benzodioxoles

Summary

Summary: Compounds based on benzene fused to oxole. They can be formed from methylated CATECHOLS such as EUGENOL.

Top Publications

  1. Ying Z, Kherada N, Kampfrath T, Mihai G, Simonetti O, Desikan R, et al. A modified sesamol derivative inhibits progression of atherosclerosis. Arterioscler Thromb Vasc Biol. 2011;31:536-42 pubmed publisher
    ..INV-403 is a novel modified lignan derivative that potently inhibits atherosclerosis progression via its effects on IKK2 and nuclear factor-?B signaling. ..
  2. Gucalp A, Sparano J, Caravelli J, Santamauro J, Patil S, Abbruzzi A, et al. Phase II trial of saracatinib (AZD0530), an oral SRC-inhibitor for the treatment of patients with hormone receptor-negative metastatic breast cancer. Clin Breast Cancer. 2011;11:306-11 pubmed publisher
    ..Based on this series, saracatinib does not appear to have significant single-agent activity for the treatment of patients with ER(-)/PR(-) MBC. ..
  3. Puls L, Eadens M, Messersmith W. Current status of SRC inhibitors in solid tumor malignancies. Oncologist. 2011;16:566-78 pubmed publisher
    ..Src inhibitors have shown little activity in monotherapy trials in unselected solid tumor patient populations. Combination studies and biomarker-driven clinical trials are under way. ..
  4. Arcaroli J, Quackenbush K, Powell R, Pitts T, Spreafico A, Varella Garcia M, et al. Common PIK3CA mutants and a novel 3' UTR mutation are associated with increased sensitivity to saracatinib. Clin Cancer Res. 2012;18:2704-14 pubmed publisher
    ..These results indicate that a personalized approach in targeting Src in PIK3CA-mutant patients with colorectal cancers may prove effective in a subset of patients with this genetic alteration. ..
  5. Fury M, Baxi S, Shen R, Kelly K, Lipson B, Carlson D, et al. Phase II study of saracatinib (AZD0530) for patients with recurrent or metastatic head and neck squamous cell carcinoma (HNSCC). Anticancer Res. 2011;31:249-53 pubmed
    ..Median overall survival was six months. The study was closed early due to lack of efficacy according to the early stopping rule. Single-agent saracatinib does not merit further study in recurrent or metastatic HNSCC. ..
  6. Nayak P, Paul P, Bansal P, Kutty N, Pai K. Sesamol prevents doxorubicin-induced oxidative damage and toxicity on H9c2 cardiomyoblasts. J Pharm Pharmacol. 2013;65:1083-93 pubmed publisher
    ..Among the different doses tested, 50??m of sesamol showed maximum protection against Dox-induced oxidative damage. This reflects the significance of sesamol in ameliorating the deleterious effects associated with cancer chemotherapy. ..
  7. Alhouayek M, Lambert D, Delzenne N, Cani P, Muccioli G. Increasing endogenous 2-arachidonoylglycerol levels counteracts colitis and related systemic inflammation. FASEB J. 2011;25:2711-21 pubmed publisher
    ..This could offer a novel pharmacological approach for the treatment of IBD based on the new protective role of 2-arachidonoylglycerol described here. ..
  8. Han H. The effects of black pepper on the intestinal absorption and hepatic metabolism of drugs. Expert Opin Drug Metab Toxicol. 2011;7:721-9 pubmed publisher
  9. Mao Q, Huang Z, Ip S, Xian Y, Che C. Protective effects of piperine against corticosterone-induced neurotoxicity in PC12 cells. Cell Mol Neurobiol. 2012;32:531-7 pubmed publisher
    ..This neuroprotective effect may be one of the acting mechanisms accounts for the in vivo antidepressant activity of piperine. ..

More Information

Publications62

  1. Chandrasekaran V, Chien S, Hsu D, Liu M. Anti-hepatotoxic effects of 3,4-methylenedioxyphenol and N-acetylcysteine in acutely acetaminophen-overdosed mice. Hum Exp Toxicol. 2011;30:1609-15 pubmed publisher
    ..We conclude that the protective effect of sesamol against acetaminophen-induced liver damage is comparable to that of N-acetylcysteine by maintaining glutathione levels and inhibiting lipid peroxidation in mice. ..
