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89459-44-9 | 4-Acridinecarboxamide,9-amino-N-[3-(dimethylamino)propyl]-
CAS No: 89459-44-9 Catalog No: AG0042FH MDL No:
Product Description
Catalog Number:
AG0042FH
Chemical Name:
4-Acridinecarboxamide,9-amino-N-[3-(dimethylamino)propyl]-
CAS Number:
89459-44-9
Molecular Formula:
C19H22N4O
Molecular Weight:
322.4042
IUPAC Name:
9-amino-N-[3-(dimethylamino)propyl]acridine-4-carboxamide
InChI:
InChI=1S/C19H22N4O/c1-23(2)12-6-11-21-19(24)15-9-5-8-14-17(20)13-7-3-4-10-16(13)22-18(14)15/h3-5,7-10H,6,11-12H2,1-2H3,(H2,20,22)(H,21,24)
InChI Key:
VNWAULKXOPRJEL-UHFFFAOYSA-N
SMILES:
CN(CCCNC(=O)c1cccc2c1nc1ccccc1c2N)C
Properties
Complexity:
428
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
322.179g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
322.412g/mol
Monoisotopic Mass:
322.179g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
71.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.5
Literature
| Title | Journal |
|---|---|
| Spectroscopic investigation on the interaction of 9-aminoacridine with certain dyes. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120901 |
| 9-Amino acridine pharmacokinetics, brain distribution, and in vitro/in vivo efficacy against malignant glioma. | Cancer chemotherapy and pharmacology 20120601 |
| Photoacoustic and luminescence characterization of nitrogen heterocyclic aromatic UV-MALDI matrices in solution. | Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20120601 |
| Synthesis and biological evaluation of acridine derivatives as antimalarial agents. | ChemMedChem 20120401 |
| MALDI imaging and structural analysis of rat brain lipid negative ions with 9-aminoacridine matrix. | Analytical chemistry 20120306 |
| Studying the interactions of a platinum(II) 9-aminoacridine complex with proteins and oligonucleotides by ESI-TOF MS. | Dalton transactions (Cambridge, England : 2003) 20120107 |
| An investigation on the fluorescence quenching of 9-aminoacridine by certain pyrimidines. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20111101 |
| Rescue of the mutant CFTR chloride channel by pharmacological correctors and low temperature analyzed by gene expression profiling. | American journal of physiology. Cell physiology 20111001 |
| DNA cleavage activity of Fe(II)N4Py under photo irradiation in the presence of 1,8-naphthalimide and 9-aminoacridine: unexpected effects of reactive oxygen species scavengers. | Inorganic chemistry 20110905 |
| Protective effects of methanol extracts from Cladonia rangiformis and Umbilicaria vellea against known mutagens sodium azide and 9-aminoacridine. | Toxicology and industrial health 20110901 |
| Imaging of complex sulfatides SM3 and SB1a in mouse kidney using MALDI-TOF/TOF mass spectrometry. | Analytical and bioanalytical chemistry 20110701 |
| Quinacrine and 9-amino acridine inhibit B-Z and B-H(l) form DNA conformational transitions. | DNA and cell biology 20110701 |
| The sequence selectivity of DNA-targeted 9-aminoacridine cisplatin analogues in a telomere-containing DNA sequence. | Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20110601 |
| Superoxide is produced by the reduced flavin in mitochondrial complex I: a single, unified mechanism that applies during both forward and reverse electron transfer. | The Journal of biological chemistry 20110520 |
| Microscale MALDI imaging of outer-layer lipids in intact egg chambers from Drosophila melanogaster. | Analytical chemistry 20110515 |
| Sphingomyelin is more sensitively detectable as a negative ion than phosphatidylcholine: a matrix-assisted laser desorption/ionization time-of-flight mass spectrometric study using 9-aminoacridine (9-AA) as matrix. | Rapid communications in mass spectrometry : RCM 20110430 |
| Use of fluorescence lifetime technology to provide efficient protection from false hits in screening applications. | Analytical biochemistry 20110201 |
| Excited state properties of 9-amino acridine surface adsorbed onto αZr-phosphate particles. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20110201 |
| Beyond DNA binding - a review of the potential mechanisms mediating quinacrine's therapeutic activities in parasitic infections, inflammation, and cancers. | Cell communication and signaling : CCS 20110101 |
| Measurement of the ΔpH and electric field developed across Arabidopsis thylakoids in the light. | Methods in molecular biology (Clifton, N.J.) 20110101 |
| Voltage-dependent and -independent block of α-amino-3-hydroxy-5-methylisoxazole-4-propionate receptor channels. | Journal of neurochemistry 20101201 |
