Summary: Cyclohexane ring substituted by one or more ketones in any position.

Top Publications

  1. Corazza O, Schifano F, Simonato P, Fergus S, Assi S, Stair J, et al. Phenomenon of new drugs on the Internet: the case of ketamine derivative methoxetamine. Hum Psychopharmacol. 2012;27:145-9 pubmed publisher
    ..Better international collaboration levels and novel forms of intervention are necessary to tackle this fast-growing phenomenon...
  2. Couce M, Dalmau J, Del Toro M, Pintos Morell G, Aldámiz Echevarría L. Tyrosinemia type 1 in Spain: mutational analysis, treatment and long-term outcome. Pediatr Int. 2011;53:985-9 pubmed publisher
    ..The aim of the present study was to review the efficacy of long-term treatment of HT1 with nitisinone, expand knowledge about the clinical spectrum of the disease and assess a possible genotype-phenotype correlation...
  3. Hofer K, Grager B, Müller D, Rauber Lüthy C, Kupferschmidt H, Rentsch K, et al. Ketamine-like effects after recreational use of methoxetamine. Ann Emerg Med. 2012;60:97-9 pubmed publisher
    ..According to this case report, user Web reports, and the chemical structure, methoxetamine produces ketamine-like effects. Complete recovery can be expected with supportive care...
  4. Thimm E, Herebian D, Assmann B, Klee D, Mayatepek E, Spiekerkoetter U. Increase of CSF tyrosine and impaired serotonin turnover in tyrosinemia type I. Mol Genet Metab. 2011;102:122-5 pubmed publisher
  5. Rosenbaum C, Carreiro S, Babu K. Here today, gone tomorrow…and back again? A review of herbal marijuana alternatives (K2, Spice), synthetic cathinones (bath salts), kratom, Salvia divinorum, methoxetamine, and piperazines. J Med Toxicol. 2012;8:15-32 pubmed publisher
    ..This paper discusses the background, pharmacology, clinical effects, detection, and management of synthetic cannabinoid, synthetic cathinone, methoxetamine, and piperazine exposures...
  6. Matsui K, Nazifi E, Kunita S, Wada N, Matsugo S, Sakamoto T. Novel glycosylated mycosporine-like amino acids with radical scavenging activity from the cyanobacterium Nostoc commune. J Photochem Photobiol B. 2011;105:81-9 pubmed publisher
    ..commune. These results suggest that these glycosylated MAAs have multiple roles as a UV protectant and an antioxidant relevant to anhydrobiosis in N. commune. ..
  7. Thimm E, Richter Werkle R, Kamp G, Molke B, Herebian D, Klee D, et al. Neurocognitive outcome in patients with hypertyrosinemia type I after long-term treatment with NTBC. J Inherit Metab Dis. 2012;35:263-8 pubmed publisher
    ..However, there are first reports of cognitive impairment in patients with elevated plasma tyrosine concentrations...
  8. la Marca G, Malvagia S, Materazzi S, Della Bona M, Boenzi S, Martinelli D, et al. LC-MS/MS method for simultaneous determination on a dried blood spot of multiple analytes relevant for treatment monitoring in patients with tyrosinemia type I. Anal Chem. 2012;84:1184-8 pubmed publisher
  9. Wood D, Davies S, Puchnarewicz M, Johnston A, Dargan P. Acute toxicity associated with the recreational use of the ketamine derivative methoxetamine. Eur J Clin Pharmacol. 2012;68:853-6 pubmed publisher
    ..We report here a case series of three individuals with acute toxicity related to the analytically confirmed use of methoxetamine...

More Information


  1. Pan Y, Wang Y, Cai L, Cai Y, Hu J, Yu C, et al. Inhibition of high glucose-induced inflammatory response and macrophage infiltration by a novel curcumin derivative prevents renal injury in diabetic rats. Br J Pharmacol. 2012;166:1169-82 pubmed publisher
    ..This novel compound is a potential anti-inflammatory agent and might be beneficial for the prevention of diabetic nephropathy. ..
