trioxsalen

Summary

Summary: Pigmenting photosensitizing agent obtained from several plants, mainly Psoralea corylifolia. It is administered either topically or orally in conjunction with ultraviolet light in the treatment of vitiligo.

Top Publications

  1. Gengyo Ando K, Mitani S. Characterization of mutations induced by ethyl methanesulfonate, UV, and trimethylpsoralen in the nematode Caenorhabditis elegans. Biochem Biophys Res Commun. 2000;269:64-9 pubmed
    ..As a pilot experiment, we could isolate actual deletion mutations at a much higher frequency than previously. ..
  2. Ljungman M, Hanawalt P. Localized torsional tension in the DNA of human cells. Proc Natl Acad Sci U S A. 1992;89:6055-9 pubmed
    ..These results document an intragenomic heterogeneity of DNA torsional tension and lend support to the twin supercoiled domain model for transcription in the genome of intact human cells. ..
  3. Calvet J, Myers J. In-vivo secondary structure analysis of the small nuclear RNA U1 using psoralen cross-linking. J Mol Biol. 1987;197:543-53 pubmed
    ..Efficient psoralen-adduct formation, which resulted in cross-linking at the U96-U116 site and monoaddition on U45, suggests that these regions are relatively accessible in the native U1 small nuclear ribonucleoprotein particle in vivo. ..
  4. Yandell M, Edgar L, Wood W. Trimethylpsoralen induces small deletion mutations in Caenorhabditis elegans. Proc Natl Acad Sci U S A. 1994;91:1381-5 pubmed
    ..TMP should be useful in generating mutations that cause complete loss of function of single genes and that are likely to result in allele-specific DNA polymorphisms. ..
  5. Toussaint M, Levasseur G, Tremblay M, Paquette M, Conconi A. Psoralen photocrosslinking, a tool to study the chromatin structure of RNA polymerase I--transcribed ribosomal genes. Biochem Cell Biol. 2005;83:449-59 pubmed
    ..In this review we focused on the studies of chromatin in ribosomal genes and how these results have helped to address the fundamental question: What is the structure of chromatin in the coding regions of genes? ..
  6. Vasquez K, Wensel T, Hogan M, Wilson J. High-efficiency triple-helix-mediated photo-cross-linking at a targeted site within a selectable mammalian gene. Biochemistry. 1996;35:10712-9 pubmed
    ..These results indicate that psorTFO1 allows for DNA damage with high precision and high efficiency, and the likely proportion of monoadducts and cross-links can be estimated from the target sequence. ..
  7. Conconi A, Widmer R, Koller T, Sogo J. Two different chromatin structures coexist in ribosomal RNA genes throughout the cell cycle. Cell. 1989;57:753-61 pubmed
    ..This suggests that the two states of chromatin are maintained independently of the transcriptional process and that they are stably propagated through the cell cycle. ..
  8. Jansen G, Hazendonk E, Thijssen K, Plasterk R. Reverse genetics by chemical mutagenesis in Caenorhabditis elegans. Nat Genet. 1997;17:119-21 pubmed
    ..Any sequenced gene in any organism that can be handled in very large numbers can possibly be targeted in this way. ..
  9. Wellinger R, Sogo J. In vivo mapping of nucleosomes using psoralen-DNA crosslinking and primer extension. Nucleic Acids Res. 1998;26:1544-5 pubmed
    ..By the use of psoralen crosslinking and primer extension, a method was developed which allows the analysis of chromatin structure in vivo. Using a yeast minichromosome, >9 nucleosomes were mapped with a resolution of at least +/-30 bp. ..

More Information

Publications62

  1. Reddy M, Christensen J, Vasquez K. Interplay between human high mobility group protein 1 and replication protein A on psoralen-cross-linked DNA. Biochemistry. 2005;44:4188-95 pubmed
    ..The abundance of HMGB1 suggests that it may play an important role in determining the sensitivity of cells to DNA damage under physiological, experimental, and therapeutic conditions. ..
  2. Shi Y, Hearst J. Wavelength dependence for the photoreactions of DNA-psoralen monoadducts. 2. Photo-cross-linking of monoadducts. Biochemistry. 1987;26:3792-8 pubmed
    ..At wavelengths above 313 nm, photoreversal of the monoadduct could not be detected, and photo-cross-linking occurred efficiently with a quantum yield of 2.4 X 10(-2). ..
  3. Sastry S, Hearst J. Studies on the interaction of T7 RNA polymerase with a DNA template containing a site-specifically placed psoralen cross-link. I. Characterization of elongation complexes. J Mol Biol. 1991;221:1091-110 pubmed
    ..Heparin caused the quantitative release of 36 (+1) RNA nucleotides within 30 seconds, but the DNA was not simultaneously released from the elongation complex under these conditions. ..
