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5578-73-4

5578-73-4 | [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (1:1)

CAS No: 5578-73-4 Catalog No: AG0038NA MDL No:MFCD00012126

Product Description

Catalog Number:
AG0038NA
Chemical Name:
[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (1:1)
CAS Number:
5578-73-4
Molecular Formula:
C20H14ClNO4
Molecular Weight:
367.7825
MDL Number:
MFCD00012126
IUPAC Name:
24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene;chloride
InChI:
InChI=1S/C20H14NO4.ClH/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21;/h2-8H,9-10H2,1H3;1H/q+1;/p-1
InChI Key:
GIZKAXHWLRYMLE-UHFFFAOYSA-M
SMILES:
C[n+]1cc2c3OCOc3ccc2c2c1c1cc3OCOc3cc1cc2.[Cl-]
UNII:
B8Z8J4400H

Properties

Complexity:
530  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
367.061g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
367.785g/mol
Monoisotopic Mass:
367.061g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
40.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0

Literature

Title Journal
Improved apoptotic cell death in drug-resistant non-small-cell lung cancer cells by tumor necrosis factor-related apoptosis-inducing ligand-based treatment. The Journal of pharmacology and experimental therapeutics 20140301
NQO1 involves in the imine bond reduction of sanguinarine and recombinant adeno-associated virus mediated NQO1 overexpression decreases sanguinarine-induced cytotoxicity in rat BRL cells. Toxicology letters 20140210
Sanguinarine induces apoptosis in human colorectal cancer HCT-116 cells through ROS-mediated Egr-1 activation and mitochondrial dysfunction. Toxicology letters 20130704
Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells. Phytochemistry 20130701
Sanguinarine inhibits growth of human cervical cancer cells through the induction of apoptosis. Oncology reports 20121201
Antibacterial activity of substituted 5-methylbenzo[c]phenanthridinium derivatives. Bioorganic & medicinal chemistry letters 20121201
In vitro antifungal activity of sanguinarine and chelerythrine derivatives against phytopathogenic fungi. Molecules (Basel, Switzerland) 20121102
Luminescence and binding properties of two isoquinoline alkaloids chelerythrine and sanguinarine with ctDNA. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120901
The anti-inflammatory effects of sanguinarine and its modulation of inflammatory mediators from peritoneal macrophages. European journal of pharmacology 20120815
Molecular basis for differential glycine transporters sensitivity to sanguinarine. Toxicology letters 20120803
Investigation of sanguinarine and chelerythrine effects on LPS-induced inflammatory gene expression in THP-1 cell line. Phytomedicine : international journal of phytotherapy and phytopharmacology 20120715
Spectroscopic, molecular modeling, and NMR-spectroscopic investigation of the binding mode of the natural alkaloids berberine and sanguinarine to human telomeric G-quadruplex DNA. ACS chemical biology 20120615
Induction of heme oxygenase-1 by Macleaya cordata extract and its constituent sanguinarine in RAW264.7 cells. Fitoterapia 20120301
The sequential exposure to jasmonate, salicylic acid and yeast extract promotes sanguinarine accumulation in Argemone mexicana cell cultures. Biotechnology letters 20120201
Microinjection of sanguinarine into the ventrolateral orbital cortex inhibits Mkp-1 and exerts an antidepressant-like effect in rats. Neuroscience letters 20120111
Inhibition of Stat3 activation by sanguinarine suppresses prostate cancer cell growth and invasion. The Prostate 20120101
Antitumor effects of the benzophenanthridine alkaloid sanguinarine in a rat syngeneic model of colorectal cancer. Anti-cancer drugs 20120101
Sanguinarine induces apoptosis of HT-29 human colon cancer cells via the regulation of Bax/Bcl-2 ratio and caspase-9-dependent pathway. International journal of toxicology 20120101
Establishment of a sanguinarine-producing cell suspension culture of Argemone mexicana L (Papaveraceae): induction of alkaloid accumulation. Methods in molecular biology (Clifton, N.J.) 20120101
Binding of the anticancer alkaloid sanguinarine with tRNA(phe): spectroscopic and calorimetric studies. Journal of biomolecular structure & dynamics 20120101
Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: binding aspects and implications for drug design. Medicinal research reviews 20111101
