L-Alanosine

CAS# 5854-93-3

L-Alanosine

Catalog No. BCN7253----Order now to get a substantial discount!

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Quality Control of L-Alanosine

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Chemical structure

L-Alanosine

3D structure

Chemical Properties of L-Alanosine

Cas No. 5854-93-3 SDF Download SDF
PubChem ID 135409347 Appearance Powder
Formula C3H7N3O4 M.Wt 149.1
Type of Compound Anthraquinones Storage Desiccate at -20°C
Synonyms Alanosine
Solubility H2O : 15 mg/mL (100.60 mM; ultrasonic and adjust pH to 8 with NaOH)
Chemical Name (Z)-[(2S)-2-amino-2-carboxyethyl]-hydroxyimino-oxidoazanium
SMILES C(C(C(=O)O)N)[N+](=NO)[O-]
Standard InChIKey AFHJQYHRLPMKHU-WEZNYRQKSA-N
Standard InChI InChI=1S/C3H7N3O4/c4-2(3(7)8)1-6(10)5-9/h2,9H,1,4H2,(H,7,8)/b6-5-/t2-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of L-Alanosine

The leaf juice of Aloe microdonta. Chiov.

Biological Activity of L-Alanosine

Description1. Aloin shows tyrosinase activity, it could be used as lightening agents in the treatment of hyperpigmentation disorders and cosmetic additives. 2. Aloe components (aloin, aloesin and aloe-gel) show anti-inflammatory effects, they can ameliorate intestinal inflammatory responses in a dextran sulfate sodium (DSS)-induced ulcerative colitis rat model. 3. Aloin is a potent proapoptotic agent, it showed a pronounced antiproliferative effect at physiological concentration (IC50 = 97 microM), caused cell cycle arrest in the S phase and markedly increased HeLaS3 cell apoptosis (to 24%).
TargetsTyrosinase | TNF-α | IL Receptor

L-Alanosine Dilution Calculator

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L-Alanosine Molarity Calculator

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Preparing Stock Solutions of L-Alanosine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.7069 mL 33.5345 mL 67.0691 mL 134.1382 mL 167.6727 mL
5 mM 1.3414 mL 6.7069 mL 13.4138 mL 26.8276 mL 33.5345 mL
10 mM 0.6707 mL 3.3535 mL 6.7069 mL 13.4138 mL 16.7673 mL
50 mM 0.1341 mL 0.6707 mL 1.3414 mL 2.6828 mL 3.3535 mL
100 mM 0.0671 mL 0.3353 mL 0.6707 mL 1.3414 mL 1.6767 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on L-Alanosine

Alanosine is an amino acid analogue and antibiotic derived from the bacterium Streptomyces alanosinicus with antimetabolite and potential antineoplastic activities. L-alanosine inhibits adenylosuccinate synthetase, which converts inosine monophospate (IMP) into adenylosuccinate, an intermediate in purine metabolism. L-alanosine-induced disruption of de novo purine biosynthesis is potentiated by methylthioadenosine phosphorylase (MTAP) deficiency. The clinical use of this agent may be limited by its toxicity profile. MTAP is a key enzyme in the adenine and methionine salvage pathways.
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References on L-Alanosine

Aloin, cinnamic acid and sophorcarpidine are potent inhibitors of tyrosinase.[Pubmed:12622939]

Chin Med J (Engl). 2002 Dec;115(12):1859-62.

OBJECTIVE: To evaluate the effects of aloin, cinnamic acid and 15 other kinds of natural chemicals on the activity of tyrosinase, in order to provide lightening agents in the treatment of hyperpigmentation disorders and cosmetic additives. METHODS: Tyrosinase activity was estimated by measuring the oxidation rate of L-dopa. Inhibition of the enzyme was deduced according to the Lineweaver-Burk plots compared to the control. RESULTS: Cadabine, paeonal, farrerol, evodin, cinnamic acid, aloin and sophorcarpidine had different levels of inhibition of tyrosinase. The inhibitory rates of cinnamic acid (2 mmol/L, 0.5 mmol/L), aloin (2 mmol/L) and the rest were significantly higher than that of hydroquinone (0.5 mmol/L) (P < 0.05). CONCLUSIONS: Tyrosinase activity can be greatly inhibited by cinnamic acid, aloin and sophorcarpidine, of which sophorcarpidine functions as an uncompetitive inhibitor, compared to aloin and cinnamic acid, which are mixed-type inhibitors.

