PF-1163A

• CAT Number: R067087
• CAS Number: 258871-59-9
• Molecular Formula: C27H43NO6
• Molecular Weight: 477.6
• Purity: ≥95%
• Synonyms: (3S,10R,13S)-3-[[4-(2-hydroxyethoxy)phenyl]methyl]-13-[(2S)-2-hydroxypentyl]-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione
• Storage: -20°C
• InChI: 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
• InChIKey: SDBGPLZSWIQIOV-VQPAQMSKSA-N
• 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

PF-1163A (CAS 258871-59-9) is a depsipeptide antifungal isolated from Penicillium that inhibits ergosterol synthesis (IC50 = 12 ng/ml). 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. It inhibits growth of C. albicans (MIC = 8 µg/ml) but not of other Candida strains, A. fumigatus, or HepG2 cells. It also acts synergistically with fluconazole to reduce growth of azole-resistant C. albicans (MICs = 1 and 0.0078 µg/ml alone and in combination, respectively). PF-1163A is a more polar form of PF-1163B.

Reference

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, Toru, et al. "PF1163A and B, new antifungal antibiotics produced by Penicilium sp. II. Physico-chemical properties and structure elucidation." The Journal of antibiotics 53.1 (2000): 38-44.
3.Okabe, Miki, et al. "Macrolides from a marine-derived fungus, Penicillium meleagrinum var. viridiflavum, showing synergistic effects with fluconazole against azole-resistant Candida albicans." Journal of natural products 79.4 (2016): 1208-1212.