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Chemical Compound Review

CID6328166     bismuth; 3,4,5-trihydroxybenzoic acid;...

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Disease relevance of Gallic acid

  • An epidemic of neurological toxicity was reported in France in the 1970's with prolonged bismuth treatment, usually bismuth subgallate and subnitrate [1].
  • Characterization of components of this protein mixture was undertaken using human autoantibodies from bullous pemphigoid (BP) patients that have been shown to recognize hemidesmosomal plaque elements (Mutasim, D. F., Y. Takahashi, R. S. Labib, G. J. Anhalt, H. P. Patel, and L. A. Diaz. 1985. J. Invest. Dermatol. 84:47-53) and by production of mAbs [2].
  • We show here that the transcriptomes of human placenta and infantile hemangioma are sufficiently similar to suggest a placental origin for this tumor, expanding on recent immunophenotypical studies that have suggested this possibility [North, P. E., et al. (2001) Arch. Dermatol. 137, 559-570] [3].
  • Xeroderma pigmentosum (XP)-C is one of the more common complementation groups of XP, but causative mutations have thus far been reported for only six cases (S. G. Khan et al., J. Investig. Dermatol., 115: 791-796, 1998; L. Li et al., Nat. Genet., 5: 413-417, 1993) [4].
  • We demonstrated previously that the expression of the c-jun family was dysregulated in metastatic melanoma cells compared with normal human melanocytes (D. T. Yamanishi et al., J. Invest. Dermatol., 97: 349-353, 1991) [5].

Psychiatry related information on Gallic acid

  • (J Am Acad Dermatol 2002;46:807-21.) Learning objective: At the conclusion of this learning activity, participants should be familiar with clinical and histologic aspects of trichotillomania and should be able to cope with the risks of medical and psychiatric complications in these patients [6].
  • The patient improved after discontinuation of bismuth subgallate; there was resolution of paranoid behavior and gustatory and olfactory functions improved [7].

High impact information on Gallic acid

  • While alpha 3 beta 1 mediates adhesion, spreading, and migration (Kreidberg, J.A. 2000. Curr. Opin. Cell Biol. 12:548--553), alpha 6 beta 4 is involved in BM anchorage via hemidesmosomes (Borradori, L., and A. Sonnenberg. 1999. J. Invest. Dermatol. 112:411--418) [8].
  • In the epidermis, VLA-3 is generally strongly expressed on the entire plasma membrane of basal cells and is not polarized towards the basement membrane (Klein, C. E., C. Cardon-Cardo, R. Soehnchen, R. J. Cote, H. F. Oettgen, M. Eisinger, and L. J. Old. 1987. J. Invest. Dermatol. 89:500-507) [9].
  • The supernatant fluid (conditioned medium) of cultured human vascular endothelial cells inhibits activation of Hageman factor (factor XII), whether by ellagic acid, bovine brain sulfatides, or bismuth subgallate; inhibition appears to be a property of one or more proteins in the culture supernates [10].
  • We have previously shown that an AP1 site located in the proximal promoter region (position -55) is essential for human loricrin promoter activity (Rossi, A., Jang, S-I., Ceci, R., Steinert, P. M., and Markova, N. G. (1998) J. Invest. Dermatol. 110, 34-40) [11].
  • To this end, routinely-processed paraffin sections of 15 typical Spitz naevi, 15 typical nodular melanomas, and five cases originally misdiagnosed as Spitz naevi but which later metastasized and were reclassified as melanoma were analysed using a method previously described (De Wit et al., J Invest Dermatol 1992; 98: 450-458) [12].

