A DNA-intercalating antitumor agent
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Luzopeptin A

Item No. 18444

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
Luzopeptin A
CAS Number
75580-37-9
Synonyms
  • BBM-928A
Molecular Formula
C64H78N14O24
Formula Weight
1427.4
Purity
≥95%
Formulation (Request formulation change)
A tan solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: soluble
SMILES
CC(O[C@@H]1[C@@](N2N=CC1)([H])C(NCC(N(C)CC(N(C)[C@@H](C(O)(C)C)C(OC[C@@H](NC(C3=NC4=CC=C(OC)C=C4C=C3O)=O)C(N5[C@]([C@@H](OC(C)=O)CC=N5)([H])C(NCC(N(C)CC(N(C)[C@@H](C(O)(C)C)C(OC[C@@H](NC(C6=NC(C=CC(OC)=C7)=C7C=C6O)=O)C2=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=
InChi Code
InChI=1S/C64H78N14O24/c1-31(79)101-43-17-19-67-77-51(43)57(89)65-25-45(83)73(7)27-47(85)75(9)54(64(5,6)96)62(94)100-30-40(72-56(88)50-42(82)24-34-22-36(98-12)14-16-38(34)70-50)60(92)78-52(44(18-20-68-78)102-32(2)80)58(90)66-26-46(84)74(8)28-48(86)76(
InChi Key
QMZVWFQMMLKHLS-LPQVFZKKSA-N
Origin
Bacterium/Actinomadura
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $369

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    Product Description

    Luzopeptin A is a cyclic depsipeptide antibiotic first isolated from an actinomycete strain.1,2 It displays antitumor activity, as it is highly active in mice against a variety of experimental tumors.1 Luzopeptin A acts as a bifunctional DNA intercalator that strongly binds DNA and forms crosslinks between DNA molecules.3 It also inhibits reverse transcriptases from HIV-1 and HIV-2 (IC50s = 7 and 68 nM, respectively), as well as cellular DNA polymerases.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ohkuma, H., Sakai, F., Nishiyama, Y., et al. BBM-928, a new antitumor antibiotic complex. I. Production, isolation, characterization and antitumor activity. J. Antibiot. (Tokyo) 33(10), 1087-1097 (1980).

    2. Konishi, M., Ohkuma, H., Sakai, F., et al. BBM-928, a new antitumor antibiotic complex. III. Structure determination of BBM-928 A, B and C. J. Antibiot. (Tokyo) 34(2), 148-159 (1981).

    3. Huang, C.H., Mirabelli, C.K., Mong, S., et al. Intermolecular cross-linking of DNA through bifunctional intercalation of an antitumor antibiotic, luzopeptin A (BBM-928A). Cancer Res. 43(6), 2718-2724 (1983).

    4. Lingham, R.B., Hsu, A.H.M., O'Brien, J.A., et al. Quinoxapeptins: A novel chromodepsipeptide inhibitors of HIV-1 and HIV-2 reverse transcriptase I. The producing organism and biological activity. J. Antibiot. (Tokyo) 49(3), 254-259 (1996).

    5. Take, Y., Inouye, Y., and Nakamura, S. Comparative studies of the inhibitory properties of antibiotics on human immunodeficiency virus and avian myeloblastosis virus reverse transcriptases and cellular DNA polymerases. J. Antibiot. (Tokyo) 42(1), 107-115 (1989).