  4. Sladek F, Melian A, Howard Flanders P. Incision by UvrABC excinuclease is a step in the path to mutagenesis by psoralen crosslinks in Escherichia coli. Proc Natl Acad Sci U S A. 1989;86:3982-6 pubmed
    ..Since crosslinks were estimated to be responsible for most of the mutations observed, we conclude that the premutagenic lesion of psoralen crosslinks is recombinagenic and therefore very likely to be the product of UvrABC incision. ..
  5. Akkari Y, Bateman R, Reifsteck C, D Andrea A, Olson S, Grompe M. The 4N cell cycle delay in Fanconi anemia reflects growth arrest in late S phase. Mol Genet Metab. 2001;74:403-12 pubmed
    ..These results indicate that the FA pathway is required for the efficient resolution of ICL-induced S-phase arrest. ..
  6. Kiec Swierczynska M, Krecisz B, Swierczynska Machura D. Occupational allergic contact dermatitis disseminated from multifunctional acrylates in ultraviolet-cured lacquers. Int J Occup Med Environ Health. 2006;19:77-8 pubmed
    ..The patient showed disseminated dermatitis, however, no hypertrophied lesions on the hand skin, a characteristic symptom in persons exposed to acrylates, were observed. ..
  7. Averbeck D, Papadopoulo D, Moustacchi E. Repair of 4,5',8-trimethylpsoralen plus light-induced DNA damage in normal and Fanconi's anemia cell lines. Cancer Res. 1988;48:2015-20 pubmed
    ..Incision of CL being progressively diminished by increasing amounts of MA in normal cells (D. Papadopoulo, D. Averbeck, and E. Moustacchi, Photochem. Photobiol., 47:321-326, 1988), we show here that it is even more so for FA cells. ..
  8. Thomas D, Svoboda D, Vos J, Kunkel T. Strand specificity of mutagenic bypass replication of DNA containing psoralen monoadducts in a human cell extract. Mol Cell Biol. 1996;16:2537-44 pubmed
    ..A model is proposed based on the preferential loopout of the monoadducted base from the strand that templates retrograde discontinuous synthesis. ..
  9. Teare J, Wollenzien P. Structures of human and rabbit beta-globin precursor messenger RNAs in solution. Biochemistry. 1989;28:6208-19 pubmed
    ..Furthermore, given the absence of strongly conserved structures, it is unlikely that there could be any strict requirements for secondary structures that influence splice site usage. ..
  10. Botta R, Gustavino B. Relationship between chromatin bridges in anaphase and chromosomal aberrations induced by TMP + UVA (365 nm) in CHO cells. Mutat Res. 1997;374:253-9 pubmed
    ..Moreover TMP + 365 nm UVA treatment shows an S-dependent clastogenic effect. The proposed hypothesis of 'conservative pairing' between DNA strands of sister chromatids is further supported. ..
  11. Kumaresan K, Lambert M. Fanconi anemia, complementation group A, cells are defective in ability to produce incisions at sites of psoralen interstrand cross-links. Carcinogenesis. 2000;21:741-51 pubmed
  12. Moroff G, Wagner S, Benade L, Dodd R. Factors influencing virus inactivation and retention of platelet properties following treatment with aminomethyltrimethylpsoralen and ultraviolet A light. Blood Cells. 1992;18:43-54; discussion 54-6 pubmed
    ..8 J/cm2. Our studies have identified two sets of conditions that provide about 5 logs of virus inactivation without extensively altering platelet in vitro properties. ..
  13. Wang Y, Zhang Q, Wang Y. Tandem mass spectrometry for the determination of the sites of DNA interstrand cross-link. J Am Soc Mass Spectrom. 2004;15:1565-71 pubmed
  14. Park Y, Hann S, Im S, Kim S. Skin concentration of 8-methoxypsoralen, 5-methoxypsoralen and 4,5,8-trimethylpsoralen in guinea pigs. J Dermatol Sci. 1993;5:19-24 pubmed
    ..5 h, with the level of 8-MOP approximately 1.3 times higher than that of 5-MOP. The level of TMP could not be measured even in the case of intraperitoneal injection. ..
  15. Guillouf C, Laquerbe A, Moustacchi E, Papadopoulo D. Mutagenic processing of psoralen monoadducts differ in normal and Fanconi anemia cells. Mutagenesis. 1993;8:355-61 pubmed
    ..Great similarities were found between normal and FA cells with respect to the nature and location of point mutation at the HPRT gene; the high proneness to deletions remains one of the major instability features of FA. ..