Chemical compound and disease context of Gallic acid

  • Treatment of Cloudman S91 melanoma cells with retinoic acid (RA) inhibits MSH-induced tyrosinase activity and melanin formation [(1990) J. Invest. Dermatol. 94, 461-464] [13].
  • In cultured melanotic melanoma, a marked decrease of pigmentation has been found to be induced by the addition of tunicamycin [Y. Mishima and G. Imokawa (1983) J. Invest. Dermatol. 81, 106-114] [14].
  • Previous work showed that broad-band UV-B (290-320 nm) radiation produced higher levels of cyclobutyl pyrimidine dimers in DNA of individuals with high UV-B sensitivity (low minimal erythema dose) than in subjects of low UV-B sensitivity [Freeman et al. (1986) J. Invest. Dermatol., 86, 34-36] [15].
  • Pigmentation-associated antigen (PAA) or gp75 is a glycoprotein localized to the melanosomes of human melanomas and melanocytes to which a mouse monoclonal antibody (AbTA99) has been produced (T. M. Thomson et al. (1985) J. Invest. Dermatol. 85, 169) [16].
  • (J Am Acad Dermatol 2003;49:171-82.)Learning objective At the conclusion of this learning activity, participants should be familiar with use of oral retinoids for childhood dermatologic conditions such as psoriasis, acne, and ichthyoses as well as safety and risks associated with oral retinoid use in children and adolescents [17].

Biological context of Gallic acid

  • This mouse model not only demonstrates the depletion of CD4(+) T cells as a useful strategy for cancer gene therapy with interleukin-12 but also provides a model for human melanoma-associated vitiligo.J Invest Dermatol 115:1059-1064 2000[18]
  • Acta Dermatol Venereol 69(suppl 151):88-92, 1989): Type I frequently shows positive family history, linkage disequilibrium for human leucocyte antigens (HLAs) Cw6, B13 and Bw57 as well as an early onset [19].
  • The psoriasis-associated fatty acid binding protein (PA-FABP, also known as FABP5) is a novel keratinocyte protein that is highly up-regulated in psoriatic plaques (P. Madsen, H. H. Rasmussen, H. Leffers, B. Honoré and J. E. Celis, J. Invest. Dermatol. 1992, 99, 299-305) [20].
  • A recent study shows that apoptosis may be a significant mechanism of regression of LyP (Arch Dermatol 133:828-833, 1997) [21].
  • Moreover, bismuth subgallate alone inhibited antibody responses to CT [22].

Anatomical context of Gallic acid

  • Culture at the liquid-air interface is known to induce morphological differentiation in a variety of culture systems designed for keratinocytes (Pruniéras, M et al., J invest dermatol 81 (1983) 28s) [3] [23].
  • The same treatment also stimulates extracellular matrix synthesis by fibroblasts (J Invest Dermatol 93:449; 94:717) [24].
  • We have previously shown that filaggrin constructs containing the linker, when transiently transfected into epithelial cells, lead to expression of a protein that resembles keratohyalin (Dale et al. J Invest Dermatol 108:179-187 1997) [25].
  • We have recently shown (Mutasim et al: J Invest Dermatol 84:47-53, 1985) that autoantibodies from the sera of patients with bullous pemphigoid bind in vitro to hemidesmosomes but not to desmosomes providing a highly specific marker for these organelles [26].
  • Few other organ systems have received such enthusiastic reviews in recent years as to the chances and prospects of gene therapy as the skin, with its excellent accessibility and its pools of--seemingly--readily manipulated epithelial stem cells (cf. Cotsarelis et al., Exp Dermatol 1999: 8: 80-88) [27].

Associations of Gallic acid with other chemical compounds


Gene context of Gallic acid

  • The results of the present and our previous study [Katagata Y, et al. J Dermatol Sci 1996;13:219-227] indicate that expression of keratin in melanoma cells may be a universal phenomenon [32].
  • In contrast, hHa1 expression in the upper transitional cell compartment is uncoupled from the nuclear co-expression of the LEF1/beta-catenin complex seen in normal hair follicles (Cribier et al., J Invest Dermatol 2004; 122: 1078) [33].
  • Periplakin has also been shown to serve as an autoantigen in a malignancy-associated autoimmune blistering disease, paraneoplastic pemphigus (Mahoney et al., 1998, J. Invest. Dermatol. 111: 308-313) [34].
  • Epidermal growth factor (EGF) stimulates ODC activity and increases the steady-state level of ODC mRNA in a dose- and time-dependent manner in these cells [Prystowsky, Clevenger and Zheng (1993) Exp. Dermatol. 2, 125-132] [35].
  • Bismuth subgallate, which is an insoluble analog of ellagic acid, lost its ability to activate Hageman factor on being exposed to BAC770 [36].

