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Chemical Compound Review

lawsonin     4-hydroxynaphthalene-1,2-dione

Synonyms: Lawsone, Mehendi, Lawson, Henna, Mendi, ...
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Disease relevance of Lawson


Psychiatry related information on Lawson

  • Throughout the year, the women were evaluated by means of the Eysenck Personality Inventory, the Profile of Mood States, the Lawson Morale Scale, and various self-perception items [6].
  • Finally, each group identified above was analysed for fit to the Lawson & Inglis (1985) principal components model of learning disability [7].
  • Replicating similar identification studies in which brief, masked pictures (Lawson & Jolicoeur, 1998) were presented, disorientation reduced the efficiency of recognition [8].

High impact information on Lawson

  • We have purified the transformation and shape change sensitive isoform of an actin associated polypeptide doublet previously described by us (Shapland, C., P. Lowings, and D. Lawson. 1988. J. Cell Biol. 107:153-161) and have shown that it is evolutionarily conserved as far back as yeast [9].
  • In this study I describe the ultrastructural distribution of epinemin (Lawson, D., 1983, J. Cell Biol., 97:1891-1905) in antibody-labelled, helium-cooled, quick-frozen, deep-etched cytoskeletons [10].
  • The degree of substitution was estimated to average 4.8 glycans per repeat, which compares to 2.6 glycosylated sites per repeat for the mucin from milk (Müller, S., Goletz, S., Packer, N., Gooley, A. A., Lawson, A. M., and Hanisch, F.-G. (1997) J. Biol. Chem. 272, 24780-24793) [11].
  • We have shown that 8-epi-PGF2 alpha, unlike other F2-isoprostanes, is a minor product of the prostaglandin endoperoxide synthase-1 (PG G/H S-1) expressed in human platelets (Praticó, D., Lawson, J. A., and Fitzgerald, G. A. (1995) J. Biol. Chem. 270, 9800-9808) [12].
  • In the present study, mitochondria harboring distinct AAC proteins and the pet9 Arg96 to HIS mutant (Lawson, J., Gawaz, M., Klingenberg, M., and Douglas, M. G. (1990) J. Biol. Chem. 265, 14195-14201) protein have been characterized [13].

Chemical compound and disease context of Lawson


Biological context of Lawson

  • Ser-88 forms a hydrogen bond with the amino group of bound tryptophan (Schevitz, R. W., Otwinowski, Z., Joachimiak, A., Lawson, C. L., and Sigler, P. B. (1985) Nature 317, 782-786), and alteration of the geometry of the side chain would be anticipated to perturb the topology of the binding site [19].
  • The research concerning the visual perception in deaf subjects has led to contradictory results: Deaf subjects have been reported to show enhanced visual perceptual skills compared to hearing subjects (Neville & Lawson, 1987) [20].
  • Regarding the consensus statement on 21-hydroxylase deficiency from the Lawson Wilkins Pediatric Endocrine Society and the European Society for Paediatric Endocrinology [21].
  • A calcium binding protein of Mr 29,000 which cross-reacts with antibodies raised against chick calbindin-D28k was previously reported to be present in rat cerebellum [Pochet, R., Parmentier, M., Lawson, D. E. M., & Pasteels, J. L. (1985) Brain Res. 345, 251-254] [22].
  • The development of gynecology as a specialty, although primarily American in origin, was influenced in large degree by Robert Lawson Tait, a brilliant Scottish/English surgeon who practiced in the late 19th century [23].

