Psammaplins from the Sponge Pseudoceratina purpurea: Inhibition of Both Histone Deacetylase and DNA Methyltransferase

Four novel bisulfide bromotyrosine derivatives, psammaplins E (9), F (10), G (11), and H (12), and two new bromotyrosine derivatives, psammaplins I (13) and J (14), were isolated from the sponge Pseudoceratina purpurea, along with known psammaplins A (4), B (6), C (7), and D (8) and bisaprasin (5)....

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Bibliographic Details
Published in:Journal of organic chemistry 2003-05, Vol.68 (10), p.3866-3873
Main Authors: PIñA, Ivette C., GAUTSCHI, Jeffrey T., WANG, Gui-Yang-Sheng, SANDERS, Miranda L., SCHMITZ, Francis J., FRANCE, Dennis, CORNELL-KENNON, Susan, SAMBUCETTI, Lidia C., REMISZEWSKI, Stacy W., PEREZ, Larry B., BAIR, Kenneth W., CREWS, Phillip
Format: Article
Language:English
Subjects:
Animals
Biological and medical sciences
Disulfides - chemistry
Disulfides - isolation & purification
Disulfides - pharmacology
DNA Modification Methylases - antagonists & inhibitors
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - isolation & purification
Enzyme Inhibitors - pharmacology
General pharmacology
Histone Deacetylase Inhibitors
Medical sciences
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Papua New Guinea
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Porifera - chemistry
Sulfuric Acid Esters - chemistry
Sulfuric Acid Esters - isolation & purification
Sulfuric Acid Esters - pharmacology
Tyrosine - analogs & derivatives
Tyrosine - chemistry
Tyrosine - isolation & purification
Tyrosine - pharmacology
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Summary:Four novel bisulfide bromotyrosine derivatives, psammaplins E (9), F (10), G (11), and H (12), and two new bromotyrosine derivatives, psammaplins I (13) and J (14), were isolated from the sponge Pseudoceratina purpurea, along with known psammaplins A (4), B (6), C (7), and D (8) and bisaprasin (5). The structures of psammaplins E (9) and F (10), which each contain an oxalyl group rarely found in marine organisms, were determined by spectroscopic analysis. Compounds 4, 5, and 10 are potent histone deacetylase inhibitors and also show mild cytotoxicity. Furthermore, compounds 4, 5, and 11 are potent DNA methyltransferase inhibitors. The biogenetic pathway previously proposed for the psammaplins class is also revisited.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034248t