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
Related Categories
General description
2-Amino-2-norbornanecarboxylic acid is a potential large amino acid transporters inhibitor. It may suppress tumor progression and apoptosis.
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.
Analysis Note
Mixture of exo- and endo-isomers.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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)
Chun Sung Kim et al.
Biological & pharmaceutical bulletin, 31(6), 1096-1100 (2008-06-04)
L-Type amino acid transporter 1 (LAT1) is highly expressed in cancer cells to support their continuous growth and proliferation. We have examined the effect of 2-aminobicyclo-(2,2,1)-heptane-2-carboxylic acid (BCH), an inhibitor of system L amino acid transporters, and the mechanism by
Ashwini L Chand et al.
Human reproduction (Oxford, England), 26(11), 3102-3108 (2011-09-15)
Little is known about metabolic processes in the developing ovarian follicle. Using mouse ovarian follicles, we investigated uptake of L-leucine by follicles at varying stages of maturity in the presence of insulin-like growth factor (IGF)-1. METHODS Mouse ovarian follicles were
Mikko Gynther et al.
Journal of medicinal chemistry, 51(4), 932-936 (2008-01-26)
The blood-brain barrier efficiently controls the entry of drug molecules into the brain. We describe a feasible means to achieve carrier-mediated drug transport into the rat brain via the specific, large neutral amino acid transporter (LAT1) by conjugating a model
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