  2. Ferroni L, Klisch M, Pancaldi S, Häder D. Complementary UV-absorption of mycosporine-like amino acids and scytonemin is responsible for the UV-insensitivity of photosynthesis in Nostoc flagelliforme. Mar Drugs. 2010;8:106-21 pubmed publisher
    ..Furthermore, this study performed with a genuinely terrestrial organism points to the relevance of marine photoprotective compounds for life on Earth, especially for the colonization of terrestrial environments...
  3. Schlune A, Thimm E, Herebian D, Spiekerkoetter U. Single dose NTBC-treatment of hereditary tyrosinemia type I. J Inherit Metab Dis. 2012;35:831-6 pubmed publisher
    ..In fact, single dose treatment may increase patients' compliance with the drug treatment and improve metabolic control...
  4. Nakhjiri M, Safavi M, Alipour E, Emami S, Atash A, Jafari Zavareh M, et al. Asymmetrical 2,6-bis(benzylidene)cyclohexanones: Synthesis, cytotoxic activity and QSAR study. Eur J Med Chem. 2012;50:113-23 pubmed publisher
    ..The results indicated that the cytotoxic activity profile against different tumor cells can be optimized by desired 4-alkoxy-3-bromo-5-methoxybenzylidene scaffold. ..
  5. Shields J, Dargan P, Wood D, Puchnarewicz M, Davies S, Waring W. Methoxetamine associated reversible cerebellar toxicity: three cases with analytical confirmation. Clin Toxicol (Phila). 2012;50:438-40 pubmed publisher
    ..We report three cases that presented to hospital with acute neurological toxicity associated with analytically confirmed methoxetamine exposure...
  6. Larochelle J, Alvarez F, Bussières J, Chevalier I, Dallaire L, Dubois J, et al. Effect of nitisinone (NTBC) treatment on the clinical course of hepatorenal tyrosinemia in Québec. Mol Genet Metab. 2012;107:49-54 pubmed publisher
    ..Nitisinone (NTBC, Orfadin ®) inhibits tyrosine degradation prior to the formation of toxic metabolites like succinylacetone and has been offered to HT1 patients in Québec since 1994...
  7. Polyak I, Reetz M, Thiel W. Quantum mechanical/molecular mechanical study on the mechanism of the enzymatic Baeyer-Villiger reaction. J Am Chem Soc. 2012;134:2732-41 pubmed publisher
  8. Yadav B, Taurin S, Rosengren R, Schumacher M, Diederich M, Somers Edgar T, et al. Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin. Bioorg Med Chem. 2010;18:6701-7 pubmed publisher
    ..This level of activity warrants further investigation for the treatment of ER-negative breast cancer and/or chronic myelogenous leukemia as prototypical cellular models for solid and liquid tumors. ..
  9. Koelink C, van Hasselt P, van der Ploeg A, van den Heuvel Eibrink M, Wijburg F, Bijleveld C, et al. Tyrosinemia type I treated by NTBC: how does AFP predict liver cancer?. Mol Genet Metab. 2006;89:310-5 pubmed
    ..Still, some patients with NTBC treatment develop liver cancer. A rise of alpha-fetoprotein (AFP) is an indicator of liver cancer...
  10. Batisson I, Crouzet O, Besse Hoggan P, Sancelme M, Mangot J, Mallet C, et al. Isolation and characterization of mesotrione-degrading Bacillus sp. from soil. Environ Pollut. 2009;157:1195-201 pubmed publisher
    ..Among several metabolites formed, 2-amino-4-methylsulfonylbenzoic acid (AMBA) accumulated in the medium. Although sulcotrione has a chemical structure closely resembling that of mesotrione, the isolates were unable to degrade it. ..
  11. Umezawa K. Inhibition of tumor growth by NF-kappaB inhibitors. Cancer Sci. 2006;97:990-5 pubmed
    ..It inhibited both canonical and non-canonical NF-kappaB activating pathways. It inhibited various carcinomas and leukemias in animal models without any toxicity, and might be useful as an anticancer agent. ..
