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Aphidicolin

(HB3690)
Data

Product overview

  • Name
    Aphidicolin
  • Short description
    DNA replication inhibitor. Useful for cell synchronization
  • Biological description

    Overview
    Aphidicolin is a potent DNA replication inhibitor which is often used to achieve cell synchronization.


    Mechanism

    Aphidicolin is a potent and specific inhibitor of B-family DNA polymerases and binds at or near the nucleotide-binding site. It prevents DNA polymerase-α from binding dNTPs without blocking the activity of DNA polymerase β or δ.


    Aphidicolin inhibits DNA replication and some forms of DNA repair. During cell culture, addition of aphidicolin induces cell cycle pause at the G1/S border. DNA synthesis stops in cells that have entered S-phase, while nondividing cells are unaffected.


    Uses
    Aphidicolin acts synergistically with vincristine and doxorubicin. In addition to its anti-mitotic effects, it exhibits antibiotic and antiviral activities.


  • Alternative names
    APC, APH, Aphidicoline, (+)-Aphidicolin, NSC234714, BRN4689958, ICI69653
  • Biological action
    Inhibitor
  • Purity
    >98%
  • Citations

Properties

  • Chemical name
    (3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol
  • Molecular Weight
    338.5
  • Chemical structure
    (+)-Aphidicolin [38966-21-1]
  • Molecular Formula
    C20H34O4
  • CAS Number
    38966-21-1
  • PubChem identifier
    457964
  • SMILES
    C[C@]12CC[C@H]([C@@]([C@@H]1CC[C@@H]3[C@@]24CC[C@@]([C@H](C3)C4)(CO)O)(C)CO)O
  • Source
    Isolated from Phoma sp. BS 7210
  • InChi
    InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
  • InChiKey
    NOFOAYPPHIUXJR-APNQCZIXSA-N
  • MDL number
    MFCD00083214
  • Appearance
    White to off-white solid

Storing and Using Your Product

  • Storage instructions
    +4°C
  • Solubility overview
    Soluble in DMSO (25 mM)
  • Handling
    This compound is light sensitive; exposure to light may affect compound performance. We therefore recommend storing the material in the dark and protecting from light. Do not store the material in solution; make up solutions and use immediately.
  • Important
    This product is for RESEARCH USE ONLY and is not intended for therapeutic or diagnostic use. Not for human or veterinary use.

References for Aphidicolin

  • Cell synchronization by inhibitors of DNA replication induces replication stress and DNA damage response: analysis by flow cytometry.

    Darzynkiewicz et al (2011) Methods Mol Biol. 761 : 85-96
    PubMedID: 21755443
  • Structural basis for inhibition of DNA replication by aphidicolin.

    Baranovskiy et al (2014) Nucleic Acids res. 42(22) : 14013-21
    PubMedID: 25429975
  • Aphidicolin inhibits the synthesis and joining of short DNA fragments but not the union of 10-kilobase DNA replication intermediates.

    Lonn et al (1983) Proc Natl Acad Sci U S A. 80(13) : 3996-9
    PubMedID: 6408640
  • Mechanism of DNA polymerase alpha inhibition by aphidicolin.

    Sheaff et al (1991) Biochemistry 30(35) : 8590-7
    PubMedID: 1909569
  • Inhibitor analysis of calf thymus DNA polymerases alpha, delta and epsilon.

    Wright et al (1994) FEBS lett. 341(1) : 128-30
    PubMedID: 8137912
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