DL-AP4  (Synonyms: 2-Amino-4-phosphonobutyric acid)

DL-AP4 (2-Amino-4-phosphonobutyric acid) is a glutamate antagonist. DL-AP4 behaves as a competitive inhibitor of glutamate binding with an apparent K_d of 66 μM. DL-AP4 can be used for the research of central nervous system and visual system^[1][2][3].

Glutamate^[1]

DL-AP4 (500 μM) reduces the tonic inward current by closing ion channels at holding potentials of -33 mV in isolated rod bipolar cells^[1].
DL-AP4 (0.1 M; 1h) antagonizes the excitatory action of glutamate applied iontophoretically to receptors present in the locust muscle membrane^[2].
DL-AP4 (compound 2) antagonizes excitatory synapses in the lateral perforant path of the rat hippocampal slice with an apparent K_d of 2.5 μM^[3].
DL-AP4 (50 µM; 0-2 seconds) blocks the light response of a series of 10 ms 405-nm flashes, at the following strengths: 3, 10, 30, 100, 300, 990, 3000, 9900 photons μm^-2[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

183.10

C₄H₁₀NO₅P

6323-99-5

Solid

White to off-white

O=C(O)C(N)CCP(O)(O)=O

Room temperature in continental US; may vary elsewhere.

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

• [1]. Cull-Candy SG, et al. 2-Amino-4-phosphonobutyric acid as a glutamate antagonist on locust muscle. Nature. 1976 Jul 29;262(5567):408-9.  [Content Brief]

  [2]. Yamashita M, et al. Responses of rod bipolar cells isolated from the rat retina to the glutamate agonist 2-amino-4-phosphonobutyric acid (APB). J Neurosci. 1991 Aug;11(8):2372-82.  [Content Brief]

  [3]. Crooks SL, et al. Cyclic analogues of 2-amino-4-phosphonobutanoic acid (APB) and their inhibition of hippocampal excitatory transmission and displacement of [3H]APB binding. J Med Chem. 1986 Oct;29(10):1988-95.  [Content Brief]

  [4]. Ellis EM, et al. Separate ON and OFF pathways in vertebrate vision first arose during the Cambrian. Curr Biol. 2020 Jun 8;30(11):R633-R634.  [Content Brief]