  2. Renouf D, Moore M, Hedley D, Gill S, Jonker D, Chen E, et al. A phase I/II study of the Src inhibitor saracatinib (AZD0530) in combination with gemcitabine in advanced pancreatic cancer. Invest New Drugs. 2012;30:779-86 pubmed publisher
    ..Saracatinib 175 mg daily in combination with gemcitabine is well tolerated but the combination did not improve efficacy over what would be expected from gemcitabine alone. ..
  3. Sumislawski J, Ramikie T, Patel S. Reversible gating of endocannabinoid plasticity in the amygdala by chronic stress: a potential role for monoacylglycerol lipase inhibition in the prevention of stress-induced behavioral adaptation. Neuropsychopharmacology. 2011;36:2750-61 pubmed publisher
    ..These data indicate that chronic stress reversibly gates eCB synaptic plasticity at inhibitory synapses in the amygdala, and in vivo augmentation of 2-AG levels prevents both behavioral and synaptic adaptations to chronic stress. ..
  4. Kinsey S, Nomura D, O Neal S, Long J, Mahadevan A, Cravatt B, et al. Inhibition of monoacylglycerol lipase attenuates nonsteroidal anti-inflammatory drug-induced gastric hemorrhages in mice. J Pharmacol Exp Ther. 2011;338:795-802 pubmed publisher
  5. Xiao X, Hu Z, Shi B, Wei S, Wu W. Larvicidal activity of lignans from Phryma leptostachya L. against Culex pipiens pallens. Parasitol Res. 2012;110:1079-84 pubmed publisher
    ..This is the first report on the mosquito larvicidal activity of the three compounds, phrymarolin-I, haedoxane A, and haedoxane E from Phyrma leptostachya L. ..
  6. Moulick K, Ahn J, Zong H, Rodina A, Cerchietti L, Gomes Dagama E, et al. Affinity-based proteomics reveal cancer-specific networks coordinated by Hsp90. Nat Chem Biol. 2011;7:818-26 pubmed publisher
    ..We further show that the abundance of the PU-H71-enriched Hsp90 species, which is not dictated by Hsp90 expression alone, is predictive of the cell's sensitivity to Hsp90 inhibition. ..
  7. Coppola M, Mondola R. 3,4-methylenedioxypyrovalerone (MDPV): chemistry, pharmacology and toxicology of a new designer drug of abuse marketed online. Toxicol Lett. 2012;208:12-5 pubmed publisher
    ..This substance, sold as bath salts, has caused many serious intoxications and some deaths in several countries. The aim of this paper is summarise the clinical, pharmacological and toxicological information about this new designer drug. ..
  8. He L, Kota P, Aleksandrov A, Cui L, Jensen T, Dokholyan N, et al. Correctors of ?F508 CFTR restore global conformational maturation without thermally stabilizing the mutant protein. FASEB J. 2013;27:536-45 pubmed publisher
    ..He, L., Kota, P., Aleksandrov, A. A., Cui, L., Jensen, T., Dokholyan, N. V., Riordan, J. R. Correctors of ?F508 CFTR restore global conformational maturation without thermally stabilizing the mutant protein. ..
  9. Venkatesh S, Durga K, Padmavathi Y, Reddy B, Mullangi R. Influence of piperine on ibuprofen induced antinociception and its pharmacokinetics. Arzneimittelforschung. 2011;61:506-9 pubmed publisher
    ..From this study it can be concluded that piperine can be used as a bioenhancer along with ibuprofen...
  10. Van Goor F, Hadida S, Grootenhuis P, Burton B, Stack J, Straley K, et al. Correction of the F508del-CFTR protein processing defect in vitro by the investigational drug VX-809. Proc Natl Acad Sci U S A. 2011;108:18843-8 pubmed publisher
    ..VX-809 was more efficacious and selective for CFTR than previously reported CFTR correctors. VX-809 represents a class of CFTR corrector that specifically addresses the underlying processing defect in F508del-CFTR...
