Summary: Derivatives of hydroquinone (1,4-dihydrobenzene) made by reduction of BENZOQUINONES.

Top Publications

  1. Bährs H, Putschew A, Steinberg C. Toxicity of hydroquinone to different freshwater phototrophs is influenced by time of exposure and pH. Environ Sci Pollut Res Int. 2013;20:146-54 pubmed publisher
    ..0, it is questionable, if polyphenols in general and quinones in particular are the effective chemicals and if litter and straw leachates are applied as means to combat algal and cyanobacterial blooms. ..
  2. Lam L, Zhang Z, Board P, Xun L. Reduction of benzoquinones to hydroquinones via spontaneous reaction with glutathione and enzymatic reaction by S-glutathionyl-hydroquinone reductases. Biochemistry. 2012;51:5014-21 pubmed publisher
    ..is uncommon in nature, the extensive presence of GS-HQRs suggests they use common GS-hydroquinones. Here we demonstrate that several benzoquinones spontaneously reacted with GSH to form GS-hydroquinones via ..
  3. Hayes R, Green A, Nissen M, Lewis K, Xun L, Kang C. Structural characterization of 2,6-dichloro-p-hydroquinone 1,2-dioxygenase (PcpA) from Sphingobium chlorophenolicum, a new type of aromatic ring-cleavage enzyme. Mol Microbiol. 2013;88:523-36 pubmed publisher
    ..A tight hydrophobic pocket provides p-hydroquinones access to the Fe(II) centre...
  4. König J, Wyllie S, Wells G, Stevens M, Wyatt P, Fairlamb A. Antitumor quinol PMX464 is a cytocidal anti-trypanosomal inhibitor targeting trypanothione metabolism. J Biol Chem. 2011;286:8523-33 pubmed publisher
    ..Thus, the quinol pharmacophore represents a novel lead structure for the development of a new drug against African sleeping sickness. ..
  5. Stratford M, Ramsden C, Riley P. The influence of hydroquinone on tyrosinase kinetics. Bioorg Med Chem. 2012;20:4364-70 pubmed publisher
    ..Secondary addition products formed in the presence of hydroquinone are shown to stimulate, rather than inhibit, the kinetics of substrate oxidation. ..
  6. van den Boorn J, Picavet D, van Swieten P, van Veen H, Konijnenberg D, van Veelen P, et al. Skin-depigmenting agent monobenzone induces potent T-cell autoimmunity toward pigmented cells by tyrosinase haptenation and melanosome autophagy. J Invest Dermatol. 2011;131:1240-51 pubmed publisher
    ..These T cells effectively eradicate melanoma in vivo, as we have reported previously. Monobenzone thereby represents a promising and readily applicable compound for immunotherapy in melanoma patients...
  7. Gordaliza M. Cytotoxic terpene quinones from marine sponges. Mar Drugs. 2010;8:2849-70 pubmed publisher
    ..The cytotoxic and antiproliferative properties of many natural sesquiterpene quinones and hydroquinones from sponges of the order Dictyoceratida, such as avarol, avarone, illimaquinone, nakijiquinone and ..
  8. Sunassee S, Davies Coleman M. Cytotoxic and antioxidant marine prenylated quinones and hydroquinones. Nat Prod Rep. 2012;29:513-35 pubmed publisher
    ..Marine prenylated quinones, hydroquinones and naphthoquinones are of mixed polyketide and terpenoid biogenesis and recent biosynthetic studies of ..
  9. Ribeiro A, Shimada A, Hebeda C, de Oliveira T, de Melo Loureiro A, Filho W, et al. In vivo hydroquinone exposure alters circulating neutrophil activities and impairs LPS-induced lung inflammation in mice. Toxicology. 2011;288:1-7 pubmed publisher
    ..Therefore, it has been shown, for the first time, that neutrophils are target of lower levels of in vivo HQ exposure, which may be considered in host defense in infectious diseases. ..

