Page last updated: 2024-11-07

tyrosyl-arginyl-phenylalanyl-lysinamide

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Description

tyrosyl-arginyl-phenylalanyl-lysinamide: dermorphin analog [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID122222
CHEMBL ID60444
SCHEMBL ID8975803
MeSH IDM0174287

Synonyms (21)

Synonym
tyr-arg-phe-lys-nh2
l-lysinamide, l-tyrosyl-d-arginyl-l-phenylalanyl-
tyrosyl-arginyl-phenylalanyl-lysinamide
dalda
CHEMBL60444 ,
68425-36-5
(s)-6-amino-2-((s)-2-{(r)-2-[(s)-2-amino-3-(4-hydroxy-phenyl)-propionylamino]-5-guanidino-pentanoylamino}-3-phenyl-propionylamino)-hexanoic acid amide
6-amino-2-[1-[1-[1-amino-2-(4-hydroxyphenyl)-(1s)-ethylcarboxamido]-4-amino(imino)methylamino-(1r)-butylcarboxamido]-2-phenyl-(1s)-ethylcarboxamido]-(2s)-hexanamide
bdbm50016867
(2s)-6-amino-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-phenylpropanoyl]amino]hexanamide
118476-85-0
nsc_122222
cas_122222
bdbm85737
unii-fs8087fl3x
fs8087fl3x ,
einecs 270-350-9
SCHEMBL8975803
HY-P3870
CS-0626328
DTXSID001045851

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"We have formulated a safe and effective, omega-3 rich polyunsaturated fatty acid containing oil-in-water nanoemulsion formulation, for encapsulating and delivering chemically-modified DALDA, a potent mu-opioid peptide analogue, to the CNS."( Analgesic efficacy and safety of DALDA peptide analog delivery to the brain using oil-in-water nanoemulsion formulation.
Amiji, MM; Ferris, C; Kulkarni, P; Shah, L, 2014
)
0.4

Pharmacokinetics

ExcerptReferenceRelevance
" These favorable pharmacokinetic properties of DALDA and [Dmt1]DALDA, together with their mu-selectivity, potency, and long duration of action, make them ideal candidates as opioid analgesics."( In vivo pharmacokinetics of selective mu-opioid peptide agonists.
Desiderio, DM; Fasolo, J; Fridland, G; Lovelace, JL; Schiller, PW; Soong, Y; Szeto, HH; Wu, D, 2001
)
0.31
" We have also examined the effect of curcumin, which is known to down-regulate efflux transporters and inhibit systemic metabolism, on the pharmacokinetic properties of the peptide."( CNS delivery and pharmacokinetic evaluations of DALDA analgesic peptide analog administered in Nano-sized oil-in-water emulsion formulation.
Amiji, MM; Gattacceca, F; Shah, L, 2014
)
0.4
"Qualitative and quantitative biodistribution and pharmacokinetic studies in mice clearly demonstrated improved plasma and brain exposure of modified DALDA when administered in nanoemulsion, thereby providing an exciting opportunity towards improved efficacy and/or lowered dose of the peptide."( CNS delivery and pharmacokinetic evaluations of DALDA analgesic peptide analog administered in Nano-sized oil-in-water emulsion formulation.
Amiji, MM; Gattacceca, F; Shah, L, 2014
)
0.4

