U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ACRIDINE ORANGE

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

HIDE SMILES / InChI

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

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Imaging beta-amyloid plaques and neurofibrillary tangles in the aging human brain.
2004
Acridine derivatives activate p53 and induce tumor cell death through Bax.
2005 Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Acridine Orange based platinum(II) complexes inducing cytotoxicity and cell cycle perturbation in spite of GSTP1 up-regulation.
2006 Jul 10
Screening of protein kinase inhibitors identifies PKC inhibitors as inhibitors of osteoclastic acid secretion and bone resorption.
2010 Oct 26
Patents

Patents

Sample Use Guides

Acridine Orange was administered once intravenously at 21, 25, 30 or 36 mg/kg
Route of Administration: Intravenous
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 Fri Dec 15 17:18:22 GMT 2023
Edited
by admin
on Fri Dec 15 17:18:22 GMT 2023
Record UNII
F30N4O6XVV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACRIDINE ORANGE
MART.  
Common Name English
ACRIDINE ORANGE [MART.]
Common Name English
ACRIDINE ORANGE [IARC]
Common Name English
RHODULINE ORANGE
Common Name English
EUCHRYSINE
Common Name English
NSC-194350
Code English
N,N,N',N'-TETRAMETHYLACRIDINE-3,6-DIAMINE
Systematic Name English
Code System Code Type Description
MESH
C019380
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
NSC
194350
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
PUBCHEM
62344
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID60197783
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
CAS
494-38-2
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
CHEBI
51739
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
FDA UNII
F30N4O6XVV
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
CHEBI
87346
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
WIKIPEDIA
ACRIDINE ORANGE
Created by admin on Fri Dec 15 17:18:22 GMT 2023 , Edited by admin on Fri Dec 15 17:18:22 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT