PF-1163A
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| Category | Antibiotics |
| Catalog number | BBF-03533 |
| CAS | 258871-59-9 |
| Molecular Weight | 477.6 |
| Molecular Formula | C27H43NO6 |
| Purity | ≥95% |
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Description
PF-1163A is an antibiotic isolated from Penicillium species. It exhibits growth inhibitory activity against pathogenic fungal strain Candida albicans and inhibits the ergosterol biosynthesis in Candida albicans.
Specification
| Synonyms | (3S,10R,13S)-3-[[4-(2-Hydroxyethoxy)phenyl]methyl]-13-[(2S)-2-hydroxypentyl]-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione |
| Canonical SMILES | CCCC(CC1CCC(CCCCC(=O)N(C(C(=O)O1)CC2=CC=C(C=C2)OCCO)C)C)O |
| 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 |
| InChI Key | SDBGPLZSWIQIOV-VQPAQMSKSA-N |
Properties
| Appearance | Oil |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 684.6±50.0 °C at 760 mmHg |
| Density | 1.1±0.1 g/cm3 |
Reference Reading
1. PF1163A and B, new antifungal antibiotics produced by Penicillium sp. II. Physico-chemical properties and structure elucidation
T Usui, K Tatsuta, S Takano, T Watanabe, A Hosoya, T Sasaki, H Nose, M Kawaguchi, S Yoshida, Y Ohtsuka, T Shomura J Antibiot (Tokyo) . 2000 Jan;53(1):38-44. doi: 10.7164/antibiotics.53.38.
The structures of new antifungal antibiotics, PF1163A and B, were elucidated by spectroscopic analyses of the degradation products and by X-ray crystallography of the de-2-hydroxyethyl derivative of PF1163B. Both antibiotics consist of a 13-membered macrocyclic structure containing a derivative of N-methyl tyrosine and a hydroxy fatty acid. PF1163A differs from PF 1163B by having an additional hydroxyl group on the side chain.
2. PF1163A and B, new antifungal antibiotics produced by Penicillium sp. I. Taxonomy of producing strain, fermentation, isolation and biological activities
S Hoshiko, A Hosoya, A Seki, H Nose, T Sasaki, T Shomura, T Yaguchi J Antibiot (Tokyo) . 2000 Jan;53(1):33-7. doi: 10.7164/antibiotics.53.33.
Two novel antifungal antibiotics, PF1163A and B, were isolated from the fermentation broth of Penicillium sp. They were purified from the solid cultures of rice media using ethyl acetate extraction, silica gel and Sephadex LH-20 column chromatographies. PF1163A and B showed potent growth inhibitory activity against pathogenic fungal strain Candida albicans but did not show cytotoxic activity against mammalian cells. These compounds inhibited the ergosterol biosynthesis in Candida albicans.
3. PF1163A, a novel antifungal agent, inhibit ergosterol biosynthesis at C-4 sterol methyl oxidase
Hideki Fushimi, Asako Seki, Shigeru Hoshiko, Hiroomi Watabe, Toru Sasaki, Hiroshi Nose J Antibiot (Tokyo) . 2002 Nov;55(11):969-74. doi: 10.7164/antibiotics.55.969.
PF1163A and B are a pair of antifungal agents isolated from a fermentation broth of Penicillium sp. PF1163A inhibited ergosterol synthesis in Saccharomyces cerevisiae, resulting in an accumulation of 4,4-dimethylzymosterol and a decrease of ergosterol. The ERG25 strain overexpressing the ERG25 gene was resistant to PF1163A. ERG25p is a C-4 sterol methyl oxidase known to be essential for the viability of yeast and fungi because of the known role of ERG25 gene disruption in S. cerevisiae-led lethality. ERG25p is the enzyme responsible for the first step in the removal of the two methyl groups at the C-4 position of sterol. From the results obtained here, we conclude that PF1163A is a novel natural antifungal that inhibits C-4 sterol methyl oxidase.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