More Information


  1. Yang E, Lee J, Yun C, Kim I. The pro-apoptotic effect of hydroquinone in human neutrophils and eosinophils. Toxicol In Vitro. 2011;25:131-7 pubmed publisher
    ..HQ exerts a cytotoxic effect in human neutrophils and eosinophils and may impair the regulation of immune responses. ..
  2. Pons M, Marin Castano M. Cigarette smoke-related hydroquinone dysregulates MCP-1, VEGF and PEDF expression in retinal pigment epithelium in vitro and in vivo. PLoS ONE. 2011;6:e16722 pubmed publisher
  3. Lee J, Yang E, Kim I. Hydroquinone-induced apoptosis of human lymphocytes through caspase 9/3 pathway. Mol Biol Rep. 2012;39:6737-43 pubmed publisher
    ..Our results demonstrated that HQ induces apoptosis by activating caspases 9/3 pathway and that the toxic effect seems to be dependent on lymphocyte metabolism. ..
  4. Shimada A, Ribeiro A, Bolonheis S, Ferraz de Paula V, Hebeda C, Farsky S. In vivo hydroquinone exposure impairs MCP-1 secretion and monocyte recruitment into the inflamed lung. Toxicology. 2012;296:20-6 pubmed publisher
  5. Funari S, Rebbin V, Marzorati L, di Vitta C. Membrane morphology modifications induced by hydroquinones. Langmuir. 2011;27:8257-62 pubmed publisher
    ..The zwitterionic POPC does not form cubic phases but instead shows lamellar structures with no clear influence of the 2,6-BATH. ..
  6. Hebeda C, Pinedo F, Bolonheis S, Ferreira Z, Muscara M, Teixeira S, et al. Intracellular mechanisms of hydroquinone toxicity on endotoxin-activated neutrophils. Arch Toxicol. 2012;86:1773-81 pubmed publisher
    ..Altogether, our data show that HQ alters the action of different LPS-activated pathways on neutrophils, which may contribute to the impaired triggering of the host innate immune reaction detected during in vivo HQ exposure. ..
  7. Chen H, Yao J, Wang F, Choi M, Bramanti E, Zaray G. Study on the toxic effects of diphenol compounds on soil microbial activity by a combination of methods. J Hazard Mater. 2009;167:846-51 pubmed publisher
    ..Our proposed methods can provide toxicological information of diphenols to soil microbes from the metabolic, microbial and biochemical point of views which are consistent with and correlated to each other. ..
  8. Jiang J, Bauer I, Paul A, Kappler A. Arsenic redox changes by microbially and chemically formed semiquinone radicals and hydroquinones in a humic substance model quinone. Environ Sci Technol. 2009;43:3639-45 pubmed
    ..6% oxidation) and pH 3 (0.5% oxidation). In addition to As(III) oxidation by semiquinone radicals, hydroquinones that were also produced during quinone reduction reduced As(V) to As(III) at neutral and acidic pH values (..
  9. Wei M, Zhang J, Liu H, Zhou N. para-Nitrophenol 4-monooxygenase and hydroxyquinol 1,2-dioxygenase catalyze sequential transformation of 4-nitrocatechol in Pseudomonas sp. strain WBC-3. Biodegradation. 2010;21:915-21 pubmed publisher
    ..Nevertheless, strain WBC-3 could completely degrade both PNP and 4-NC when PNP was used as the inducer, demonstrating its potential in bioremediation of the environment polluted by both 4-NC and PNP...
  10. Long J, Manchandia T, Ban K, Gao S, Miller C, Chandra J. Adaphostin cytoxicity in glioblastoma cells is ROS-dependent and is accompanied by upregulation of heme oxygenase-1. Cancer Chemother Pharmacol. 2007;59:527-35 pubmed
    ..Taken together, our data indicate that a cell's ability to cope with ROS dictates sensitivity to adaphostin and conceivably other chemotherapies that cause redox perturbations. ..
