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Chemical Structure
Chemical Structure
Chemical Structure

GE23077 A1/B1 [752989-44-9, 752989-45-0, 752989-46-1]

Research Use Only
AG-CN2-0305
AdipoGen Life Sciences
Estimated Purity>70% (HPLC, for A1/B1)
Product group Chemicals
Molecular Weight805.8 [A1]803.8 [B1]
Price on request
Packing Size
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    GE23077 A1/B1 [752989-44-9, 752989-45-0, 752989-46-1]
  • Delivery Days Customer
    10
  • Certification
    Research Use Only
  • Estimated Purity
    >70% (HPLC, for A1/B1)
  • Hazard Information
    Non-hazardous
  • Molecular Formula
    C31H51N9O16 [A1] C31H49N9O16 [B1]
  • Molecular Weight
    805.8 [A1]803.8 [B1]
  • Scientific Description
    Chemical. CAS: 752989-46-1 [Mixture A1/B1], 752989-45-0 [A1]752989-44-9 [B1]. Formula: C31H51N9O16 [A1], C31H49N9O16 [B1]. MW: 805.8 [A1]803.8 [B1]. Isolated from Actinomadura sp. Cyclic heptapeptide antibiotic. Potent and selective inhibitor of bacterial RNA polymerase (RNAP). Inhibits Gram-positive (Bacillus subtilis) and Gram-negative (Escherichia coli) RNAPs with IC50 ~20nM, whereas it is not active on E. coli DNA polymerase or on eukaryotic (wheat germ) RNAP II (IC50 values >100microM). Even though of its potent activity in vitro on purified bacterial RNAPs, it shows a narrow spectrum of antimicrobial activity in vivo on Gram-positive and Gram-negative bacteria, due to lack of memmbrane permeability. Acts at the level of transcription initiation. Binds directly to the bacterial RNA polymerase (RNAP) active-center i and i+1 nucleotide binding sites, preventing the binding of initiating nucleotides and thereby preventing transcription initiation. Tool for mechanistic studies on bacterial RNAP and for potential anti-infective drug discovery. - Cyclic heptapeptide antibiotic. Potent and selective inhibitor of bacterial RNA polymerase (RNAP). Inhibits Gram-positive (Bacillus subtilis) and Gram-negative (Escherichia coli) RNAPs with IC50 ~20nM, whereas it is not active on E. coli DNA polymerase or on eukaryotic (wheat germ) RNAP II (IC50 values >100microM). Even though of its potent activity in vitro on purified bacterial RNAPs, it shows a narrow spectrum of antimicrobial activity in vivo on Gram-positive and Gram-negative bacteria, due to lack of membrane permeability. Acts at the level of transcription initiation. Binds directly to the bacterial RNA polymerase (RNAP) active-center i and i+1 nucleotide binding sites, preventing the binding of initiating nucleotides and thereby preventing transcription initiation. Tool for mechanistic studies on bacterial RNAP and for potential anti-infective drug discovery.
  • SMILES
    O=C1NC(CNC(/C(C)=C/C)=O)C(NC(CO)C(NC(C(C)C)C(NC(C(NC(C(C)O)C(NCC(O)C(NC1C(O)=O)=O)=O)=O)C(C(C(N)=O)O)O)=O)=O)=O.O=C2NC(CNC(C(C)CC)=O)C(NC(CO)C(NC(C(C)C)C(NC(C(NC(C(C)O)C(NCC(O)C(NC2C(O)=O)=O)=O)=O)C(C(C(N)=O)O)O)=O)=O)=O
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

References

  • Antibiotics GE23077, novel inhibitors of bacterial RNA polymerase. I. Taxonomy, isolation and characterization: I. Ciciliato, et al.; J. Antibiot. 57, 210 (2004)
  • Mode of action of the microbial metabolite GE23077, a novel potent and selective inhibitor of bacterial RNA polymerase: E. Sarubbi, et al.; Eur. J. Biochem. 271, 3146 (2004)
  • Antibiotics GE23077, novel inhibitors of bacterial RNA polymerase. II. Structure elucidation: A. Marazzi, et al.; J. Antibiot. 58, 260 (2005)
  • Antibiotics GE23077, novel inhibitors of bacterial RNA polymerase. Part 3: Chemical derivatization: R. Mariani, et al.; Bioorg. Med. Chem. Lett. 15, 3748 (2005)
  • GE23077 binds to the RNA polymerase 'i' and 'i+1' sites and prevents the binding of initiating nucleotides: Y. Zhang, et al.; Elife 3, e02450 (2014)