Compounds > 4-(9-acridinylamino)aniline
Page last updated: 2024-12-06

4-(9-acridinylamino)aniline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-(9-acridinylamino)aniline, also known as Acridine Orange, is a fluorescent dye commonly used in microscopy and cell biology. It is a cationic dye that intercalates into DNA and RNA, making it useful for staining nucleic acids. Its synthesis typically involves the reaction of acridine with aniline under acidic conditions. Acridine Orange exhibits metachromasia, meaning it can emit different colors depending on the concentration and environment. It is widely used for visualizing DNA and RNA in cells, for flow cytometry, and for studying the structure and function of nucleic acids. It has also been investigated for its potential therapeutic applications, such as in cancer treatment and antimicrobial therapy.'

4-(9-acridinylamino)aniline: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID42803
CHEMBL ID289352
SCHEMBL ID17154450
MeSH IDM0109598

Synonyms (19)

Synonym
acridine, 9-(p-aminoanilino)-
4-(9-acridinylamino)aniline
9-(4-aminoanilino)acridine
ccris 4549
9-(p-aminoanilino)acridine
1,4-benzenediamine, n-9-acridinyl-
brn 0414107
sn 7281
NCI60_001275
NCISTRUC1_001873
NCISTRUC2_001616
CHEMBL289352
4-n-acridin-9-ylbenzene-1,4-diamine
58658-11-0
SCHEMBL17154450
DTXSID80207353
1-n-acridin-9-ylbenzene-1,4-diamine
n1-(acridine-9yl)benzene-1,4-diamine
n1-(acridin-9-yl)benzene-1,4-diamine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID24209Association constant for binding to poly [d(G-C)]1981Journal of medicinal chemistry, Feb, Volume: 24, Issue:2
Potential antitumor agents. 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring.
AID46149Inhibitory concentration against ethidium binding to DNA1981Journal of medicinal chemistry, Feb, Volume: 24, Issue:2
Potential antitumor agents. 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring.
AID24208Association constant for binding to poly [d(A-T)]1981Journal of medicinal chemistry, Feb, Volume: 24, Issue:2
Potential antitumor agents. 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring.
AID215154Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-5 M concentration in dark conditions1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID95454Concentration required to reduce growth of human jurkat leukemia cells to 50% of control cultures, determined using a 72 hr continuous exposure1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.
AID1149743Half life in mouse L1210 cells allografted C3H/DBA2 F1 hybrid hybrid mouse1977Journal of medicinal chemistry, Aug, Volume: 20, Issue:8
Potential antitumor agents. 23. 4'-(9-Acridinylamino)alkanesulfonanilide congeners bearing hydrophilic functionality.
AID210610In vitro therapeutic index calculated as the IC50 ratio of Jurkat cells to that of Leishmania major.1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines.
AID235013In vitro therapeutic index value is the ratio between IC50 values of [J] and [P]1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.
AID1150556Antitumor activity against mouse L1210 cells allografted in ip dosed C3H/DBA2 F1 mouse assessed as optimum dose required to increase in maximum life span administered as qd for 5 days1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Potential antitumor agents. 17. 9-Anilino-10-methylacridinium salts.
AID215159Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-6 M concentration in dark conditions1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID100306Dose of the drug (mol /kg) providing a 50% life extension in L1210 assays when given at qd 1-5 schedule. 1987Journal of medicinal chemistry, Mar, Volume: 30, Issue:3
Redox chemistry of the 9-anilinoacridine class of antitumor agents.
AID215156Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-5 M concentration in presence of light1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID116415Maximum percent increase in life span of mice was determined by L1210 assay1981Journal of medicinal chemistry, Feb, Volume: 24, Issue:2
Potential antitumor agents. 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring.
AID1150557Antitumor activity against mouse L1210 cells allografted in C3H/DBA2 F1 mouse assessed as increase in life span at optimum dose, ip qd administered for 5 days relative to control1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Potential antitumor agents. 17. 9-Anilino-10-methylacridinium salts.
AID98490Inhibitory concentration to reduce the growth of L1210 cells by 50% after 70 hr. 1987Journal of medicinal chemistry, Mar, Volume: 30, Issue:3
Redox chemistry of the 9-anilinoacridine class of antitumor agents.
AID26375Ionisation constant (pKa)1981Journal of medicinal chemistry, Feb, Volume: 24, Issue:2
Potential antitumor agents. 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring.
AID100911Concentration required to reduce incorporation of [3H]TdR in drug-treated cultures of intracellular Leishmania major to 50% of controls1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines.
AID25559Ionization constant (pKa)1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.
AID158039Inhibitory concentration IC50 against Plasmodium falciparum K1 by [3H]hypoxanthine uptake over 24 hr1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.
AID215160Trypanocidal activity against Trypanosoma brucei, exposur of parasites to compound prior to injection into mice at 10 e-6 M concentration in presence of light1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID18955Lipophilicity index (substitution method)1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines.
AID214997Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-4 M concentration in presence of light1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID214996Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-4 M concentration in dark conditions1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID95456Concentration required to reduce the growth of human Jurkat cells to 50% of control cultures1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines.
AID98819Drug concentration in mole/kg/day providing 50% extension of life in intraperitoneally implanted leukemia L1210 mice.1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.
AID97604Tumor cell selectivity determined as maximal percent increase in life span (ILSmax) at LD10 dosage level in L1210 cells1982Journal of medicinal chemistry, Aug, Volume: 25, Issue:8
Structure-antitumor activity relationships of 9-anilinoacridines using pattern recognition.
AID210614Compound concentration in mole/kg/day lethal to 10% of mice1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.
AID116709Drug dose that is lethal to 10% of animals was measured1981Journal of medicinal chemistry, Feb, Volume: 24, Issue:2
Potential antitumor agents. 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (80.00)18.7374
1990's2 (20.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.91

