C-1027

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C-1027 or Lidamycin is a antitumor antibiotic consisting of a complex of an enediyne chromophore and an apoprotein.[1][2][3][4] [5][6] It shows antibiotic activity against most Gram-positive bacteria.[7] It is one of the most potent cytotoxic molecules known, due to its induction of a higher ratio of DNA double-strand breaks than single-strand breaks.

C-1027’s chromophore contains a nine-membered enediyne that is responsible for most of the molecule’s biological activity.[7] Unlike other enediynes, this molecule contains no triggering mechanism. It is already primed to undergo the cycloaromatization reaction without external activation to produce the toxic 1,4-benzenoid diradical species. C-1027 can induce oxygen-independent interstrand DNA crosslinks in addition to the oxygen-dependent single- and double-stranded DNA breaks typically generated by other enediynes. This unique oxygen-independent mechanism suggests that C-1027 may be effective against hypoxic tumor cells.[8]

C-1027 Mechanism

C-1027 shows promise as an anticancer drug and is currently undergoing phase II clinical trials in China,[9] with a 30% success rate.[10] It can induce apoptosis in many cancer cells and recent studies have indicated that it induces unusual DNA damage responses to double-strand breaks, including altering cell cycle progression and inducing chromosomal aberrations.[6]

References[edit | edit source]

  1. ↑ , A new macromolecular antitumor antibiotic, C-1027. I. Discovery, taxonomy of producing organism, fermentation and biological activity., The Journal of Antibiotics, 1988, Vol. 41(Issue: 11), pp. 1575–1579, DOI: 10.7164/antibiotics.41.1575, PMID: 3198491,
  2. ↑ , A new macromolecular antitumor antibiotic, C-1027. II. Isolation and physico-chemical properties., The Journal of Antibiotics, 1988, Vol. 41(Issue: 11), pp. 1580–1585, DOI: 10.7164/antibiotics.41.1580, PMID: 3198492,
  3. ↑ , A new macromolecular antitumor antibiotic, C-1027. III. Antitumor activity., The Journal of Antibiotics, 1989, Vol. 42(Issue: 8), pp. 1294–1298, DOI: 10.7164/antibiotics.42.1294, PMID: 2759910,
  4. ↑ , Structure and cycloaromatization of a novel enediyne, C-1027 chromophore, Tetrahedron Lett., 1993, Vol. 34(Issue: 16), pp. 2637–2640, DOI: 10.1016/S0040-4039(00)77644-1,
  5. ↑ , Complexity and simplicity in the biosynthesis of enediyne natural products, Natural Product Reports, Vol. 27(Issue: 4), pp. 499–528, DOI: 10.1039/b908165h, PMID: 20336235,
  6. ↑ 6.0 6.1 , Lidamycin shows highly potent cytotoxic to myeloma cells and inhibits tumor growth in mice, Acta Pharmacologica Sinica, Vol. 30(Issue: 7), pp. 1025–32, DOI: 10.1038/aps.2009.75, PMID: 19575006, PMC: 4006655,
  7. ↑ 7.0 7.1 , C1027 chromophore, a potent new enediyne antitumor antibiotic, induces sequence-specific double-strand DNA cleavage, Biochemistry, Vol. 33(Issue: 19), pp. 5947–54, PMID: 8180224,
  8. ↑ , Improvement of the enediyne antitumor antibiotic C-1027 production by manipulating its biosynthetic pathway regulation in Streptomyces globisporus, Journal of Natural Products, Vol. 74(Issue: 3), pp. 420–4, DOI: 10.1021/np100825y, PMID: 21250756, PMC: 3064734,
  9. ↑ , Draft genome sequence of Streptomyces globisporus C-1027, which produces an antitumor antibiotic consisting of a nine-membered enediyne with a chromoprotein, Journal of Bacteriology, Vol. 194(Issue: 15), pp. 4144, DOI: 10.1128/JB.00797-12, PMID: 22815456, PMC: 3416545,
  10. ↑ , Enediynes: Exploration of microbial genomics to discover new anticancer drug leads, Bioorganic & Medicinal Chemistry Letters, Vol. 25(Issue: 1), pp. 9–15, DOI: 10.1016/j.bmcl.2014.11.019, PMID: 25434000, PMC: 4480864,



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Contributors: Prab R. Tumpati, MD