l-canaline base

Names

[ CAS No. ]:
496-93-5

[ Name ]:
l-canaline base

[Synonym ]:
L-2-amino-4-(aminooxy)butyric acid
O-Amino-homoserin
Canaline
O-amino-homoserine
O-amino-DL-homoserine
O-Amino-DL-homoserin
2-amino-4-aminooxybutanoic acid
L-a-amino-g-(aminooxy)-n-butyric acid
(S)-2-Amino-4-(aminooxy)butanoic acid
L-2-amino-4-(aminooxy)butyrate
L-Homoserine,O-amino
O-Amino-L-homoserine
L-Canaline

Biological Activity

[Description]:

L-Canaline is a nonprotein amino acid stored in many leguminous plants. L-Canaline is a cytotoxic metabolite catalyzed by L-canavanine and its arginase. L-Canaline is a potent and irreversible inhibitor of ornithine aminotransferase. L-Canaline inhibits the growth of the malaria parasite Plasmodium falciparum with an IC50 of 297 nM. L-Canaline has anticancer and antiproliferative effects[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

[Target]

IC50: 297 nM (Plasmodium falciparum)[3]; Ornithine aminotransferase[1]

[In Vitro]

L-Canaline treatment inhibits the proliferation of PBMCs after stimulation by phorbol 12-myristate-13-acetate (PMA) or via the mixed lymphocyte reaction. The greatest effect is seen with PMA-stimulated cells, where L-canaline has an IC50 of 0.26 mM. L-Canaline is slightly less toxic to PBMCs stimulated via the mixed lymphocyte reaction (IC50 of 0.54 mM)[1].L-canaline inhibits L-lysine flux competitively (Ki of 4.6 mM) in astrocytes and astrocytoma cells[2].

[In Vivo]

L-Canaline decreases the aspartic acid content of tissues of the medulla oblongata of male Wistar rats, but it does not affect the evoked release of this nonprotein amino acid into these tissues[2]. Intraseptal injection of 100 μg of L-canaline into male Sprague-Dawley rats causes a 90% decrease in the omithine aminotransferase activity of the septum tissues evaluated from animals killed 1 h later[2].

[References]

[1]. Bence AK, et al. The antiproliferative and immunotoxic effects of L-canavanine and L-canaline. Anticancer Drugs. 2002 Mar;13(3):313-20.

[2]. Rosenthal GA. L-canaline: a potent antimetabolite and anti-cancer agent from leguminous plants. Life Sci. 1997;60(19):1635-41.

[3]. Berger BJ. Antimalarial activities of aminooxy compounds. Antimicrob Agents Chemother. 2000 Sep;44(9):2540-2.

Chemical & Physical Properties

[ Density]:
1.298g/cm3

[ Boiling Point ]:
378.1ºC at 760mmHg

[ Molecular Formula ]:
C₄H₁₀N₂O₃

[ Molecular Weight ]:
134.13400

[ Flash Point ]:
182.5ºC

[ Exact Mass ]:
134.06900

[ PSA ]:
98.57000

[ LogP ]:
0.07930

[ Vapour Pressure ]:
9.22E-07mmHg at 25°C

[ Index of Refraction ]:
1.51

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ HS Code ]:
2922509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922509090

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%