An antibiotic with diverse biological activites
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Chartreusin

Item No. 23773

Technical Information
Formal Name
10-[[6-deoxy-2-O-(6-deoxy-3-O-methyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]oxy]-6-hydroxy-1-methyl-benzo[h][1]benzopyrano[5,4,3-cde][1]benzopyran-5,12-dione
CAS Number
6377-18-0
Synonyms
  • Antibiotic X 465A
  • Lambdamycin
  • NSC 5159
Molecular Formula
C32H32O14
Formula Weight
Purity
≥98%
A crystalline solid
Acetone: SolubleDMSO: 10 mg/mlMethanol: Slightly soluble
λmax
236, 268, 331, 400, 423 nm
SMILES
OC1=C(C(OC2=C3C(C(O4)=O)=C(C)C=C2)=O)C3=C4C5=C1C=CC=C5O[C@@H]6O[C@H](C)[C@H](O)[C@H](O)[C@H]6O[C@]7([H])[C@H](O)[C@@H](OC)[C@@H](O)[C@@H](C)O7
InChi Code
InChI=1S/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3/t11-,12-,21+,22+,24+,25-,27+,28-,31-,32+/m1/s1
InChi Key
PONPPNYZKHNPKZ-RYBWXQSLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Chartreusin is an antibiotic originally isolated from S. chartreusis with diverse biological activities.1 It inhibits growth of S. aureus, B. subtilis, M. luteus, M. flavus, B. fragilis, C. difficile, C. perfringens, and P. acnes (MICs = 0.4-12.5 μg/ml).2 Chartreusin binds to DNA and induces electrophoretic shifts in both supercoiled and nicked plasmid DNA.3 It also inhibits strand-passing activity of topoisomerase II in a P4 unknotting assay. Chartreusin inhibits protein synthesis in chick embryo fibroblasts (CEFs) and mouse fibroblast 3T6 cells (IC50s = 7 and 70 μM, respectively).4 It is cytotoxic to human lung carcinoma A549 cells in vitro (IC50 = 95 nM) and increases median survival in P388 leukemia and B16 melanoma mouse tumor models when administered at a dose of 10 mg/kg per day.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Leach, B.E., Calhoun, K.M., Johnson, L.E., et alChartreusin, a new antibiotic produced by Streptomyces chartreusis, a new species. J. Am. Chem. Soc. 75(16), 4011-4012 (1953).

    2. Konishi, M., Sugawara, K., Kofu, F., et alElsamicins, new antitumor antibiotics related to chartreusin. I. Production, isolation, characterization and antitumor activity. J. Antibiot. (Tokyo) 39(6), 784-791 (1986).

    3. Lorico, A., and Long, B.H. Biochemical characterisation of elsamicin and other coumarin-related antitumour agents as potent inhibitors of human topoisomerase II. Eur. J. Cancer 29A(14), 1985-1991 (1993).

    4. Contreras, A., Vazquez, D., and Carrasco, L. Inhibition, by selected antibiotics, of protein synthesis in cells growing in tissue cultures. J. Antibiot. (Tokyo) 31(6), 598-602 (1978).