Chiral HPLC studies on chemical behavior of 6-methoxydihydrosanguinarine in alcoholic solvent system. Journal of pharmaceutical and biomedical analysis 20111101
Sanguinarine is an allosteric activator of AMP-activated protein kinase. Biochemical and biophysical research communications 20110923
Embryonic toxicity of sanguinarine through apoptotic processes in mouse blastocysts. Toxicology letters 20110910
Evaluation of anticancer activities of benzo[c]phenanthridine alkaloid sanguinarine in oral squamous cell carcinoma cell line. Anticancer research 20110901
In vitro potentiation of ampicillin, oxacillin, norfloxacin, ciprofloxacin, and vancomycin by sanguinarine against methicillin-resistant Staphylococcus aureus. Foodborne pathogens and disease 20110801
The mechanism of action of sanguinarine against methicillin-resistant Staphylococcus aureus. The Journal of toxicological sciences 20110601
X-Ray diffraction analyses of the natural isoquinoline alkaloids Berberine and Sanguinarine complexed with double helix DNA d(CGTACG). Chemical communications (Cambridge, England) 20110507
Differential effect of the benzophenanthridine alkaloids sanguinarine and chelerythrine on glycine transporters. Neurochemistry international 20110501
Identification of benzo[c]phenanthridine metabolites in human hepatocytes by liquid chromatography with electrospray ion-trap and quadrupole time-of-flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110501
Structural modification of sanguinarine and chelerythrine and their antibacterial activity. Natural product research 20110501
Interaction of berberine, palmatine, coralyne, and sanguinarine to quadruplex DNA: a comparative spectroscopic and calorimetric study. Biochimica et biophysica acta 20110401
In vitro and in vivo evaluation of sanguinarine liposomes prepared by a remote loading method with three different ammonium salts. Die Pharmazie 20110401
[Study on the alkaloids from the stem of Zanthoxylum dissitum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110401
Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana. Archives of biochemistry and biophysics 20110301
The actions of benzophenanthridine alkaloids, piperonyl butoxide and (S)-methoprene at the G-protein coupled cannabinoid CB₁ receptor in vitro. European journal of pharmacology 20110301
Inclusion complex formation of sanguinarine alkaloid with cucurbit[7]uril: inhibition of nucleophilic attack and photooxidation. Organic & biomolecular chemistry 20110221
[Study on liver injury of Oncomelania hupensis caused by Eomecon chinanthe sanguinarine]. Zhongguo xue xi chong bing fang zhi za zhi = Chinese journal of schistosomiasis control 20110201
Human telomere d[(TTAGGG)4] undergoes a conformational transition to the Na+-form upon binding with sanguinarine in presence of K+. Biochemical and biophysical research communications 20110107
Interaction of the anticancer plant alkaloid sanguinarine with bovine serum albumin. PloS one 20110101
Potentiation of tumour promotion by topical application of argemone oil/isolated sanguinarine alkaloid in a model of mouse skin carcinogenesis. Chemico-biological interactions 20101205
Distinct G-quadruplex structures of human telomeric DNA formed by the induction of sanguinarine and nitidine under salt-deficient condition. Fitoterapia 20101201
Fluorescence of sanguinarine: spectral changes on interaction with amino acids. Physical chemistry chemical physics : PCCP 20101007
Effect of sanguinarine from the leaves of Macleaya cordata against Ichthyophthirius multifiliis in grass carp (Ctenopharyngodon idella). Parasitology research 20101001
In vitro growth-inhibitory effect of plant-derived extracts and compounds against Paenibacillus larvae and their acute oral toxicity to adult honey bees. Veterinary microbiology 20100928
Sanguinarine induces apoptosis of human osteosarcoma cells through the extrinsic and intrinsic pathways. Biochemical and biophysical research communications 20100827
Metabolism of sanguinarine in human and in rat: characterization of oxidative metabolites produced by human CYP1A1 and CYP1A2 and rat liver microsomes using liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis 20100708
Fusarium oxysporum homogenates and jasmonate induce limited sanguinarine accumulation in Argemone mexicana cell cultures. Biotechnology letters 20100701
