ACRIFLAVINE

Names

[ Name ]:
ACRIFLAVINE

[Synonym ]:
ACRIFLAVINE
EUFLAVINE
3,6-Diamino-10-methylacridinium chloride - 3,6-acridinediamine (1:1:1)
3,6-Diamino-10-methylacridinium Chloride mixt with 3,6-Acridine Diamine
3,6-Diamino-10-methylacridinium chloride 3,6-acridinediamine (1:1:1)
diacrid
3,6-Diamino-10-methylacridinium chloride 3,6-acridinediamine (1:1)
flavipin
Trypaflavine
Acridinium, 3,6-diamino-10-methyl-, chloride, mixt. with 3,6-acridinediamine
gonacin
3,6-Diamino-10-methylacridinium chloride - acridine-3,6-diamine (1:1:1)
flavine
Neutroflavine
EUFLAVIN
angiflan
Neutral Acriflavine
flavisept
isravin
MFCD00064307

Biological Activity

[Description]:

Acriflavine is a fluorescent dye for labeling high molecular weight RNA. It is also a topical antiseptic.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> HIF/HIF Prolyl-Hydroxylase

Research Areas >> Cancer

Dye Reagents

Research Areas >> Infection

[In Vitro]

Acriflavine is identified as a potent inhibitor of the MCT4 that can inhibit the binding between Basigin and MCT4. Acriflavine significantly inhibits growth and self-renewal potential of several glioblastoma neurosphere lines[1]. The HIF-1 inhibitor acriflavine decreases survival and growth of CML cells. It targets stem cell potential of CML cells[2].

[In Vivo]

Acriflavine treatment inhibits intratumoral expression of VEGF and tumor vascularization[1]. In a murine CML model, acriflavine decreases leukemia development and reduces LSC maintenance[2]. Acriflavine retards tumor growth in a murine model of breast cancer. The combination of sunitinib with acriflavine significantly decreases vascular endothelial growth factor and TGF-β expression and reduces tumor vasculature followed by increased intratumor necrosis and apoptosis[3].

[Animal admin]

Mice: CML mice are treated daily with acriflavine (8 mg/kg) or PBS via intraperitoneal injection, for 10 days starting from day 7 after bone marrow transplantation[2].

[References]

[1]. Voss DM, et al. Disruption of the monocarboxylate transporter-4-basigin interaction inhibits the hypoxic response, proliferation, and tumor progression. Sci Rep. 2017 Jun 27;7(1):4292.

[2]. Cheloni G, et al. Targeting chronic myeloid leukemia stem cells with the hypoxia-inducible factor inhibitor acriflavine. Blood. 2017 Jun 2. pii: blood-2016-10-745588.

[3]. Yin T, et al. HIF-1 Dimerization Inhibitor Acriflavine Enhances Antitumor Activity of Sunitinib in Breast Cancer Model. Oncol Res. 2014;22(3):139-45.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
179-181 °C

[ Molecular Formula ]:
C₁₄H₁₄ClN₃

[ Molecular Weight ]:
259.73

[ PSA ]:
120.85000

[ LogP ]:
3.86310

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AR9660000

CHEMICAL NAME :: Acridinium, 3,6-diamino-10-methyl-, chloride mixed with 3,6-acridinediamine

CAS REGISTRY NUMBER :: 8048-52-0

LAST UPDATED :: 199706

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C14-H14-N3.Cl.C13-H11-N3

MOLECULAR WEIGHT :: 469.03

WISWESSER LINE NOTATION :: T C666 BKJ B1 EZ MZ &G &T C666 BNJ EZ MZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 160 mg/kg/60W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

TYPE OF TEST :: Dominant lethal test

MUTATION DATA

TYPE OF TEST :: Morphological transformation

TEST SYSTEM :: Rodent - hamster Kidney

DOSE/DURATION :: 25 mg/L

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 19,55,1981 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,31,1977 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,31,1977 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X1531 No. of Facilities: 10 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 40 (estimated) No. of Female Employees: 10 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

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

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

[ Hazard Codes ]:
Xn:Harmful;N:Dangerousfortheenvironment;

[ Risk Phrases ]:
R22;R37/38;R41;R50/53

[ Safety Phrases ]:
S26-S39-S60-S61

[ RIDADR ]:
UN 3077 9/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
AR9660000

[ HS Code ]:
38249064

Customs

[ HS Code ]: 38249064

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