  11. Espinosa Heidmann D, Suner I, Catanuto P, Hernandez E, Marin Castano M, Cousins S. Cigarette smoke-related oxidants and the development of sub-RPE deposits in an experimental animal model of dry AMD. Invest Ophthalmol Vis Sci. 2006;47:729-37 pubmed
    ..This study was an investigation of the effects of cigarette smoke (CS) and HQ in the development of sub-RPE deposits in an experimental mouse model...
  12. Li J, Johnson D, Calkins M, Wright L, Svendsen C, Johnson J. Stabilization of Nrf2 by tBHQ confers protection against oxidative stress-induced cell death in human neural stem cells. Toxicol Sci. 2005;83:313-28 pubmed
    ..Nrf2 stabilization by pharmacological modulation or adenovirus-mediated Nrf2 overexpression, therefore, might be viable strategies to prevent a wide-spectrum of oxidative stress-related neuronal cell injuries. ..
  13. McGregor D. Hydroquinone: an evaluation of the human risks from its carcinogenic and mutagenic properties. Crit Rev Toxicol. 2007;37:887-914 pubmed
  14. Nordlund J, Grimes P, Ortonne J. The safety of hydroquinone. J Eur Acad Dermatol Venereol. 2006;20:781-7 pubmed
    ..This article reviews the evidence for the safety of hydroquinone in the treatment of hyperpigmentation conditions. ..
  15. Kim E, Kang B, Kim T. Inhibition of interleukin-12 production in mouse macrophages by hydroquinone, a reactive metabolite of benzene, via suppression of nuclear factor-kappaB binding activity. Immunol Lett. 2005;99:24-9 pubmed
    ..These findings suggest that HQ may, at least in part, enhance allergic immune responses by inhibiting the production of IL-12 in macrophages. ..
  16. Orsolic N, Golemovic M, Quintas Cardama A, Scappini B, Manshouri T, Chandra J, et al. Adaphostin has significant and selective activity against chronic and acute myeloid leukemia cells. Cancer Sci. 2006;97:952-60 pubmed
    ..In conclusion, adaphostin showed significant and selective activity against CML and AML cells and its development for clinical testing is warranted. ..
  17. Qiu Y, Wang X. A new sesquiterpenoid hydroquinone from the marine sponge Dysidea arenaria. Molecules. 2008;13:1275-81 pubmed
    ..Compounds 3 -6 displayed moderate inhibitory activity, with IC(50)values of 239.7, 16.4, 176.1, and 130.4 microM, respectively, while 1 and 2 were found to be inactive against the same biological target...
  18. Lee J, Kim J, Lee Y, Shin W, Chun T, Rhee M, et al. Hydroquinone, a reactive metabolite of benzene, reduces macrophage-mediated immune responses. Mol Cells. 2007;23:198-206 pubmed
    ..Therefore, our data suggest that hydroquinone inhibits macrophage-mediated immune responses by modulating intracellular signaling and protective mechanisms. ..
  19. Tziveleka L, Abatis D, Paulus K, Bauer R, Vagias C, Roussis V. Marine polyprenylated hydroquinones, quinones, and chromenols with inhibitory effects on leukotriene formation. Chem Biodivers. 2005;2:901-9 pubmed
    A series of polyprenylated hydroquinones, quinones, and chromenols were isolated from the extracts of the marine sponge Ircinia spinosula and the brown alga Taonia atomaria, which gave rise to the constituents 1-4 and 5-8, respectively...
  20. Moonen M, Synowsky S, van den Berg W, Westphal A, Heck A, van den Heuvel R, et al. Hydroquinone dioxygenase from pseudomonas fluorescens ACB: a novel member of the family of nonheme-iron(II)-dependent dioxygenases. J Bacteriol. 2008;190:5199-209 pubmed publisher
    ..HQDO was activated by iron(II) ions and catalyzed the ring fission of a wide range of hydroquinones to the corresponding 4-hydroxymuconic semialdehydes...