  16. Smith J, Boeke J. An unusual form of transcriptional silencing in yeast ribosomal DNA. Genes Dev. 1997;11:241-54 pubmed
    ..Deletion of SIR2 resulted in increased psoralen cross-linking of the rDNA in vivo, suggesting that a specific chromatin structure in rDNA down-regulates polymerase II promoters. ..
  17. Vos J, Hanawalt P. DNA interstrand cross-links promote chromosomal integration of a selected gene in human cells. Mol Cell Biol. 1989;9:2897-905 pubmed
  18. Hurt D, Winestock K, O Connor M, Johnston M. Antibody-nucleic acid interactions. Antibodies to psoralen-modified RNA as probes of RNA structure. Nucleic Acids Res. 1987;15:9057-73 pubmed
    Antisera elicited by immunization of rabbits with 4'-aminomethyl-trioxsalen (AMT)-modified poly(A,U) complexed with methylated bovine serum albumin was characterized in competition radioimmunoassays (RIA) and enzyme-linked immunosorbent ..
  19. Dardare N, Platz M. Binding affinities of commonly employed sensitizers of viral inactivation. Photochem Photobiol. 2002;75:561-4 pubmed
  20. Piette J. Molecular analysis of mutations induced by 4'-hydroxymethyl-4,5',8-trimethylpsoralen and UVA in the mouse HPRT gene. J Photochem Photobiol B. 1992;12:37-55 pubmed
    ..Using polymerase chain reaction (PCR) amplification and agarose gel electrophoresis, deletions in the HPRT promoter have been observed and correlated to deficient enzyme expression. ..
  21. Wang Y, Wang Y. Structure elucidation of DNA interstrand cross-link by a combination of nuclease P1 digestion with mass spectrometry. Anal Chem. 2003;75:6306-13 pubmed
    ..We believe that the method described in this paper can be generally applicable for investigating the structures of other DNA ICLs. ..
  22. Keane T, Petros J, Velimirovich B, Yue K, Graham S. Methoxypsoralen phototherapy of transitional cell carcinoma. Urology. 1994;44:842-6 pubmed
    ..This therapy may prove to be effective in clinical early stage transitional cell carcinoma and warrants further assessment. ..
  23. Christensen L, Wang H, Van Houten B, Vasquez K. Efficient processing of TFO-directed psoralen DNA interstrand crosslinks by the UvrABC nuclease. Nucleic Acids Res. 2008;36:7136-45 pubmed publisher
    ..As mutagenesis by TFO-directed ICLs requires nucleotide excision repair, the efficient processing of these lesions supports the use of triplex technology to direct DNA damage for genome modification. ..
  24. Lee B, Blake K, Miller P. Interaction of psoralen-derivatized oligodeoxyribonucleoside methylphosphonates with synthetic DNA containing a promoter for T7 RNA polymerase. Nucleic Acids Res. 1988;16:10681-97 pubmed
    ..Oligomers did not crosslink to ds-DNA undergoing transcription nor did they inhibit the transcription reaction. ..
  25. Kitayama S, Kohoroku M, Takagi A, Itoh H. Mutation of D. radiodurans in a gene homologous to ruvB of E. coli. Mutat Res. 1997;385:151-7 pubmed
    ..coli homologue. The mutant was transformed with exogenous DNA at the same rate as the wild-type cells, but it was moderately sensitive to UV, gamma-rays and to interstrand cross-linking reagents...
  26. Papadopoulo D, Porfirio B, Moustacchi E. Mutagenic response of Fanconi's anemia cells from a defined complementation group after treatment with photoactivated bifunctional psoralens. Cancer Res. 1990;50:3289-94 pubmed
    ..It is suggested that the chromosomal instability characteristic of Fanconi's anemia is responsible for the cancer proneness rather than the mutability at the gene level. ..
  27. Shlyakhtenko L, Gall A, Weimer J, Hawn D, Lyubchenko Y. Atomic force microscopy imaging of DNA covalently immobilized on a functionalized mica substrate. Biophys J. 1999;77:568-76 pubmed
    ..This suggests that UV cross-linking does not induce formation of a noticeable number of single-stranded breaks in DNA molecules. ..
  28. Groene W, Shaw R. Psoralen preparation of antigenically intact noninfectious rotavirus particles. J Virol Methods. 1992;38:93-102 pubmed
    ..The lack of viral replication following inactivation was determined with an immunohistochemical focus assay. The antigenic authenticity of the particles was determined by monoclonal antibody ELISA and a viral hemagglutination assay. ..