  11. Periasamy S, Hsu D, Chen S, Yang S, Chandrasekaran V, Liu M. Therapeutic sesamol attenuates monocrotaline-induced sinusoidal obstruction syndrome in rats by inhibiting matrix metalloproteinase-9. Cell Biochem Biophys. 2011;61:327-36 pubmed publisher
    ..We conclude that a single dose of sesamol therapeutically attenuated SOS by decreasing the recruitment of inflammatory cells, downregulating MMP-9, and upregulating TIMP-1 expression. ..
  12. Busquets Garcia A, Puighermanal E, Pastor A, de la Torre R, Maldonado R, Ozaita A. Differential role of anandamide and 2-arachidonoylglycerol in memory and anxiety-like responses. Biol Psychiatry. 2011;70:479-86 pubmed publisher
    ..These results dissociate the role of anandamide and 2-arachidonoylglycerol in memory consolidation and anxiety and reveal the interest of cannabinoid receptor 2 as a novel target for the treatment of anxiety-related disorders. ..
  13. Mackay H, Au H, McWhirter E, Alcindor T, Jarvi A, Macalpine K, et al. A phase II trial of the Src kinase inhibitor saracatinib (AZD0530) in patients with metastatic or locally advanced gastric or gastro esophageal junction (GEJ) adenocarcinoma: a trial of the PMH phase II consortium. Invest New Drugs. 2012;30:1158-63 pubmed publisher
    ..Further development in gastric cancer would require rational drug combinations or identification of a tumor phenotype sensitive to Src inhibition. ..
  14. Johnson J, Nihal M, Siddiqui I, Scarlett C, Bailey H, Mukhtar H, et al. Enhancing the bioavailability of resveratrol by combining it with piperine. Mol Nutr Food Res. 2011;55:1169-76 pubmed publisher
    ..However, further detailed research is needed to study the mechanism of improved bioavailability of resveratrol via its combination with piperine as well as its effect on resveratrol metabolism. ..
  15. Vennila L, Pugalendi K. Efficacy of sesamol on plasma and tissue lipids in isoproterenol-induced cardiotoxicity in Wistar rats. Arch Pharm Res. 2012;35:1465-70 pubmed publisher
    ..The protective role of sesamol against isoproterenol-induced myocardial infarction was further confirmed by histopathological examination. These results suggest that sesamol has antihyperlipidaemic effect against cardiotoxicity...
  16. Cinelli M, Reddy P, Lv P, Liang J, Chen L, Agama K, et al. Identification, synthesis, and biological evaluation of metabolites of the experimental cancer treatment drugs indotecan (LMP400) and indimitecan (LMP776) and investigation of isomerically hydroxylated indenoisoquinoline analogues as topoisomerase I . J Med Chem. 2012;55:10844-62 pubmed publisher
    ..Differences in activity resulting from the placement of the hydroxyl group are explained by molecular modeling analyses. ..
  17. Clancy J, Rowe S, Accurso F, Aitken M, Amin R, Ashlock M, et al. Results of a phase IIa study of VX-809, an investigational CFTR corrector compound, in subjects with cystic fibrosis homozygous for the F508del-CFTR mutation. Thorax. 2012;67:12-8 pubmed publisher
    ..Additional data are needed to determine how improvements detected in CFTR function secondary to VX-809 in the sweat gland relate to those measurable in the respiratory tract and to long-term measures of clinical benefit. NCT00865904. ..
  18. Hwang Y, Yun H, Kim H, Han E, Choi J, Chung Y, et al. Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by piperine via the inhibition of PKC?/ERK1/2-dependent matrix metalloproteinase-9 expression. Toxicol Lett. 2011;203:9-19 pubmed publisher
    ..Thus, piperine has potential as a potent anti-cancer drug in therapeutic strategies for fibrosarcoma metastasis. ..
  19. Dong M, Rice L, Lepler S, Pampo C, Siemann D. Impact of the Src inhibitor saracatinib on the metastatic phenotype of a fibrosarcoma (KHT) tumor model. Anticancer Res. 2010;30:4405-13 pubmed
    ..0 to 5.0 (p<0.05) and less than 1.0 (p<0.01), respectively. These findings suggest that Src inhibition by saracatinib may reduce the metastatic activity of tumor cells. ..
