A glycopeptide antibiotic with diverse biological activities
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Phleomycin

Item No. 15549

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3S,4S,5R,6R)-2-(((2R,3S,4S,5S,6S)-2-(2-(6-amino-2-(3-amino-1-((2,3-diamino-3-oxopropyl)amino)-3-oxopropyl)-5-methylpyrimidine-4-carboxamido)-3-((5-((1-((2-(4-((4-guanidinobutyl)carbamoyl)-4',5'-dihydro-[2,4'-bithiazol]-2'-yl)ethyl)amino)-3-hydroxy-1-oxobutan-2-yl)amino)-3-hydroxy-4-methyl-5-oxopentan-2-yl)amino)-1-(1H-imidazol-4-yl)-3-oxopropoxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl carbamate, copper(II) salt, monohydrochloride
CAS Number
11006-33-0
Synonyms
  • PLM-D1
Molecular Formula
C55H84N20O21S2Cu • HCl
Formula Weight
1525.5
Purity
≥95% (mixture of phleomycins)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
λmax
242, 300 nm
SMILES
NC(CNC(CC(N)=O)C1=NC(N)=C(C(C(NC(C(NC(C(C(C)C(NC(C(NCCC2=NC(C3=NC(C(NCCCCNC(N)=N)=O)=CS3)CS2)=O)C(O)C)=O)O)C)=O)C(O[C@H]4[C@]([H])([C@H]([C@@H]([C@@H](O4)CO)O)O)O[C@H]5O[C@@H]([C@H]([C@@H]([C@@H]5O)OC(N)=O)[O-])C[O-])C6=CNC=N6)=O)=N1)C)C(N)=O.[Cu+2].Cl
InChi Code
InChI=1S/C55H84N20O21S2.ClH.Cu/c1-19-32(72-45(75-43(19)58)24(11-30(57)79)67-12-23(56)44(59)85)49(89)74-34(40(25-13-63-18-68-25)94-53-42(38(83)36(81)28(14-76)93-53)95-52-39(84)41(96-55(62)91)37(82)29(15-77)92-52)50(90)69-21(3)35(80)20(2)46(86)73-33(22(4)78)48(88)65-10-7-31-70-27(17-97-31)51-71-26(16-98-51)47(87)64-8-5-6-9-66-54(60)61;;/h13,16,18,20-24,27-29,33-42,52-53,67,76,78,80-81,83-84H,5-12,14-15,17,56H2,1-4H3,(H2,57,79)(H2,59,85)(H2,62,91)(H,63,68)(H,64,87)(H,65,88)(H,69,90)(H,73,86)(H,74,89)(H2,58,72,75)(H4,60,61,66);1H;/q-2;;+2/t20?,21?,22?,23?,24?,27?,28-,29+,33?,34?,35?,36+,37+,38-,39-,40?,41-,42-,52+,53-;;/m0../s1
InChi Key
QZGJYYBUEYHNGV-GEYAUAICSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Phleomycin is a glycopeptide antibiotic that has been found in S. verticillus and has diverse biological activities.1,2,3,4,5 It induces chromosomal breaks in S. cerevisiae when used at concentrations ranging from 1 to 2 µM.1 Phleomycin (5 or 10 µg/ml) reduces proliferation, DNA synthesis, and the percentage of cells entering mitosis in HeLa cervical cancer cells.2 In vivo, phleomycin (1 mg/kg per day), in combination with the purine analog LS34, increases survival time in an Ehrlich mouse ascites tumor model.3 It has been used as an antibiotic selection agent for successfully transformed cells in genetic engineering experiments.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Moore, C.W. Internucleosomal cleavage and chromosomal degradation by bleomycin and phleomycin in yeast. Cancer Res. 48(23), 6837-6843 (1988).

    2. Kajiwara, K., Kim, U.H., and Mueller, G.C. Phleomycin, an inhibitor of replication of HeLa cells. Cancer Res. 26(2), 233-236 (1966).

    3. Allen, T.E., Brown, D.J., Cowden, W.B., et al. Amplification of the antitumor activity of phleomycins in rats and mice by heterocyclic analogues of purines. J. Antibiot. (Tokyo) 37(4), 376-383 (1984).

    4. Wenzel, T.J., Migliazza, A., Steensma, H.Y., et al. Efficient selection of phleomycin-resistant Saccharomyces cerevisiae transformants. Yeast 8(8), 667-668 (1992).

    5. Vickers, C.E., Bydder, S.F., and Nielsen, L.K. Dual gene expression cassette vectors with antibiotic selection markers for engineering in Saccharomyces cerevisiae. Microb. Cell Fact. 12, 96 (2013).