Dosage Studied

ExcerptRelevanceReference
"01-micrograms dosage was associated with hyperactivity."( Behavioral effects of the mu-opioid peptide agonists DAMGO, DALDA, and PL017 on locomotor activities.
Meyer, ME, 1993
)
0.29
" The various dosing regimens tested for modified DALDA solution and curcumin nanoemulsion directed towards a novel combination strategy for improved systemic delivery of peptides across the BBB."( CNS delivery and pharmacokinetic evaluations of DALDA analgesic peptide analog administered in Nano-sized oil-in-water emulsion formulation.
Amiji, MM; Gattacceca, F; Shah, L, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)Ki0.00010.00000.419710.0000AID1872031
Delta-type opioid receptorHomo sapiens (human)Ki19.20000.00000.59789.9300AID1872032
Kappa-type opioid receptorHomo sapiens (human)Ki4.23000.00000.362410.0000AID1872033
Mu-type opioid receptorMus musculus (house mouse)IC50 (µMol)0.78100.00081.699210.0000AID1872058
Mu-type opioid receptorCavia porcellus (domestic guinea pig)IC50 (µMol)0.25400.00020.660310.0000AID1872057
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (52)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMu-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
sensory perceptionMu-type opioid receptorHomo sapiens (human)
negative regulation of cell population proliferationMu-type opioid receptorHomo sapiens (human)
sensory perception of painMu-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
behavioral response to ethanolMu-type opioid receptorHomo sapiens (human)
positive regulation of neurogenesisMu-type opioid receptorHomo sapiens (human)
negative regulation of Wnt protein secretionMu-type opioid receptorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeMu-type opioid receptorHomo sapiens (human)
calcium ion transmembrane transportMu-type opioid receptorHomo sapiens (human)
cellular response to morphineMu-type opioid receptorHomo sapiens (human)
regulation of cellular response to stressMu-type opioid receptorHomo sapiens (human)
regulation of NMDA receptor activityMu-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayMu-type opioid receptorHomo sapiens (human)
immune responseDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerDelta-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
adult locomotory behaviorDelta-type opioid receptorHomo sapiens (human)
negative regulation of gene expressionDelta-type opioid receptorHomo sapiens (human)
negative regulation of protein-containing complex assemblyDelta-type opioid receptorHomo sapiens (human)
positive regulation of CREB transcription factor activityDelta-type opioid receptorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationDelta-type opioid receptorHomo sapiens (human)
response to nicotineDelta-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
eating behaviorDelta-type opioid receptorHomo sapiens (human)
regulation of mitochondrial membrane potentialDelta-type opioid receptorHomo sapiens (human)
regulation of calcium ion transportDelta-type opioid receptorHomo sapiens (human)
cellular response to growth factor stimulusDelta-type opioid receptorHomo sapiens (human)
cellular response to hypoxiaDelta-type opioid receptorHomo sapiens (human)
cellular response to toxic substanceDelta-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayDelta-type opioid receptorHomo sapiens (human)
immune responseKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
chemical synaptic transmissionKappa-type opioid receptorHomo sapiens (human)
sensory perceptionKappa-type opioid receptorHomo sapiens (human)
locomotory behaviorKappa-type opioid receptorHomo sapiens (human)
sensory perception of painKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
response to insulinKappa-type opioid receptorHomo sapiens (human)
positive regulation of dopamine secretionKappa-type opioid receptorHomo sapiens (human)
negative regulation of luteinizing hormone secretionKappa-type opioid receptorHomo sapiens (human)
response to nicotineKappa-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
maternal behaviorKappa-type opioid receptorHomo sapiens (human)
eating behaviorKappa-type opioid receptorHomo sapiens (human)
response to estrogenKappa-type opioid receptorHomo sapiens (human)
estrous cycleKappa-type opioid receptorHomo sapiens (human)
response to ethanolKappa-type opioid receptorHomo sapiens (human)
regulation of saliva secretionKappa-type opioid receptorHomo sapiens (human)
behavioral response to cocaineKappa-type opioid receptorHomo sapiens (human)
sensory perception of temperature stimulusKappa-type opioid receptorHomo sapiens (human)
defense response to virusKappa-type opioid receptorHomo sapiens (human)
cellular response to lipopolysaccharideKappa-type opioid receptorHomo sapiens (human)
cellular response to glucose stimulusKappa-type opioid receptorHomo sapiens (human)
positive regulation of p38MAPK cascadeKappa-type opioid receptorHomo sapiens (human)
positive regulation of potassium ion transmembrane transportKappa-type opioid receptorHomo sapiens (human)
response to acrylamideKappa-type opioid receptorHomo sapiens (human)
positive regulation of eating behaviorKappa-type opioid receptorHomo sapiens (human)
conditioned place preferenceKappa-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
G-protein alpha-subunit bindingMu-type opioid receptorHomo sapiens (human)
G protein-coupled receptor activityMu-type opioid receptorHomo sapiens (human)
beta-endorphin receptor activityMu-type opioid receptorHomo sapiens (human)
voltage-gated calcium channel activityMu-type opioid receptorHomo sapiens (human)
protein bindingMu-type opioid receptorHomo sapiens (human)
morphine receptor activityMu-type opioid receptorHomo sapiens (human)
G-protein beta-subunit bindingMu-type opioid receptorHomo sapiens (human)
neuropeptide bindingMu-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor activityDelta-type opioid receptorHomo sapiens (human)
protein bindingDelta-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingDelta-type opioid receptorHomo sapiens (human)
G protein-coupled enkephalin receptor activityDelta-type opioid receptorHomo sapiens (human)
neuropeptide bindingDelta-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor activityKappa-type opioid receptorHomo sapiens (human)
protein bindingKappa-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingKappa-type opioid receptorHomo sapiens (human)
dynorphin receptor activityKappa-type opioid receptorHomo sapiens (human)
neuropeptide bindingKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (23)

