Biocatalytic and semisynthetic optimization of the anti-invasive tobacco (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol
Autor: | Anne Hebert, Danielle Bagaley, Anbalagan Muralidharan, Khalid A. El Sayed, Surat Laphookhieo, Frederick A. Rainey, Girish V. Shah, Shibu Thomas, Muhammad Yousaf, Hany N. Baraka |
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Rok vydání: | 2007 |
Předmět: |
Male
Stereochemistry Bioconversion Clinical Biochemistry Diol Pharmaceutical Science Antineoplastic Agents Bacillus Biochemistry chemistry.chemical_compound Structure-Activity Relationship Cell Line Tumor Drug Discovery Tobacco Animals Humans Neoplasm Invasiveness Molecular Biology Natural product biology Negombata magnifica Organic Chemistry Prostatic Neoplasms biology.organism_classification Semisynthesis Terpenoid Porifera chemistry Biocatalysis Molecular Medicine Diterpenes Drug Screening Assays Antitumor Bacteria |
Zdroj: | Bioorganicmedicinal chemistry. 16(6) |
ISSN: | 1464-3391 |
Popis: | Tobacco cembranoids were reported to inhibit tumorigenesis. Biocatalysis of (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (1) using the symbiotic Bacillus sp. NC5, Bacillus sp. NK8, and Bacillus sp. NK7, isolated from the Red Sea sponge Negombata magnifica, afforded two new and four known hydroxylated metabolites 3-8. The use of symbiotic marine bacteria as biocatalysts for bioactive natural product scaffolds is very rare. Cembranoid 1 carbamate analogs 9-11 were prepared by its reaction with corresponding isocyanates. Cembranoid 1 and its bioconversion and carabamate products show anti-invasive activity against the human highly metastatic prostate PC-3M cancer cell line at 10-50 nM doses in Matrigel assay. |
Databáze: | OpenAIRE |
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