A polyketide enediyne
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Calicheamicin γ1

Item No. 40830

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1R,4Z,8S,13E)-8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-D-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-β-D-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-carbamic acid, methyl ester
CAS Number
108212-75-5
Synonyms
  • Calicheamicin γ1I
Molecular Formula
C55H74IN3O21S4
Formula Weight
1368.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly Soluble: 0.1-1 mg/mlDMSO: Sparingly Soluble: 1-10 mg/mlMethanol: Slightly Soluble: 0.1-1 mg/mlWater: Sparingly Soluble: 1-10 mg/ml
SMILES
C[C@H]1O[C@@H](O[C@H]2C#C/C=C\C#C[C@]3(O)CC(C(NC(OC)=O)=C2/C3=C\CSSSC)=O)[C@H](O[C@@H]4OC[C@H](NCC)[C@@H](OC)C4)[C@@H](O)[C@@H]1NO[C@@H]5O[C@H](C)[C@@H](SC(C6=C(C)C(I)=C(O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](OC)[C@H]7O)C(OC)=C6OC)=O)[C@@H](O)C5
InChi Code
InChI=1S/C55H74IN3O21S4/c1-12-57-30-24-73-35(22-34(30)68-6)78-48-43(63)40(26(3)75-53(48)77-33-17-15-13-14-16-19-55(67)23-32(61)41(58-54(66)72-10)38(33)29(55)18-20-82-84-81-11)59-80-36-21-31(60)50(28(5)74-36)83-51(65)37-25(2)39(56)46(49(71-9)45(37)69-7)79-52-44(64)47(70-8)42(62)27(4)76-52/h13-14,18,26-28,30-31,33-36,40,42-44,47-48,50,52-53,57,59-60,62-64,67H,12,20-24H2,1-11H3,(H,58,66)/b14-13-,29-18+/t26-,27+,28-,30+,31+,33+,34+,35+,36+,40-,42+,43+,44-,47-,48-,50-,52+,53+,55+/m1/s1
InChi Key
HXCHCVDVKSCDHU-PJKCJEBCSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Calicheamicin γ1 is a polyketide synthase-derived enediyne that has been found in M. echinospora.1 It is composed of carbohydrate and aromatic moieties, which bind to the minor groove in DNA, and a warhead moiety that aromatizes and oxidatively induces double-stranded DNA scission in cell-free assays.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bhardwaj, M., Cui, Z., Daniel Hankore, E., et al. A discrete intermediate for the biosynthesis of both the enediyne core and the anthraquinone moiety of enediyne natural products. Proc. Natl. Acad. Sci. USA 120(9), e2220468120 (2023).

    2. Ahlert, J., Shepard, E., Lomovskaya, N., et al. The calicheamicin gene cluster and its iterative type I enediyne PKS. Science 297(5584), 1173-1176 (2002).

    3. Zein, N.N., Sinha, A.M., McGahren, W.J., et al. Calicheamicin γ1I: An antitumor antibiotic that cleaves double-stranded DNA site specifically. Science 240(4856), 1198-1201 (1988).