Processvia Protein(s)Taxonomy
endosomeMu-type opioid receptorHomo sapiens (human)
endoplasmic reticulumMu-type opioid receptorHomo sapiens (human)
Golgi apparatusMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
axonMu-type opioid receptorHomo sapiens (human)
dendriteMu-type opioid receptorHomo sapiens (human)
perikaryonMu-type opioid receptorHomo sapiens (human)
synapseMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
neuron projectionMu-type opioid receptorHomo sapiens (human)
plasma membraneDelta-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneDelta-type opioid receptorHomo sapiens (human)
dendrite membraneDelta-type opioid receptorHomo sapiens (human)
presynaptic membraneDelta-type opioid receptorHomo sapiens (human)
axon terminusDelta-type opioid receptorHomo sapiens (human)
spine apparatusDelta-type opioid receptorHomo sapiens (human)
postsynaptic density membraneDelta-type opioid receptorHomo sapiens (human)
neuronal dense core vesicleDelta-type opioid receptorHomo sapiens (human)
plasma membraneDelta-type opioid receptorHomo sapiens (human)
neuron projectionDelta-type opioid receptorHomo sapiens (human)
nucleoplasmKappa-type opioid receptorHomo sapiens (human)
mitochondrionKappa-type opioid receptorHomo sapiens (human)
cytosolKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
membraneKappa-type opioid receptorHomo sapiens (human)
sarcoplasmic reticulumKappa-type opioid receptorHomo sapiens (human)
T-tubuleKappa-type opioid receptorHomo sapiens (human)
dendriteKappa-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneKappa-type opioid receptorHomo sapiens (human)
presynaptic membraneKappa-type opioid receptorHomo sapiens (human)
perikaryonKappa-type opioid receptorHomo sapiens (human)
axon terminusKappa-type opioid receptorHomo sapiens (human)
postsynaptic membraneKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
neuron projectionKappa-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorMus musculus (house mouse)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID1311262Displacement of [3H]DSLET from delta-type opioid receptor in rat brain membranes incubated for 2 hrs2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
[Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1.
AID138522Ke value for naloxone as antagonist (compound) was measured by using Mouse vas deferens (MVD) assay.1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID77509The relative potency of compound was measured by comparing the potency of compound to the [Leu]enkephalin in Guinea pig ileum(GPI) assay.1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID1872031Binding affinity to MOP (unknown origin)2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.
AID1872092Antinociceptive activity in rat administered IT2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.
AID1137677Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes2014ACS medicinal chemistry letters, Apr-10, Volume: 5, Issue:4
In Vitro Membrane Permeation Studies and in Vivo Antinociception of Glycosylated Dmt
AID78873Concentration of compound to inhibit 50% (IC50) electrically evoked contractions was tested in Guinea pig ileum(GPI) assay.1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID1311260Agonist activity at mu opioid receptor in guinea pig ileum assessed as inhibition of electrically-stimulated muscle contraction2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
[Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1.
AID1311269Agonist activity at delta opioid receptor in albino mouse vas deferens assessed as inhibition of electrically-stimulated muscle contraction2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
[Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1.
AID1311265Selectivity ratio of Ki for kappa-type opioid receptor in guniea pig brain membranes to Ki for mu-type opioid receptor in rat brain membranes2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
[Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1.
AID1872094Antinociceptive activity in thermal hyperalgesia mouse model administered sc2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.
AID149312Ratio of binding affinity of opioid receptor mu and opioid receptor delta1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID1872032Binding affinity to DOP (unknown origin)2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.
AID1137680Agonist activity at mu opioid receptor in guinea pig ileum2014ACS medicinal chemistry letters, Apr-10, Volume: 5, Issue:4
In Vitro Membrane Permeation Studies and in Vivo Antinociception of Glycosylated Dmt
AID138345Concentration of compound to inhibit 50% (IC50) electrically evoked contractions was tested in Mouse vas deferens (MVD) assay.1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID149292Binding affinity against opioid receptor mu by displacement of radioligand [3H]DAGO in rat brain membrane1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID1872058Antagonist activity at mouse vas deferns MOP2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.
AID79202Ke value for naloxon as antagonist (compound) was measured by using Guinea pig ileum assay.1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID1311264Selectivity ratio of Ki for delta-type opioid receptor in rat brain membranes to Ki for mu-type opioid receptor in rat brain membranes2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
[Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1.
AID149342Binding affinity against opioid receptor delta by displacement of radioligand [3H]DSLET in rat brain membrane1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID118325The relative potency of compound was measured by comparing the potency of compound to the [Leu]enkephalin in Mouse vas deferens (MVD) assay.1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID1872057Antagonist activity at guinea pig ileum MOP2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.
AID1311263Displacement of [3H]U69,593 from kappa-type opioid receptor in guniea pig brain membranes incubated for 2 hrs2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
[Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1.
AID1872093Antinociceptive activity in mechanical allodynia mouse model administered sc2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.
AID1872033Binding affinity to KOP (unknown origin)2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.
AID1311261Displacement of [3H]DAMGO from mu-type opioid receptor in rat brain membranes incubated for 2 hrs2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
[Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1.
AID149318The relative potency of compound was measured against Opioid receptor mu to that of [Leu]enkephalin in [3H]DAGO binding assay.1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID149359The relative potency of compound was measured against opioid receptor delta to that of [Leu]enkephalin in [3H]DSLET binding assay.1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
AID229266Ratio of IC50 in Mouse vas deferens and Guinea pig ileum assay1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Dermorphin analogues carrying an increased positive net charge in their "message" domain display extremely high mu opioid receptor selectivity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (66)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (1.52)18.7374
1990's23 (34.85)18.2507
2000's25 (37.88)29.6817
2010's12 (18.18)24.3611
2020's5 (7.58)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.83

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.83 (24.57)
Research Supply Index4.32 (2.92)
Research Growth Index6.15 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.35%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other73 (98.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]