  20. Matsuda D, Ohte S, Ohshiro T, Jiang W, Rudel L, Hong B, et al. Molecular target of piperine in the inhibition of lipid droplet accumulation in macrophages. Biol Pharm Bull. 2008;31:1063-6 pubmed
    ..Thus, it was suggested that piperine inhibited macrophage ACAT to decrease CE synthesis, leading to a reduction of lipid droplets. ..
  21. Alig L, Alsenz J, Andjelkovic M, Bendels S, Benardeau A, Bleicher K, et al. Benzodioxoles: novel cannabinoid-1 receptor inverse agonists for the treatment of obesity. J Med Chem. 2008;51:2115-27 pubmed publisher
    ..including pharmacophore compliance, chemical tractability, and drug likeness, allowed the identification of benzodioxoles as a novel CB1R inverse agonist series...
  22. Long J, Nomura D, Cravatt B. Characterization of monoacylglycerol lipase inhibition reveals differences in central and peripheral endocannabinoid metabolism. Chem Biol. 2009;16:744-53 pubmed publisher
    ..Collectively, these studies indicate that MAGL exerts tissue-dependent control over endocannabinoid and monoglyceride metabolism and designate JZL184 as a selective tool to characterize the functions of MAGL in vivo. ..
  23. Chu P, Hsu D, Hsu P, Liu M. Sesamol down-regulates the lipopolysaccharide-induced inflammatory response by inhibiting nuclear factor-kappa B activation. Innate Immun. 2010;16:333-9 pubmed publisher
    ..7 cells. By inhibiting TNF-?, IL-1?, and nitrite levels, and interfering with the NF?B pathway, sesamol down-regulated the LPS-initiated inflammatory response. ..
  24. Bezerra D, de Castro F, Alves A, Pessoa C, de Moraes M, Silveira E, et al. In vitro and in vivo antitumor effect of 5-FU combined with piplartine and piperine. J Appl Toxicol. 2008;28:156-63 pubmed
    ..These findings indicate that piplartine may enhance the therapeutic effectiveness of chemotherapeutic drugs, and moreover, this combination could improve immunocompetence hampered by 5-FU. ..
  25. Chen P, Lee C, Chang H, Tsai C. Sesamol regulates plasminogen activator gene expression in cultured endothelial cells: a potential effect on the fibrinolytic system. J Nutr Biochem. 2005;16:59-64 pubmed
    ..As for PAI-1, none of the nutrients induced any evident response. These findings suggest that the overall vascular fibrinolytic capacity may be enhanced by using sesamol to regulate PA gene expression. ..
  26. Bhardwaj R, Glaeser H, Becquemont L, Klotz U, Gupta S, Fromm M. Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4. J Pharmacol Exp Ther. 2002;302:645-50 pubmed
  27. Hiwale A, Dhuley J, Naik S. Effect of co-administration of piperine on pharmacokinetics of beta-lactam antibiotics in rats. Indian J Exp Biol. 2002;40:277-81 pubmed
    ..tmax, Cmax, t(1/2) and AUC, of these antibiotics. The increased bioavailability could be attributed to the effect of piperine on microsomal metabolising enzymes or enzymes system. ..
  28. Selvendiran K, Thirunavukkarasu C, Singh J, Padmavathi R, Sakthisekaran D. Chemopreventive effect of piperine on mitochondrial TCA cycle and phase-I and glutathione-metabolizing enzymes in benzo(a)pyrene induced lung carcinogenesis in Swiss albino mice. Mol Cell Biochem. 2005;271:101-6 pubmed
    ..Piprine administration to benzo(a)pyrene induced animals significantly increased the activities of mitochondrial enzymes, thereby suggesting its role in mitochondrial energy production. ..
  29. Baselga J, Cervantes A, Martinelli E, Chirivella I, Hoekman K, Hurwitz H, et al. Phase I safety, pharmacokinetics, and inhibition of SRC activity study of saracatinib in patients with solid tumors. Clin Cancer Res. 2010;16:4876-83 pubmed publisher
    ..A reduction in tumor Src activity was observed. PK data show that saracatinib is suitable for once-daily oral dosing. Based on this study, the recommended dose for the phase II studies was chosen to be 175 mg/d. ..