  21. Zhang J, Liu H, Xiao Y, Zhang X, Zhou N. Identification and characterization of catabolic para-nitrophenol 4-monooxygenase and para-benzoquinone reductase from Pseudomonas sp. strain WBC-3. J Bacteriol. 2009;191:2703-10 pubmed publisher
    ..J. Moonen, N. M. Kamerbeek, A. H. Westphal, S. A. Boeren, D. B. Janssen, M. W. Fraaije, and W. J. van Berkel, J. Bacteriol. 190:5190-5198, 2008), suggesting that the genes involved in PNP degradation are physically linked. ..
  22. Horita M, Wang D, Tsutsui K, Sano K, Masuoka N, Kira S. Involvement of oxidative stress in hydroquinone-induced cytotoxicity in catalase-deficient Escherichia coli mutants. Free Radic Res. 2005;39:1035-41 pubmed
    ..The present results suggest that H2O2 is probably involved in hydroquinone-induced cytotoxicity in catalase-deficient E. coli mutants and catalase plays an important role in protection of the cells against hydroquinone toxicity. ..
  23. Koh K, Cha Y, Kim S, Kim J. tBHQ inhibits LPS-induced microglial activation via Nrf2-mediated suppression of p38 phosphorylation. Biochem Biophys Res Commun. 2009;380:449-53 pubmed publisher
    ..This suggested that prior activation of Nrf2 in microglia may inhibit microglial hyperactivation and prevent neuronal death. ..
  24. Sladic D, Gasic M. Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida. Molecules. 2006;11:1-33 pubmed
    ..Examples of the recognition of validated core structures and synthesis of structurally simplified compounds retaining modes of activity are analyzed. ..
  25. Benites J, Valderrama J, Rivera F, Rojo L, Campos N, Pedro M, et al. Studies on quinones. Part 42: Synthesis of furylquinone and hydroquinones with antiproliferative activity against human tumor cell lines. Bioorg Med Chem. 2008;16:862-8 pubmed
    The preparation of furyl-1,4-quinone and hydroquinones by reaction of 2-furaldehyde N,N-dimethylhydrazone with benzo- and naphthoquinones is reported...
  26. Strunnikova N, Zhang C, Teichberg D, Cousins S, Baffi J, Becker K, et al. Survival of retinal pigment epithelium after exposure to prolonged oxidative injury: a detailed gene expression and cellular analysis. Invest Ophthalmol Vis Sci. 2004;45:3767-77 pubmed
    ..RPE cells avoided cell death and recovered from prolonged oxidative injury by activating a host of defense mechanisms while simultaneously triggering genes and cellular responses that may be involved in RPE disease development. ..
  27. Rudi A, Benayahu Y, Kashman Y. Likonides A and B: new ansa farnesyl quinols from the marine sponge Hyatella sp. Org Lett. 2004;6:4013-6 pubmed
    ..The compounds are of a unique ansa structure. The structures and stereochemistry of the compounds were elucidated by interpretation of MS, two-dimensional NMR, and CD experiments. ..
  28. Zhao C, Wood T, Bruckenstein S. Shifts in protein charge state distributions with varying redox reagents in nanoelectrospray triple quadrupole mass spectrometry. J Am Soc Mass Spectrom. 2005;16:409-16 pubmed
    ..The results observed with ubiquitin upon adding quinhydrone were analogous to those observed with cytochrome c. ..
  29. Kim A, Cho J, Lee J, Choi J, Chung H. Hydroquinone modulates reactivity of peroxynitrite and nitric oxide production. J Pharm Pharmacol. 2005;57:475-81 pubmed
    ..The results suggest that hydroquinone may potently modulate reactivity of ONOO(-) and may therefore be a useful agent against ONOO(-) mediated diseases. ..
  30. Shih A, Imbeault S, Barakauskas V, Erb H, Jiang L, Li P, et al. Induction of the Nrf2-driven antioxidant response confers neuroprotection during mitochondrial stress in vivo. J Biol Chem. 2005;280:22925-36 pubmed
    ..We conclude that Nrf2 may underlie a feedback system limiting oxidative load during chronic metabolic stress. ..
