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2447-54-3

2447-54-3 | [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-

CAS No: 2447-54-3 Catalog No: AG002O8W MDL No:MFCD00064925

Product Description

Catalog Number:
AG002O8W
Chemical Name:
[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-
CAS Number:
2447-54-3
Molecular Formula:
C20H14NO4+
Molecular Weight:
332.3295
MDL Number:
MFCD00064925
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
InChI:
InChI=1S/C20H14NO4/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/q+1
InChI Key:
INVGWHRKADIJHF-UHFFFAOYSA-N
SMILES:
C[n+]1cc2c3OCOc3ccc2c2c1c1cc3OCOc3cc1cc2
EC Number:
219-503-3
UNII:
AV9VK043SS

Properties

Complexity:
530  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
332.092g/mol
Formal Charge:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
332.335g/mol
Monoisotopic Mass:
332.092g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
40.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.4  

Literature

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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
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. Chemico-biological interactions 20130905
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Differential induction of protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cultures by methyl jasmonate and yeast extract. Journal of microbiology and biotechnology 20080201
Conventional protein kinase C isoenzymes undergo dephosphorylation in neutrophil-like HL-60 cells treated by chelerythrine or sanguinarine. Cell biology and toxicology 20080101
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Sanguinarine-induced apoptosis in human leukemia U937 cells via Bcl-2 downregulation and caspase-3 activation. Chemotherapy 20080101
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Enhanced benzophenanthridine alkaloid production and protein expression with combined elicitor in Eschscholtzia californica suspension cultures. Biotechnology letters 20071201
Conserved regulation of MAP kinase expression by PUF RNA-binding proteins. PLoS genetics 20071201
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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
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Knockdown of berberine bridge enzyme by RNAi accumulates (S)-reticuline and activates a silent pathway in cultured California poppy cells. Transgenic research 20070601
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HPLC quantification of seven quaternary benzo[c]phenanthridine alkaloids in six species of the family Papaveraceae. Journal of pharmaceutical and biomedical analysis 20070509
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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
Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism. Planta 20070401
Variability in the yield of benzophenanthridine alkaloids in wildcrafted vs cultivated bloodroot (Sanguinaria canadensis L.). Journal of agricultural and food chemistry 20070221
Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica. The FEBS journal 20070201
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
Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis 20060918
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
A simple and sensitive method of nonaqueous capillary electrophoresis with laser-induced native fluorescence detection for the analysis of chelerythrine and sanguinarine in Chinese herbal medicines. Talanta 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
Safety evaluation studies on argemone oil through dietary exposure for 90days in rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060701
Cytokine-induced monocyte adhesion to endothelial cells involves platelet-activating factor: suppression by conjugated linoleic acid. Biochimica et biophysica acta 20060701
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
Development of a kinetic metabolic model: application to Catharanthus roseus hairy root. Bioprocess and biosystems engineering 20060501
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
Anticariogenic activity of macelignan isolated from Myristica fragrans (nutmeg) against Streptococcus mutans. Phytomedicine : international journal of phytotherapy and phytopharmacology 20060301
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
Differential effects of selected natural compounds with anti-inflammatory activity on the glucocorticoid receptor and NF-kappaB in HeLa cells. Chemico-biological interactions 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
Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. BMC cancer 20060101
Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine. BMC cell biology 20060101
Biosynthesis of antitumoral and bactericidal sanguinarine. Journal of biomedicine & biotechnology 20060101
Analysis of secondary metabolites from eschscholtzia californica by high-performance liquid chromatography. Phytochemical analysis : PCA 20060101
[Effect of alkaloids from celandine on calcium accumulation and oxidative phosphorylation in mitochondria depending on their DNA intercalating properties]. Ukrains'kyi biokhimichnyi zhurnal (1999 ) 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
Identification and evaluation of potential anti-cancer drugs on human neuroendocrine tumor cell lines. Anticancer research 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
A rapid and reliable solid-phase extraction method for high-performance liquid chromatographic analysis of opium alkaloids from papaver plants. Chemical & pharmaceutical bulletin 20051101
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
Capillary zone electrophoretic studies of interactions of some quaternary isoquinoline alkaloids with DNA constituents and DNA. Electrophoresis 20050501
Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment. Plant physiology 20050501