Anatomical context of Lawson


Associations of Lawson with other chemical compounds


Gene context of Lawson

  • Mcm2, a protein important for ARS activity, as well as Aac2, one of the three isoforms of the mitochondrial ATP/ADP carrier, were previously described (Yan et al., 1991; Lawson and Douglas, 1988) [33].
  • The differences in backbone chemical shifts between the two subunits within each dimer of delta 2-7 trpR reflect dimer-dimer contacts involving the helix-turn-helix domains and N-terminal residues consistent with a previously determined crystal structure [Lawson and Carey (1993) Nature, 366, 178-182] [34].
  • Ribose 1,5-bisphosphate (Rib-1,5-P2), a newly discovered activator of rat brain phosphofructokinase, forms rapidly during the initiation of glycolytic flux and disappears within 20 s (Ogushi, S., Lawson, J.W. R., Dobson, G.P., Veech, R.L., and Uyeda, K. (1990) J. Biol. Chem. 265, 10943-10949) [35].
  • This confirms that Tyr-7 is involved in the interaction between Trp repressor dimers, as seen in the crystal structure (Lawson and Carey, 1993) [36].
  • At a lawsone concentration of 2.8 x 10-3 mol/L, blood from 15 healthy adults formed MHb percentages of 7.4% +/- 3.3% (+/- 1 SD); in blood from 4 G6PD A- adults, percentages were 44.5%, 40.6%, 41.3%, and 42.8% [29].

Analytical, diagnostic and therapeutic context of Lawson

  • Using density gradient ultracentrifugation, we have previously found that in A431 cells the predominant PI4K activity arises from a type II alpha enzyme that is localized to a buoyant membrane fraction of unknown origin [Waugh, Lawson, Tan and Hsuan (1998) J. Biol. Chem. 273, 17115-17121] [37].
  • In our patient with advanced prostate carcinoma, after the usual method of placement of a ureteral stent had failed, antegrade percutaneous ureteroneocystostomy with placement of a double-J performed by means of the Lawson retrograde nephrostomy set [38].
  • Retrograde percutaneous nephrolithotomy using the Lawson technique for management of complex nephrolithiasis [39].
  • To grow L. intracellularisin vitro, the cell culture method of Lawson et al [40].
  • The famous abdominal surgeon Lawson Tait appeared to be a strong opponent of cholecystectomy, maintaining cholecystostomy as the procedure of choice [41].