  29. al Aboosi M, Ajam Z. Oral photochemotherapy in vitiligo: follow-up, patient compliance. Int J Dermatol. 1995;34:206-8 pubmed
    ..The scoring system is a simple practical measure applicable to patients that proved eventually to be very useful for providing more effective treatment and a good response. ..
  30. Yamayoshi A, Kato K, Suga S, Ichinoe A, Arima T, Matsuda T, et al. Specific apoptosis induction in human papillomavirus-positive cervical carcinoma cells by photodynamic antisense regulation. Oligonucleotides. 2007;17:66-79 pubmed
    ..These results suggest that the photodynamic antisense strategy has the great therapeutic potential in HPV-positive cervical cancers. ..
  31. Oroskar A, Lambert C, Peak M. Effects of hydroxyl radical scavengers on relaxation of supercoiled DNA by aminomethyl-trimethyl-psoralen and monochromatic UVA photons. Free Radic Biol Med. 1996;20:751-6 pubmed
  32. Nivsarkar M, Desai A, Mokal R. Free radical induced biophysical modification of membrane lipids: a novel mechanism proposed for a haemorheological alteration induced by 4,5' 8-trimethyl psoralen. Biochem Mol Biol Int. 1996;38:625-33 pubmed
  33. Kodadek T, Gamper H. Efficient synthesis of a supercoiled M13 DNA molecule containing a site specifically placed psoralen adduct and its use as a substrate for DNA replication. Biochemistry. 1988;27:3210-5 pubmed
  34. Tamanini A, Borgatti M, Finotti A, Piccagli L, Bezzerri V, Favia M, et al. Trimethylangelicin reduces IL-8 transcription and potentiates CFTR function. Am J Physiol Lung Cell Mol Physiol. 2011;300:L380-90 pubmed publisher
    ..In conclusion, TMA is a dual-acting compound reducing excessive IL-8 expression and potentiating CFTR function. ..
  35. Chen J, Berenbaum M, Schuler M. Amino acids in SRS1 and SRS6 are critical for furanocoumarin metabolism by CYP6B1v1, a cytochrome P450 monooxygenase. Insect Mol Biol. 2002;11:175-86 pubmed
    ..Conservation of Phe116 and His117 in an array of lepidopteran CYP6B proteins implies that these amino acids serve a similar function in other monooxygenases of the insect CYP6B subfamily. ..
  36. Wilson D, Rieckher M, Williams A, Schumacher B. Systematic analysis of DNA crosslink repair pathways during development and aging in Caenorhabditis elegans. Nucleic Acids Res. 2017;45:9467-9480 pubmed publisher
    ..elegans mutants, we identify DNA repair factors that protect against the genotoxicity of ICLs generated by trioxsalen/ultraviolet A (TMP/UVA) during development and aging...
  37. Mojica F, Higgins C. Localized domains of DNA supercoiling: topological coupling between promoters. Mol Microbiol. 1996;22:919-28 pubmed
  38. Raha M, Wang G, Seidman M, Glazer P. Mutagenesis by third-strand-directed psoralen adducts in repair-deficient human cells: high frequency and altered spectrum in a xeroderma pigmentosum variant. Proc Natl Acad Sci U S A. 1996;93:2941-6 pubmed
    ..These results may help to elucidate the repair deficiency in XPV, and they raise the possibility that genetic manipulation via triplex-targeted mutagenesis may be enhanced by modulation of the XPV-associated activity in normal cells. ..
  39. Carlin A, Simmons J, el Arini S, Shiu G. Determination of khellin in serum by gas chromatography. J Chromatogr. 1993;614:324-7 pubmed
    ..Using a DB-17 capillary column and a simple chloroform extraction, khellin and an internal standard, trioxsalen, were separated from endogenous substances without further clean-up. Spiked serum samples in the range 0.11-1...
  40. Toth K, Csik G, Ronto G. Dark and photoreactivity of 4'-aminomethyl-4,5',8-trimethylpsoralen with T7 phage. J Photochem Photobiol B. 1990;5:167-78 pubmed
    ..Mono- and di-adducts influence DNA stability differently; biologically both types of adducts are genotoxic as measured by action spectra...
  41. Inadomi T, Ross P. Effects of nuclear isolation on psoralen affinity for chromatin. Biochem Biophys Res Commun. 1989;163:1384-9 pubmed
    ..However, in nuclei, as in purified DNA, both sequences were just as sensitive as total DNA. Apparently, chromatin in cells exists within diverse TMP-binding environments and some of this diversity was lost upon nuclear isolation. ..
