A depsipeptide antifungal
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PF-1163A

Item No. 22065

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,10R,13S)-3-[[4-(2-hydroxyethoxy)phenyl]methyl]-13-[(2S)-2-hydroxypentyl]-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione
CAS Number
258871-59-9
Molecular Formula
C27H43NO6
Formula Weight
477.6
Purity
≥95%
Formulation (Request formulation change)
An oil
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C(N(C)[C@H]1CC2=CC=C(OCCO)C=C2)CCCC[C@@H](C)CC[C@@H](C[C@@H](O)CCC)OC1=O
InChi Code
InChI=1S/C27H43NO6/c1-4-7-22(30)19-24-13-10-20(2)8-5-6-9-26(31)28(3)25(27(32)34-24)18-21-11-14-23(15-12-21)33-17-16-29/h11-12,14-15,20,22,24-25,29-30H,4-10,13,16-19H2,1-3H3/t20-,22+,24+,25+/m1/s1
InChi Key
SDBGPLZSWIQIOV-VQPAQMSKSA-N
Origin
Fungus/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    500 µg

    $248

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    2.5 mg

    $1,052

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    Product Description

    PF-1163A is a depsipeptide antifungal isolated from Penicillium that inhibits ergosterol synthesis (IC50 = 12 ng/ml).1,2 In S. cerevisiae transfected with ERG biosynthesis genes, PF-1163 inhibits ERG25p, a C-4 methyl oxidase in the ERG biosynthetic pathway, with a MIC value of 12.5 µg/ml, while a strain overexpressing ERG25p is resistant.3 It inhibits growth of C. albicans (MIC = 8 µg/ml) but not of other Candida strains, A. fumigatus, or HepG2 cells.1 It also acts synergistically with fluconazole (Item No. 11594) to reduce growth of azole-resistant C. albicans (MICs = 1 and 0.0078 µg/ml alone and in combination, respectively).4 PF-1163A is a more polar form of PF-1163B (Item No. 22066).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nose, H., Seki, A., Yaquchi, T., et al. PF1163A and B, new antifungal antibiotics produced by Penicillium sp. I. Taxonomy of producing strain, fermentation, isolation and biological activities. J. Antibiot. (Tokyo) 53(1), 33-37 (2000).

    2. Sasaki, T., Nose, H., Hosoya, A., et al. PF1163A and B, new antifungal antibiotics produced by Penicillium sp. II. Physico-chemical properties and structure elucidation. J. Antibiot. (Tokyo) 53(1), 38-44 (2000).

    3. Nose, H., Fushimi, H., Seki, A., et al. PF1163A, a novel antifungal agent, inhibit ergosterol biosynthesis at C-4 sterol methyl oxidase. J. Antibiot. (Tokyo) 55(11), 969-974 (2002).

    4. Okabe, M., Sugita, T., Kinoshita, K., et al. Macrolides from a marine-derived fungus, Penicillium meleagrinum var. viridiflavum, showing synergistic effects with fluconazole against azole-resistant Candida albicans. J. Nat. Prod. 79(4), 1208-1212 (2016).