In situ extraction strategy affects benzophenanthridine alkaloid production fluxes in suspension cultures of Eschscholtzia californica. Biotechnology and bioengineering 20050205
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
Reversal of a full-length mutant huntingtin neuronal cell phenotype by chemical inhibitors of polyglutamine-mediated aggregation. BMC neuroscience 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 some isoquinoline alkaloids on enzymatic activity of acetylcholinesterase and monoamine oxidase]. Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20050101
[Effect of alkaloid sanguinarine and a pharmaceutical preparation ukrain on modulation of vesicular membrane fusion and actin cytoskeleton of macrophages]. Tsitologiia 20050101
Unequivocal evidence of genotoxic potential of argemone oil in mice. International journal of cancer 20041210
Aggregation and other intermolecular interactions of biological buffers observed by capillary electrophoresis and UV photometry. Journal of chromatography. A 20041008
Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis. The Plant journal : for cell and molecular biology 20041001
Effect of chemopreventive agents on glutathione S-transferase P1-1 gene expression mechanisms via activating protein 1 and nuclear factor kappaB inhibition. Biochemical pharmacology 20040915
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
Isopanduratin A from Kaempferia pandurata as an active antibacterial agent against cariogenic Streptococcus mutans. International journal of antimicrobial agents 20040401
Natural antimycobacterial metabolites: current status. Phytochemistry 20040401
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
[Biosynthesis of poppy isoquinoline alkaloids in nature and in vitro culture. 2. Bracteum poppy (Papaver bracteatum Lindl.)]. Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20040101
Inhibition of mouse liver respiration by Chelidonium majus isoquinoline alkaloids. Toxicology letters 20031215
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
A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy. The Plant cell 20031101
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 susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis. Phytotherapy research : PTR 20030301
Achiral and chiral determination of benzophenanthridine alkaloids from methanol extracts of Hylomecon species by high performance liquid chromatography. Archives of pharmacal research 20030201
In vitro effect of sanguinarine alkaloid on binding of [3H]candesartan to the human angiotensin AT1 receptor. European journal of pharmacology 20030105
Modulation of berberine bridge enzyme levels in transgenic root cultures of California poppy alters the accumulation of benzophenanthridine alkaloids. Plant molecular biology 20030101
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
Argemone oil induced cellular damage in the reproductive tissues of transgenic Drosophila melanogaster: protective role of 70 kDa heat shock protein. Journal of biochemical and molecular toxicology 20030101
Sensitivity of lysosomal enzymes to the plant alkaloid sanguinarine: comparison with other SH-specific agents. Cell biology international 20030101
[Biosynthesis of poppy isoquinoline alkaloids in nature and in vitro culture. 1. Opium poppy (Papaver somniferum L.)]. Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20030101
[Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs]. Tsitologiia 20030101
Influence of DNA structures on the conversion of sanguinarine alkanolamine form to iminium form. Journal of biomolecular structure & dynamics 20021201
Inhibitory effect of isoquinoline alkaloids on movement of second-stage larvae of Toxocara canis. Biological & pharmaceutical bulletin 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
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
The alkaloid sanguinarine is effective against multidrug resistance in human cervical cells via bimodal cell death. Biochemical pharmacology 20020415
Epidemic dropsy: observations on pathophysiology and clinical features during the Delhi epidemic of 1998. Tropical doctor 20020401
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
Capillary electrophoresis of phytochemical substances. Journal of pharmaceutical and biomedical analysis 20020201
Antisense RNA-mediated suppression of benzophenanthridine alkaloid biosynthesis in transgenic cell cultures of California poppy. Plant physiology 20020201
The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis. Journal of ethnopharmacology 20020101
Effect of a homeopathic drug, Chelidonium, in amelioration of p-DAB induced hepatocarcinogenesis in mice. BMC complementary and alternative medicine 20020101
[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
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense. Planta medica 20011001
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
Benzo[c]phenanthridine bases and their antituberculosis activity. Medicinal research reviews 20010101
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
[The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives]. Tsitologiia 20010101
Isoquinoline alkaloid production by transformed cultures of Papaver somniferum. Kokuritsu Iyakuhin Shokuhin Eisei Kenkyujo hokoku = Bulletin of National Institute of Health Sciences 20010101
Sanguinaria-related leukoplakia: epidemiologic and clinicopathologic features of a recently described entity. General dentistry 20010101
Alkaloid biosynthesis in Papaver sp. cells in culture and during organogenesis. Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20010101
Relationship between oral pain and ethanol concentration in mouthrinses. Journal of periodontal research 19950501
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products 19910101

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