Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H19N3 |
Molecular Weight | 265.3529 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C1=CC2=NC3=C(C=CC(=C3)N(C)C)C=C2C=C1
InChI
InChIKey=DPKHZNPWBDQZCN-UHFFFAOYSA-N
InChI=1S/C17H19N3/c1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14/h5-11H,1-4H3
Molecular Formula | C17H19N3 |
Molecular Weight | 265.3529 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28708430 | https://www.ncbi.nlm.nih.gov/pubmed/24982218
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28708430 | https://www.ncbi.nlm.nih.gov/pubmed/24982218
Acridine Orange is a cell-permeant nucleic acid binding dye that emits green fluorescence when bound to double-stranded DNA and red fluorescence when bound to single-stranded DNA or RNA. This unique characteristic makes acridine orange useful for cell-cycle studies. Acridine orange has been widely accepted and used in many different areas, such as epifluorescence microscopy, the assessment of sperm chromatin quality. Acridine orange stain is particularly useful in the rapid screening of normally sterile specimens, and its recommended for the use of fluorescent microscopic detection of microorganisms in direct smears prepared from clinical and nonclinical materials. The staining has to be performed at an acid pH in order to obtain this differential staining effect with bacteria showing orange stain and tissue components yellow to green. Acridine orange can be used in conjunction with ethidium bromide to differentiate between viable, apoptotic and necrotic cells. Additionally, acridine orange may be used on blood samples to cause bacterial DNA to fluoresce, aiding in the clinical diagnosis of bacterial infection once serum and debris have been filtered. Acridine orange can be used in photodynamic Cancer Therapy.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL345 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28986738 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Imaging beta-amyloid plaques and neurofibrillary tangles in the aging human brain. | 2004 |
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Acridine derivatives activate p53 and induce tumor cell death through Bax. | 2005 Aug |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Acridine Orange based platinum(II) complexes inducing cytotoxicity and cell cycle perturbation in spite of GSTP1 up-regulation. | 2006 Jul 10 |
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Screening of protein kinase inhibitors identifies PKC inhibitors as inhibitors of osteoclastic acid secretion and bone resorption. | 2010 Oct 26 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24982218
Acridine Orange was administered once intravenously at 21, 25, 30 or 36 mg/kg
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28262028
Melanoma cells Me 30966 were plated at 4 x 10^4 cells per well in 12-well plates in 1 ml of buffered RPMI medium. Cells were treated with increasing doses of Acridine Orange (1, 0.5, 0.25 and 0.10 mg/ml) for 30 minutes, 3 and 6 h. After treatment, samples were washed with PBS and excited with light at 466 nm for 10 s. Then cells were collected by pooling them from the medium (i.e., dead cells) and adherent cells following trypsinization. Cells were then collected (five minutes at 500xg), resuspended in PBS/0.4% trypan blue 1:1 (vol/vol). After 10 minutes, cells were analyzed by FACS on a Becton Dickinson FACScalibur using CellQuestPro software
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:18:22 GMT 2023
by
admin
on
Fri Dec 15 17:18:22 GMT 2023
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Record UNII |
F30N4O6XVV
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Record Status |
Validated (UNII)
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Record Version |
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C019380
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194350
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DTXSID60197783
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494-38-2
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51739
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F30N4O6XVV
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87346
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ACRIDINE ORANGE
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admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
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