H-D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2 (Disulfide bond between Cys2 and Pen7)

Names

[ Name ]:
H-D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2 (Disulfide bond between Cys2 and Pen7)

[Synonym ]:
CYS2,TYR3,ARG5,PEN7-AMIDE
D-Phe-L-Cys-L-Tyr-D-Trp-L-Arg-L-Thr-L-Pen-L-Thr-NH2
M.W. 1104.30 C51H69N13O11S2
1,2-Dithia-5,8,11,14,17-pentaazacycloeicosane-4-carboxamide, N-[(1S,2R)-1-(aminocarbonyl)-2-hydroxypropyl]-10-[3-[(aminoiminomethyl)amino]propyl]-19-[[(2R)-2-amino-1-oxo-3-phenylpropyl]amino]-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-, (4R,7S,10S,13R,16S,19R)-
cyclic D-Pen-Cys-Tyr-D-Trp-Arg-ThrPen-Thr-NH2
1,2-Dithia-5,8,11,14,17-pentaazacycloeicosane-4-carboxamide, N-[(1S,2R)-1-(aminocarbonyl)-2-hydroxypropyl]-10-[3-[(aminoiminomethyl)amino]propyl]-19-[[(2R)-2-amino-1-oxo-3-phenylpropyl]amino]-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-, (7S,10S,13R,16S,19R)-
H-D-PHE-CYS-TYR-D-TRP-ARG-THR-PEN-THR-NH2
(7S,10S,13R,16S,19R)-N-[(2S,3R)-1-Amino-3-hydroxy-1-oxo-2-butanyl]-10-(3-carbamimidamidopropyl)-16-(4-hydroxybenzyl)-7-[(1R)-1-hydroxyethyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-19-(D-phenylalanylamino)-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
(4R,7S,10S,13R,16S,19R)-N-[(2S,3R)-1-Amino-3-hydroxy-1-oxo-2-butanyl]-10-(3-carbamimidamidopropyl)-16-(4-hydroxybenzyl)-7-[(1R)-1-hydroxyethyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-19-(D-phenylalanylamino)-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2

Biological Activity

[Description]:

CTAP is a potent, highly selective, and brain penetrant μ opioid receptor antagonist (IC50=3.5 nM) and displays over 1200-fold selectivity over δ opioid (IC50=4500 nM) and somatostatin receptors. CTAP can be used for the study of L-DOPA-induced dyskinesia (LID)[1].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Opioid Receptor

Signaling Pathways >> Neuronal Signaling >> Opioid Receptor

Research Areas >> Neurological Disease

[Target]

IC50: 3.5 nM (μ opioid receptor) IC50: 4500 nM (δ opioid receptor)[1]

[References]

[1]. Mitchell J Bartlett, et al. Highly-selective µ-opioid Receptor Antagonism Does Not Block L-DOPA-induced Dyskinesia in a Rodent Model.BMC Res Notes

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Molecular Formula ]:
C₅₁H₆₉N₁₃O₁₁S₂

[ Molecular Weight ]:
1104.304

[ Exact Mass ]:
1103.468140

[ PSA ]:
461.79000

[ LogP ]:
0.44

[ Index of Refraction ]:
1.699

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3.0

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Buprenorphine decreases the CCL2-mediated chemotactic response of monocytes.

J. Immunol. 194(7) , 3246-58, (2015)

Despite successful combined antiretroviral therapy, ∼ 60% of HIV-infected people exhibit HIV-associated neurocognitive disorders (HAND). CCL2 is elevated in the CNS of infected people with HAND and me...

Effect of μ-opioid agonist DAMGO on surface CXCR4 and HIV-1 replication in TF-1 human bone marrow progenitor cells.

BMC Res. Notes 7 , 752, (2014)

Approximately one-third of the AIDS cases in the United States have been attributed to the use of injected drugs, frequently involving the abuse of opioids. Consequently, it is critical to address whe...

Dopamine/Tyrosine Hydroxylase Neurons of the Hypothalamic Arcuate Nucleus Release GABA, Communicate with Dopaminergic and Other Arcuate Neurons, and Respond to Dynorphin, Met-Enkephalin, and Oxytocin.

J. Neurosci. 35 , 14966-82, (2015)

We employ transgenic mice with selective expression of tdTomato or cre recombinase together with optogenetics to investigate whether hypothalamic arcuate (ARC) dopamine/tyrosine hydroxylase (TH) neuro...