Analytical, diagnostic and therapeutic context of Gallic acid

  • The skin cancer risk associated with narrowband (NB) phototherapy is not yet known although mathematical models have been created to quantify the risk (Diffey BL. Factors affecting the choice of a ceiling on the number of exposures with TL01 ultraviolet B phototherapy. Br J Dermatol 2003; 149: 428-30) [37].
  • (J Am Acad Dermatol 2000;43:571-91.) Learning objective: At the conclusion of this learning activity, participants should be familiar with the clinical spectrum of CP, the histopathologic and immunopathologic characteristics, the differential diagnosis, the treatment, and the natural history of the disease [38].
  • (J Am Acad Dermatol 2000;42:159-74.) LEARNING OBJECTIVE: At the conclusion of this learning activity, participants should be familiar with the various serologic tests for CTD, should understand the associations of specific antibodies with individual CTD, and should identify the factors that influence the predictive value of these serologic tests [39].
  • Bismuth subgallate, an agent that initiates clotting via activation of factor XII, has been advocated for use in controlling bleeding during tonsillectomy and adenoidectomy [40].
  • DATA SOURCES: MEDLINE (January 1966-October 1999) and Current Contents (January 1997-October 1999) were searched, using bismuth subgallate, adenoidectomy, tonsillectomy, and adenotonsillectomy as search terms [41].