| 9-Aminoacridine peptide derivatives as versatile reporter systems for use in fluorescence lifetime assays. | Chemical communications (Cambridge, England) 20101007 |
| Mononuclear Fe(II)-N4Py complexes in oxidative DNA cleavage: structure, activity and mechanism. | Dalton transactions (Cambridge, England : 2003) 20100914 |
| MALDI-TOF/MS analysis of archaebacterial lipids in lyophilized membranes dry-mixed with 9-aminoacridine. | Journal of lipid research 20100901 |
| Lipidomic analysis of porcine olfactory epithelial membranes and cilia. | Lipids 20100701 |
| Selective desorption/ionization of sulfatides by MALDI-MS facilitated using 9-aminoacridine as matrix. | Journal of lipid research 20100601 |
| Significant sensitivity improvements by matrix optimization: a MALDI-TOF mass spectrometric study of lipids from hen egg yolk. | Chemistry and physics of lipids 20100601 |
| The intact muscle lipid composition of bulls: an investigation by MALDI-TOF MS and 31P NMR. | Chemistry and physics of lipids 20100201 |
| Modulation of mdm2 pre-mRNA splicing by 9-aminoacridine-PNA (peptide nucleic acid) conjugates targeting intron-exon junctions. | BMC cancer 20100101 |
| Phosphatidylcholines and -ethanolamines can be easily mistaken in phospholipid mixtures: a negative ion MALDI-TOF MS study with 9-aminoacridine as matrix and egg yolk as selected example. | Analytical and bioanalytical chemistry 20091201 |
| Synthesis, inhibition potency, binding mode, and antiprotozoal activities of fluorescent inhibitors of trypanothione reductase based on mepacrine-conjugated diaryl sulfide scaffolds. | ChemMedChem 20091201 |
| Identification of potent chemotypes targeting Leishmania major using a high-throughput, low-stringency, computationally enhanced, small molecule screen. | PLoS neglected tropical diseases 20091101 |
| Synthesis and evaluation of 9-aminoacridines derived from benzyne click chemistry. | Bioorganic & medicinal chemistry letters 20091015 |
| Binding of TCA to the prion protein: mechanism, implication for therapy, and application as probe for complex formation of bio-macromolecules. | Journal of biomolecular structure & dynamics 20091001 |
| Polyanion hydrophobicity and protein basicity affect protein stability in protein-polyanion complexes. | Biomacromolecules 20090914 |
| Quantitation of the tacrine analogue octahydroaminoacridine in human plasma by liquid chromatography-tandem mass spectrometry. | Journal of pharmaceutical and biomedical analysis 20090908 |
| On the role of topoisomerase I in mediating the cytotoxicity of 9-aminoacridine-based anticancer agents. | Bioorganic & medicinal chemistry letters 20090801 |
| In situ primary metabolites localization on a rat brain section by chemical mass spectrometry imaging. | Analytical chemistry 20090701 |
| Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates. | Bioorganic & medicinal chemistry letters 20090401 |
| 9-Aminoacridine-based anticancer drugs target the PI3K/AKT/mTOR, NF-kappaB and p53 pathways. | Oncogene 20090226 |
| Blockade of NMDA receptor channels by 9-aminoacridine and its derivatives. | Neuroscience letters 20090213 |
| 9-Aminoacridine inhibition of HIV-1 Tat dependent transcription. | Virology journal 20090101 |
| Inhibition of RNA recruitment and replication of an RNA virus by acridine derivatives with known anti-prion activities. | PloS one 20090101 |
| Matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of cellular glycerophospholipids enabled by multiplexed solvent dependent analyte-matrix interactions. | Analytical chemistry 20081001 |
| New palladium(II) and platinum(II) complexes with 9-aminoacridine: structures, luminiscence, theoretical calculations, and antitumor activity. | Inorganic chemistry 20080804 |
| Isolation and characterization of novel phenotype CHO cell mutants defective in peroxisome assembly, using ICR191 as a potent mutagenic agent. | Cell biochemistry and function 20080801 |
| Attenuation of acridine mutagen ICR-191--DNA interactions and DNA damage by the mutagen interceptor chlorophyllin. | Biophysical chemistry 20080601 |
| Negative ion mode matrix-assisted laser desorption/ionisation time-of-flight mass spectrometric analysis of oligosaccharides using halide adducts and 9-aminoacridine matrix. | Rapid communications in mass spectrometry : RCM 20080401 |
| Drug 9AA reactivates p21/Waf1 and Inhibits HIV-1 progeny formation. | Virology journal 20080101 |
| Transformation of MCF-10A cells by random mutagenesis with frameshift mutagen ICR191: a model for identifying candidate breast-tumor suppressors. | Molecular cancer 20080101 |