Dietary aloin, aloesin, or aloe-gel exerts anti-inflammatory activity in a rat colitis model.[Pubmed:21277867]

Life Sci. 2011 Mar 14;88(11-12):486-92.

AIMS: Aloe has been a very popular folk remedy for inflammation-related pathological conditions despite the lack of studies reporting its efficacy in vivo. The present study evaluated the anti-inflammatory effects of aloe components (aloin, aloesin and aloe-gel) known to be biologically active in the rat model of colitis. MAIN METHODS: Male Sprague Dawley rats were fed experimental diets for 2 weeks before and during the induction of colitis. Drinking water containing 3% dextran sulfate sodium (DSS) was provided for 1 week to induce colitis. At the end of the experimental period, clinical and biochemical markers were compared. KEY FINDINGS: Plasma leukotriene B(4) (LTB(4)) and tumor necrosis factor-alpha (TNF-alpha) concentrations were significantly decreased in all groups supplemented with aloe components compared to the colitis control group (p<0.05). Animals fed both a 0.1% and 0.5% aloesin supplemented diet showed colonic myeloperoxidase (MPO) activities which were decreased by 32.2% and 40.1%, respectively (p<0.05). Colonic mucosa TNF-alpha and interleukin-1ss (IL-1beta) mRNA expressions were significantly reduced in all animals fed aloin, aloesin, or aloe-gel (p<0.05). SIGNIFICANCE: Dietary supplementation of aloe components ameliorates intestinal inflammatory responses in a DSS-induced ulcerative colitis rat model. In particular, aloesin was the most potent inhibitor. Further studies are required for a more complete understanding of the specific mechanism of the action of these supplements.

Antitumor effects of a natural anthracycline analog (Aloin) involve altered activity of antioxidant enzymes in HeLaS3 cells.[Pubmed:17726368]

Cancer Biol Ther. 2007 Aug;6(8):1200-5. Epub 2007 May 4.

The antiproliferative and cytotoxic potential of the natural anthracycline aloin from Aloe vera was tested on human uterine carcinoma HeLaS3 cells. Aloin showed a pronounced antiproliferative effect at physiological concentration (IC50 = 97 microM), caused cell cycle arrest in the S phase and markedly increased HeLaS3 cell apoptosis (to 24%). In the concentration range of 20-100 microM, its action was accompanied by remarkable changes in the activity of almost all antioxidant enzymes: MnSOD activity was increased many fold, while CuZnSOD and iNOS activities were inhibited. Moreover, inhibition of CuZnSOD was shown to occur by direct aloin interaction with the enzyme. As catalase activity was not changed, it is suggested that such conditions were responsible for antiproliferative and cytotoxic effects owing to accumulation of H2O2. Aloin alone was a more potent proapoptotic agent than a 2 Gy fractional dose of ionizing radiation or a combination of the two. Compared to other currently used therapeutics, aloin, due to its less undesirable side effects and antimetastatic potential, may prove to be the agent of choice on which clinical protocols for the treatment of human cervical carcinoma should rely in future.

Description

L-Alanosine (NSC-153353), an antibiotic from Streptomyces alanosinicus, has antineoplastic activity. L-Alanosine (NSC-153353) inhibits adenylosuccinate synthetase, which converts inosine monophospate (IMP) into adenylosuccinate. L-Alanosine (NSC-153353) blocks the common de novo purine biosynthesis pathway and, thereby, inhibits tumor cells with MTAP deficiency.

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