An antiprotozoan antibiotic
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Ikarugamycin

Item No. 15386

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3R,7Z,14S,19E)-3-ethyl-2,3,3aS,5aR,5bS,6,10,11,12,13,14,15,20aS,21,21aR,21bR-hexadecahydro-22-hydroxy-2-methyl-14,17-metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione
CAS Number
36531-78-9
Molecular Formula
C29H38N2O4
Formula Weight
478.6
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: Slightly solubleMethanol: Slightly soluble
SMILES
O=C(C1=C(O)[C@H](CCCN2)NC1=O)/C=C/[C@@H]3C[C@@]4([H])[C@@](C=C[C@]5([H])[C@]4([H])C[C@@H](C)[C@H]5CC)([H])[C@H]3C/C=C\C2=O
InChi Code
InChI=1S/C29H38N2O4/c1-3-18-16(2)14-22-20(18)10-11-21-19-6-4-8-26(33)30-13-5-7-24-28(34)27(29(35)31-24)25(32)12-9-17(19)15-23(21)22/h4,8-12,16-24,34H,3,5-7,13-15H2,1-2H3,(H,30,33)(H,31,35)/b8-4-,12-9+/t16-,17-,18-,19+,20+,21-,22+,23+,24+/m1/s1
InChi Key
WSUGGLXIPUHOSG-QOMLVTEJSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $197

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    2.5 mg

    $885

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    Product Description

    Ikarugamycin is a macrocyclic antibiotic first isolated from Streptomyces sp. that demonstrates potent antiprotozoal activity.1 It exhibits cytotoxic effects in cancer cell lines, inhibiting cell proliferation (IC50 = 221.3 nM in HL-60 cells) through genotoxicity and by inducing apoptosis and activation of caspases.2 It also was shown to significantly inhibit oxidized low-density lipoprotein-induced accumulation of cholesteryl esters in macrophages at 1-4 μM.3 Additionally, ikarugamycin is used to inhibit clathrin-coated pit-mediated endocytosis.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jomon, K., Kuroda, Y., Ajisaka, M., et al. A new antibiotic, ikarugamycin. J. Antibiot. (Tokyo) 25(5), 271-280 (1972).

    2. Popescu, R., Heiss, E.H., Ferk, F., et al. Ikarugamycin induces DNA damage, intracellular calcium increase, p38 MAP kinase activation and apoptosis in HL-60 human promyelocytic leukemia cells. Mutat. Res. 709-710, 60-66 (2011).

    3. Hasumi, K., Shinohara, C., Naganuma, S., et al. Inhibition of the uptake of oxidized low-density lipoprotein in macrophage J774 by the antibiotic ikarugamycin. Eur. J. Biochem. 205(2), 841-846 (1992).

    4. Luo, T., Fredericksen, B.L., Hasumi, K., et al. Human immunodeficiency virus type 1 Nef-induced CD4 cell surface downregulation is inhibited by ikarugamycin. J. Virol. 75(5), 2488-2492 (2001).