  31. Mukhopadhyay I, Sausville E, Doroshow J, Roy K. Molecular mechanism of adaphostin-mediated G1 arrest in prostate cancer (PC-3) cells: signaling events mediated by hepatocyte growth factor receptor, c-Met, and p38 MAPK pathways. J Biol Chem. 2006;281:37330-44 pubmed
    ..These findings suggest that the tyrphostin member has a broader spectrum of activity than originally predicted. ..
  32. Barnes D, De S, van Hensbergen P, Moravcsik E, Melo J. Different target range and cytotoxic specificity of adaphostin and 17-allylamino-17-demethoxygeldanamycin in imatinib-resistant and sensitive cell lines. Leukemia. 2007;21:421-6 pubmed
    ..We suggest that both compounds may prove useful in the treatment of CML but caution that undesirable side-effects may result from the inhibition of multiple cell signalling proteins. ..
  33. Nordin K, Unell M, Jansson J. Novel 4-chlorophenol degradation gene cluster and degradation route via hydroxyquinol in Arthrobacter chlorophenolicus A6. Appl Environ Microbiol. 2005;71:6538-44 pubmed
  34. Yan D, Dong J, Sulik K, Chen S. Induction of the Nrf2-driven antioxidant response by tert-butylhydroquinone prevents ethanol-induced apoptosis in cranial neural crest cells. Biochem Pharmacol. 2010;80:144-9 pubmed publisher
    ..These results clearly demonstrate that the activation of Nrf2 signaling confers protection against ethanol-induced apoptosis in NCCs. ..
  35. Chen H, Yao J, Wang F, Zhou Y, Chen K, Zhuang R, et al. Toxicity of three phenolic compounds and their mixtures on the gram-positive bacteria Bacillus subtilis in the aquatic environment. Sci Total Environ. 2010;408:1043-9 pubmed publisher
    ..The experimental results of microcalorimetry show no significant difference on the toxicity of the phenolic compound mixtures from that predicted by CA. However, IA prediction underestimated the mixture effects in all the experiments. ..
  36. Sarkar C, Mitra P, Saha S, Nayak C, Chakraborty R. Effect of copper-hydroquinone complex on oxidative stress-related parameters in human erythrocytes (in vitro). Toxicol Mech Methods. 2009;19:86-93 pubmed publisher
    ..This suggests hydroquinone in the presence of copper does not contribute to erythrocyte membrane lipid peroxidation seen in smokers. Criteria for ideal antioxidant supplementation in smokers were suggested. ..
  37. Bertram K, Baglole C, Phipps R, Libby R. Molecular regulation of cigarette smoke induced-oxidative stress in human retinal pigment epithelial cells: implications for age-related macular degeneration. Am J Physiol Cell Physiol. 2009;297:C1200-10 pubmed publisher
    ..These data support the hypothesis that cigarette smoke contributes to AMD pathogenesis by causing oxidative damage and cell death to RPE cells. ..
  38. Yang S, Ma H, Yu L, Yu C. On the mechanism of quinol oxidation at the QP site in the cytochrome bc1 complex: studied using mutants lacking cytochrome bL or bH. J Biol Chem. 2008;283:28767-76 pubmed publisher
    ..Both mutant complexes produce as much superoxide as does antimycin A-treated wild-type complex. Ascorbate eliminates all superoxide generating activity in the intact or antimycin inhibited wild-type or mutant complexes. ..
  39. Luo L, Jiang L, Geng C, Cao J, Zhong L. Hydroquinone-induced genotoxicity and oxidative DNA damage in HepG2 cells. Chem Biol Interact. 2008;173:1-8 pubmed publisher
    ..All these results demonstrate that HQ exerts genotoxic effects in HepG2 cells, probably through DNA damage by oxidative stress. GSH, as a main intracellular antioxidant, is responsible for cellular defense against HQ-induced DNA damage. ..
