L-Canavanine sulfate

Names

[ Name ]:
L-Canavanine sulfate

[Synonym ]:
CANAVANINE SULFATE,L
L-Canavanine sulphate
L-Canavanine Sulfate Hydrate
L-CANAVANINE SULFATE
O-Guanidino-L-homoserin,Sulfat
L-Homoserine, O-[(diaminomethylene)amino]-, sulfate (1:1)
O-[(Diaminomethylene)amino]-L-homoserine sulfate (1:1)
Canavanine sulfate
EINECS 218-728-4
O-guanidino-L-homoserine,sulfate
L-Canavanine sulfate salt
L-HOMOSERINE, O-((AMINOIMINOMETHYL)AMINO)-, SULFATE (1:1)
MFCD00012618
canavanine sulphate

Biological Activity

[Description]:

L-Canavanine sulfate is a selective inhibitor of inducible NO synthase.

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

Research Areas >> Cancer

[Target]

NO synthase[1]

[In Vitro]

L-Canavanine sulfate (L-CAV) causes only a limited degree of cytotoxicity in HeLa, Hep G2, and SK-HEP-1 cells when given alone in arginine-rich media with IC50 values ranging from 5 to 10 mM. In HaCaT keratinocyte cell line, IC50 of L-Canavanine sulfate exceeds the concentration of 10 mM, indicating low cytotoxicity in normal cells in vitro. In arginine-free media, IC50 of L-Canavanine sulfate in HeLa, Hep G2, and SK-HEP-1 cells are 0.21±0.04; 0.64±0.16; and 1.18±0.14 mM, respectively. L-Canavanine sulfate, which is hardly toxic alone, potentiates the cytotoxicity of vinblastine (VIN) and paclitaxel (PTX) in HeLa and hepatocellular carcinoma cells[2].

[In Vivo]

Administration of L-Canavanine sulfate (100 mg/kg) produces a moderate increase in mean arterial pressure of 20 mm Hg, returns blood pressure to near basal levels and completely attenuates the lipopolysaccharide-induced hypotension. All, but one, endotoxaemic rats dosed with L-Canavanine sulfate (100 mg/kg) survive for 6 h post lipopolysaccharide, after which time the experiment is terminated (n=7)[1]. L-canavanine inhibits DNA synthesis by Li 210 cells in vivo and significantly increases the lifespan of animals bearing the Li 210 leukemia. An optimal dose of 18 g/kg produces a peak increase in lifespan of 44%. The therapeutic dose range is narrow, and a dose of 24 g/kg causes death due to drug toxicity[3].

[Cell Assay]

A dose-dependent cytotoxicity is examined using the MTT assay. Into each well of 96-well plates, 2×104 of cells are seeded, and after 24 h incubation, cells are incubated with test compounds (including L-Canavanine sulfate). After 24 h, 0.5 mg/mL of MTT is added to each well of HeLa, Caco-2, MIA PaCa-2, BxPC-3 and SK-HEP-1 cells, while MTT is added to Hep G2 after 48 h incubation with test compounds (including L-Canavanine sulfate). The cells are then incubated for 3 h so that the viable cells could produce formazan crystals; they are then dissolved in 100 μL DMSO. After incubation for 10 min in a shaker, the absorption of the formazan is measured at 570 nm using a reader[2].

[Animal admin]

Male rats weighing 295 to 305 g are used. After a period of stabilization, 6 mg lipopolysaccharide/kg is administered intravenously in 0.3 mL over 2 min, and cardiovascular parameters are monitored over 5 to 6 h. L-Canavanine sulfate is administered intravenously in a 0.2 mL volume bolus injection at 100 mg/kg[1]. Mice: L-Canavanine is dissolved in phosphate-buffered saline[1]. L-Canavanine (100 mg/mb) is infused at a rate of 0.1 mL/hr through a catheter implanted S.C. over the back. Groups of 5 mice are treated at each dose beveltogether with 6 to 8 control animals and are inspected twice per day for median time of death[1].

[References]

[1]. Teale DM, et al. L-canavanine restores blood pressure in a rat model of endotoxic shock. Eur J Pharmacol. 1994 Dec 12;271(1):87-92.

[2]. Nurcahyanti AD, et al. Cytotoxic potentiation of vinblastine and paclitaxel by L-canavanine in human cervical cancer and hepatocellular carcinoma cells. Phytomedicine. 2015 Dec 15;22(14):1232-7.

[3]. Green MH, et al. Antitumor activity of L-canavanine against L1210 murine leukemia. Cancer Res. 1980 Mar;40(3):535-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
574ºC at 760mmHg

[ Melting Point ]:
160-165 °C (dec.)

[ Molecular Formula ]:
C₅H₁₄N₄O₇S

[ Molecular Weight ]:
274.252

[ Flash Point ]:
300.9ºC

[ Exact Mass ]:
274.058319

[ PSA ]:
217.43000

[ LogP ]:
0.52230

[ Appearance of Characters ]:
powder | white

[ Vapour Pressure ]:
1.21E-08mmHg at 25°C

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: 100 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

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

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S36

[ RIDADR ]:
2811

[ WGK Germany ]:
3

[ HS Code ]:
2925290090

Customs

[ HS Code ]: 2925290090

[ Summary ]:
2925290090 other imines and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

Articles

Determination of L-canavanine and other free amino acids in Vicia disperma (Fabaceae) seeds by precolumn derivatization using diethyl ethoxymethylenemalonate and reversed-phase high-performance liquid chromatography.

Talanta 131 , 95-8, (2014)

A method for determination of the non-protein amino acid l-α-amino-γ-(guanidinooxy)-n-butyric acid (L-canavanine) and other free amino acids in Vicia disperma is presented. Seed extracts were derivati...

Quality control of a transcriptional regulator by SUMO-targeted degradation.

Mol. Cell. Endocrinol. 29 , 1694-706, (2009)

Slx5 and Slx8 are heterodimeric RING domain-containing proteins that possess SUMO-targeted ubiquitin ligase (STUbL) activity in vitro. Slx5-Slx8 and its orthologs are proposed to target SUMO conjugate...

Dissection of genetically complex traits with extremely large pools of yeast segregants.

Nanotechnology 464 , 1039-42, (2010)

Most heritable traits, including many human diseases, are caused by multiple loci. Studies in both humans and model organisms, such as yeast, have failed to detect a large fraction of the loci that un...