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Structural analysis of bengamide derivatives as inhibitors of methionine aminopeptidases.

Xu W, Lu JP, Ye QZ
J Med Chem 55 8021-7 (2012)
Related entries: 4fli, 4flj, 4flk

Cited: 12 times
EuropePMC logo PMID: 22913487

Abstract

Natural-product-derived bengamides possess potent antiproliferative activity and target human methionine aminopeptidases (MetAPs) for their cellular effects. Several derivatives were designed, synthesized, and evaluated as MetAP inhibitors. Here, we present four new X-ray structures of human MetAP1 in complex with the inhibitors. Together with the previous structures of bengamide derivatives with human MetAP2 and tubercular MtMetAP1c, analysis of the interactions of these inhibitors at the active site provides structural basis for further modification of these bengamide inhibitors for improved potency and selectivity as anticancer and antibacterial therapeutics.

Articles - 4fll mentioned but not cited (1)

  1. Structural analysis of bengamide derivatives as inhibitors of methionine aminopeptidases. Xu W, Lu JP, Ye QZ. J Med Chem 55 8021-8027 (2012)


Reviews citing this publication (6)

  1. Marine-derived angiogenesis inhibitors for cancer therapy. Wang YQ, Miao ZH. Mar Drugs 11 903-933 (2013)
  2. Chemistry and biology of bengamides and bengazoles, bioactive natural products from Jaspis sponges. García-Ruiz C, Sarabia F. Mar Drugs 12 1580-1622 (2014)
  3. The Bengamides: A Mini-Review of Natural Sources, Analogues, Biological Properties, Biosynthetic Origins, and Future Prospects. White KN, Tenney K, Crews P. J Nat Prod 80 740-755 (2017)
  4. Marine Natural Products from New Caledonia--A Review. Motuhi SE, Mehiri M, Payri CE, La Barre S, Bach S. Mar Drugs 14 E58 (2016)
  5. Computational Approaches to Enzyme Inhibition by Marine Natural Products in the Search for New Drugs. Gago F. Mar Drugs 21 100 (2023)
  6. The Development of the Bengamides as New Antibiotics against Drug-Resistant Bacteria. Porras-Alcalá C, Moya-Utrera F, García-Castro M, Sánchez-Ruiz A, López-Romero JM, Pino-González MS, Díaz-Morilla A, Kitamura S, Wolan DW, Prados J, Melguizo C, Cheng-Sánchez I, Sarabia F. Mar Drugs 20 373 (2022)

Articles citing this publication (5)

  1. Decoding the Function of Expansion Segments in Ribosomes. Fujii K, Susanto TT, Saurabh S, Barna M. Mol Cell 72 1013-1020.e6 (2018)
  2. An array of bengamide E analogues modified at the terminal olefinic position: synthesis and antitumor properties. Martín-Gálvez F, García-Ruiz C, Sánchez-Ruiz A, Valeriote FA, Sarabia F. ChemMedChem 8 819-831 (2013)
  3. Novel reversible methionine aminopeptidase-2 (MetAP-2) inhibitors based on purine and related bicyclic templates. Heinrich T, Buchstaller HP, Cezanne B, Rohdich F, Bomke J, Friese-Hamim M, Krier M, Knöchel T, Musil D, Leuthner B, Zenke F. Bioorg Med Chem Lett 27 551-556 (2017)
  4. Design, synthesis and cytotoxicity of bengamide analogues and their epimers. Phi TD, Doan Thi Mai H, Tran VH, Truong BN, Tran TA, Vu VL, Chau VM, Pham VC. Medchemcomm 8 445-451 (2017)
  5. Bengamide Analogues Show A Potent Antitumor Activity against Colon Cancer Cells: A Preliminary Study. García-Pinel B, Porras-Alcalá C, Cabeza L, Ortiz R, Prados J, Melguizo C, Cheng-Sánchez I, López-Romero JM, Sarabia F. Mar Drugs 18 E240 (2020)


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