1,2-DIAMINOANTHRAQUINONE

Names

[ Name ]:
1,2-DIAMINOANTHRAQUINONE

[Synonym ]:
EINECS 217-156-2
1,2-diamino-9,10-anthraquinone
1,2-diaminoanthracene-9,10-dione
1,2-diamino-anthraquinon
DAA
MFCD00001219
1,2-Diaminoanthraquinone
1,2-diamino-10-anthracenedione
diamino-anthraquinone
10-Anthracenedione,1,2-diamino-9

Biological Activity

[Description]:

1,2-Diaminoanthraquinone is a sensitivity, specificity and nontoxic nitric oxide (NO) fluorescent probe. 1,2-Diaminoanthraquinone can be used to detect NO productions in live cell and animals with a maximum of absorption at about 540 nm and a detection limit of 5 μM for NO[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vitro]

1,2-Diaminoanthraquinone and the product formed upon its reaction with NO, DAA-TZ, can be spectrally resolved using fluorescence spectroscopy and confocal microscopy[1]. Immunofluorescence[1] Cell Line: Raw 264.7 macrophage cells Concentration: 27.4 μM Incubation Time: 20 min Result: Reacted with NO in the presence of oxygen in the intracellular environment to yield DAA-TZ.

[References]

[1]. María J Marín, et al. Fluorescence of 1,2-diaminoanthraquinone and its nitric oxide reaction product within macrophage cells. Chembiochem. 2011 Nov 4;12(16):2471-7.

[2]. Francisco Galindo, et al. Spectroscopic studies of 1,2-diaminoanthraquinone (DAQ) as a fluorescent probe for the imaging of nitric oxide in living cells. Photochem Photobiol Sci. 2008 Jan;7(1):126-30.

Chemical & Physical Properties

[ Density]:
1.456 g/cm3

[ Boiling Point ]:
548.8ºC at 760 mmHg

[ Melting Point ]:
289-291 °C(lit.)

[ Molecular Formula ]:
C₁₄H₁₀N₂O₂

[ Molecular Weight ]:
238.24100

[ Flash Point ]:
285.7ºC

[ Exact Mass ]:
238.07400

[ PSA ]:
86.18000

[ LogP ]:
2.78880

[ Vapour Pressure ]:
4.26E-12mmHg at 25°C

[ Index of Refraction ]:
1.757

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CB6200000

CHEMICAL NAME :: Anthraquinone, 1,2-diamino-

CAS REGISTRY NUMBER :: 1758-68-5

BEILSTEIN REFERENCE NO. :: 2125604

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C14-H10-N2-O2

MOLECULAR WEIGHT :: 238.26

WISWESSER LINE NOTATION :: L C666 BV IVJ DZ EZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 320 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 100 ug/plate

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 40,203,1976

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CB6200000

[ HS Code ]:
2922399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922399090

[ Summary ]:
2922399090 other amino-aldehydes, amino-ketones and amino-quinones, other than those containing more than one kind of oxygen function; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles

[Detection of NO-synthase activity of lactobacilli by fluorescent staining].

Mikrobiologiia 76(4) , 570-2, (2007)

Spatial nitric oxide imaging using 1,2-diaminoanthraquinone to investigate the involvement of nitric oxide in long-term potentiation in rat brain slices.

Neuroimage 15(3) , 633-9, (2002)

Long-term potentiation (LTP), a model of activity-dependent synaptic plasticity, involves the persistent enhancement of excitatory neurotransmission. Several recent studies have suggested a critical r...

Floral transition and nitric oxide emission during flower development in Arabidopsis thaliana is affected in nitrate reductase-deficient plants.

Plant Cell Physiol. 49(7) , 1112-21, (2008)

The nitrate reductase (NR)-defective double mutant of Arabidopsis thaliana (nia1 nia2) has previously been shown to present a low endogenous content of NO in its leaves compared with the wild-type pla...