Phe-Gly-OH
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Phe-Gly-OH

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Category
Others
Catalog number
BAT-006529
CAS number
721-90-4
Molecular Formula
C11H14N2O3
Molecular Weight
222.24
Phe-Gly-OH
IUPAC Name
2-[[(2S)-2-amino-3-phenylpropanoyl]amino]acetic acid
Synonyms
L-Phenylalanylglycine; (S)-2-(2-amino-3-phenylpropanamido)acetic acid; ((S)-2-Amino-3-phenyl-propionylamino)-acetic acid; Phe Gly OH
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.259g/cm3
Melting Point
260 °C(dec.)
Boiling Point
512.5°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H14N2O3/c12-9(11(16)13-7-10(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1
InChI Key
GLUBLISJVJFHQS-VIFPVBQESA-N
Canonical SMILES
C1=CC=C(C=C1)CC(C(=O)NCC(=O)O)N
1. Opioid receptor labeling with the chloromethyl ketone derivative of [3H]Tyr-D-Ala-Gly-(Me)Phe-Gly-ol (DAMGO) II: Covalent labeling of mu opioid binding site by 3H-Tyr-D-Ala-Gly-(Me)Phe chloromethyl ketone
H A Oktem, J Moitra, S Benyhe, G Toth, A Lajtha, A Borsodi Life Sci. 1991;48(18):1763-8. doi: 10.1016/0024-3205(91)90214-v.
Opioid receptors of rat brain membranes were prelabeled with 3H-Tyr-D-Ala2-(Phe4)-Gly-CH2Cl, a chloromethyl ketone derivative of enkephalin, and solubilized in 1% digitonin. Hydrodynamic parameters of the receptor detergent complex derived from gel filtration and sucrose density gradient ultracentrifugation were found to be 51 A and 8.7 S, respectively, and the size was estimated to be about 200 kDa. Sodium dodecyl sulfate gel electrophoresis followed by fluorography revealed specific alkylation of a major protein at 58 kDa.
2. CB1 receptor-independent actions of SR141716 on G-protein signaling: coapplication with the mu-opioid agonist Tyr-D-Ala-Gly-(NMe)Phe-Gly-ol unmasks novel, pertussis toxin-insensitive opioid signaling in mu-opioid receptor-Chinese hamster ovary cells
Resat Cinar, Mária Szücs J Pharmacol Exp Ther. 2009 Aug;330(2):567-74. doi: 10.1124/jpet.109.152710. Epub 2009 May 15.
The CB(1) cannabinoid receptor antagonist N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride (SR141716) has been shown by many investigators to inhibit basal G-protein activity, i.e., to display inverse agonism at high concentrations. However, it is not clear whether this effect is cannabinoid CB(1) receptor-mediated. Using the ligand-stimulated [(35)S]guanosine 5'-3-O-(thio)triphosphate (GTPgammaS) assay, we have found that 10 microM SR141716 slightly but significantly decreases the basal [(35)S]GTPgammaS binding in membranes of the wild-type and CB(1) receptor knockout mouse cortex, parental Chinese hamster ovary (CHO) cells, and CHO cells stably transfected with micro-opioid receptors, MOR-CHO. Accordingly, we conclude that the inverse agonism of SR141716 is CB(1) receptor-independent. Although the specific MOR agonist Tyr-D-Ala-Gly-(NMe)Phe-Gly-ol (DAMGO) saturably and concentration-dependently stimulated [(35)S]GTPgammaS binding, SR141716 (10 microM) inhibited the basal by 25% and competitively inhibited DAMGO stimulation in the mouse cortex. In MOR-CHO membranes, DAMGO caused a 501 +/- 29% stimulation of the basal activity, which was inhibited to 456 +/- 22% by 10 microM SR141716. The inverse agonism of SR141716 was abolished, and DAMGO alone displayed weak, naloxone-insensitive stimulation, whereas the combination of DAMGO and SR141716 (10 microM each) resulted in a 169 +/- 22% stimulation of the basal activity (that was completely inhibited by the prototypic opioid antagonist naloxone) because of pertussis toxin (PTX) treatment to uncouple MORs from G(i)/G(o) proteins. SR141716 proved to bind directly to MORs with low affinity (IC(50) = 5.7 microM). These results suggest the emergence of novel, PTX-insensitive G-protein signaling that is blocked by naloxone when MORs are activated by the combination of DAMGO and SR141716.
3. Opioid receptor labeling with the chloromethyl ketone derivative of (3)H-Tyr-D-Ala-Gly-(Me)Phe-Gly-ol (DAMGO) I: Binding properties of 3H-Tyr-D-Ala-Gly-(Me)Phe chloromethyl
H A Oktem, E Varga, J Hepp, K Medzihradzky, A Lajtha, A Borsodi Life Sci. 1991;48(18):1757-62. doi: 10.1016/0024-3205(91)90213-u.
We prepared a tritiated chloromethyl ketone derivative of Tyr-D-Ala-Gly(Me)Phe-Gly-ol 3H-D-Ala-Gly-(Me)Phe-chloromethyl ketone, and studied its binding characteristics in rat brain membranes. A significant portion (about 70%) of the binding becomes wash-resistant after 60 min of incubation. The binding of the ligand is highly stereospecific and mu-opioid receptor selective. These characteristics of the ligand, together with its high specific radioactivity (57 Ci/mmol) makes it a good candidate for biochemical characterization and covalent labeling of mu opioid receptors.
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