  12. Ohsugi T, Horie R, Kumasaka T, Ishida A, Ishida T, Yamaguchi K, et al. In vivo antitumor activity of the NF-kappaB inhibitor dehydroxymethylepoxyquinomicin in a mouse model of adult T-cell leukemia. Carcinogenesis. 2005;26:1382-8 pubmed
    ..These results suggest that DHMEQ induces apoptosis in HTLV-I-transformed cells in vivo, resulting in inhibition of tumor formation and organ infiltration, thereby enhancing survival. ..
  13. Takatsuna H, Asagiri M, Kubota T, Oka K, Osada T, Sugiyama C, et al. Inhibition of RANKL-induced osteoclastogenesis by (-)-DHMEQ, a novel NF-kappaB inhibitor, through downregulation of NFATc1. J Bone Miner Res. 2005;20:653-62 pubmed
    ..Our results also indicate the possibility of (-)-DHMEQ becoming a new therapeutic strategy against bone erosion. ..
  14. Conde F, Churio M, Previtali C. The deactivation pathways of the excited-states of the mycosporine-like amino acids shinorine and porphyra-334 in aqueous solution. Photochem Photobiol Sci. 2004;3:960-7 pubmed
    ..97%) of the absorbed energy is promptly delivered to the surroundings as heat, consistently with the low photodecomposition and emission yields observed. ..
  15. Gissen P, Preece M, Willshaw H, McKiernan P. Ophthalmic follow-up of patients with tyrosinaemia type I on NTBC. J Inherit Metab Dis. 2003;26:13-6 pubmed
    ..Despite high plasma tyrosine concentrations in some patients, they did not experience symptoms or signs of ocular toxicity...
  16. Chiba T, Kondo Y, Shinozaki S, Kaneko E, Ishigami A, Maruyama N, et al. A selective NFkappaB inhibitor, DHMEQ, reduced atherosclerosis in ApoE-deficient mice. J Atheroscler Thromb. 2006;13:308-13 pubmed
    ..A new NFkappaB inhibitor, dehydroxymethylepoxyquinomicin, reduced atherosclerosis without affecting plasma lipid levels in apoE-deficient mice. ..
  17. Charles R, Schröder E, May G, Free P, Gaffney P, Wait R, et al. Protein sulfenation as a redox sensor: proteomics studies using a novel biotinylated dimedone analogue. Mol Cell Proteomics. 2007;6:1473-84 pubmed
    ..Cardiac proteins that were sulfenated during oxidative stress were purified with avidin-agarose and identified by separation of tryptic digests by liquid chromatography with on-line analysis by mass spectrometry. ..
  18. Mukherjee A, Huber K, Evans H, Lakhani N, Martin S. A cellular and molecular investigation of the action of PMX464, a putative thioredoxin inhibitor, in normal and colorectal cancer cell lines. Br J Pharmacol. 2007;151:1167-75 pubmed
    ..The Trx1 system is an important target in tumour cells and can be inhibited by PMX464. Quiescent HUVEC and fibroblasts are relatively resistant conferring a therapeutic benefit when targeting Trx1. ..
  19. Wells G, Berry J, Bradshaw T, Burger A, Seaton A, Wang B, et al. 4-Substituted 4-hydroxycyclohexa-2,5-dien-1-ones with selective activities against colon and renal cancer cell lines. J Med Chem. 2003;46:532-41 pubmed
    ..Analogue 7a also showed in vivo antitumor activity against human RXF 944XL renal xenografts in nude NMRI mice and is the focus of further study. ..
  20. Michalek R, NELSON K, Holbrook B, Yi J, Stridiron D, Daniel L, et al. The requirement of reversible cysteine sulfenic acid formation for T cell activation and function. J Immunol. 2007;179:6456-67 pubmed
    ..Together, these results demonstrate that reversible cysteine sulfenic acid formation is an important regulatory mechanism by which CD8(+) T cells are able to modulate signaling, proliferation, and function. ..
  21. Carignan M, Cardozo K, Oliveira Silva D, Colepicolo P, Carreto J. Palythine-threonine, a major novel mycosporine-like amino acid (MAA) isolated from the hermatypic coral Pocillopora capitata. J Photochem Photobiol B. 2009;94:191-200 pubmed publisher
    ..From structural considerations we suggest that palythine-threonine is formed by decarboxylation of porphyra-334 followed by demethylation of mycosporine-methylamine-threonine...
