DAMGO TFA is a μ-opioid receptor (μ-OPR ) selective agonist with a Kd of 3.46 nM for native μ-OPR. An enkephalin analog that selectively binds to the MU OPIOID RECEPTOR. It is used as a model for drug permeability experiments.
CAT No: R1969
CAS No:950492-85-0
Synonyms/Alias:DAMGO;DAGO;78123-71-4;glyol;Dagol;DAMGE;2-Ala-4-mephe-5-gly-enkephalin;Tyr-ala-gly-(nme)phe-gly-ol;RX 783006;(D-Ala(2)-mephe(4)-gly-ol(5))enkephalin;(2S)-2-amino-N-[(2R)-1-[[2-[[(2S)-1-(2-hydroxyethylamino)-1-oxo-3-phenylpropan-2-yl]-methylamino]-2-oxoethyl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide;Enkephalin, ala(2)-mephe(4)-gly(5)-;CHEBI:272;CHEMBL38874;Tyr-D-Ala-Gly-MePhe-Gly-ol;Enkephalin, alanyl(2)-methylphenylalanyl(4)-glycine(5)-;950492-85-0;[3H]DAMGO;Tyr-D-Ala-Gly-MePhe-Gly(ol);Tyr-D-Ala-Gly-NMe-Phe-Gly-ol;Tyr-D-Ala-Gly-(NMe)Phe-Gly-ol;Tyr-D-Ala-Gly-N(Me)Phe-Gly-ol;Tyr-D-Ala-Gly-N-Me-Phe-Gly-ol;Ala(2)-mephe(4)-gly-ol(5) enkephalin;Tyr-D-Ala-Gly-N-Methyl-Phe-Gly-ol;D-Ala2-MePhe4-Met(0)5-enkephalin-ol;Enkephalin, Ala(2)-MePhe(4)-Gly-ol(5)-;C26H35N5O6;H-Tyr-D-Ala-Gly-N-Me-Phe-Glycinol;[D-Ala2, NMe-Phe4, Gly-ol5]-enkephalin;2YM5VT3MNR;RX783006;Dagol;L-Phenylalaninamide, L-tyrosyl-D-alanylglycyl-N-(2-hydroxyethyl)-Nalpha-methyl-;Tyr-DAla-Gly-MePhe-Gly-ol;SCHEMBL725750;GTPL1647;Tyr-D-Ala-Gly-NMePhe-Gly-ol;BDBM21015;H-Tyr-D-Ala-Gly-MePhe-Gly-ol;Tyr-D-Ala2-Gly-NMePhe-Gly-ol;DTXSID30228775;HPZJMUBDEAMBFI-WTNAPCKOSA-N;HY-P0210;Tyr-D-Ala-Gly-N(CH3)Phe-Gly-ol;H-Tyr-D-Ala-Gly-N(Me)Phe-Gly-ol;HB2409;AKOS024456435;NCGC00167303-01;(2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]-methylamino]-N-(2-hydroxyethyl)-3-phenylpropanamide;AS-83278;BD173150;BD174973;DA-72545;CS-0021316;G12226;Q5204254;[tyrosyl-3,5-3H(N)]-D-Ala2-Mephe4-glyol5-enkephalin;3: PN: WO2009046859 PAGE: 98 CLAIMED PROTEIN;158: PN: US20030176421 PAGE: 54-55 CLAIMED PROTEIN;L-TYROSYL-D-ALANYLGLYCYL-N-(2-HYDROXYETHYL)-N.ALPHA.-METHYL-L-PHENYLALANINAMIDE;L-Tyrosyl-D-alanylglycyl-N-(2-hydroxyethyl)-Nalpha-methyl-L-phenylalaninamide;(2S)-2-{2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-N-methylacetamido}-N-(2-hydroxyethyl)-3-phenylpropanamide;(2S)-2-amino-N-[(1R)-2-[[2-[[(1S)-1-benzyl-2-(2-hydroxyethylamino)-2-oxo-ethyl]-methyl-amino]-2-oxo-ethyl]amino]-1-methyl-2-oxo-ethyl]-3-(4-hydroxyphenyl)propanamide;(S)-2-amino-N-((R)-1-(2-(((S)-1-(2-hydroxyethylamino)-1-oxo-3-phenylpropan-2-yl)(methyl)amino)-2-oxoethylamino)-1-oxopropan-2-yl)-3-(4-hydroxyphenyl)propanamide;Benzenepropanimidic?acid, .alpha.-amino-4-hydroxy-N-[(1R,2Z)-2-hydroxy-2-[[2-[[(1S,2Z)-2-hydroxy-2-[(2-hydroxyethyl)imino]-1-(phenylmethyl)ethyl]methylamino]-2-oxoethyl]imino]-1-methylethyl]-, (.alpha.S)-;
Chemical Name:(2S)-2-amino-N-[(2R)-1-[[2-[[(2S)-1-(2-hydroxyethylamino)-1-oxo-3-phenylpropan-2-yl]-methylamino]-2-oxoethyl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide
DAMGO TFA, also known as [D-Ala2, N-MePhe4, Gly-ol]-enkephalin trifluoroacetate salt, is a synthetic peptide agonist that exhibits high selectivity and affinity for the μ-opioid receptor (MOR). Structurally derived from the endogenous opioid peptide enkephalin, DAMGO TFA is widely employed in neuropharmacological and biochemical research to elucidate the functional mechanisms of opioid receptor signaling. Its chemical modifications confer enhanced metabolic stability and receptor specificity, making it a valuable investigative tool for dissecting the role of μ-opioid pathways in diverse physiological and cellular contexts.
