A macrolide antibiotic
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Nargenicin

Item No. 25456

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
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
CAS Number
70695-02-2
Synonyms
  • Antibiotic 47444
  • CP 47,444
  • NSC 355066
Molecular Formula
C28H37NO8
Formula Weight
515.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
λmax
267 nm
SMILES
C/C([C@]1(O2)[C@](C[C@@H]3OC)([H])C=C[C@@]4([H])[C@@H]2[C@H](OC(C5=CC=CN5)=O)[C@H](C)[C@@H](O)[C@]41[H])=C\[C@@H](C)[C@]([C@@H](C)O)([H])OC3=O
InChi Code
InChI=1S/C28H37NO8/c1-13-11-14(2)28-17(12-20(34-5)27(33)35-23(13)16(4)30)8-9-18-21(28)22(31)15(3)24(25(18)37-28)36-26(32)19-7-6-10-29-19/h6-11,13,15-18,20-25,29-31H,12H2,1-5H3/b14-11+/t13-,15-,16-,17-,18-,20+,21+,22-,23+,24-,25-,28+/m1/s1
InChi Key
YEUSSARNQQYBKH-SIMZXIQRSA-N
Origin
Bacterium/Nocardia argentinensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product 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).1 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.2 In murine BV-2 microglial cells, nargenicin (1 μM) inhibits cytokine expression and nitric oxide production induced by LPS.3 Nargenicin (200 μM), when used in combination with 1,25-dihydroxyvitamin D3 or all-trans retinoic acid (Item No. 11017), reduces cell proliferation by 37-47% and increases cell differentiation by 82-85% in HL-60 human myeloid leukemia cells.4 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.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sohng, J.K., Yamaguchi, T., Seong, C.N., et al. Production, isolation and biological activity of nargenicin from Nocardia sp. CS682. Arch. Pharm. Res. 31(10), 1339-1345 (2008).

    2. Painter, R.E., Adam, G.C., Arocho, M., et al. Elucidation of DnaE as the antibacterial target of the natural product, nargenicin. Chem. Biol. 22(10), 1362-1373 (2015).

    3. Yoo, J.C., Cho, H.S., Park, E., et al. Nargenicin attenuates lipopolysaccharide-induced inflammatory responses in BV-2 cells. Neuroreport 20(11), 1007-1012 (2009).

    4. Kim, S.H., Yoo, J.C., and Kim, T.S. Nargenicin enhances 1,25-dihydroxyvitamin D3- and all-trans retinoic acid-induced leukemia cell differentiation via PKCβI/MAPK pathways. Biochem. Pharmacol. 77(11), 1694-1701 (2009).