  1. Bismuth therapy in gastrointestinal diseases. Gorbach, S.L. Gastroenterology (1990) [Pubmed]
  2. Immunochemical characterization of three components of the hemidesmosome and their expression in cultured epithelial cells. Klatte, D.H., Kurpakus, M.A., Grelling, K.A., Jones, J.C. J. Cell Biol. (1989) [Pubmed]
  3. Evidence by molecular profiling for a placental origin of infantile hemangioma. Barnés, C.M., Huang, S., Kaipainen, A., Sanoudou, D., Chen, E.J., Eichler, G.S., Guo, Y., Yu, Y., Ingber, D.E., Mulliken, J.B., Beggs, A.H., Folkman, J., Fishman, S.J. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  4. Mutations in the XPC gene in families with xeroderma pigmentosum and consequences at the cell, protein, and transcript levels. Chavanne, F., Broughton, B.C., Pietra, D., Nardo, T., Browitt, A., Lehmann, A.R., Stefanini, M. Cancer Res. (2000) [Pubmed]
  5. Activation of nuclear factor-kappa B in human metastatic melanomacells and the effect of oxidative stress. Meyskens, F.L., Buckmeier, J.A., McNulty, S.E., Tohidian, N.B. Clin. Cancer Res. (1999) [Pubmed]
  6. Trichotillomania. Hautmann, G., Hercogova, J., Lotti, T. J. Am. Acad. Dermatol. (2002) [Pubmed]
  7. Encephalopathy associated with bismuth subgallate therapy. Friedland, R.P., Lerner, A.J., Hedera, P., Brass, E.P. Clinical neuropharmacology. (1993) [Pubmed]
  8. Inhibitory role of alpha 6 beta 4-associated erbB-2 and phosphoinositide 3-kinase in keratinocyte haptotactic migration dependent on alpha 3 beta 1 integrin. Hintermann, E., Bilban, M., Sharabi, A., Quaranta, V. J. Cell Biol. (2001) [Pubmed]
  9. Integrin VLA-3: ultrastructural localization at cell-cell contact sites of human cell cultures. Kaufmann, R., Frösch, D., Westphal, C., Weber, L., Klein, C.E. J. Cell Biol. (1989) [Pubmed]
  10. Inhibition of the activation of Hageman factor (factor XII) by human vascular endothelial cell culture supernates. Ratnoff, O.D., Everson, B., Embury, P., Ziats, N.P., Anderson, J.M., Emanuelson, M.M., Malemud, C.J. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  11. Loricrin expression in cultured human keratinocytes is controlled by a complex interplay between transcription factors of the Sp1, CREB, AP1, and AP2 families. Jang, S.I., Steinert, P.M. J. Biol. Chem. (2002) [Pubmed]
  12. DNA in situ hybridization as a diagnostic tool in the discrimination of melanoma and Spitz naevus. De Wit, P.E., Kerstens, H.M., Poddighe, P.J., Van Muijen, G.N., Ruiter, D.J. J. Pathol. (1994) [Pubmed]
  13. Stimulation of the receptor for melanocyte-stimulating hormone by retinoic acid. Chakraborty, A.K., Orlow, S.J., Pawelek, J.M. FEBS Lett. (1990) [Pubmed]
  14. Purification of hamster melanoma tyrosinases and structural studies of their asparagine-linked sugar chains. Ohkura, T., Yamashita, K., Mishima, Y., Kobata, A. Arch. Biochem. Biophys. (1984) [Pubmed]
  15. Do pyrimidine dimer yields correlate with erythema induction in human skin irradiated in situ with ultraviolet light (275-365 nm)? Hacham, H., Freeman, S.E., Gange, R.W., Maytum, D.J., Sutherland, J.C., Sutherland, B.M. Photochem. Photobiol. (1991) [Pubmed]
  16. Glycosylation characteristics of pigmentation-associated antigen (GP75): an intracellular glycoprotein of human melanocytes and malignant melanomas. Roux, L., Lloyd, K.O. Arch. Biochem. Biophys. (1986) [Pubmed]
  17. Oral retinoid therapy for dermatologic conditions in children and adolescents. Brecher, A.R., Orlow, S.J. J. Am. Acad. Dermatol. (2003) [Pubmed]
  18. Elimination of CD4(+) T cells enhances anti-tumor effect of locally secreted interleukin-12 on B16 mouse melanoma and induces vitiligo-like coat color alteration. Nagai, H., Hara, I., Horikawa, T., Oka, M., Kamidono, S., Ichihashi, M. J. Invest. Dermatol. (2000) [Pubmed]
  19. Type I and type II psoriasis show a similar usage of T-cell receptor variable regions. Schmitt-Egenolf, M., Boehncke, W.H., Christophers, E., Ständer, M., Sterry, W. J. Invest. Dermatol. (1991) [Pubmed]
  20. Expression of recombinant psoriasis-associated fatty acid binding protein in Escherichia coli: gel electrophoretic characterization, analysis of binding properties and comparison with human serum albumin. Vorum, H., Madsen, P., Svendsen, I., Cells, J.E., Honoré, B. Electrophoresis (1998) [Pubmed]