  30. Schlosburg J, Blankman J, Long J, Nomura D, Pan B, Kinsey S, et al. Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system. Nat Neurosci. 2010;13:1113-9 pubmed publisher
    ..Thus, individual endocannabinoids generate distinct analgesic profiles that are either sustained or transitory and associated with agonism and functional antagonism of the brain cannabinoid system, respectively. ..
  31. Bianchini A, Monserrat J. Effects of methyl parathion on Chasmagnathus granulatus hepatopancreas: protective role of sesamol. Ecotoxicol Environ Saf. 2007;67:100-8 pubmed
  32. Kim S, Lee Y. Piperine inhibits eosinophil infiltration and airway hyperresponsiveness by suppressing T cell activity and Th2 cytokine production in the ovalbumin-induced asthma model. J Pharm Pharmacol. 2009;61:353-9 pubmed publisher
  33. Parihar V, Prabhakar K, Veerapur V, Kumar M, Reddy Y, Joshi R, et al. Effect of sesamol on radiation-induced cytotoxicity in Swiss albino mice. Mutat Res. 2006;611:9-16 pubmed
    ..There was no protection at a dose less than 25mg/kg bw. ..
  34. Chen Y, Lin S, Chang J, Cheng Y, Tsai N, Chen S, et al. In vitro and in vivo studies of a novel potential anticancer agent of isochaihulactone on human lung cancer A549 cells. Biochem Pharmacol. 2006;72:308-19 pubmed
    ..These findings indicate isochaihulactone is a promising new antimitotic anticancer compound with potential for clinical application in the future. ..
  35. Pathak N, Khandelwal S. Modulation of cadmium induced alterations in murine thymocytes by piperine: oxidative stress, apoptosis, phenotyping and blastogenesis. Biochem Pharmacol. 2006;72:486-97 pubmed
  36. Selvendiran K, Padmavathi R, Magesh V, Sakthisekaran D. Preliminary study on inhibition of genotoxicity by piperine in mice. Fitoterapia. 2005;76:296-300 pubmed
    ..A significant suppression (33.9-66.5%) in the micronuclei formation induced by benzo(a)pyrene and cyclophosphamide was reduced following oral administration of piperine at doses of 25, 50 and 75 mg/kg in mice. ..
  37. Lee C, Han E, Kim Y. Piperine inhibition of 1-methyl-4-phenylpyridinium-induced mitochondrial dysfunction and cell death in PC12 cells. Eur J Pharmacol. 2006;537:37-44 pubmed
    ..The effects may be ascribed to its inhibitory action on the formation of reactive oxygen species and depletion of GSH. ..
  38. Pattanaik S, Hota D, Prabhakar S, Kharbanda P, Pandhi P. Pharmacokinetic interaction of single dose of piperine with steady-state carbamazepine in epilepsy patients. Phytother Res. 2009;23:1281-6 pubmed publisher
    ..Piperine could significantly enhance the oral bioavailability of carbamazepine, possibly by decreasing the elimination and/or by increasing its absorption. ..
  39. Wattanathorn J, Chonpathompikunlert P, Muchimapura S, Priprem A, Tankamnerdthai O. Piperine, the potential functional food for mood and cognitive disorders. Food Chem Toxicol. 2008;46:3106-10 pubmed publisher
    ..Therefore, piperine may be served as the potential functional food to improve brain function. However, further investigations about precise underlying mechanism are still required. ..
  40. Pathak N, Khandelwal S. Comparative efficacy of piperine, curcumin and picroliv against Cd immunotoxicity in mice. Biometals. 2008;21:649-61 pubmed publisher
    ..The ameliorative potential was in order of piperine > curcumin > picroliv and former could be considered the drug of choice under immunocompromised conditions. ..
  41. Zhao J, Du G, Xiong Y, Wen Y, Bhadauria M, Nirala S. Attenuation of beryllium induced hepatorenal dysfunction and oxidative stress in rodents by combined effect of gallic acid and piperine. Arch Pharm Res. 2007;30:1575-83 pubmed
    ..We concluded that gallic acid exerts a synergistic effect when administered with piperine and provides a more pronounced therapeutic potential in reducing beryllium-induced hepatorenal dysfunction and oxidative stress consequences...