  22. Wakamatsu K, Nanki T, Miyasaka N, Umezawa K, Kubota T. Effect of a small molecule inhibitor of nuclear factor-kappaB nuclear translocation in a murine model of arthritis and cultured human synovial cells. Arthritis Res Ther. 2005;7:R1348-59 pubmed
  23. Schlump J, Perot C, Ketteler K, Schiff M, Mayatepek E, Wendel U, et al. Severe neurological crisis in a patient with hereditary tyrosinaemia type I after interruption of NTBC treatment. J Inherit Metab Dis. 2008;31 Suppl 2:S223-5 pubmed publisher
    ..After re-introduction of NTBC the patient slowly regained normal neurological functions and recovered completely...
  24. Singh S, Klisch M, Sinha R, Hader D. Genome mining of mycosporine-like amino acid (MAA) synthesizing and non-synthesizing cyanobacteria: A bioinformatics study. Genomics. 2010;95:120-8 pubmed publisher
    ..Based on the results we propose that YP_324358 and YP_324357 gene products are involved in the biosynthesis of the common core (deoxygadusol) of all MAAs. ..
  25. Kyte B, Rouvière P, Cheng Q, Stewart J. Assessing the substrate selectivities and enantioselectivities of eight novel Baeyer-Villiger monooxygenases toward alkyl-substituted cyclohexanones. J Org Chem. 2004;69:12-7 pubmed
    ..NCIB 9871, was used to oxidize 15 different alkyl-substituted cyclohexanones. The panel of substrates included equal numbers of 2-, 3-, and 4-alkyl-substituted compounds to probe each ..
  26. Miyajima A, Kosaka T, Seta K, Asano T, Umezawa K, Hayakawa M. Novel nuclear factor kappa B activation inhibitor prevents inflammatory injury in unilateral ureteral obstruction. J Urol. 2003;169:1559-63 pubmed
    ..Specific inhibition of nuclear factor kappa B can prevent inflammatory renal responses, suggesting that targeting nuclear factor kappa B activation may be feasible for preventing inflammatory kidney diseases. ..
  27. Chiu C, Chang H, Chuang D, Chang F, Chang Y, Cheng Y, et al. Fern plant-derived protoapigenone leads to DNA damage, apoptosis, and G(2)/m arrest in lung cancer cell line H1299. DNA Cell Biol. 2009;28:501-6 pubmed publisher
    ..57 microM for 24 h sample were shown to be apoptosis using Annexin V-immunofluorescence/propidium iodide staining. These results suggest protoapigenone is a potential chemotherapeutic agent for lung cancers. ..
  28. Conde F, Churio M, Previtali C. The photoprotector mechanism of mycosporine-like amino acids. Excited-state properties and photostability of porphyra-334 in aqueous solution. J Photochem Photobiol B. 2000;56:139-44 pubmed
    ..These results support the photoprotective role assigned to this MAA in living systems. ..
  29. Singh S, Sinha R, Klisch M, Hader D. Mycosporine-like amino acids (MAAs) profile of a rice-field cyanobacterium Anabaena doliolum as influenced by PAR and UVR. Planta. 2008;229:225-33 pubmed publisher
    ..It seems that A. doliolum is able to protect its cell machinery from UVR by synthesizing a complex set of MAAs and thus is able to survive successfully during the summer in its natural brightly lit habitats...
  30. Grompe M, Lindstedt S, Al Dhalimy M, Kennaway N, Papaconstantinou J, Torres Ramos C, et al. Pharmacological correction of neonatal lethal hepatic dysfunction in a murine model of hereditary tyrosinaemia type I. Nat Genet. 1995;10:453-60 pubmed
    ..The adult FAH-/- mouse will serve as useful model for studies of the pathophysiology and treatment of hereditary tyrosinaemia type I as well as hepatic cancer. ..
  31. Turell L, Botti H, Carballal S, Ferrer Sueta G, Souza J, Duran R, et al. Reactivity of sulfenic acid in human serum albumin. Biochemistry. 2008;47:358-67 pubmed
    ..6 +/- 0.2, 2.9 +/- 0.5, 9.3 +/- 0.9, and 55 +/- 3 M-1 s-1 (25 degrees C, pH 7.4), respectively, supporting a role for HSA-SOH in the formation of mixed disulfides. ..
