• Carbenicillin disodium, USP packaged and labeled.

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SKU: C126

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Description

Carbenicillin Disodium, USP is a carboxypenicillin antibiotic routinely used for gene selection.  The compound interferes with peptidoglycan synthesis, thus it can also be used to study the role of penicillin-sensitive transpeptidases in the formation of cell walls.  The carboxycillins are susceptible to degradation by beta-lactamase enzymes.  The compound is water-soluble.

Carbenicillin Disodium USP conforms to United States Pharmacopoeia specifications.

    CAS Number

    4800-94-6

    Molecular Formula

    C17H16N2Na2O6S

    Molecular Weight

    422.36 g/mol

    Mechanism of Action

    Carbenicillin interferes with PBP (penicillin binding protein) activity involved in the final phase of peptidoglycan synthesis. PBP’s are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to β-lactams is commonly due to cells containing plasmid encoded β-lactamases.

    Storage Conditions

    -20°C

    Tariff Code

    2941.10.5000

    Spectrum

    The activity of carbenicillin is limited to primarily Gram-negative bacteria including Pseudomonas aeruginosa and common enteric bacteria.

Applications

    Microbiology Applications

    Carbenicillin disodium is often used to select for cells that have been transformed with a plasmid containing the ampR gene which confers resistance to ampicillin and carbenicillin. Carbenicillin disodium can be substituted for ampicillin sodium for better stability and to avoid formation of satellite colonies.

    Carbenicillin disodium is a preferred alternative to ampicillin due to its increased stability in the presence of heat and low pH environments. Substituting carbenicillin disodium for ampicillin also reduces the risk of satellite colonies appearing on growth media during extended periods of incubation.

    Plant Biology Applications

    Carbenicillin Disodium, USP is routinely used in Agrobacterium mediated transformation protocols to select for resistant Agrobacterium and transformed plants. Carbenicillin disodium demonstrates low toxicity to plant tissues.

    RNA-guided genome editing using the CRISPR/Cas9 system was used with tobacco protoplasts and whole-plant transformation. Using multiplexing gRNA, Two genes (NtPDS and NtPDR6) were mutated and transgenic tobacco plants with successfully obtained containing both mutations (Gao et al, 2015).

Specifications

    Form

    Powder

    Appearance

    White or off-white powder

    Source

    Semi-synthetic

    Water Content (Karl Fischer)

    ≤6.0%

    Potency (on a dry basis)

    ≥770 µg/mg

    pH

    6.5-8.0

References

    References

    Bourhis E, Hymowitz SG and Cochran AG (2007). The mitotic regulator Survivin binds as a monomer to its functional interactor Borealin. J. Biol. Chem 282(48):35018-35023 PMID 17881355

    Bush K and Bradford PA (2016) B-Lactams and B-Lactamase inhibitors: An overview. Cold Spring Harb.Perspect. Med 6(8): pii: a025247 PMID 27329032

    Gao J et al (2015) CRISPR/Cas9-mediated targeted mutagenesis in Nicotiana tabacum. Plant Mol. Biol 87(1):99-110 PMID 25344637

    Matsuda N, Isuzugawa K, Gao M, Takshina T and Nishimura K. (2004)  Development of Agrobacterium-mediated transformation system in pear cultivars with low-regeneration Frequency. Hortsci. 39(4)

    Pitout JD, Sanders CC, Sanders WE (1997) Antimicrobial resistance with focus on beta-lactam resistance in gram-negative bacilli. Am J Med 103:51-59 PMID 9236486

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