  21. Cutaneous CD30+ lymphoproliferative disorders: expression of bcl-2 and proteins of the tumor necrosis factor receptor superfamily. Paulli, M., Berti, E., Boveri, E., Kindl, S., Bonoldi, E., Gambini, C., Rosso, R., Borroni, G., Straccapansa, V., Magrini, U., DeCoteau, J.E., Krammer, P.H., Möller, P., Kadin, M.E. Hum. Pathol. (1998) [Pubmed]
  22. Effect of bismuth salts on systemic and mucosal immune responses to orally administered cholera toxin. Horowitz, N.S., Staats, H.F., Palker, T.J. Immunopharmacology (1995) [Pubmed]
  23. Epidermal morphogenesis and induction of the 67 kD keratin polypeptide by culture of human keratinocytes at the liquid-air interface. Asselineau, D., Bernhard, B., Bailly, C., Darmon, M. Exp. Cell Res. (1985) [Pubmed]
  24. Induction of proliferation of growth-inhibited keratinocytes and fibroblasts in monolayer culture by sodium lauryl sulfate: comparison with all-trans retinoic acid. Varani, J., Astrom, A., Griffiths, C.E., Voorhees, J.J. J. Invest. Dermatol. (1991) [Pubmed]
  25. Profilaggrin requires both linker and filaggrin peptide sequences to form granules: implications for profilaggrin processing in vivo. Kuechle, M.K., Thulin, C.D., Presland, R.B., Dale, B.A. J. Invest. Dermatol. (1999) [Pubmed]
  26. The use of human pemphigoid autoantibodies to study the fate of epidermal basal cell hemidesmosomes after trypsin dissociation. Takahashi, Y., Mutasim, D.F., Patel, H.P., Anhalt, G.J., Labib, R.S., Diaz, L.A. J. Invest. Dermatol. (1985) [Pubmed]
  27. How realistic is cutaneous gene therapy? Hengge, U.R., Taichman, L.B., Kaur, P., Rogers, G., Jensen, T.G., Goldsmith, L.A., Rees, J.L., Christiano, A.M. Exp. Dermatol. (1999) [Pubmed]
  28. Stimulation of protein phosphorylation by epidermal growth factor in pig skin (epidermis). Aoyagi, T., Adachi, K., Halprin, K.M., Levine, V. J. Invest. Dermatol. (1980) [Pubmed]
  29. Effect of bismuth subgallate on nitric oxide and prostaglandin E2 production by macrophages. Lin, C.Y., Shen, Y.H., Wu, S.H., Lin, C.H., Hwang, S.M., Tsai, Y.C. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  30. Bicyclic monoterpene diols induce differentiation of S91 melanoma and PC12 pheochromocytoma cells by a cyclic guanosine-monophosphate-dependent pathway. Brown, D.A., Lesiak, K., Ren, W.Y., Strzelecki, K.L., Khorlin, A.A. Pigment Cell Res. (1999) [Pubmed]
  31. MDI 301, a non-irritating retinoid, induces changes in human skin that underlie repair. Varani, J., Fay, K., Perone, P. Arch. Dermatol. Res. (2007) [Pubmed]
  32. Keratin expression and its significance in five cultured melanoma cell lines derived from primary, recurrent and metastasized melanomas. Katagata, Y., Kondo, S. FEBS Lett. (1997) [Pubmed]
  33. Expression patterns of hair and epithelial keratins and transcription factors HOXC13, LEF1, and beta-catenin in a malignant pilomatricoma: a histological and immunohistochemical study. Cribier, B., Worret, W.I., Braun-Falco, M., Peltre, B., Langbein, L., Schweizer, J. J. Cutan. Pathol. (2006) [Pubmed]
  34. Human periplakin: genomic organization in a clonally unstable region of chromosome 16p with an abundance of repetitive sequence elements. Aho, S., Rothenberger, K., Tan, E.M., Ryoo, Y.W., Cho, B.H., McLean, W.H., Uitto, J. Genomics (1999) [Pubmed]
  35. Phorbol 12-myristate 13-acetate inhibits epidermal growth factor signalling in human keratinocytes, leading to decreased ornithine decarboxylase activity. Xue, G.Z., Zheng, Z.S., Chen, R.Z., Lloyd, M.B., Prystowsky, J.H. Biochem. J. (1996) [Pubmed]
  36. Inhibitory action of amyloid precursor protein against human Hageman factor (factor XII). Niwano, H., Embury, P.B., Greenberg, B.D., Ratnoff, O.D. J. Lab. Clin. Med. (1995) [Pubmed]
  37. Abstract No. 4 Many patients receiving high-dose phototherapy are not being reviewed. Mackintosh, L., Ashton, C., Bilsland, D. Br. J. Dermatol. (2006) [Pubmed]
  38. Cicatricial pemphigoid. Fleming, T.E., Korman, N.J. J. Am. Acad. Dermatol. (2000) [Pubmed]
  39. A practical guide for serologic evaluation of autoimmune connective tissue diseases. Mutasim, D.F., Adams, B.B. J. Am. Acad. Dermatol. (2000) [Pubmed]
  40. Respiratory difficulty following bismuth subgallate aspiration. Murray, A.D., Gibbs, S.R., Billings, K.R., Biavati, M.J. Arch. Otolaryngol. Head Neck Surg. (2000) [Pubmed]
  41. Bismuth subgallate-epinephrine paste in adenotonsillectomies. Hatton, R.C. The Annals of pharmacotherapy. (2000) [Pubmed]
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