  32. Starenki D, Namba H, Saenko V, Ohtsuru A, Maeda S, Umezawa K, et al. Induction of thyroid cancer cell apoptosis by a novel nuclear factor kappaB inhibitor, dehydroxymethylepoxyquinomicin. Clin Cancer Res. 2004;10:6821-9 pubmed
    ..Our results show the potential usefulness of the novel NF-kappaB inhibitor, DHMEQ, in future therapeutic strategies for the treatment of thyroid cancers that do not respond to conventional approaches. ..
  33. Neve P, Powles S. Recurrent selection with reduced herbicide rates results in the rapid evolution of herbicide resistance in Lolium rigidum. Theor Appl Genet. 2005;110:1154-66 pubmed
    ..The potential genetic basis of the observed response and implications of reduced herbicide application rates for management of herbicide resistance are discussed. ..
  34. Chang H, Su J, Yeh Y, Lee Y, Chen H, Wu Y, et al. Protoapigenone, a novel flavonoid, inhibits ovarian cancer cell growth in vitro and in vivo. Cancer Lett. 2008;267:85-95 pubmed publisher
    ..Taken together, protoapigenone showed a significant anti-ovarian cancer activity with low toxicity, suggesting its potential to be developed as a chemotherapeutic agent. ..
  35. Mihovilovic M, Chen G, Wang S, Kyte B, Rochon F, Kayser M, et al. Asymmetric Baeyer-Villiger oxidations of 4-mono- and 4,4-disubstituted cyclohexanones by whole cells of engineered Escherichia coli. J Org Chem. 2001;66:733-8 pubmed
    ..monooxygenase have been used for the Baeyer-Villiger oxidations of a variety of 4-mono- and 4,4-disubstituted cyclohexanones. In cases where comparisons were possible, this new biocatalytic reagent provided lactones with chemical ..
  36. Baudoux J, Blake A, Simpkins N. Rapid access to the Welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones. Org Lett. 2005;7:4087-9 pubmed
    ..One of the bridged indole intermediates was further transformed into an oxindole having the essential skeleton of the Welwitindolinone alkaloids. ..
  37. Liang G, Li X, Chen L, Yang S, Wu X, Studer E, et al. Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin. Bioorg Med Chem Lett. 2008;18:1525-9 pubmed publisher
  38. Chaabane H, Vulliet E, Joux F, Lantoine F, Conan P, Cooper J, et al. Photodegradation of sulcotrione in various aquatic environments and toxicity of its photoproducts for some marine micro-organisms. Water Res. 2007;41:1781-9 pubmed
    ..Toxicological studies on two marine heterotrophic bacteria and one cyanobacterium showed absence of effects up to 100 microgL(-1) for both sulcotrione and its photoproducts. ..
  39. Kikuchi E, Horiguchi Y, Nakashima J, Kuroda K, Oya M, Ohigashi T, et al. Suppression of hormone-refractory prostate cancer by a novel nuclear factor kappaB inhibitor in nude mice. Cancer Res. 2003;63:107-10 pubmed
    ..c. tumor growth in nude mice without any side effects. Our result indicates the possibility of using a novel NFkappaB activation inhibitor, DHMEQ, as a new treatment strategy against hormone-refractory prostate cancer. ..
  40. Watanabe M, Dewan M, Okamura T, Sasaki M, Itoh K, Higashihara M, et al. A novel NF-kappaB inhibitor DHMEQ selectively targets constitutive NF-kappaB activity and induces apoptosis of multiple myeloma cells in vitro and in vivo. Int J Cancer. 2005;114:32-8 pubmed
    ..Therefore, our study presents a new molecular target therapy in MM. ..