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.91 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.91)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
amsacrine
Amsacrine: An aminoacridine derivative that intercalates into DNA and is used as an antineoplastic agent.. amsacrine : A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity.		3.3570acridines;
aromatic ether;
sulfonamide		antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
diminazene
Diminazene: An effective trypanocidal agent.. diminazene : A triazene derivative that is triazene in which each of the terminal nitrogens is substituted by a 4-carbamimidoylphenyl group.		1.9610carboxamidine;
triazene derivative		antiparasitic agent;
trypanocidal drug
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		1.9810aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
mefloquine hydrochloride
[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol : An organofluorine compound that consists of quinoline bearing trifluoromethyl substituents at positions 2 and 8 as well as a (2-piperidinyl)hydroxymethyl substituent at position 4.		1.9810organofluorine compound;
piperidines;
quinolines;
secondary alcohol
acriflavine chloride
3,6-diamino-10-methylacridinium chloride : The 10-methochloride salt of 3,6-diaminoacridine. Note that a mixture of this compound with 3,6-diaminoacridine (proflavine) is known as acriflavine or neutral acriflavine.		1.9610organic chloride saltantibacterial agent;
antiseptic drug;
carcinogenic agent;
histological dye;
intercalator
proflavine
Proflavine: Topical antiseptic used mainly in wound dressings.. 3,6-diaminoacridine : An aminoacridine that is acridine that is substituted by amino groups at positions 3 and 6. A slow-acting bacteriostat that is effective against many Gram-positive bacteria (but ineffective against spores), its salts were formerly used for treatment of burns and infected wounds.		1.9610aminoacridinesantibacterial agent;
antiseptic drug;
carcinogenic agent;
chromophore;
intercalator
9-anilinoacridine
[no description available]		3.2160
nitracrine
Nitracrine: Acridine antineoplastic agent used in mammary and ovarian tumors. It inhibits RNA synthesis.		1.9610acridines
9-(4-methylanilino)-acridine
9-(4-methylanilino)-acridine: RN given refers to parent cpd; structure in first source		2.8840
4'-(9-acridinylamino)methanesulfonanilide
4'-(9-acridinylamino)methanesulfonanilide: structure		3.2160
4'-(9-acridinylamino)methanesulfon-o-anisidide
4'-(9-acridinylamino)methanesulfon-o-anisidide: 30-90 times less potent in killing L1210 cells & 200 times less potent in producing single-strand breaks in DNA than m-AMSA; RN given refers to parent cpd; structure in first source		2.3720
pyronaridine
[no description available]		1.9810aminoquinoline
3,6-diamino-9-(4-(methylsulfonyl)aminophenyl)aminoacridine
[no description available]		2.3720
1-nitro-9-aminoacridine
[no description available]		1.9610
jp-1302
[no description available]		1.9610
quinine
[no description available]		1.9810cinchona alkaloidantimalarial;
muscle relaxant;
non-narcotic analgesic
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		02.3520