Binding of the anticancer alkaloid sanguinarine to double stranded RNAs: insights into the structural and energetics aspects. Molecular bioSystems 20100701
Interaction of sanguinarine and its dihydroderivative with the Na+/K+-ATPase. Complex view on the old problem. Toxicology letters 20100616
Structure and mechanism of sanguinarine reductase, an enzyme of alkaloid detoxification. The Journal of biological chemistry 20100611
[Identification of differentially expressed proteins in the liver of Oncomelania snails induced by Eomecon chinanthe sanguinarine]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20100601
Study on the inclusion interaction of cucurbit[n]urils with sanguinarine by spectrofluorimetry and its analytical application. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20100201
Racemization of 6-methoxydihydrosanguinarine in methanol investigated by enantioselective dynamic HPLC. Journal of pharmaceutical and biomedical analysis 20100105
Skin tumor promotion by argemone oil/alkaloid in mice: evidence for enhanced cell proliferation, ornithine decarboxylase, cyclooxygenase-2 and activation of MAPK/NF-kappaB pathway. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100101
The cytotoxic agents NSC-95397, brefeldin A, bortezomib and sanguinarine induce apoptosis in neuroendocrine tumors in vitro. Anticancer research 20100101
Sanguinarine as a potent and specific inhibitor of protein phosphatase 2C in vitro and induces apoptosis via phosphorylation of p38 in HL60 cells. Bioscience, biotechnology, and biochemistry 20100101
Involvement of lipoxygenase in elicitor-stimulated sanguinarine accumulation in Papaver somniferum suspension cultures. Plant physiology and biochemistry : PPB 20100101
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. BMC plant biology 20100101
Inactivation of the Ecs ABC transporter of Staphylococcus aureus attenuates virulence by altering composition and function of bacterial wall. PloS one 20100101
A mutant of SWAP-70, a phosphatidylinositoltrisphosphate binding protein, transforms mouse embryo fibroblasts, which is inhibited by sanguinarine. PloS one 20100101
Antiproliferative and antiangiogenic effects of the benzophenanthridine alkaloid sanguinarine in melanoma. Biochemical pharmacology 20091201
Sanguinarine sensitizes human gastric adenocarcinoma AGS cells to TRAIL-mediated apoptosis via down-regulation of AKT and activation of caspase-3. Anticancer research 20091101
Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding. Bioorganic & medicinal chemistry letters 20091001
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Nature chemical biology 20091001
Phenotype of hepatic xenobiotic metabolizing enzymes and CYP450 isoforms of sanguinarine treated rats: effect of P450 inducers on its toxicity. Toxicology mechanisms and methods 20091001
Antifungal activity of the benzo[c]phenanthridine alkaloids from Chelidonium majus Linn against resistant clinical yeast isolates. Journal of ethnopharmacology 20090925
Fluorescence of sanguinarine: fundamental characteristics and analysis of interconversion between various forms. Analytical and bioanalytical chemistry 20090901
Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells. Toxicology in vitro : an international journal published in association with BIBRA 20090601
Anti-invasive activity of sanguinarine through modulation of tight junctions and matrix metalloproteinase activities in MDA-MB-231 human breast carcinoma cells. Chemico-biological interactions 20090515
Food contamination. Disease-a-month : DM 20090501
Effect of argemone oil and argemone alkaloid, sanguinarine on Sertoli-germ cell coculture. Toxicology letters 20090425
Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry. Journal of chromatography. A 20090313
Sanguinarine induces apoptosis in A549 human lung cancer cells primarily via cellular glutathione depletion. Toxicology in vitro : an international journal published in association with BIBRA 20090301
Sanguinarine interacts with chromatin, modulates epigenetic modifications, and transcription in the context of chromatin. Chemistry & biology 20090227
Plant defense responses in opium poppy cell cultures revealed by liquid chromatography-tandem mass spectrometry proteomics. Molecular & cellular proteomics : MCP 20090101
Sanguinarine cytotoxicity on mouse melanoma K1735-M2 cells--nuclear vs. mitochondrial effects. Biochemical pharmacology 20081201
Natural feed additive of Macleaya cordata: safety assessment in rats a 90-day feeding experiment. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20081201
Ligand binding to tandem G quadruplexes from human telomeric DNA. Chembiochem : a European journal of chemical biology 20081103
Induction of hepatotoxicity by sanguinarine is associated with oxidation of protein thiols and disturbance of mitochondrial respiration. Journal of applied toxicology : JAT 20081101
Site-specific binding of chelerythrine and sanguinarine to single pyrimidine bulges in hairpin DNA. Analytical and bioanalytical chemistry 20081001
Production of hydrogen peroxide and redox cycling can explain how sanguinarine and chelerythrine induce rapid apoptosis. Archives of biochemistry and biophysics 20080901
Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2). Journal of medicinal chemistry 20080612
Sanguinarine-induced apoptosis: generation of ROS, down-regulation of Bcl-2, c-FLIP, and synergy with TRAIL. Journal of cellular biochemistry 20080601
Macleaya cordata extract and Sangrovit genotoxicity. Assessment in vivo. Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia 20080601
Separation of sanguinarine and chelerythrine in Macleaya cordata (Willd) R. Br. based on methyl acrylate-co-divinylbenzene macroporous adsorbents. Journal of chromatography. A 20080523
A decisive role of mitochondria in defining rate and intensity of apoptosis induction by different alkaloids. Toxicology letters 20080401
Histopathologic findings and diagnostic difficulties posed with use of escharotic agents for treatment of skin lesions: a case report and review of the literature. Journal of cutaneous pathology 20080401
Sanguinarine-induced G1-phase arrest of the cell cycle results from increased p27KIP1 expression mediated via activation of the Ras/ERK signaling pathway in vascular smooth muscle cells. Archives of biochemistry and biophysics 20080315
Sanguinarine causes DNA damage and p53-independent cell death in human colon cancer cell lines. Chemico-biological interactions 20080310
Apoptogenic activity of two benzophenanthridine alkaloids from Chelidonium majus L. does not correlate with their DNA damaging effects. Toxicology in vitro : an international journal published in association with BIBRA 20080301
Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells. Cell biology international 20080201
Conventional protein kinase C isoenzymes undergo dephosphorylation in neutrophil-like HL-60 cells treated by chelerythrine or sanguinarine. Cell biology and toxicology 20080101
Sanguinarine. Cardiovascular therapeutics 20080101
Sanguinarine-induced apoptosis in human leukemia U937 cells via Bcl-2 downregulation and caspase-3 activation. Chemotherapy 20080101
Sanguinarine, a benzophenanthridine alkaloid, induces apoptosis in MDA-MB-231 human breast carcinoma cells through a reactive oxygen species-mediated mitochondrial pathway. Chemotherapy 20080101
Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives. Medicinal research reviews 20070901
Specific binding and self-structure induction to poly(A) by the cytotoxic plant alkaloid sanguinarine. Biochimica et biophysica acta 20070901
Induction of apoptosis by sanguinarine in C6 rat glioblastoma cells is associated with the modulation of the Bcl-2 family and activation of caspases through downregulation of extracellular signal-regulated kinase and Akt. Anti-cancer drugs 20070901
Berberine suppresses inflammatory agents-induced interleukin-1beta and tumor necrosis factor-alpha productions via the inhibition of IkappaB degradation in human lung cells. Pharmacological research 20070901
The plant alkaloid sanguinarine is a potential inhibitor of follicular angiogenesis. The Journal of reproduction and development 20070601
Sanguinarine induces apoptosis of human pancreatic carcinoma AsPC-1 and BxPC-3 cells via modulations in Bcl-2 family proteins. Cancer letters 20070508
Disposition of sanguinarine in the rat. Xenobiotica; the fate of foreign compounds in biological systems 20070501
Sanguinarine-dependent induction of apoptosis in primary effusion lymphoma cells. Cancer research 20070415
Antiplatelet effect of sanguinarine is correlated to calcium mobilization, thromboxane and cAMP production. Atherosclerosis 20070401
