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103222-11-3

103222-11-3 structure
103222-11-3 structure
  • Name: Vapreotide acetate salt
  • Chemical Name: rc 160
  • CAS Number: 103222-11-3
  • Molecular Formula: C57H70N12O9S2
  • Molecular Weight: 1131.371
  • Catalog: Biochemical Peptide
  • Create Date: 2018-10-03 12:51:33
  • Modify Date: 2024-01-02 08:06:47
  • Vapreotide is a NK1R antagonist, with an IC50 of 330 nM. Sequence: Phe-Cys-Tyr-Trp-Lys-Val-Cys-Trp-NH2(Disulfide bridge: Cys2-Cys7).
Name rc 160
Synonyms D-PHE-CYS-TYR-D-TRP-LYS-VAL-CYS-TRP-NH2
1H-indole-3-propanamide, α-[[[(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-[[(2R)-2-amino-1-oxo-3-phenylpropyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-7-(1-methylethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloeicos-4-yl]carbonyl]amino]-, (αS)-
H-D-Phe-Cys-Tyr-D-Trp-Lys-Val-Cys-Trp-NH2
Octastatin
(4R,7S,10S,13R,16S,19R)-10-(4-Aminobutyl)-N-[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-16-(4-hydroxybenzyl)-13-(1H-indol-3-ylmethyl)-7-isopropyl-6,9,12,15,18-pentaoxo-19-(D-phenylalanylamino)-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
Vapreotide Acetate
(4R,7S,10S,13R,16S,19R)-10-(4-Aminobutyl)-N-[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxo-2-propanyl]-16-(4-hydroxybenzyl)-13-(1H-indol-3-ylmethyl)-7-isopropyl-6,9,12,15,18-pentaoxo-19-(D-phenylalanylamino)-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
1H-Indole-3-propanamide, α-[[[(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-[[(2R)-2-amino-1-oxo-3-phenylpropyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-7-(1-methylethyl)-6,9,12 ,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloeicos-4-yl]carbonyl]amino]-, (αS)-
vapreotide
FCYWKVCW-NH2
(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-N-[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-16-(4-hydroxybenzyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-19-(D-phenylalanylamino)-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
RC-160
D-Phenylalanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-tryptophanamide Cyclic (2®7)-Disulfide
Description Vapreotide is a NK1R antagonist, with an IC50 of 330 nM. Sequence: Phe-Cys-Tyr-Trp-Lys-Val-Cys-Trp-NH2(Disulfide bridge: Cys2-Cys7).
Related Catalog
Target

330 nM (NK1R)[1].

In Vitro Vapreotide attenuates the effect of SP on calcium release in a concentration-dependent manner. The concentration required for Vapreotide to completely inhibit the effect of SP is about 100 times higher than that required for the NK1R antagonist aprepitant. The effect of Vapreotide on cell proliferation is mediated primarily by SSTR2. In order to further establish the NK1R antagonist effect of Vapreotide, U373MG cells are pretreated with SSTR2 selective antagonist CYN followed by incubation with Vapreotide and SP stimulation. The results show that pretreatment with CYN does not reverse the inhibitory effect of Vapreotide on SP-stimulated IL-8 mRNA expression. Vapreotide reduces HIV-1 replication in MDM as indicated by limited HIV gag mRNA expression compared to control MDM. In addition, SP treatment (10 μM) reverses Vapreotide inhibition of HIV-1 replication in MDM. This observation indicates that the inhibition of HIV-1 replication by Vapreotide is most likely due to its interaction with NK1R[1].
Cell Assay The HEK293-NK1R cells and U373MG cells are incubated with or without Vapreotide (0, 5, 10, 20 μM) for 10 minutes and then incubated with or without SP for 3 hours. In some experiments, cells are first incubated with CYN for 10 minutes, and then Vapreotide is added and incubated for an additional 10 minutes, followed by stimulation with SP for 3 hours. Mock treated cells are used as controls[1].
References

[1]. Spitsin S et al. Analog of somatostatin vapreotide exhibits biological effects in vitro via interaction with neurokinin-1 receptor. Neuroimmunomodulation. 2013;20(5):247-55.
Density 1.4±0.1 g/cm3
Boiling Point 1540.9±65.0 °C at 760 mmHg
Molecular Formula C57H70N12O9S2
Molecular Weight 1131.371
Flash Point 885.7±34.3 °C
Exact Mass 1130.483032
PSA 401.24000
LogP 3.47
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.699
Storage condition −20°C
Safety Phrases 22-24/25

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