  40. Chen Y, Yu K, Wu J, Shen Z, Jiang S, Hu X, et al. [Apoptosis induced by hydroquinone in bone marrow mononuclear cells in vitro]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2004;22:161-4 pubmed
    ..Hydroquinone can induce apoptosis of bone marrow mononuclear cells in vitro with dose-effect and time-effect relationship. ..
  41. Suzuki M, Hunt C, Houtman C, Dalebroux Z, Hammel K. Fungal hydroquinones contribute to brown rot of wood. Environ Microbiol. 2006;8:2214-23 pubmed
    ..trabeum, drives Fenton chemistry on defined media by reducing Fe(3+) and O(2) with two extracellular hydroquinones, 2,5-dimethoxyhydroquinone (2,5-DMHQ) and 4,5-dimethoxycatechol (4,5-DMC)...
  42. Le S, Hailer M, Buhrow S, Wang Q, Flatten K, Pediaditakis P, et al. Inhibition of mitochondrial respiration as a source of adaphostin-induced reactive oxygen species and cytotoxicity. J Biol Chem. 2007;282:8860-72 pubmed
  43. West L, Faulkner D. Hexaprenoid hydroquinones from the sponge Haliclona (aka Adocia) sp. J Nat Prod. 2006;69:1001-4 pubmed
    Three new hexaprenoid hydroquinones, adociaquinol (1), adociasulfate 11 (2), and adociasulfate 12 (3), together with the known adociasulfates 2, 4, and 6, were isolated from the marine sponge Haliclona (aka Adocia) sp...
  44. O Donoghue J. Hydroquinone and its analogues in dermatology - a risk-benefit viewpoint. J Cosmet Dermatol. 2006;5:196-203 pubmed
  45. Hariharan V, Klarquist J, Reust M, Koshoffer A, McKee M, Boissy R, et al. Monobenzyl ether of hydroquinone and 4-tertiary butyl phenol activate markedly different physiological responses in melanocytes: relevance to skin depigmentation. J Invest Dermatol. 2010;130:211-20 pubmed publisher
    ..As the mode of cell death defines the nature of the immune response that follows, these findings help to explain the relative efficacy of these agents in mediating depigmentation. ..
  46. Berry J, Bradshaw T, Fichtner I, Ren R, Schwalbe C, Wells G, et al. Quinols as novel therapeutic agents. 2.(1) 4-(1-Arylsulfonylindol-2-yl)-4-hydroxycyclohexa-2,5-dien-1-ones and related agents as potent and selective antitumor agents. J Med Chem. 2005;48:639-44 pubmed
    ..In vivo, significant antitumor activity was recorded (day 28) in mice bearing subcutaneously implanted MDA-MB-435 xenografts, following intraperitoneal treatment of mice with compound 1a at 50 mg/kg. ..
  47. Inayat Hussain S, Ross D. Intrinsic pathway of hydroquinone induced apoptosis occurs via both caspase-dependent and caspase-independent mechanisms. Chem Res Toxicol. 2005;18:420-7 pubmed
    ..Our results emphasize that both caspase-dependent and independent mechanisms should be considered in the intrinsic apoptotic pathway induced by HQ. ..
  48. Tozlovanu M, Faucet Marquis V, Pfohl Leszkowicz A, Manderville R. Genotoxicity of the hydroquinone metabolite of ochratoxin A: structure-activity relationships for covalent DNA adduction. Chem Res Toxicol. 2006;19:1241-7 pubmed
    ..These results establish structure-activity relationships for OTA-mediated DNA adduction and provide new evidence for the potential role of the OTQ/OTHQ redox couple in OTA-induced genotoxicity. ..