Variability in the yield of benzophenanthridine alkaloids in wildcrafted vs cultivated bloodroot (Sanguinaria canadensis L.). Journal of agricultural and food chemistry 20070221
Metabolism of sanguinarine: the facts and the myths. Current drug metabolism 20070201
Aurintricarboxylic acid inhibits protein synthesis independent, sanguinarine-induced apoptosis and oncosis. Toxicologic pathology 20070201
Induction of necrosis and apoptosis to KB cancer cells by sanguinarine is associated with reactive oxygen species production and mitochondrial membrane depolarization. Toxicology and applied pharmacology 20070115
Sanguinarine inhibits VEGF-induced Akt phosphorylation. Annals of the New York Academy of Sciences 20070101
Sanguinarine inhibits VEGF-induced angiogenesis in a fibrin gel matrix. BioFactors (Oxford, England) 20070101
Protective effect of sanguinarine on ultraviolet B-mediated damages in SKH-1 hairless mouse skin: implications for prevention of skin cancer. Photochemistry and photobiology 20070101
Chelerythrine and sanguinarine dock at distinct sites on BclXL that are not the classic BH3 binding cleft. Journal of molecular biology 20061201
Protective effect of bioantioxidants on argemone oil/sanguinarine alkaloid induced genotoxicity in mice. Cancer letters 20061128
The effect of chelerythrine on cell growth, apoptosis, and cell cycle in human normal and cancer cells in comparison with sanguinarine. Cell biology and toxicology 20061101
The prokaryotic cytoskeleton: a putative target for inhibitors and antibiotics? Applied microbiology and biotechnology 20061101
Cytotoxicity of sanguinarine in primary rat hepatocytes is attenuated by dioxin and phenobarbital. Toxicology letters 20060910
Quaternary benzo[c]phenathridine alkaloids sanguinarine and chelerythrine do not affect transcriptional activity of aryl hydrocarbon receptor: analyses in rat hepatoma cell line H4IIE.luc. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060901
DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine. Bioorganic & medicinal chemistry 20060815
Sanguinarine overcomes P-glycoprotein-mediated multidrug-resistance via induction of apoptosis and oncosis in CEM-VLB 1000 cells. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20060801
Sanguinarine downregulates AT1a gene expression in a hypertensive rat model. Journal of cardiovascular pharmacology 20060801
Effects of sanguinarine and chelerythrine on the cell cycle and apoptosis. Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia 20060701
Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. Cancer letters 20060608
The benzophenanthridine alkaloid sanguinarine perturbs microtubule assembly dynamics through tubulin binding. A possible mechanism for its antiproliferative activity. The FEBS journal 20060501
The plant alkaloid Sanguinarine affects swine granulosa cell activity. Reproductive toxicology (Elmsford, N.Y.) 20060401
Cyclooxygenase 2 rescues LNCaP prostate cancer cells from sanguinarine-induced apoptosis by a mechanism involving inhibition of nitric oxide synthase activity. Cancer research 20060401
Investigation of sanguinarine and chelerythrine effects on CYP1A1 expression and activity in human hepatoma cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060201
Enhancement of UVB radiation-mediated apoptosis by sanguinarine in HaCaT human immortalized keratinocytes. Molecular cancer therapeutics 20060201
Sanguinarine reductase, a key enzyme of benzophenanthridine detoxification. Plant, cell & environment 20060201
A liquid chromatographic-mass spectrometric evidence of dihydrosanguinarine as a first metabolite of sanguinarine transformation in rat. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060102
Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine. BMC cell biology 20060101
Analysis of secondary metabolites from eschscholtzia californica by high-performance liquid chromatography. Phytochemical analysis : PCA 20060101
Rapid determination of protopine, allocryptopine, sanguinarine and chelerythrine in fruits of Macleaya cordata by microwave-assisted solvent extraction and HPLC-ESI/MS. Phytochemical analysis : PCA 20060101
Site-specific binding of chelerythrine to single cytosine and thymine bulges in DNA hairpins. Nucleic acids symposium series (2004) 20060101