  42. Gamper H, Cimino G, Hearst J. Solution hybridization of crosslinkable DNA oligonucleotides to bacteriophage M13 DNA. Effect of secondary structure on hybridization kinetics and equilibria. J Mol Biol. 1987;197:349-62 pubmed
    ..Using crosslinkable oligonucleotide probes hybridized and irradiated near the melting temperature of the respective probe-target complex one can partially overcome these secondary structure effects. ..
  43. Vassilev L, Russev G. Kinetics of replicon initiation during S phase of Chinese hamster ovary cells. Biochim Biophys Acta. 1988;949:138-42 pubmed
    ..At different times after release from the block, cells were treated with trioxsalen and long-wavelength ultraviolet light to crosslink DNA in vivo and were labelled with [3H]thymidine for 30 min...
  44. Chu Y, Wollenzien P, Cantor C. Use of psoralen monoadducts to compare the structure of 16S rRNA in active and inactive 30S ribosomal subunits. J Biomol Struct Dyn. 1983;1:647-56 pubmed
  45. Sanchez Ruderisch H, Aryee Boi J, Schwarz C, Radenhausen M, Tebbe B. Shower PUVA: a novel variant of photochemotherapy. Distribution of photosensitivity and accumulation of trioxsalen in the skin. Skin Pharmacol Physiol. 2004;17:129-32 pubmed
    Shower PUVA is a new variant of photochemotherapy suitable for therapy of various skin disorders. Psoralen, e.g. trioxsalen-containing water recirculates in a closed shower system and wets the skin continuously...
  46. Fengquin X, Nielsen H, Zhen W, Nielsen P. 8-Methoxypsoralen DNA interstrand cross-linking of the ribosomal RNA genes in Tetrahymena thermophila. Distribution, repair and effect on rRNA synthesis. Photochem Photobiol. 1993;58:238-45 pubmed
    ..The majority of the cells also go through one to two cell divisions in this period but do not survive. ..
  47. Bermúdez I, García Martínez J, Pérez Ortín J, Roca J. A method for genome-wide analysis of DNA helical tension by means of psoralen-DNA photobinding. Nucleic Acids Res. 2010;38:e182 pubmed publisher
    ..Genome-wide analysis of psoralen-DNA PB can be, therefore, a useful approach to uncover a trait of the chromosome architecture not amenable to other techniques. ..
  48. Snellman E, Rantanen T. Concentration-dependent phototoxicity in trimethylpsoralen bath psoralen ultraviolet A. Br J Dermatol. 2001;144:490-4 pubmed
    ..6-fold. With regard to the safety and practicality of the TMP bath PUVA, the lower concentrations of TMP may be of clinical importance, and this needs to be validated in future controlled clinical trials. ..
  49. Weightman S, Banks M. Photochemical inactivation of recombinant baculovirus. J Virol Methods. 1999;81:179-82 pubmed
    ..The photochemical inactivation method proved simple, rapid and effective with minimal loss of biological activity in a recombinant protein subsequently used in an ELISA. ..
  50. Benade L, Shumaker J, Xu Y, Chen X, Dodd R. Inactivation of free and cell-associated human immunodeficiency virus in platelet suspensions by aminomethyltrimethylpsoralen and ultraviolet light. Transfusion. 1994;34:680-4 pubmed
    ..2 J per cm2 of UVA (with 40 micrograms/mL AMT) exposure. These data suggest that AMT and UVA is an effective antiviral treatment for free and cell-associated HIV in platelet suspensions. ..
  51. Wagner S, White R, Wolf L, Chapman J, Robinette D, Lawlor T, et al. Determination of residual 4'-aminomethyl-4,5',8-trimethylpsoralen and mutagenicity testing following psoralen plus UVA treatment of platelet suspensions. Photochem Photobiol. 1993;57:819-24 pubmed
    ..6 J/cm2 UVA irradiation, and 8 to 10% of total AMT was associated with saline-washed irradiated platelets and is presumably tightly bound.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  52. Man I, McKinlay J, Dawe R, Ferguson J, Ibbotson S. An intraindividual comparative study of psoralen-UVA erythema induced by bath 8-methoxypsoralen and 4, 5', 8-trimethylpsoralen. J Am Acad Dermatol. 2003;49:59-64 pubmed
    ..In view of the steeper dose-response curve for TMP PUVA, a lower UVA incremental regimen should be considered compared with that for 8-MOP PUVA. ..
  53. Faergemann J, Larko O. Phototoxicity of skin microorganisms tested with a new model. Arch Dermatol Res. 1988;280:168-70 pubmed
    ..The growth inhibition was markedly enhanced after UVA irradiation, indicating phototoxicity. The phototoxic effect of P. orbiculare may play a role in the ecology of the human skin flora. ..