| Thermodynamic analysis of binding between drugs and glycosaminoglycans by isothermal titration calorimetry and fluorescence spectroscopy. | European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20071001 |
| A role of the 9-aminoacridines and their conjugates in a life science. | Current protein & peptide science 20071001 |
| The electrochemical behavior and direct determination of tyrosine at a glassy carbon electrode modified with poly (9-aminoacridine). | Annali di chimica 20071001 |
| Frameshift mutations produced by 9-aminoacridine in wild-type, uvrA and recA strains of Escherichia coli; specificity within a hotspot. | Journal of radiation research 20070901 |
| Identification of an aminoacridine derivative that binds to RNA tetraloops. | Journal of medicinal chemistry 20070823 |
| Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions. | The Journal of organic chemistry 20070706 |
| Exciton self-trapping in tetrafluoro-dimethyl-aminoacridine single crystals. | The Journal of chemical physics 20070621 |
| [Attempts to reduce drug resistance of bacteria and cancer cells]. | Orvosi hetilap 20070603 |
| Tautomerism of acridin-9-amines substituted at the exocyclic nitrogen atom: spectroscopic investigations and theoretical studies. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20070401 |
| Discriminating between cellular and misfolded prion protein by using affinity to 9-aminoacridine compounds. | The Journal of general virology 20070401 |
| Intermittent preventive treatment for malaria in pregnancy in Africa: what's new, what's needed? | Malaria journal 20070101 |
| Effectiveness of a honey dressing for healing pressure ulcers. | Journal of wound, ostomy, and continence nursing : official publication of The Wound, Ostomy and Continence Nurses Society 20070101 |
| Quantitative detection of metabolites using matrix-assisted laser desorption/ionization mass spectrometry with 9-aminoacridine as the matrix. | Rapid communications in mass spectrometry : RCM 20070101 |
| In silico chemical library screening and experimental validation of a novel 9-aminoacridine based lead-inhibitor of human S-adenosylmethionine decarboxylase. | Journal of chemical information and modeling 20070101 |
| Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity. | Bioinorganic chemistry and applications 20070101 |
| Isolation and characterization of dominant and recessive IL-3-independent hematopoietic transformants. | Oncogene 20061026 |
| Structure-activity relationship study of 9-aminoacridine compounds in scrapie-infected neuroblastoma cells. | Bioorganic & medicinal chemistry letters 20060915 |
| New peptide conjugates with 9-aminoacridine: synthesis and binding to DNA. | Journal of peptide science : an official publication of the European Peptide Society 20060701 |
| A modified Vibrio harveyi mutagenicity assay based on bioluminescence induction. | Letters in applied microbiology 20060601 |
| PsbS enhances nonphotochemical fluorescence quenching in the absence of zeaxanthin. | FEBS letters 20060403 |
| Study on the inclusion behavior of p-sulphonatocalix[4]arene with 9-amino-acridine by spectrofluorometric titrations. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060201 |
| Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum. | Bioorganic & medicinal chemistry 20060115 |
| Mutagenesis. | Methods in molecular biology (Clifton, N.J.) 20060101 |
| Rational design and synthesis of a double-stranded DNA-binder library. | Biopolymers 20060101 |
| Synergistic interaction between proton pump inhibitors and resistance modifiers: promoting effects of antibiotics and plasmid curing. | In vivo (Athens, Greece) 20060101 |
| Acridin-9-yl exchange: a proposal for the action of some 9-aminoacridine drugs. | Biopolymers 20060101 |
| An aminoacridine derivative for radionuclide therapy: DNA binding properties studied in a novel cell-free in vitro assay. | International journal of oncology 20051101 |
| Frameshift mutations induced by the acridine mustard ICR-191 in embryos and in the adult gill and hepatopancreas of rpsL transgenic zebrafish. | Mutation research 20051015 |
| Induced mutation spectra at the upp locus in Salmonella typhimurium: response of the target gene in the FU assay to mechanistically different mutagens. | Mutation research 20051015 |
| Fluorescence of acridinic dyes in anionic surfactant solution. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20051001 |
| Excited-state intramolecular charge transfer in 9-aminoacridine derivative. | The journal of physical chemistry. A 20050714 |