  42. Jin M, Han H. Effect of piperine, a major component of black pepper, on the intestinal absorption of fexofenadine and its implication on food-drug interaction. J Food Sci. 2010;75:H93-6 pubmed publisher
  43. Rajeshkumar N, Tan A, de Oliveira E, Womack C, Wombwell H, Morgan S, et al. Antitumor effects and biomarkers of activity of AZD0530, a Src inhibitor, in pancreatic cancer. Clin Cancer Res. 2009;15:4138-46 pubmed publisher
    ..One gene pair (LRRC19 and IGFBP2) identified by the K-TSP classifier has high predictive power for AZD0530 sensitivity, suggesting the potential for this gene pair as biomarker for pancreatic tumor sensitivity to AZD0530. ..
  44. Gupta A, Sharma S, Kaur I, Chopra K. Renoprotective effects of sesamol in ferric nitrilotriacetate-induced oxidative renal injury in rats. Basic Clin Pharmacol Toxicol. 2009;104:316-21 pubmed publisher
    ..Present findings strongly suggest the pivotal role of oxidative stress in the ferric nitrilotriacetate-induced renal dysfunction and points towards the renoprotective potential of sesamol in oxidative renal pathologies...
  45. Jacklin A, Ratledge C, Welham K, Bilko D, Newton C. The sesame seed oil constituent, sesamol, induces growth arrest and apoptosis of cancer and cardiovascular cells. Ann N Y Acad Sci. 2003;1010:374-80 pubmed
    ..By conducting preliminary studies on the effect of sesamol alone, it was clear that the compound demonstrated marked cytotoxicity. This paper describes the experiments performed. ..
  46. Naidu K, Thippeswamy N. Inhibition of human low density lipoprotein oxidation by active principles from spices. Mol Cell Biochem. 2002;229:19-23 pubmed
    ..These data suggest that the above spice active principles, which constitute about 1-4% of above spices, are effective antioxidants and offer protection against oxidation of human LDL. ..
  47. Kaur I, Saini A. Sesamol exhibits antimutagenic activity against oxygen species mediated mutagenicity. Mutat Res. 2000;470:71-6 pubmed
    ..Since active oxygen species are involved in multiple stage processes of carcinogenicity, this compound may also exhibit anticarcinogenic properties. ..
  48. Vijayakumar R, Nalini N. Piperine, an active principle from Piper nigrum, modulates hormonal and apo lipoprotein profiles in hyperlipidemic rats. J Basic Clin Physiol Pharmacol. 2006;17:71-86 pubmed
  49. Chen P, Tsai C, Chang H, Liu T, Lee C. Sesamol induces nitric oxide release from human umbilical vein endothelial cells. Lipids. 2005;40:955-61 pubmed
    ..The results demonstrate that sesamol induces NOS signaling pathways in HUVEC and suggest a role for sesamol in cardiovascular reactivity in vivo. ..
  50. Joshi R, Kumar M, Satyamoorthy K, Unnikrisnan M, Mukherjee T. Free radical reactions and antioxidant activities of sesamol: pulse radiolytic and biochemical studies. J Agric Food Chem. 2005;53:2696-703 pubmed
    ..These antioxidant and free radical scavenging activities of sesamol have been reported in the paper. ..
  51. Pradeep C, Kuttan G. Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells. Int Immunopharmacol. 2004;4:1795-803 pubmed
    ..We found that the nuclear translocation of p65, p50, c-Rel subunits of NF-kappaB and other transcription factors such as ATF-2, c-Fos and CREB were inhibited by the treatment of piperine. ..
  52. Lambert J, Hong J, Kim D, Mishin V, Yang C. Piperine enhances the bioavailability of the tea polyphenol (-)-epigallocatechin-3-gallate in mice. J Nutr. 2004;134:1948-52 pubmed
    ..The present study demonstrates the modulation of the EGCG bioavailablity by a second dietary component and illustrates a mechanism for interactions between dietary chemicals. ..
  53. Mittal R, Gupta R. In vitro antioxidant activity of piperine. Methods Find Exp Clin Pharmacol. 2000;22:271-4 pubmed
    ..23 mM. The results depict that piperine possesses direct antioxidant activity against various free radicals. This study also opens newer views on the potential efficacy of piperine in protecting tissues from peroxidative damage. ..