Sanguinarine blocks cytokinesis in bacteria by inhibiting FtsZ assembly and bundling. Biochemistry 20051220
Correlation of DNA damage in epidemic dropsy patients to carcinogenic potential of argemone oil and isolated sanguinarine alkaloid in mice. International journal of cancer 20051210
Randomized controlled clinical trials on agents used for chemical plaque control. International journal of dental hygiene 20051101
Effects of the limited analyte solubility on its mobility and zone shape: electrophoretic behavior of sanguinarine and chelerythrine around pH 7. Electrophoresis 20050901
Sanguinarine activates polycyclic aromatic hydrocarbon associated metabolic pathways in human oral keratinocytes and tissues. Toxicology letters 20050814
Sanguinarine activates polycyclic aromatic hydrocarbon associated metabolic pathways in human oral keratinocytes and tissues. Toxicology letters 20050728
Effects of sanguinaria in fluoride-containing dentifrices on the remineralisation of subsurface carious lesion in vitro. International dental journal 20050601
Study of the inhibition of alpha-amylase by the benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine. Journal of enzyme inhibition and medicinal chemistry 20050601
The benzo[c]phenanthridine alkaloid, sanguinarine, is a selective, cell-active inhibitor of mitogen-activated protein kinase phosphatase-1. The Journal of biological chemistry 20050513
Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment. Plant physiology 20050501
Immunohistochemical assessment of Viadent-associated leukoplakia. Oral oncology 20050201
In vivo DNA damaging potential of sanguinarine alkaloid, isolated from argemone oil, using alkaline Comet assay in mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20050101
Induction of contracture and extracellular Ca2+ influx in cardiac muscle by sanguinarine: a study on cardiotoxicity of sanguinarine. Journal of biomedical science 20050101
[Effect of alkaloid sanguinarine and a pharmaceutical preparation ukrain on modulation of vesicular membrane fusion and actin cytoskeleton of macrophages]. Tsitologiia 20050101
Aggregation and other intermolecular interactions of biological buffers observed by capillary electrophoresis and UV photometry. Journal of chromatography. A 20041008
Sanguinarine: an evaluation of in vivo cytogenetic activity. Mutation research 20040912
Sanguinarine causes cell cycle blockade and apoptosis of human prostate carcinoma cells via modulation of cyclin kinase inhibitor-cyclin-cyclin-dependent kinase machinery. Molecular cancer therapeutics 20040801
Involvement of cytochrome P450 1A in sanguinarine detoxication. Toxicology letters 20040715
Chelerythrine and other benzophenanthridine alkaloids block the human P2X7 receptor. British journal of pharmacology 20040701
Capillary electrophoretic studies of acid-base properties of sanguinarine and chelerythrine alkaloids. Journal of chromatography. A 20040618
Suppression of angiogenesis by the plant alkaloid, sanguinarine. Biochemical and biophysical research communications 20040430
Hairy root induction of Papaver somniferum var. album, a difficult-to-transform plant, by A rhizogenes LBA 9402. Planta 20040301
Quantitative liquid chromatographic determination of sanguinarine in cell culture medium and in rat urine and plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040125
Sanguinarine is a potent inhibitor of oxidative burst in DMSO-differentiated HL-60 cells by a non-redox mechanism. Chemico-biological interactions 20040115
Sanguinarine and chelerythrine: assessment of safety on pigs in ninety days feeding experiment. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040101
Local anti-infective therapy: pharmacological agents. A systematic review. Annals of periodontology 20031201
Electrophoretic investigation of interactions of sanguinarine and chelerythrine with molecules containing mercapto group. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20031125
Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy. Phytochemistry 20030901
Activation of prodeath Bcl-2 family proteins and mitochondrial apoptosis pathway by sanguinarine in immortalized human HaCaT keratinocytes. Clinical cancer research : an official journal of the American Association for Cancer Research 20030801
Sanguinarine-induced apoptosis is associated with an early and severe cellular glutathione depletion. Cancer chemotherapy and pharmacology 20030601
