Page last updated: 2024-12-07
tyrosyl-arginyl-phenylalanyl-lysinamide
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
tyrosyl-arginyl-phenylalanyl-lysinamide: dermorphin analog [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 122222 |
| CHEMBL ID | 60444 |
| SCHEMBL ID | 8975803 |
| MeSH ID | M0174287 |
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
| Excerpt | Reference | Relevance |
|---|---|---|
| "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
| Excerpt | Reference | Relevance |
|---|---|---|
| " 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
| Excerpt | Relevance | Reference |
|---|---|---|
| "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
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Mu-type opioid receptor | Homo sapiens (human) | Ki | 0.0001 | 0.0000 | 0.4197 | 10.0000 | AID1872031 |
| Delta-type opioid receptor | Homo sapiens (human) | Ki | 19.2000 | 0.0000 | 0.5978 | 9.9300 | AID1872032 |
| Kappa-type opioid receptor | Homo sapiens (human) | Ki | 4.2300 | 0.0000 | 0.3624 | 10.0000 | AID1872033 |
| Mu-type opioid receptor | Mus musculus (house mouse) | IC50 (µMol) | 0.7810 | 0.0008 | 1.6992 | 10.0000 | AID1872058 |
| Mu-type opioid receptor | Cavia porcellus (domestic guinea pig) | IC50 (µMol) | 0.2540 | 0.0002 | 0.6603 | 10.0000 | AID1872057 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (52)
Molecular Functions (12)
Ceullar Components (23)
Bioassays (29)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1311262 | Displacement of [3H]DSLET from delta-type opioid receptor in rat brain membranes incubated for 2 hrs | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | [Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1. |
| AID138522 | Ke value for naloxone as antagonist (compound) was measured by using Mouse vas deferens (MVD) assay. | 1989 | Journal 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. |
| AID77509 | The relative potency of compound was measured by comparing the potency of compound to the [Leu]enkephalin in Guinea pig ileum(GPI) assay. | 1989 | Journal 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. |
| AID1872031 | Binding affinity to MOP (unknown origin) | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources. |
| AID1872092 | Antinociceptive activity in rat administered IT | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources. |
| AID1137677 | Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes | 2014 | ACS medicinal chemistry letters, Apr-10, Volume: 5, Issue:4 | In Vitro Membrane Permeation Studies and in Vivo Antinociception of Glycosylated Dmt |
| AID78873 | Concentration of compound to inhibit 50% (IC50) electrically evoked contractions was tested in Guinea pig ileum(GPI) assay. | 1989 | Journal 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. |
| AID1311260 | Agonist activity at mu opioid receptor in guinea pig ileum assessed as inhibition of electrically-stimulated muscle contraction | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | [Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1. |
| AID1311269 | Agonist activity at delta opioid receptor in albino mouse vas deferens assessed as inhibition of electrically-stimulated muscle contraction | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | [Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1. |
| AID1311265 | Selectivity ratio of Ki for kappa-type opioid receptor in guniea pig brain membranes to Ki for mu-type opioid receptor in rat brain membranes | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | [Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1. |
| AID1872094 | Antinociceptive activity in thermal hyperalgesia mouse model administered sc | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources. |
| AID149312 | Ratio of binding affinity of opioid receptor mu and opioid receptor delta | 1989 | Journal 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. |
| AID1872032 | Binding affinity to DOP (unknown origin) | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources. |
| AID1137680 | Agonist activity at mu opioid receptor in guinea pig ileum | 2014 | ACS medicinal chemistry letters, Apr-10, Volume: 5, Issue:4 | In Vitro Membrane Permeation Studies and in Vivo Antinociception of Glycosylated Dmt |
| AID138345 | Concentration of compound to inhibit 50% (IC50) electrically evoked contractions was tested in Mouse vas deferens (MVD) assay. | 1989 | Journal 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. |
| AID149292 | Binding affinity against opioid receptor mu by displacement of radioligand [3H]DAGO in rat brain membrane | 1989 | Journal 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. |
| AID1872058 | Antagonist activity at mouse vas deferns MOP | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources. |
| AID79202 | Ke value for naloxon as antagonist (compound) was measured by using Guinea pig ileum assay. | 1989 | Journal 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. |
| AID1311264 | Selectivity ratio of Ki for delta-type opioid receptor in rat brain membranes to Ki for mu-type opioid receptor in rat brain membranes | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | [Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1. |
| AID149342 | Binding affinity against opioid receptor delta by displacement of radioligand [3H]DSLET in rat brain membrane | 1989 | Journal 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. |
| AID118325 | The relative potency of compound was measured by comparing the potency of compound to the [Leu]enkephalin in Mouse vas deferens (MVD) assay. | 1989 | Journal 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. |
| AID1872057 | Antagonist activity at guinea pig ileum MOP | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources. |
| AID1311263 | Displacement of [3H]U69,593 from kappa-type opioid receptor in guniea pig brain membranes incubated for 2 hrs | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | [Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1. |
| AID1872093 | Antinociceptive activity in mechanical allodynia mouse model administered sc | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources. |
| AID1872033 | Binding affinity to KOP (unknown origin) | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources. |
| AID1311261 | Displacement of [3H]DAMGO from mu-type opioid receptor in rat brain membranes incubated for 2 hrs | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | [Dmt(1)]DALDA analogues modified with tyrosine analogues at position 1. |
| AID149318 | The relative potency of compound was measured against Opioid receptor mu to that of [Leu]enkephalin in [3H]DAGO binding assay. | 1989 | Journal 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. |
| AID149359 | The relative potency of compound was measured against opioid receptor delta to that of [Leu]enkephalin in [3H]DSLET binding assay. | 1989 | Journal 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. |
| AID229266 | Ratio of IC50 in Mouse vas deferens and Guinea pig ileum assay | 1989 | Journal 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)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (1.52) | 18.7374 |
| 1990's | 23 (34.85) | 18.2507 |
| 2000's | 25 (37.88) | 29.6817 |
| 2010's | 12 (18.18) | 24.3611 |
| 2020's | 5 (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.
| This Compound (11.83) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (1.35%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 73 (98.65%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||