BCH

Names

[ CAS No. ]:
20448-79-7

[ Name ]:
BCH

[Synonym ]:
2-aminonorbornane-2-carboxylic acid
MFCD00167580
b-BCH
2-AMINO-2-NORBORNANE-CARBOXYLIC ACID

Biological Activity

[Description]:

LAT1-IN-1 (BCH) is a selective and competitive inhibitor of large neutral amino acid transporter 1 (LAT1) significantly inhibit cellular uptake of amino acids and mTOR phosphorylation, which induces the suppression of cancer growth and apoptosis[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[Target]

LAT1[1]

[In Vitro]

LAT1-IN-1 (1-100 mM; 3 days; KYSE30 and KYSE150 esophageal cancer cells) treatment suppresses cell proliferation in a dose-dependent manner[1]. LAT1-IN-1 (30 mM; 24 and 48 hours; KYSE30 and KYSE150 cells) treatment significantly increases cell population in the G0/G1 phase in both KYSE30 and KYSE150 cells, indicating that LAT1-IN-1 induces cell cycle arrest at G1 phase[1]. LAT1-IN-1 (30 mM; 0-24 hours; KYSE30 and KYSE150 cells) treatment decreases phosphorylation of 4E-BP1 and p70S6K at 30 minutes and the decrease is continued for 24 hours. The amount of mTOR, 4E-BP1, and p70S6K proteins is slightly decreased[1]. Cell Proliferation Assay[1] Cell Line: KYSE30 and KYSE150 esophageal cancer cells Concentration: 1 mM, 3 mM, 5 mM, 10 mM, 20 mM, 30 mM, 40 mM, 50 mM, or 100 mM Incubation Time: 3 days Result: Cell proliferation was suppressed in a dose-dependent manner. Cell Cycle Analysis[1] Cell Line: KYSE30 and KYSE150 cells Concentration: 30 mM Incubation Time: 24 and 48 hours Result: Cell cycle arrest. Western Blot Analysis[1] Cell Line: KYSE30 and KYSE150 cells Concentration: 30 mM Incubation Time: 0 hour, 0.5 hour, 1 hour, 3 hours, 6 hours, 24 hours Result: Phosphorylation of 4E-BP1 and p70S6K was decreased. The amount of mTOR, 4E-BP1, and p70S6K proteins was slightly decreased.

[In Vivo]

LAT1-IN-1 (200 mg/kg; intravenous injection; daily; for 14 days; male BALB/c nude mice) treatment significantly delays tumor growth and decreases glucose metabolism, indicating that LAT1 inhibition potentially suppresses esophageal cancer growth in vivo[1]. Animal Model: Male BALB/c nude mice (5-week-old) with KYSE150 cells[1] Dosage: 200 mg/kg Administration: Intravenous injection; daily; for 14 days Result: Significantly delayed tumor growth and decreased glucose metabolism.

[References]

[1]. Ohshima Y, et al. Efficacy of system l amino acid transporter 1 inhibition as a therapeutic target in esophageal squamous cell carcinoma. Cancer Sci. 2016 Oct;107(10):1499-1505.

[2]. Singh N, et al. Discovery of Potent Inhibitors for the Large Neutral Amino Acid Transporter 1 (LAT1) by Structure-Based Methods. Int J Mol Sci. 2018 Dec 21;20(1).

[3]. Wang Q, et al. L-type amino acid transport and cancer: targeting the mTORC1 pathway to inhibit neoplasia. Am J Cancer Res. 2015 Mar 15;5(4):1281-94. eCollection 2015.

Chemical & Physical Properties

[ Density]:
1.256g/cm3

[ Boiling Point ]:
295.5ºC at 760 mmHg

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₈H₁₃NO₂

[ Molecular Weight ]:
155.19400

[ Flash Point ]:
132.5ºC

[ Exact Mass ]:
155.09500

[ PSA ]:
63.32000

[ LogP ]:
1.28880

[ Vapour Pressure ]:
0.000369mmHg at 25°C

[ Index of Refraction ]:
1.559

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2922499990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922499990

[ Summary ]:
HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

Articles

Dietary methionine can sustain cytosolic redox homeostasis in the mouse liver.

Nat. Commun. 6 , 6479, (2015)

Across phyla, reduced nicotinamide adenine dinucleotide phosphate (NADPH) transfers intracellular reducing power to thioredoxin reductase-1 (TrxR1) and glutathione reductase (GR), thereby supporting f...

Development of a cell-based screening method for compounds that inhibit or are transported by large neutral amino acid transporter 1, a key transporter at the blood-brain barrier.

Anal. Biochem. 486 , 81-5, (2015)

Large neutral amino acid transporter 1 (LAT1) transports neutral amino acids with aromatic or branched side chains as well as their derivatives or prodrugs. Because the transporter is highly expressed...

Effects of gabapentin and pregabalin on K+-evoked 3H-GABA and 3H-glutamate release from human neocortical synaptosomes.

Naunyn Schmiedebergs Arch. Pharmacol. 379(4) , 361-9, (2009)

One site of action of the anticonvulsant, analgesic, and anxiolytic drugs gabapentin and pregabalin is the alpha(2)delta-subunit of voltage-sensitive Ca(2+) channels (VSCC). We therefore analyzed the ...

Related Compounds

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