Home Other Building Blocks DERMORPHIN ACETATE

DERMORPHIN ACETATE

CAS No.:
77614-16-5
Catalog Number:
AG00G85K
Molecular Formula:
C40H50N8O10
Molecular Weight:
802.8726
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$157
- +
5mg
99%
1 week
United States
$240
- +
10mg
99%
1 week
United States
$357
- +
25mg
99%
1 week
United States
$707
- +
Product Description
Catalog Number:
AG00G85K
Chemical Name:
DERMORPHIN ACETATE
CAS Number:
77614-16-5
Molecular Formula:
C40H50N8O10
Molecular Weight:
802.8726
MDL Number:
MFCD00076694
IUPAC Name:
(2S)-N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]-1-[(2S)-2-[[2-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxamide
InChI:
InChI=1S/C40H50N8O10/c1-23(44-37(55)29(41)18-25-9-13-27(50)14-10-25)36(54)46-30(19-24-6-3-2-4-7-24)38(56)43-21-34(52)45-31(20-26-11-15-28(51)16-12-26)40(58)48-17-5-8-33(48)39(57)47-32(22-49)35(42)53/h2-4,6-7,9-16,23,29-33,49-51H,5,8,17-22,41H2,1H3,(H2,42,53)(H,43,56)(H,44,55)(H,45,52)(H,46,54)(H,47,57)/t23-,29+,30+,31+,32+,33+/m1/s1
InChI Key:
FHZPGIUBXYVUOY-VWGYHWLBSA-N
SMILES:
OCC(C(=O)N)NC(=O)C1CCCN1C(=O)C(Cc1ccc(cc1)O)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(Cc1ccc(cc1)O)N)C)Cc1ccccc1
UNII:
2SEC01B703
Properties
Complexity:
1410  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
0
Exact Mass:
802.365g/mol
Formal Charge:
0
Heavy Atom Count:
58  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
10  
Isotope Atom Count:
0
Molecular Weight:
802.886g/mol
Monoisotopic Mass:
802.365g/mol
Rotatable Bond Count:
19  
Topological Polar Surface Area:
296A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0
Literature
Title Journal
Variation of the net charge, lipophilicity, and side chain flexibility in Dmt(1)-DALDA: Effect on Opioid Activity and Biodistribution. Journal of medicinal chemistry 20121126
Magic angle spinning NMR study of interaction of N-terminal sequence of dermorphin (Tyr-d-Ala-Phe-Gly) with phospholipids. Biochimica et biophysica acta 20121101
A stereochemical switch in the aDrs model system, a candidate for a functional amyloid. Archives of biochemistry and biophysics 20120615
Substrate specificity of a peptidyl-aminoacyl-L/D-isomerase from frog skin. Amino acids 20120501
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Asymmetric synthesis and conformational analysis by NMR spectroscopy and MD of Aba- and α-MeAba-containing dermorphin analogues. ChemMedChem 20111104
Synthesis, biological evaluation, and automated docking of constrained analogues of the opioid peptide H-Dmt-D-Ala-Phe-Gly-NH₂ using the 4- or 5-methyl substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one scaffold. Journal of medicinal chemistry 20111013
Tight binding of transition-state analogues to a peptidyl-aminoacyl-L/D-isomerase from frog skin. Chembiochem : a European journal of chemical biology 20110905
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Desirability function combining metabolic stability and functionality of peptides. Journal of peptide science : an official publication of the European Peptide Society 20110501
Emerging knowledge of regulatory roles of D-amino acids in bacteria. Cellular and molecular life sciences : CMLS 20110301
Dermorphin tetrapeptide analogs as potent and long-lasting analgesics with pharmacological profiles distinct from morphine. Peptides 20110201
Involvement of mouse μ-opioid receptor splice variants in the spinal antinociception induced by the dermorphin tetrapeptide analog amidino-TAPA. European journal of pharmacology 20110125
Ligand-directed functional selectivity at the mu opioid receptor revealed by label-free integrative pharmacology on-target. PloS one 20110101
Analytical characterization and comparison of the blood-brain barrier permeability of eight opioid peptides. Peptides 20100701
Opioid receptor internalization contributes to dermorphin-mediated antinociception. Neuroscience 20100630
AntiBP2: improved version of antibacterial peptide prediction. BMC bioinformatics 20100101
Discovery of dermorphin-based affinity labels with subnanomolar affinity for mu opioid receptors. Journal of medicinal chemistry 20091210
Evaluation of side effects through selective ablation of the mu opioid receptor expressing descending nociceptive facilitatory neurons in the rostral ventromedial medulla with dermorphin-saporin. Neurotoxicology 20091101
Synthesis and receptor binding of opioid peptide analogues containing beta3-homo-amino acids. Journal of peptide science : an official publication of the European Peptide Society 20091101
Partial ablation of mu-opioid receptor rich striosomes produces deficits on a motor-skill learning task. Neuroscience 20090929
Purification and functional reconstitution of monomeric mu-opioid receptors: allosteric modulation of agonist binding by Gi2. The Journal of biological chemistry 20090925
