First syntheses of melophlins P, Q, and R, and effects of melophlins on the growth of microorganisms and tumor cells

Chem Biodivers. 2008 Nov;5(11):2423-30. doi: 10.1002/cbdv.200890207.

Abstract

The marine tetramic acid (=1,5-dihydro-4-hydroxy-2H-pyrrol-2-ones) derivatives melophlin P, Q, and R (1p-1r, resp.) were synthesized for the first time in only four steps. Together with the congenerous melophlins A-C and G, they were also tested for antimicrobial and cytotoxic effects. Melophlins B, C, P, Q, and R, which share a 5-Me residue, showed some antibacterial activity, mainly in Gram-positive bacteria. Melophlins B, C, and R, which have Me-branched 3-acyl side chains in common, inhibited the growth of cells of human KB-3-1 cervix carcinoma, A-498 kidney carcinoma, and U-937 leukemia with IC(50) values <10 muM. They were similar in activity to cisplatin. Melophlin Q, also Me-branched, was astoundingly specific in inhibiting A-498 kidney cancer cells, while melophlin P inhibited U-937 leukemia cells particularly well. The position of the Me branch is decisive for the magnitude of the antiproliferative effect of the melophlin couples B/C and R/Q.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Humans
  • Inhibitory Concentration 50
  • Mice
  • Pyrrolidinones / chemical synthesis*
  • Pyrrolidinones / chemistry
  • Pyrrolidinones / pharmacology*
  • Tumor Cells, Cultured

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Pyrrolidinones