Opioid receptor pharmacology: DAMGO TFA is extensively utilized in studies of opioid receptor pharmacology, particularly for characterizing the binding properties, activation profiles, and downstream signaling events associated with the μ-opioid receptor. Researchers employ the compound in radioligand binding assays, functional receptor activation studies, and G-protein coupling investigations to delineate the molecular determinants of opioid ligand-receptor interactions. Its high selectivity enables precise dissection of μ-opioid-specific effects, minimizing confounding influences from other opioid receptor subtypes.
Signal transduction analysis: The peptide is frequently used to probe intracellular signaling cascades initiated by μ-opioid receptor engagement. By applying DAMGO TFA to neuronal and non-neuronal cell models, investigators can monitor changes in second messenger systems such as cyclic AMP, calcium flux, and kinase activation. These studies provide critical insights into the modulation of synaptic transmission, neuronal excitability, and gene expression patterns governed by opioid receptor signaling, supporting both basic neuroscience and pharmacological research.
Electrophysiological research: DAMGO TFA serves as a standard tool in electrophysiological experiments aimed at understanding the impact of μ-opioid receptor activation on neuronal activity. Patch-clamp recordings, field potential measurements, and synaptic plasticity assays often incorporate this peptide to elucidate opioid-mediated modulation of ion channels, synaptic strength, and network excitability. The use of DAMGO TFA in such contexts facilitates the mapping of opioid effects at both cellular and circuit levels within the central and peripheral nervous systems.
Peptide-receptor interaction studies: Owing to its defined sequence and receptor selectivity, DAMGO TFA is employed in structural and biophysical studies investigating peptide-receptor interactions. Techniques such as X-ray crystallography, NMR spectroscopy, and molecular docking simulations utilize this ligand to reveal the conformational dynamics and binding determinants of the μ-opioid receptor. These insights contribute to rational drug design efforts targeting opioid receptors with improved efficacy and reduced side effect profiles.
Opioid system functional assays: DAMGO TFA is also applied in functional assays designed to evaluate the physiological consequences of μ-opioid receptor activation in various tissue and organ systems. Isolated tissue preparations, organotypic slice cultures, and ex vivo models benefit from the use of this peptide to assess opioid-induced modulation of neurotransmitter release, muscle contractility, and other relevant biological endpoints. Such studies advance the understanding of endogenous and exogenous opioid regulation across a range of experimental systems.
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