Protective effect of dermorphin analogue sedatin on indomethacin-induced injury to the gastric mucosa. Bulletin of experimental biology and medicine 20090701
D-amino acid detection in peptides by MALDI-TOF-TOF. Analytical chemistry 20090601
[Significance of opioid receptors in regulation of cardiac tolerance in pathogenic impact of long-term ischemia-reperfusion in vivo]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20090601
Neuropathic pain is maintained by brainstem neurons co-expressing opioid and cholecystokinin receptors. Brain : a journal of neurology 20090301
Conformation-activity relationships of cyclo-constrained mu/delta opioid agonists derived from the N-terminal tetrapeptide segment of dermorphin/deltorphin. Advances in experimental medicine and biology 20090101
Conformation-activity relationships of cyclo-constrained micro/delta opioid agonists derived from the N-terminal tetrapeptide segment of dermorphin/deltorphin. Journal of peptide science : an official publication of the European Peptide Society 20080801
Amygdala intercalated neurons are required for expression of fear extinction. Nature 20080731
Blood-brain barrier penetration by two dermorphin tetrapeptide analogues: role of lipophilicity vs structural flexibility. Journal of medicinal chemistry 20080424
The use of tritium-labeled dermorphin for studying the interactions of C-terminal dermorphin fragment Tyr-Pro-Ser-NH2 and its stereoisomer Tyr-D-Pro-Ser-NH2 with opioid receptors. Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections 20080101
Multiple ligands in opioid research. Protein and peptide letters 20080101
Methylnaltrexone in the treatment of opioid-induced constipation. Clinical and experimental gastroenterology 20080101
Effect of synthetic dermorphin analogues on tissue homeostasis in the myocardium of newborn albino rats. Bulletin of experimental biology and medicine 20071001
Effect of sedatin (synthetic dermorphin analog) on the development of Acipenser schrenckii young fish. Bulletin of experimental biology and medicine 20071001
Mechanisms for the effect of arginine-containing dermorphin analogue on proliferative processes in the gastric mucosa of albino rats. Bulletin of experimental biology and medicine 20070901
Ureido group containing cyclic dermorphin(1-7) analogues: synthesis, biology and conformation. Journal of peptide science : an official publication of the European Peptide Society 20070801
Receptor binding properties and antinociceptive effects of chimeric peptides consisting of a micro-opioid receptor agonist and an ORL1 receptor antagonist. Biological & pharmaceutical bulletin 20070701
Supranodose vagotomy eliminates respiratory depression evoked by dermorphin in anaesthetized rats. European journal of pharmacology 20070601
Involvement of endogenous opioid peptides in the antinociception induced by the novel dermorphin tetrapeptide analog amidino-TAPA. European journal of pharmacology 20070410
Novel glycosylated [Lys(7)]-dermorphin analogues: synthesis, biological activity and conformational investigations. Journal of peptide science : an official publication of the European Peptide Society 20070301
[Comparative analysis of analgesic activities of dermorphin, [DPro6]-dermorphin, and their C-terminal tripeptides]. Izvestiia Akademii nauk. Seriia biologicheskaia 20070101
[Synthesis, pharmacokinetics, and metabolism of the C-terminal tripeptide of dermorphin and its diastereomer]. Bioorganicheskaia khimiia 20070101
Dependence of the analgesic activities of dermorphin, metenkephalin, and dynorphin A on the ambient temperature. Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections 20070101
[The relationship between the structure of dermorphines and their thermoregulatory activity]. Izvestiia Akademii nauk. Seriia biologicheskaia 20070101
Effects of the intravenous administration of [Lys7]dermorphin on local cerebral glucose utilization in the rat. European journal of pharmacology 20060821
Descending facilitation from the rostral ventromedial medulla maintains nerve injury-induced central sensitization. Neuroscience 20060721
Involvement of spinal mu1-opioid receptors on the Tyr-d-Arg-Phe-sarcosine-induced antinociception. European journal of pharmacology 20060701
Targeted drug delivery crossing cytoplasmic membranes of intended cells via ligand-grafted sterically stabilized liposomes. Journal of controlled release : official journal of the Controlled Release Society 20060221
Cyclic dermorphin tetrapeptide analogues obtained via ring-closing metathesis. Acta biochimica Polonica 20060101
Conversion of the potent delta-opioid agonist H-Dmt-Tic-NH-CH(2)-bid into delta-opioid antagonists by N(1)-benzimidazole alkylation(1). Journal of medicinal chemistry 20051229