Spectroscopic and thermodynamic studies on the binding of sanguinarine and berberine to triple and double helical DNA and RNA structures. Journal of biomolecular structure & dynamics 20030401
In vitro effect of sanguinarine alkaloid on binding of [3H]candesartan to the human angiotensin AT1 receptor. European journal of pharmacology 20030105
Quaternary benzo[c]phenanthridine alkaloids as inhibitors of dipeptidyl peptidase IV-like activity baring enzymes in human blood plasma and glioma cell lines. Physiological research 20030101
Sensitivity of lysosomal enzymes to the plant alkaloid sanguinarine: comparison with other SH-specific agents. Cell biology international 20030101
Influence of DNA structures on the conversion of sanguinarine alkanolamine form to iminium form. Journal of biomolecular structure & dynamics 20021201
Inhibitory activity on binding of specific ligands to the human angiotensin II AT(1) and endothelin 1 ET(A) receptors: bioactive benzo[c]phenanthridine alkaloids from the root of Bocconia frutescens. Planta medica 20020901
DNA adduct formation from quaternary benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine as revealed by the 32P-postlabeling technique. Chemico-biological interactions 20020815
[Effect of a fungal elicitor on levels of sanguinarine and polyphenoloxidase activity in a suspension culture of Papaver somniferum L]. Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 20020701
The alkaloid sanguinarine is effective against multidrug resistance in human cervical cells via bimodal cell death. Biochemical pharmacology 20020415
Interaction of sanguinarine with double stranded RNA structures. Indian journal of biochemistry & biophysics 20020401
Quaternary benzo[c]phenanthridine alkaloids as inhibitors of aminopeptidase N and dipeptidyl peptidase IV. Phytotherapy research : PTR 20020201
Antisense RNA-mediated suppression of benzophenanthridine alkaloid biosynthesis in transgenic cell cultures of California poppy. Plant physiology 20020201
[Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood]. Zhurnal evoliutsionnoi biokhimii i fiziologii 20020101
The association between Viadent use and oral leukoplakia--results of a matched case-control study. Journal of public health dentistry 20020101
White patch of maxillary vestibule. Sanguinarine-associated leukoplakia. General dentistry 20020101
Cytotoxicity of natural compounds in hepatocyte cell culture models. The case of quaternary benzo[c]phenanthridine alkaloids. Toxicology letters 20011215
The association between Viadent use and oral leukoplakia. Epidemiology (Cambridge, Mass.) 20011101
Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant. Planta 20011001
Argemone mexicana and epidemic dropsy: phytopharmacology and putative sequelae and therapy. The Journal of the Association of Physicians of India 20011001
Bax, Bcl-2, and NF-kappaB expression in sanguinarine induced bimodal cell death. Experimental and molecular pathology 20010801
Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain. Phytotherapy research : PTR 20010301
Influence of natural and synthetic compounds on cell surface expression of cell adhesion molecules, ICAM-1 and VCAM-1. Planta medica 20010301
Sanguinarine induces K+ outflow from yeast cells expressing mammalian sodium pumps. Naunyn-Schmiedeberg's archives of pharmacology 20010201
Mechanisms underlying the induction of vasorelaxation in rat thoracic aorta by sanguinarine. Japanese journal of pharmacology 20010101
Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells. Cell biology and toxicology 20010101
Molecular aspects on the interaction of sanguinarine with B-form, Z-form and HL-form DNA structures. Indian journal of biochemistry & biophysics 20010101
Sanguinarine induces bimodal cell death in K562 but not in high Bcl-2-expressing JM1 cells. Pathology, research and practice 20010101
Role of Bcl-2 family proteins and caspase-3 in sanguinarine-induced bimodal cell death. Cell biology and toxicology 20010101
Sanguinaria-related leukoplakia: epidemiologic and clinicopathologic features of a recently described entity. General dentistry 20010101
Relationship between oral pain and ethanol concentration in mouthrinses. Journal of periodontal research 19950501

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