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Bastadins, cyclic tetramers of brominated-tyrosine derivatives, selectively inhibit the proliferation of endothelial cells

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Abstract

Eight bastadins, tetramers of brominated-tyrosine derivatives, were isolated from the marine sponge Ianthella basta, and their anti-proliferative activities against endothelial cells were examined. A structure-activity relationship study of these compounds revealed that a macrocyclic structure was crucial, and a bastarane-type skeleton was important for the selective activity of these bastadins against endothelial cells. A conformational analysis of the bastadins was also carried out by molecular mechanics calculation.

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References

  1. Folkman J (1995) Clinical applications of research on angiogenesis. N Eng J Med 333:1757–1763

    Article  CAS  Google Scholar 

  2. Carmeliet P, Jain RK (2000) Angiogenesis in cancer and other disease. Nature 407:249–258

    Article  CAS  PubMed  Google Scholar 

  3. Folkman J, Shing Y (1992) Angiogenesis. J Biol Chem 267:10931–10934

    CAS  PubMed  Google Scholar 

  4. Aoki S, Cho S-H, Ono M, Kuwano T, Nakao S, Kuwano M, Nakagawa S, Gao J-Q, Mayumi T, Shibuya M, Kobayashi M (2006) Bastadin 6, a spongean brominated tyrosine derivative, inhibits tumor angiogenesis by inducing selective apoptosis to endothelial cells. Anti-Cancer Drugs 17:269–278

    Article  CAS  PubMed  Google Scholar 

  5. Kotoku N, Tsujita H, Hiramatsu A, Mori C, Koizumi N, Kobayashi M (2005) Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge. Tetrahedron 61:7211–7218

    Article  CAS  Google Scholar 

  6. Kazlaukas R, Lidgard RO, Murphy PT, Wells RJ, Blount JF (1981) Brominated tyrosine-derived metabolites from the sponge Ianthella basta. Aust J Chem 34:765–786

    Article  Google Scholar 

  7. Pordesimo EO, Schmitz FJ (1990) New bastadins from the sponge Ianthella basta. J Org Chem 55:4704–4709

    Article  CAS  Google Scholar 

  8. Butler MS, Lim TK, Capon RJ, Hammond LS (1991) The bastadins revisited: new chemistry from the Australian marine sponge Ianthella basta. Aust J Chem 44:287–296

    Article  CAS  Google Scholar 

  9. Mack MM, Molinski TF, Buck ED, Pessah IN (1994) Novel modulators of skeletal-muscle FKBP12 calcium-channel complex from Ianthella basta. J Biol Chem 269:23236–23249

    CAS  PubMed  Google Scholar 

  10. Chang G, Guida WC, Still WC (1989) An internal coordinate Monte-Carlo method for searching conformational space. J Am Chem Soc 111:4379–4386

    Article  CAS  Google Scholar 

  11. Halgren TA (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94*. J Comput Chem 17:490–519

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the Takeda Science Foundation and the Ministry of Education, Culture, Sports, Science, and Technology of Japan for financial support.

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan

    Shunji Aoki, Seok-hwan Cho, Atsushi Hiramatsu, Naoyuki Kotoku & Motomasa Kobayashi

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  1. Shunji Aoki
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  2. Seok-hwan Cho
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  3. Atsushi Hiramatsu
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  4. Naoyuki Kotoku
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  5. Motomasa Kobayashi
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Correspondence to Motomasa Kobayashi.

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Aoki, S., Cho, Sh., Hiramatsu, A. et al. Bastadins, cyclic tetramers of brominated-tyrosine derivatives, selectively inhibit the proliferation of endothelial cells . J Nat Med 60, 231–235 (2006). https://doi.org/10.1007/s11418-006-0045-3

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  • DOI: https://doi.org/10.1007/s11418-006-0045-3

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