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5652-28-8

5652-28-8 structure
5652-28-8 structure
  • Name: DL-AP3
  • Chemical Name: 2-amino-3-phosphonopropanoic acid
  • CAS Number: 5652-28-8
  • Molecular Formula: C3H8NO5P
  • Molecular Weight: 169.073
  • Catalog: Signaling Pathways GPCR/G Protein mGluR
  • Create Date: 2017-01-25 02:26:41
  • Modify Date: 2024-02-01 12:08:37
  • DL-AP3 is a competitive mGluR1 and mGluR5 antagonist. DL-AP3 is also an inhibitor of phosphoserine phosphatase. DL-AP3 has neuroprotective effect[1][2][3].

Name 2-amino-3-phosphonopropanoic acid
Synonyms Alanine, 3-phosphono-
DL-2-Amino-3-phosphonopropionic acid
2-Amino-3-phosphonopropionic acid
D,L-2-Amino-3-phosphonopropionic Acid
(+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST
2-amino-3-phosphopropanoic acid
3-Phosphonoalanine
UNII:0H89G8110O
3-Phosphono-DL-alanine
Aminophosphonopropionic acid
DL-2-Amino-4-phosphonopropionic acid
(±)-2-Amino-3-phosphonopropionic acid
2-amino-3-phosphonopropionate
2-amino-3-phosphonopropanoic acid
2-AP3
Description DL-AP3 is a competitive mGluR1 and mGluR5 antagonist. DL-AP3 is also an inhibitor of phosphoserine phosphatase. DL-AP3 has neuroprotective effect[1][2][3].
Related Catalog
Target

mGluR 1

mGluR 5

In Vitro DL-AP3 (10 µM,6 小时) 减轻原代神经元中氧-葡萄糖剥夺 (OGD) 引起的损伤 (细胞活力)[1]。 DL-AP3 (10 µM,6 小时) 恢复原代神经元中 OGD 诱导的 p-Akt1 水平降低和细胞色素 C 增加[1]。 DL-AP3 (1-100 µM) 抑制大鼠脑磷酸丝氨酸磷酸酶的活性[2]。 DL-AP3 (10μM, 10min) 联合 SKF81297 (5μM) 在 Fmr1 KO 小鼠的切片中诱导显著的的长时程增强 (LTP)[3]。 Western Blot Analysis[1] Cell Line: Primary neurons Concentration: 10 µM Incubation Time: 6 h Result: Increased the decreased levels of p-Akt1, and decreased the increase of cytochrome C.
In Vivo DL-AP3 (4 mg/kg, i.p., 持续 5 周) 联合 SKF81297 (1 mg/kg, i.p.) 减少 Fmr1 KO 小鼠多动表型[3]。 DL-AP3 (i.c.v.) 阻断绵羊内脏痛症状的发展,以及血浆中神经内分泌学变化[4]。 Animal Model: Fmr1 KO mice[3] Dosage: 4 mg/kg with SKF81297 (1 mg/kg) Administration: i.p., for 5 weeks. Result: Reduced the distance traveled by Fmr1 KO mice (open-field test). Reduced the swim latency on the final day in the Fmr1 KO mice (Morris Water Maze test).
References

[1]. Cui D, et al. DL-2-amino-3-phosphonopropionic acid protects primary neurons from oxygen-glucose deprivation induced injury. Bosn J Basic Med Sci. 2017 Feb 21;17(1):12-16.  

[2]. Hawkinson JE, et al. The metabotropic glutamate receptor antagonist L-2-amino-3-phosphonopropionic acid inhibits phosphoserine phosphatase. Eur J Pharmacol. 1996 Jun 27;307(2):219-25.  

[3]. Xu ZH, et al. Group I mGluR antagonist rescues the deficit of D1-induced LTP in a mouse model of fragile X syndrome. Mol Neurodegener. 2012 May 28;7:24.  

[4]. B.F. Kania, et al. Supraspinal basis of analgesic and clinical effects of the metabotropic glutamate mGluR1 antagonist during colonic distension in sheep. Small Ruminant Research. 2014. 117 (1).

Density 1.8±0.1 g/cm3
Boiling Point 481.6±55.0 °C at 760 mmHg
Molecular Formula C3H8NO5P
Molecular Weight 169.073
Flash Point 245.1±31.5 °C
Exact Mass 169.014008
PSA 130.66000
LogP -2.29
Vapour Pressure 0.0±2.6 mmHg at 25°C
Index of Refraction 1.559
Precursor  0

DownStream  1