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  2. Molecular basis for atovaquone binding to the cytochrome bc1 complex. Kessl, J.J., Lange, B.B., Merbitz-Zahradnik, T., Zwicker, K., Hill, P., Meunier, B., Pálsdóttir, H., Hunte, C., Meshnick, S., Trumpower, B.L. J. Biol. Chem. (2003) [Pubmed]
  3. Drug-induced hyperkalemia. Ponce, S.P., Jennings, A.E., Madias, N.E., Harrington, J.T. Medicine (Baltimore) (1985) [Pubmed]
  4. Oxygen-insensitive nitroreductases NfsA and NfsB of Escherichia coli function under anaerobic conditions as lawsone-dependent Azo reductases. Rau, J., Stolz, A. Appl. Environ. Microbiol. (2003) [Pubmed]
  5. Phylogenetic analysis of Fusobacterium prausnitzii based upon the 16S rRNA gene sequence and PCR confirmation. Wang, R.F., Cao, W.W., Cerniglia, C.E. Int. J. Syst. Bacteriol. (1996) [Pubmed]
  6. Comparative psychologic effects of estrogen administration on institutional and noninstitutional elderly women. Kantor, H.J., Milton, L.J., Ernst, M.L. Journal of the American Geriatrics Society. (1978) [Pubmed]
  7. Cognitive profiles of groups of poor readers and dyslexic children on the British Ability Scales. Tyler, S., Elliott, C.D. British journal of psychology (London, England : 1953) (1988) [Pubmed]
  8. The effect of prior experience on recognition thresholds for plane-disoriented pictures of familiar objects. Lawson, R., Jolicoeur, P. Memory & cognition. (1999) [Pubmed]
  9. Purification and properties of transgelin: a transformation and shape change sensitive actin-gelling protein. Shapland, C., Hsuan, J.J., Totty, N.F., Lawson, D. J. Cell Biol. (1993) [Pubmed]
  10. Distribution of epinemin in colloidal gold-labelled, quick-frozen, deep-etched cytoskeletons. Lawson, D. J. Cell Biol. (1984) [Pubmed]
  11. High density O-glycosylation on tandem repeat peptide from secretory MUC1 of T47D breast cancer cells. Müller, S., Alving, K., Peter-Katalinic, J., Zachara, N., Gooley, A.A., Hanisch, F.G. J. Biol. Chem. (1999) [Pubmed]
  12. Generation of 8-epiprostaglandin F2alpha by human monocytes. Discriminate production by reactive oxygen species and prostaglandin endoperoxide synthase-2. Praticó, D., FitzGerald, G.A. J. Biol. Chem. (1996) [Pubmed]
  13. Structure-function studies of adenine nucleotide transport in mitochondria. II. Biochemical analysis of distinct AAC1 and AAC2 proteins in yeast. Gawaz, M., Douglas, M.G., Klingenberg, M. J. Biol. Chem. (1990) [Pubmed]
  14. Cytotoxic properties of iron-hydroxynaphthoquinone complexes in rat hepatocytes. Kumbhar, A., Padhye, S., Ross, D. Biometals (1996) [Pubmed]
  15. In vivo exposure of Dreissena polymorpha mussels to the quinones menadione and lawsone: menadione is more toxic to mussels than lawsone. Osman, A.M., Rotteveel, S., den Besten, P.J., van Noort, P.C. Journal of applied toxicology : JAT. (2004) [Pubmed]
  16. Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. Didry, N., Dubreuil, L., Pinkas, M. Die Pharmazie. (1994) [Pubmed]
  17. Antipruritic and antidermatitic effect of extract and compounds of Impatiens balsamina L. in atopic dermatitis model NC mice. Oku, H., Ishiguro, K. Phytotherapy research : PTR. (2001) [Pubmed]
  18. Degradation of 1,4-naphthoquinones by Pseudomonas putida. Müller, U., Lingens, F. Biol. Chem. Hoppe-Seyler (1988) [Pubmed]
  19. Serine to cysteine mutations in trp repressor protein alter tryptophan and operator binding. Chou, W.Y., Matthews, K.S. J. Biol. Chem. (1989) [Pubmed]
  20. Do deaf people see better? Texture segmentation and visual search compensate in adult but not in juvenile subjects. Rettenbach, R., Diller, G., Sireteanu, R. Journal of cognitive neuroscience. (1999) [Pubmed]
  21. Regarding the consensus statement on 21-hydroxylase deficiency from the Lawson Wilkins Pediatric Endocrine Society and the European Society for Paediatric Endocrinology. Creighton, S., Ransley, P., Duffy, P., Wilcox, D., Mushtaq, I., Cuckow, P., Woodhouse, C., Minto, C., Crouch, N., Stanhope, R., Hughes, I., Dattani, M., Hindmarsh, P., Brain, C., Achermann, J., Conway, G., Liao, L.M., Barnicoat, A., Perry, L. J. Clin. Endocrinol. Metab. (2003) [Pubmed]
