Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

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Structure-Activity Relationship of Biakamide, Selective Growth Inhibitors under Nutrient-starved Condition from Marine Sponge
Ryosuke IshidaHirokazu MatsumotoSayaka IchiiMotomasa KobayashiMasayoshi AraiNaoyuki Kotoku
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JOURNAL FREE ACCESS Advance online publication

Article ID: c18-00587


The tumor microenvironment is considered as one of the important targets for anticancer drug discovery. In particular, nutrient deficiency may be observed in tumor microenvironment; biakamides A-D (1-4) isolated from marine sponge Petrosaspongia sp. as growth inhibitors against cancer cells adapted to glucose-deprived conditions have potential as new drugs and tools for elucidating adaptation mechanisms to these conditions. In this paper, we investigated structure-activity relationship (SAR) of biakamide to create easily accessible analog and gain insights about participation of the substructures to growth-inhibitory activity toward development of anticancer drug. This work revealed that 14,15-dinor-biakamide C (5), which is easily accessible, has similar activity to natural biakamide C (3). In addition, detailed SAR study showed the terminal acyl chain is important for interacting with target molecule and amide part including thiazole ring has acceptability to convert structures without losing activity.

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© 2018 The Pharmaceutical Society of Japan