Synthesis and biological evaluation of constrained analogues of the opioid peptide H-Tyr-D-Ala-Phe-Gly-NH2 using the 4-amino-2-benzazepin-3-one scaffold. The journal of peptide research : official journal of the American Peptide Society 20051101
Inhibitory control of the acute mu-withdrawal response by indirectly activated adenosine A1 and kappa-opioid systems in the Guinea-pig ileum; reversal by cholecystokinin. Neurotoxicology 20051001
Distinguishing and quantifying peptides and proteins containing D-amino acids by tandem mass spectrometry. Analytical chemistry 20050715
Cyclic enkephalin and dermorphin analogues containing a carbonyl bridge. Journal of peptide science : an official publication of the European Peptide Society 20050601
Abbreviated nomenclature for cyclic and branched homo- and hetero-detic peptides. The journal of peptide research : official journal of the American Peptide Society 20050601
6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides. Bioorganic & medicinal chemistry letters 20050516
New tris-alkoxycarbonyl arginine derivatives for peptide synthesis. Journal of peptide science : an official publication of the European Peptide Society 20050101
Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in organic solvents. The journal of peptide research : official journal of the American Peptide Society 20050101
[Study of thermoregulatory activity of a fragment of natural dermorphin precursor Arg-dermorphin and its analogs]. Izvestiia Akademii nauk. Seriia biologicheskaia 20050101
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[Thermoregulatory activity of dermorphin fragments]. Izvestiia Akademii nauk. Seriia biologicheskaia 20040101
Human brain cathepsin H as a neuropeptide and bradykinin metabolizing enzyme. Peptides 20031201
Synthesis, conformation and biological activity of dermorphin and deltorphin I analogues containing N-alkylglycine in place of residues in position 1, 3, 5 and 6. Journal of peptide science : an official publication of the European Peptide Society 20031001
Potent side-chain to side-chain cyclized dermorphin analogues containing a carbonyl bridge. Journal of peptide science : an official publication of the European Peptide Society 20031001
Enhanced evoked excitatory transmitter release in experimental neuropathy requires descending facilitation. The Journal of neuroscience : the official journal of the Society for Neuroscience 20030910
Opioid peptides: synthesis and biological properties of [(N gamma-glucosyl,N gamma-methoxy)-alpha, gamma-diamino-(S)-butanoyl]4-deltorphin-1-neoglycopeptide and related analogues. Organic & biomolecular chemistry 20030907
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The delta-selective opioid peptide dermenkephalin and the mu-selective hybrid peptide dermenkephalin-[1-4]-dermophin-[5-7] display strikingly different conformations despite identical tetrapeptide N-termini. A quantitative 2-D NMR and molecular modeling analysis. Journal of biomolecular structure & dynamics 19991201
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Opioid activity of dermenkephalin analogues in the guinea-pig myenteric plexus and the hamster vas deferens. British journal of pharmacology 19911001
Identification of a D-alanine-containing polypeptide precursor for the peptide opioid, dermorphin. The Journal of biological chemistry 19910405
Different profile of electrocortical power spectrum changes after micro-infusion into the locus coeruleus of selective agonists at various opioid receptor subtypes in rats. British journal of pharmacology 19901101
Characterisation and visualisation of [3H]dermorphin binding to mu opioid receptors in the rat brain. Combined high selectivity and affinity in a natural peptide agonist for the morphine (mu) receptor. European journal of biochemistry 19900520
Molecular determinants of receptor affinity and selectivity of the natural delta-opioid agonist, dermenkephalin. The Journal of biological chemistry 19891015
Differential contribution of C-terminal regions of dermorphin and dermenkephalin to opioid-sites selection and binding potency. Biochemical and biophysical research communications 19890915
Dermenkephalin (Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2): a potent and fully specific agonist for the delta opioid receptor. Molecular pharmacology 19890601
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Structure-activity relationships of dermorphin tetrapeptides carrying a ketomethylene linkage. Arzneimittel-Forschung 19850101
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Stimulatory effect of dermorphin, a new synthetic potent opiate-like peptide, on human growth hormone secretion. Neuroendocrinology 19831001
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Synthesis of dermorphins, a new class of opiate-like peptides. International journal of peptide and protein research 19810201
Properties