  22. Brain calbindin-D28k and an Mr 29,000 calcium binding protein in cerebellum are different but related proteins: evidence obtained from sequence analysis by tandem mass spectrometry. Gabrielides, C., McCormack, A.L., Hunt, D.F., Christakos, S. Biochemistry (1991) [Pubmed]
  23. Lawson Tait: the forgotten gynecologist. Golditch, I.M. Obstetrics and gynecology. (2002) [Pubmed]
  24. Role of oxidant stress in lawsone-induced hemolytic anemia. McMillan, D.C., Sarvate, S.D., Oatis, J.E., Jollow, D.J. Toxicol. Sci. (2004) [Pubmed]
  25. Lawsone (2-OH-1,4-naphthoquinone) derived form the henna plant increases the oxygen affinity of sickle cell blood. Chang, H., Suzuka, S.E. Biochem. Biophys. Res. Commun. (1982) [Pubmed]
  26. 2-Hydroxy-1,4-naphthoquinone, the natural dye of Henna, is non-genotoxic in the mouse bone marrow micronucleus test and does not produce oxidative DNA damage in Chinese hamster ovary cells. Marzin, D., Kirkland, D. Mutat. Res. (2004) [Pubmed]
  27. Some aspects of activity profile of sodium lawsonate in mice and rats. Kelkar, V.V., Dhumal, V.R., Bhavsar, V.H., Mardikar, B.R. Archives internationales de pharmacodynamie et de thérapie. (1986) [Pubmed]
  28. Conservative surgical treatment for acute pancreatitis: the Lawson procedure. Hesselink, E.J., Slooff, M.J., Bleichrodt, R.P., Van Schilfgaarde, R. The Netherlands journal of surgery. (1987) [Pubmed]
  29. Henna: a potential cause of oxidative hemolysis and neonatal hyperbilirubinemia. Zinkham, W.H., Oski, F.A. Pediatrics (1996) [Pubmed]
  30. Interconversion of NAD(H) to NADP(H). A cellular response to quinone-induced oxidative stress in isolated hepatocytes. Stubberfield, C.R., Cohen, G.M. Biochem. Pharmacol. (1989) [Pubmed]
  31. Role of humic acid and ouinone model compounds in bromate reduction by zerovalent iron. Xie, L., Shang, C. Environ. Sci. Technol. (2005) [Pubmed]
  32. Isoxazoles. VI: Aspects of the chemical stability of a new naphthoquinone-amine in acidic aqueous solution. Longhi, M.R., de Bertorello, M.M. Journal of pharmaceutical sciences. (1990) [Pubmed]
  33. Analysis of a 17.4 kb DNA segment of yeast chromosome II encompassing the ribosomal protein L19 as well as proteins with homologies to components of the hnRNP and snRNP complexes and to the human proliferation-associated p120 antigen. Van Dyck, L., Jonniaux, J.L., de Melo Barreiros, T., Kleine, K., Goffeau, A. Yeast (1994) [Pubmed]
  34. Subunit-specific backbone NMR assignments of a 64 kDa trp repressor/DNA complex: a role for N-terminal residues in tandem binding. Shan, X., Gardner, K.H., Muhandiram, D.R., Kay, L.E., Arrowsmith, C.H. J. Biomol. NMR (1998) [Pubmed]
  35. Activation of mammalian phosphofructokinases by ribose 1,5-bisphosphate. Ishikawa, E., Ogushi, S., Ishikawa, T., Uyeda, K. J. Biol. Chem. (1990) [Pubmed]
  36. Co-operative binding of two Trp repressor dimers to alpha- or beta-centred trp operators. Günes, C., Staacke, D., von Wilcken-Bergmann, B., Müller-Hill, B. Mol. Microbiol. (1996) [Pubmed]
  37. Localization of a highly active pool of type II phosphatidylinositol 4-kinase in a p97/valosin-containing-protein-rich fraction of the endoplasmic reticulum. Waugh, M.G., Minogue, S., Anderson, J.S., Balinger, A., Blumenkrantz, D., Calnan, D.P., Cramer, R., Hsuan, J.J. Biochem. J. (2003) [Pubmed]
  38. Percutaneous transrenal ureteroneocystostomy. Rosdy, E. J. Endourol. (1999) [Pubmed]
  39. Retrograde percutaneous nephrolithotomy using the Lawson technique for management of complex nephrolithiasis. Mokulis, J.A., Peretsman, S.J. J. Endourol. (1997) [Pubmed]
  40. Diagnosis of porcine proliferative enteropathy: detection of Lawsonia intracellularis by pathological examinations, polymerase chain reaction and cell culture inoculation. Dittmar, M., Hoelzle, L.E., Hoelzle, K., Sydler, T., Corboz, L., Miserez, R., Wittenbrink, M.M. J. Vet. Med. B Infect. Dis. Vet. Public Health (2003) [Pubmed]
  41. Langenbuch's cholecystectomy, once a remarkably controversial operation. van Gulik, T.M. The Netherlands journal of surgery. (1986) [Pubmed]
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