Preussin
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| Category | Antibiotics |
| Catalog number | BBF-03612 |
| CAS | 119463-16-0 |
| Molecular Weight | 317.51 |
| Molecular Formula | C21H35NO |
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Description
Preussin is extracted from Aspergillus ochraceus. It has the effect of anti-filamentous fungi and yeast, its antifungal spectrum is wider than anisomycin, and the activity is stronger than anisomycin.
Specification
| Synonyms | 3-Pyrrolidinol, 1-methyl-5-nonyl-2-(phenylemthyl)- |
| IUPAC Name | 2-benzyl-1-methyl-5-nonylpyrrolidin-3-ol |
| Canonical SMILES | CCCCCCCCCC1CC(C(N1C)CC2=CC=CC=C2)O |
| InChI | InChI=1S/C21H35NO/c1-3-4-5-6-7-8-12-15-19-17-21(23)20(22(19)2)16-18-13-10-9-11-14-18/h9-11,13-14,19-21,23H,3-8,12,15-17H2,1-2H3 |
| InChI Key | GBCXKHLKJHRTAB-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | fungi; yeast |
| Boiling Point | 432.1°C at 760 mmHg |
| Density | 0.967 g/cm3 |
Reference Reading
1. Addition of Lithium Anion of (Acetylmethylene)triphenylphosphorane to Nonracemic Sulfinimines: Total Synthesis of (+)-241D and Formal Total Synthesis of (+)-Preussin
Sopan P Khandare, Polimera Obula Reddy, Kavirayani R Prasad Org Lett. 2020 Sep 18;22(18):7273-7277. doi: 10.1021/acs.orglett.0c02608. Epub 2020 Aug 27.
The addition of lithium anion of (acetylmethylene)triphenylphosphorane to nonracemic sulfinimines was investigated. It was found that the addition proceeded with good diastereoselectivity and further reaction of the formed sulfinimidophosphorane with several aldehydes afforded the β-sulfinamido substituted enones in good yields. The resultant enones were elaborated to the synthesis of alkaloid (+)-241D, to the formal total synthesis of (+)-preussin, and to the synthesis of aminocyclopentenol.
2. Alkoxyallene-based syntheses of preussin and its analogs and their cytotoxicity
Arndt Hausherr, Gerhard Siemeister, Hans-Ulrich Reissig Org Biomol Chem. 2018 Dec 19;17(1):122-134. doi: 10.1039/c8ob02645a.
Short syntheses of oxa-preussin, racemic preussin and (-)-preussin are reported. Starting from a racemic 3-nonyl-substituted methoxyallene derivative, its lithiation and addition to phenylethanal provided the corresponding allenyl alcohol that was converted into two diastereomeric dihydrofuran derivatives by silver nitrate-catalyzed 5-endo-trig cyclization. The acid hydrolysis of the enol ether moiety gave heterocyclic ketones and subsequent highly stereoselective reductions with l-selectride furnished 2-benzyl-5-nonylfuran-3-ol derivatives in good overall yield. The major all-cis-diastereomer has the skeleton and relative configuration of preussin and is hence called oxa-preussin. An analogous sequence with the same allene, but an N-sulfonyl imine as the electrophile, finally led to racemic preussin. The stereoselectivities of the individual steps are discussed in detail. With an enantiopure 2-benzyl-5-nonylpyrrolidin-3-one intermediate the preparation of (-)-preussin with an enantiomeric ratio of >95 : 5 could be accomplished in a few steps. The sign of the optical rotation of this product finally proved the absolute configurations of its precursors and demonstrated that our chiral auxiliary-based route led to the antipode of the natural product. The cytotoxicity of several of the prepared heterocycles against MCF-7 tumor cells was investigated and five compounds, including racemic and enantiopure (-)-preussin, were identified as highly cytotoxic with IC50 values in the range of 3-6 μM.
3. Cytotoxic and Antiproliferative Effects of Preussin, a Hydroxypyrrolidine Derivative from the Marine Sponge-Associated Fungus Aspergillus candidus KUFA 0062, in a Panel of Breast Cancer Cell Lines and Using 2D and 3D Cultures
Fernanda Malhão, Alice A Ramos, Suradet Buttachon, Tida Dethoup, Anake Kijjoa, Eduardo Rocha Mar Drugs. 2019 Jul 30;17(8):448. doi: 10.3390/md17080448.
Preussin, a hydroxyl pyrrolidine derivative isolated from the marine sponge-associated fungus Aspergillus candidus KUFA 0062, displayed anticancer effects in some cancer cell lines, including MCF7. Preussin was investigated for its cytotoxic and antiproliferative effects in breast cancer cell lines (MCF7, SKBR3, and MDA-MB-231), representatives of major breast cancers subtypes, and in a non-tumor cell line (MCF12A). Preussin was first tested in 2D (monolayer), and then in 3D (multicellular aggregates), cultures, using a multi-endpoint approach for cytotoxicity (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), resazurin and lactate dehydrogenase (LDH)) and proliferative (5-bromo-2'-deoxyuridine (BrdU)) assays, as well as the analysis of cell morphology by optical/electron microscopy and immunocytochemistry for caspase-3 and ki67. Preussin affected cell viability and proliferation in 2D and 3D cultures in all cell lines tested. The results in the 3D culture showed the same tendency as in the 2D culture, however, cells in the 3D culture were less responsive. The effects were observed at different concentrations of preussin, depending on the cell line and assay method. Morphological study of preussin-exposed cells revealed cell death, which was confirmed by caspase-3 immunostaining. In view of the data, we recommend a multi-endpoint approach, including histological evaluation, in future assays with the tested 3D models. Our data showed cytotoxic and antiproliferative activities of preussin in breast cancer cell lines in 2D and 3D cultures, warranting further studies for its anticancer potential.
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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 ╳
