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70695-02-2

70695-02-2 Structure

70695-02-2 Structure
IdentificationBack Directory
[Name]

nargenicin A1
[CAS]

70695-02-2
[Synonyms]

CP-47444
NSC 355066
Antibiotic 47444
Antibiotic CP-47444
Nargenicin A1 DISCONTINUED
Nodusmicin 9-(1H-pyrrole-2-carboxylate)
1H-Pyrrole-2-carboxylic acid, (1E,3R,4S,7S,8aS,10aR,11R,12R,13R,14R,14aS,14bS)-3,4,6,7,8,8a,10a,11,12,13,14,14a-dodecahydro-14-hydroxy-4-[(1R)-1-hydroxyethyl]-7-methoxy-1,3,13-trimethyl-6-oxo-11,14b-epoxy-14bH-naphth[2,1-e]oxecin-12-yl ester
[Molecular Formula]

C28H37NO8
[MDL Number]

MFCD08702706
[MOL File]

70695-02-2.mol
[Molecular Weight]

515.599
Chemical PropertiesBack Directory
[Boiling point ]

718.3±60.0 °C(Predicted)
[density ]

1.31±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C,protect from light
[solubility ]

DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
[form ]

Off-white powder.
[pka]

14.03±0.20(Predicted)
[color ]

Off-white
Hazard InformationBack Directory
[Description]

Nargenicin is a macrolide antibiotic that selectively inhibits the growth of S. aureus, methicilin resistant S. aureus (MRSA), and M. luteus (MICs = 0.6, 0.3, and 2.5 μg/ml, respectively) over a panel of 11 Gram-positive and Gram-negative bacteria (MICs = >80 μg/ml). It dose-dependently inhibits S. aureus DnaE in the presence of DNase I-activated DNA and E. coli DnaE when used at concentrations of 0.00001-0.1 and 0.01-100 μg/mL, respectively. In murine BV-2 microglial cells, nargenicin (1 μM) inhibits cytokine expression and nitric oxide production induced by LPS. Nargenicin (200 μM), when used in combination with 1,25-dihydroxyvitamin D3 or all-trans retinoic acid , reduces cell proliferation by 37-47% and increases cell differentiation by 82-85% in HL-60 human myeloid leukemia cells. In vivo, nargenicin (50 mg/kg, p.o.) reduces the number of colony-forming units (CFUs) in infected kidneys by 100,000-fold in a murine model of S. aureus infection.
[Uses]

Nargenicin A1 is an antibiotic with a broad efficacy.
[storage]

+4°C
[References]

[1] JAE KYUNG SOHNG. Production, isolation and biological activity of nargenicin from Nocardia sp. CS682[J]. Archives of Pharmacal Research, 2008, 31 10: 1339-1345. DOI: 10.1007/s12272-001-2115-0
[2] RONALD E PAINTER. Elucidation of DnaE as the Antibacterial Target of the Natural Product, Nargenicin.[J]. Chemistry & biology, 2015, 22 10: 1362-1373. DOI: 10.1016/j.chembiol.2015.08.015
[3] JIN CHEOL YOO. Nargenicin attenuates lipopolysaccharide-induced inflammatory responses in BV-2 cells.[J]. Neuroreport, 2009, 20 11: 1007-1012. DOI: 10.1097/wnr.0b013e32832d2239
[4] SEUNG HYUN KIM  Tae S K  Jin Cheol Yoo. Nargenicin enhances 1,25-dihydroxyvitamin D3- and all-trans retinoic acid-induced leukemia cell differentiation via PKCβI/MAPK pathways[J]. Biochemical pharmacology, 2009, 77 11: Pages 1694-1701. DOI: 10.1016/j.bcp.2009.03.004
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