A7902
2-Amino-2-norbornanecarboxylic acid
suitable for ligand binding assays
Synonym(s):
BCH, 2-Aminobicyclo[2.2.1]heptane-2-carboxylic acid
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About This Item
Empirical Formula (Hill Notation):
C8H13NO2
CAS Number:
Molecular Weight:
155.19
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.26
MDL number:
Product Name
2-Amino-2-norbornanecarboxylic acid, amino acid transport inhibitor
SMILES string
NC1(C[C@@H]2CC[C@H]1C2)C(O)=O
InChI
1S/C8H13NO2/c9-8(7(10)11)4-5-1-2-6(8)3-5/h5-6H,1-4,9H2,(H,10,11)/t5-,6+,8?/m1/s1
InChI key
MPUVBVXDFRDIPT-RSHNMJPRSA-N
form
powder
technique(s)
ligand binding assay: suitable
color
white to off-white
mp
>300 °C (lit.)
Quality Level
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Analysis Note
Mixture of exo- and endo-isomers.
Application
- Thyroid Hormone Transporters in a Human Placental Cell Model.: This study investigates the role of 2-Amino-2-norbornanecarboxylic acid in the transport of thyroid hormones in placental cells, offering insights that could improve understanding of fetal development and maternal health (Chen et al., 2022).
- Metabolic adaptations to hypoxia in the neonatal mouse forebrain can occur independently of the transporters SLC7A5 and SLC3A2.: Research explores how 2-Amino-2-norbornanecarboxylic acid affects metabolic responses to hypoxia in neonatal brain development, providing a foundation for future studies on brain health and neurodevelopment (Fitzgerald et al., 2021).
- Hemocompatible LAT1-inhibitor can induce apoptosis in cancer cells without affecting brain amino acid homeostasis.: This article assesses the potential of 2-Amino-2-norbornanecarboxylic acid as a selective inhibitor that could lead to new treatments for cancer while preserving critical brain functions (Markowicz-Piasecka et al., 2020).
- Regulation of Melanogenesis by the Amino Acid Transporter SLC7A5.: Research demonstrates the utility of 2-Amino-2-norbornanecarboxylic acid in regulating skin pigmentation processes, which could have implications for disorders related to pigmentation (Gaudel et al., 2020).
- Structure of the human LAT1-4F2hc heteromeric amino acid transporter complex.: This study utilizes 2-Amino-2-norbornanecarboxylic acid to elucidate the structure of a key amino acid transporter, which is crucial for understanding nutrient uptake and its implications in various diseases (Yan et al., 2019).
Biochem/physiol Actions
2-Amino-2-norbornanecarboxylic acid (BCH) is a Na(+)-independent system L specific substrate used with other system specific substrates such as the system A specific substrate α-(methylamino) isobutyric acid and system N specific substrate L-glutamic acid gamma-monohydroxamate to help identify, differentiate and characterize amino acid transport systems in cells.
General description
2-Amino-2-norbornanecarboxylic acid is a potential large amino acid transporters inhibitor. It may suppress tumor progression and apoptosis.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Discovery of Potent Inhibitors for the Large Neutral Amino Acid Transporter 1 (LAT1) by Structure-Based Methods
Singh N, et al.
International Journal of Molecular Sciences, 20(1), 27-27 (2019)
Hiroyuki Okudaira et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 52(5), 822-829 (2011-05-04)
Trans-1-amino-3-(18)F-fluorocyclobutanecarboxylic acid (anti-(18)F-FACBC) is an amino acid PET tracer that has shown promise for visualizing prostate cancer. Therefore, we aimed to clarify the anti-(18)F-FACBC transport mechanism in prostate cancer cells. We also studied the fate of anti-(18)F-FACBC after it is
M M Sánchez del Pino et al.
The Journal of biological chemistry, 267(36), 25951-25957 (1992-12-25)
Endothelial cell membranes, the site of the blood-brain barrier, were obtained from the capillaries of cow brain. The luminal and abluminal membranes were separated by centrifugation on a discontinuous Ficoll gradient. Electron microscopy revealed that the membrane preparations consisted almost
Chem. Abstr., 117, 64436p-64436p (1992)
Hisao Imai et al.
Anticancer research, 30(12), 4819-4828 (2010-12-29)
L-type amino acid transporter 1 (LAT1) is highly expressed in various human neoplasms. Antitumor activity of inhibiting LAT1 was analyzed in non-small cell lung cancer (NSCLC). Expression of LAT1 mRNA in 54 lung cancer cell lines was examined by RT-PCR.
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