| Metabolomic analysis of eukaryotic tissue and prokaryotes using negative mode MALDI time-of-flight mass spectrometry. | Analytical chemistry 20050401 |
| Binding of an aminoacridine derivative to a GAAA RNA tetraloop. | Bioorganic & medicinal chemistry letters 20041206 |
| Antigenotoxic potential of glucomannan on four model test systems. | Cell biology and toxicology 20041101 |
| Self-assembling peptide nanotubes from enantiomeric pairs of cyclic peptides with alternating D and L amino acid residues. | Journal of the American Chemical Society 20040324 |
| Chloroplast mutations induced by 9-aminoacridine hydrochloride are independent of the plastome mutator in Oenothera. | TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik 20040201 |
| Anti-stress activity of Propionibacterium freudenreichii : identification of a reactivative protein. | Antonie van Leeuwenhoek 20040101 |
| A transient product of DNA alkylation can be stabilized by binding localization. | Journal of the American Chemical Society 20031119 |
| Quinoline and cyanine dyes--putative anti-MRSA drugs. | International journal of antimicrobial agents 20031101 |
| Alleviation of mutagenic effects of polycyclic aromatic agents (quinacrine mustard, ICR-191 and ICR-170) by caffeine and pentoxifylline. | Mutation research 20030929 |
| Enhancement of plasmid curing by 9-aminoacridine and two phenothiazines in the presence of proton pump inhibitor 1-(2-benzoxazolyl)-3,3,3-trifluoro-2-propanone. | International journal of antimicrobial agents 20030901 |
| Study of T-cell signaling by somatic cell mutagenesis and complementation cloning. | Journal of immunological methods 20030701 |
| Superior duplex DNA strand invasion by acridine conjugated peptide nucleic acids. | Journal of the American Chemical Society 20030528 |
| Changes in [Ca2+]i induced by several glucose transport-enhancing stimuli in rat epitrochlearis muscle. | Journal of applied physiology (Bethesda, Md. : 1985) 20030501 |
| Acridine mutagenesis of zebrafish (Danio rerio). | Mutation research 20030409 |
| Lipid membrane with low proton permeability. | Biochimica et biophysica acta 20030401 |
| 9-Aminoacridine: an efficient reagent to improve human and plant chromosome banding patterns and to standardize chromosome image analysis. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20030101 |
| Analysis of 2-aminoacridone-derivatized complex oligosaccharides using micellar electrokinetic capillary chromatography and laser-induced fluorescence detection. | Methods in molecular biology (Clifton, N.J.) 20030101 |
| Interaction of antitumoral 9-aminoacridine drug with DNA and dextran sulfate studied by fluorescence and surface-enhanced Raman spectroscopy. | Biopolymers 20030101 |
| Frameshift mutations induced by three classes of acridines in the lacZ reversion assay in Escherichia coli: potency of responses and relationship to slipped mispairing models. | Environmental and molecular mutagenesis 20030101 |
| Staggering of subunits in NMDAR channels. | Biophysical journal 20021201 |
| Inhibition of the U1A-RNA complex by an aminoacridine derivative. | Bioorganic & medicinal chemistry letters 20021021 |
| Effects of DNA structure on oxopropenylation by the endogenous mutagens malondialdehyde and base propenal. | Biochemistry 20020416 |
| Molecular rearrangements of the extracellular vestibule in NMDAR channels during gating. | Neuron 20020103 |
| Anacardic acid-mediated changes in membrane potential and pH gradient across liposomal membranes. | Biochimica et biophysica acta 20020102 |
| Blocker studies of the functional architecture of the NMDA receptor channel. | Neuroscience and behavioral physiology 20020101 |
| Determination of nitrite by inhibition of the chemiluminescence of acriflavine in a flow-injection assembly. | The Analyst 20010801 |
| Extravascular transport of the DNA intercalator and topoisomerase poison N-[2-(Dimethylamino)ethyl]acridine-4-carboxamide (DACA): diffusion and metabolism in multicellular layers of tumor cells. | The Journal of pharmacology and experimental therapeutics 20010601 |
| Surface-enhanced Raman and steady fluorescence study of interaction between antitumoral drug 9-aminoacridine and trypsin-like protease related to metastasis processes, guanidinobenzoatase. | Biopolymers 20010101 |
| [Synthesis and antibacterial activity of the new 9-aminoacridine, 10,11-dihydro-5H-dibenzo[b,f]azepine, polyfluoro 5,6-dihydro-1,3,5-oxadiazine derivatives]. | Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] 20010101 |
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