  49. Rich P. The quinone chemistry of bc complexes. Biochim Biophys Acta. 2004;1658:165-71 pubmed
  50. Laube T, Bernet A, Dahse H, Jacobsen I, Seifert K. Synthesis and pharmacological activities of some sesquiterpene quinones and hydroquinones. Bioorg Med Chem. 2009;17:1422-7 pubmed publisher
    Synthesis of protected siphonodictyal C was achieved via drim-7-en-11-al. Some sesquiterpene quinones and hydroquinones were tested for their pharmacological activities in assays in search of antiproliferative, cytotoxic, antiphlogistic, ..
  51. Shanafelt T, Lee Y, Bone N, Strege A, Narayanan V, Sausville E, et al. Adaphostin-induced apoptosis in CLL B cells is associated with induction of oxidative stress and exhibits synergy with fludarabine. Blood. 2005;105:2099-106 pubmed
    ..Further preclinical development of adaphostin as a novel agent for the treatment of CLL appears warranted...
  52. Marin Castano M, Striker G, Alcazar O, Catanuto P, Espinosa Heidmann D, Cousins S. Repetitive nonlethal oxidant injury to retinal pigment epithelium decreased extracellular matrix turnover in vitro and induced sub-RPE deposits in vivo. Invest Ophthalmol Vis Sci. 2006;47:4098-112 pubmed
    ..This study suggests that HQ may be another type of oxidant that causes injury to the RPE and may explain the association between environmental oxidants and early AMD. ..
  53. Wang X, Hayes J, Higgins L, Wolf C, Dinkova Kostova A. Activation of the NRF2 signaling pathway by copper-mediated redox cycling of para- and ortho-hydroquinones. Chem Biol. 2010;17:75-85 pubmed publisher
    ..Thus, the oxidation of para- and ortho-hydroquinones to quinones represents the rate-limiting step in the activation of Nrf2.
  54. Huang C, Fang W, Lin L, Chiou R, Kan L, Chi N, et al. Anticancer activity of botanical alkyl hydroquinones attributed to topoisomerase II poisoning. Toxicol Appl Pharmacol. 2008;227:331-8 pubmed publisher
    ..These results indicated that HQ17(3) is a potential anticancer agent, and its structural features could be a model for anticancer drug design. ..
  55. Terasaka H, Morshed S, Hashimoto K, Sakagami H, Fujisawa S. Hydroquinone-induced apoptosis in HL-60 cells. Anticancer Res. 2005;25:161-70 pubmed
    ..The activation of caspase-3 by HQ/NAC combinations suggests that NAC, a precursor of intracellular glutathione synthesis, acts as a co-catalyst during HQ-induced apoptosis. ..
  56. Ibuki Y, Goto R. Dysregulation of apoptosis by benzene metabolites and their relationships with carcinogenesis. Biochim Biophys Acta. 2004;1690:11-21 pubmed
    ..These findings suggested that benzene metabolites induced dysregulation of apoptosis due to caspase-3 inhibition, which contributes to carcinogenesis. ..
  57. Shiga T, Suzuki H, Yamamoto A, Yamamoto H, Yamamoto K. Hydroquinone, a benzene metabolite, induces Hog1-dependent stress response signaling and causes aneuploidy in Saccharomyces cerevisiae. J Radiat Res. 2010;51:405-15 pubmed
    ..These data indicate that the hydroquinone-induced G2/M transition checkpoint, which is activated by the Hog1-Swe1 pathway, plays a role in the formation of aneuploidy. ..
  58. Levitt J. The safety of hydroquinone: a dermatologist's response to the 2006 Federal Register. J Am Acad Dermatol. 2007;57:854-72 pubmed
    ..Therefore, the proposed ban appears to be unnecessarily extreme. ..
  59. Bradshaw T, Matthews C, Cookson J, Chew E, Shah M, Bailey K, et al. Elucidation of thioredoxin as a molecular target for antitumor quinols. Cancer Res. 2005;65:3911-9 pubmed
    ..Results are consistent with a mechanism of action of novel antitumor quinols involving inhibition of the small redox protein thioredoxin. ..
