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SML2807

Sigma-Aldrich

JP4-039

≥98% (HPLC)

Synonyme(s) :

4-[[(3E,5S)-5-[[(1,1-Dimethylethoxy)carbonyl]amino]-7-methyl-1-oxo-3-octen-1-yl]amino]-2,2,6,6-tetramethyl-1-piperidinyloxy, JP 4-039

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About This Item

Formule empirique (notation de Hill):
C23H42N3O4
Numéro CAS:
1205492-16-5
Poids moléculaire :
424.60
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

powder

Couleur

faint yellow to dark orange

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

O=C(C/C=C/[C@@H](NC(OC(C)(C)C)=O)CC(C)C)NC1CC(C)(C)N([O])C(C)(C)C1

InChI

1S/C23H42N3O4/c1-16(2)13-17(25-20(28)30-21(3,4)5)11-10-12-19(27)24-18-14-22(6,7)26(29)23(8,9)15-18/h10-11,16-18H,12-15H2,1-9H3,(H,24,27)(H,25,28)/b11-10+/t17-/m1/s1

Clé InChI

AJHRJWQXDNEJAG-SXSDINLZSA-N

Actions biochimiques/physiologiques

JP4-039 is an electron-/reactive oxygen species (ROS)-scavenging GS-nitroxide composed of 4-amino-TEMPO and a truncated gramicidin S (GS) mitochrondria-targeting sequence. JP4-039 is a superior irradiation mitigator than XJB-5-131 (33% vs. 20% mice survial rate on day 35 with respective compound; 23.6 μmol/kg iv. 24 hr post 9.5 Gy whole body irradiation), while displaying weaker anti-ferroptotic potency (EC50 = 3.58 μM/1.27 μM against 10 μM erastin-/2 μM RSL3-induced HT-1080 ferroptosis vs. 114 nM/68 nM with XJB-5-131) due to lower lipophilicity & mitochondria enrichment. Typical dosing range: 40 nM-10 μM in cultures and 10-20 mg/kg in mice (im., ip., iv.) in vivo.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

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Mark E Bernard et al.
Radiation research, 176(5), 603-612 (2011-09-24)
Fanconi anemia (FA) is an inherited disorder characterized by defective DNA repair and cellular sensitivity to DNA crosslinking agents. Clinically, FA is associated with high risk for marrow failure, leukemia and head and neck squamous cell carcinoma (HNSCC). Radiosensitivity in
Liang Wei et al.
Scientific reports, 8(1), 2072-2072 (2018-02-03)
Total body irradiation (TBI) leads to dose- and tissue-specific lethality. In the current study, we demonstrate that a mitochondrion-targeted nitroxide JP4-039 given once 24 hours after 9-10 Gy TBI significantly improves mouse survival, and the recovery of intestinal barrier, differentiation and stem
Michael W Epperly et al.
In vivo (Athens, Greece), 24(6), 811-819 (2010-12-18)
this study evaluated esophageal radioprotection by the Gramicidin S (GS) derived-nitroxide, JP4-039, a mitochondrial targeting peptide-isostere covalently-linked to 4-amino-Tempo, delivered in a novel swallowed oil-based (F15) formulation. C57BL/6HNsd female mice received intraesophageal F15 formulation containing JP4-039 (4 mg/ml in 100
Michael W Epperly et al.
In vivo (Athens, Greece), 32(5), 1009-1023 (2018-08-29)
The mitochondrial targeted GS-nitroxide, JP4-039, is an effective total body irradiation (TBI) mitigator when delivered intravenously (IV) up to 72 h after exposure. Effective systemic and localized administration to oral cavity/oropharynx and esophagus has been demonstrated. The objective of the
Julie P Goff et al.
In vivo (Athens, Greece), 25(3), 315-323 (2011-05-18)
Total-body irradiation (TBI) doses in the range of 2-8 Gy are associated with a drop in peripheral blood counts, decreased bone marrow cellularity, and hematopoietic syndrome. Radiation mitigators must be safe for individuals likely to recover spontaneously. Female C57BL/6HNsd mice
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