  41. Mukherjee A, Westwell A, Bradshaw T, Stevens M, Carmichael J, Martin S. Cytotoxic and antiangiogenic activity of AW464 (NSC 706704), a novel thioredoxin inhibitor: an in vitro study. Br J Cancer. 2005;92:350-8 pubmed
    ..In contrast, bFGF levels are unaffected, suggesting possible involvement of HIF1alpha. Thus, AW464 is a promising chemotherapeutic drug that may have enhanced potency under hypoxic conditions and also additional antiangiogenic activity. ..
  42. Sinha R, Singh S, Hader D. Database on mycosporines and mycosporine-like amino acids (MAAs) in fungi, cyanobacteria, macroalgae, phytoplankton and animals. J Photochem Photobiol B. 2007;89:29-35 pubmed
    ..Tables 1S and 2S are available online as Supplementary material in the electronic copy of the journal as well as on our server <>.). ..
  43. El Karaksy H, Rashed M, El Sayed R, El Raziky M, El Koofy N, El Hawary M, et al. Clinical practice. NTBC therapy for tyrosinemia type 1: how much is enough?. Eur J Pediatr. 2010;169:689-93 pubmed publisher
    ..Succinylacetone was undetectable in urine on these doses...
  44. Arora N, Stumper O, Wright J, Kelly D, McKiernan P. Cardiomyopathy in tyrosinaemia type I is common but usually benign. J Inherit Metab Dis. 2006;29:54-7 pubmed
    ..Tyrosinaemia type I (TTI) is an inherited multisystemic disorder of tyrosine metabolism. In addition to hepatic and renal involvement, cardiomyopathy is an important clinical manifestation...
  45. Saurin A, Neubert H, Brennan J, Eaton P. Widespread sulfenic acid formation in tissues in response to hydrogen peroxide. Proc Natl Acad Sci U S A. 2004;101:17982-7 pubmed
    ..These approaches may find widespread utility in the study of oxidative stress, particularly because hydrogen peroxide is used extensively in models of disease or redox signaling. ..
  46. 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
  47. Somers Edgar T, Taurin S, Larsen L, Chandramouli A, Nelson M, Rosengren R. Mechanisms for the activity of heterocyclic cyclohexanone curcumin derivatives in estrogen receptor negative human breast cancer cell lines. Invest New Drugs. 2011;29:87-97 pubmed publisher
    ..These new derivatives provide a platform for the further development of drugs for the treatment of ER-negative breast cancer. ..
  48. Yu Q, Collavo A, Zheng M, Owen M, Sattin M, Powles S. Diversity of acetyl-coenzyme A carboxylase mutations in resistant Lolium populations: evaluation using clethodim. Plant Physiol. 2007;145:547-58 pubmed
  49. Yamamoto M, Horie R, Takeiri M, Kozawa I, Umezawa K. Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues. J Med Chem. 2008;51:5780-8 pubmed publisher
    ..These findings may explain the highly selective inhibition of NF-kappaB and the low toxic effect of (-)-DHMEQ in cells and animals. ..
  50. Lock E, Gaskin P, Ellis M, Provan W, Smith L. Tyrosinemia produced by 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione (NTBC) in experimental animals and its relationship to corneal injury. Toxicol Appl Pharmacol. 2006;215:9-16 pubmed
  51. Kayser M, Clouthier C. New bioorganic reagents: evolved cyclohexanone monooxygenase--why is it more selective?. J Org Chem. 2006;71:8424-30 pubmed
    ..of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified...
  52. Ariga A, Namekawa J, Matsumoto N, Inoue J, Umezawa K. Inhibition of tumor necrosis factor-alpha -induced nuclear translocation and activation of NF-kappa B by dehydroxymethylepoxyquinomicin. J Biol Chem. 2002;277:24625-30 pubmed
    ..Taken together, these data indicate that DHMEQ is a unique inhibitor of NF-kappaB acting at the level of nuclear translocation. ..
  53. Dimmock J, Kumar P, Nazarali A, Motaganahalli N, Kowalchuk T, Beazely M, et al. Cytotoxic 2,6-bis(arylidene)cyclohexanones and related compounds. Eur J Med Chem. 2000;35:967-77 pubmed
    A number of 2-arylidenecyclohexanones 1, 2, 6-bis(arylidene)cyclohexanones 2 and related Mannich bases 3-5 were prepared...