  60. Bahia P, Rattray M, Williams R. Dietary flavonoid (-)epicatechin stimulates phosphatidylinositol 3-kinase-dependent anti-oxidant response element activity and up-regulates glutathione in cortical astrocytes. J Neurochem. 2008;106:2194-204 pubmed publisher
    ..Together, this suggests that flavonoids may be cytoprotective by increasing anti-oxidant gene expression. ..
  61. Dasmahapatra G, Nguyen T, Dent P, Grant S. Adaphostin and bortezomib induce oxidative injury and apoptosis in imatinib mesylate-resistant hematopoietic cells expressing mutant forms of Bcr/Abl. Leuk Res. 2006;30:1263-72 pubmed
    ..These findings indicate that adaphostin+/-bortezomib circumvent imatinib resistance due to Bcr/Abl point mutations most likely through ROS generation. ..
  62. Chew E, Matthews C, Zhang J, McCarroll A, Hagen T, Stevens M, et al. Antitumor quinols: role of glutathione in modulating quinol-induced apoptosis and identification of putative cellular protein targets. Biochem Biophys Res Commun. 2006;346:242-51 pubmed
  63. Chen Y, Y Y R, Lin T, Huang C, Tang W, Chen S, et al. Identification of an Alkylhydroquinone from Rhus succedanea as an Inhibitor of Tyrosinase and Melanogenesis. J Agric Food Chem. 2009;57:2200-5 pubmed publisher
    ..As tyrosinase activity accounts for postharvest browning of botanical products and animal skin melanogenesis, HQ17(1) could be useful for the preservation of these products or as a skin-whitening cosmetic. ..
  64. Hose C, Kaur G, Sausville E, Monks A. Transcriptional profiling identifies altered intracellular labile iron homeostasis as a contributing factor to the toxicity of adaphostin: decreased vascular endothelial growth factor secretion is independent of hypoxia-inducible factor-1 regulation. Clin Cancer Res. 2005;11:6370-81 pubmed
    ..Thus, adaphostin remains an interesting agent with the ability to kill tumor cells directly and modulate angiogenesis. ..
  65. Niedermeyer T, Mikolasch A, Lalk M. Nuclear amination catalyzed by fungal laccases: reaction products of p-hydroquinones and primary aromatic amines. J Org Chem. 2005;70:2002-8 pubmed
    reaction: see text] Nuclear amination of p-hydroquinones with primary aromatic amines was catalyzed by fungal laccases (EC from Trametes spec. and Myceliophthora thermophila...
  66. Chandra J, Tracy J, Loegering D, Flatten K, Verstovsek S, Beran M, et al. Adaphostin-induced oxidative stress overcomes BCR/ABL mutation-dependent and -independent imatinib resistance. Blood. 2006;107:2501-6 pubmed
    ..Collectively, these data suggest that ROS generation by adaphostin overcomes even the most potent imatinib resistance in CML and Ph+ ALL. ..
  67. Chew E, Lu J, Bradshaw T, Holmgren A. Thioredoxin reductase inhibition by antitumor quinols: a quinol pharmacophore effect correlating to antiproliferative activity. FASEB J. 2008;22:2072-83 pubmed publisher
    ..From the results obtained, we propose that TrxR inhibition is a critical cellular event that contributes to the proapoptotic effects of quinols. ..
  68. Lion C, Matthews C, Wells G, Bradshaw T, Stevens M, Westwell A. Antitumour properties of fluorinated benzothiazole-substituted hydroxycyclohexa-2,5-dienones ('quinols'). Bioorg Med Chem Lett. 2006;16:5005-8 pubmed
  69. Satoh T, Saitoh S, Hosaka M, Kosaka K. Simple ortho- and para-hydroquinones as compounds neuroprotective against oxidative stress in a manner associated with specific transcriptional activation. Biochem Biophys Res Commun. 2009;379:537-41 pubmed publisher
    ..ability of a compound to bind to a cysteine on bovine serum albumin, by which we found that neuroprotective hydroquinones [TBHQ (para-) and CA (ortho-)] had distinctive patterns of cysteine binding compared with other electrophilic ..