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Isolation, Synthesis, and Biological Activity of Aphrocallistin, an Adenine-Substituted Bromotyramine Metabolite from the Hexactinellida Sponge Aphrocallistes beatrix

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Center for Marine Biomedical and Biotechnology Research, Harbor Branch Oceanographic Institute at Florida Atlantic University, 5600 US 1 North, Ft. Pierce, Florida 34946, and Burnham Institute for Medical Research at Lake Nona, Conrad Prebys Center for Chemical Genomics, 6400 Sanger Road, Orlando, Florida 32827
* To whom correspondence should be addressed. Isolation, tumor biology: Wright. Tel: 772-465-2400, ext 459. Fax: 772-461-2221. E-mail: [email protected]. Synthesis, pharmacology: Roth. Tel: 407-745-2062. Fax: 407-745-2001. E-mail: [email protected]
†Harbor Branch Oceanographic Institute at Florida Atlantic University.
‡Burnham Institute for Medical Research at Lake Nona.
Cite this: J. Nat. Prod. 2009, 72, 6, 1178–1183
Publication Date (Web):May 21, 2009
https://doi.org/10.1021/np900183v
Copyright © 2009 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    A new adenine-substituted bromotyrosine-derived metabolite designated as aphrocallistin (1) has been isolated from the deep-water Hexactinellida sponge Aphrocallistes beatrix. Its structure was elucidated on the basis of spectral data and confirmed through a convergent, modular total synthetic route that is amenable toward future analogue preparation. Aphrocallistin inhibits the growth of a panel of human tumor cell lines with IC50 values ranging from 7.5 to >100 μM and has been shown to induce G1 cell cycle arrest in the PANC-1 pancreatic carcinoma cell line. Aphrocallistin has been fully characterized in the NCI cancer cell line panel and has undergone in vitro ADME pharmacological profiling.

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    Copies of the 1H and 13C NMR spectra along with selected 2D NMR spectra (g-DQF-COSY, edited-g-HSQC, g-HMBC, g-NOESY) for the natural product; the 1H NMR spectrum and LC-MS analysis of synthetic aphrocallistin; details of preparation of compound 6; and details of the pharmacological testing are available free of charge via the Internet at http://pubs.acs.org.

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