The British journal of dermatology 20010301
The effects of singlet oxygen produced by photodynamic action on the mitochondrial permeability transition differ in accordance with the localization of the sensitizer. Archives of biochemistry and biophysics 20010215
Zygotic expression of the caudal homolog pal-1 is required for posterior patterning in Caenorhabditis elegans embryogenesis. Developmental biology 20010101
Yeast U1 snRNP-pre-mRNA complex formation without U1snRNA-pre-mRNA base pairing. RNA (New York, N.Y.) 20010101
Furanocoumarins in celery and parsnips: method and multiyear Canadian survey. Journal of AOAC International 20010101
Kinetics of phototoxicity in trioxysalen bath psoralen plus ultraviolet A photochemotherapy. Acta dermato-venereologica 20010101
Can a mixed damage interfere with DNA-protein cross-links repair? Journal of cellular and molecular medicine 20010101
Reverse genetics by chemical mutagenesis in Caenorhabditis elegans. Nature genetics 19970901
The effect of etretinate compared with different regimens of PUVA in the treatment of persistent palmoplantar pustulosis. The British journal of dermatology 19850401
Letter: Suntanned Hallucinations. The American journal of psychiatry 19750701

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