Synthesis, antibacterial and antiviral properties of curcumin bioconjugates bearing dipeptide, fatty acids and folic acid

Eur J Med Chem. 2010 Mar;45(3):1078-86. doi: 10.1016/j.ejmech.2009.12.002. Epub 2010 Jan 19.

Abstract

Curcumin bioconjugates, viz. di-O-tryptophanylphenylalanine curcumin (2), di-O-decanoyl curcumin (3), di-O-pamitoyl curcumin (4), di-O-bis-(gamma,gamma)folyl curcumin (6), C(4)-ethyl-O-gamma-folyl curcumin (8) and 4-O-ethyl-O-gamma-folyl curcumin (10) have been synthesized and tested for their antibacterial and antiviral activities. The conjugates 2, 3, 4, 6 and 8 have shown very promising antibacterial activity with MIC ranging between 0.09 and 0.67 microM against Gram-positive cocci and Gram-negative bacilli. Further, the conjugates 2, 3, 6, 8 and 10 have been screened for their antiviral activities against HSV, VSV, FIPV, PIV-3, RSV and FHV and the molecules 2 and 3 have shown good results with EC(50) 0.011 microM and 0.029 microM against VSV and FIPV/FHV, respectively. However, the molecules did not show expected results against HIV-1 III(B) and ROD strains in MTT assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Antiviral Agents* / chemical synthesis
  • Antiviral Agents* / chemistry
  • Antiviral Agents* / pharmacology
  • Bacteria / drug effects*
  • Cells, Cultured
  • Curcumin* / analogs & derivatives
  • Curcumin* / chemical synthesis
  • Curcumin* / pharmacology
  • Dipeptides* / chemical synthesis
  • Dipeptides* / chemistry
  • Fatty Acids* / chemical synthesis
  • Fatty Acids* / chemistry
  • Folic Acid* / chemical synthesis
  • Folic Acid* / chemistry
  • HIV-1 / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure

Substances

  • Anti-Bacterial Agents
  • Antiviral Agents
  • Dipeptides
  • Fatty Acids
  • Folic Acid
  • Curcumin