Design and synthesis of potent Quillaja saponin vaccine adjuvants

J Am Chem Soc. 2010 Feb 17;132(6):1939-45. doi: 10.1021/ja9082842.

Abstract

The success of antitumor and antiviral vaccines often requires the use of an adjuvant, a substance that significantly enhances the immune response to a coadministered antigen. Only a handful of adjuvants have both sufficient potency and acceptable toxicity for clinical investigation. One promising adjuvant is QS-21, a saponin natural product that is the immunopotentiator of choice in many cancer and infectious disease vaccine clinical trials. However, the therapeutic promise of QS-21 adjuvant is curtailed by several factors, including its scarcity, difficulty in purification to homogeneity, dose-limiting toxicity, and chemical instability. Here, we report the design, synthesis, and evaluation of chemically stable synthetic saponins. These novel, amide-modified, non-natural substances exhibit immunopotentiating effects in vivo that rival or exceed that of QS-21 in evaluations with the GD3-KLH melanoma conjugate vaccine. The highly convergent synthetic preparation of these novel saponins establishes new avenues for discovering improved molecular adjuvants for specifically tailored vaccine therapies.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis*
  • Adjuvants, Immunologic / isolation & purification
  • Animals
  • Cell Line, Tumor
  • Drug Design*
  • Female
  • Mice
  • Mice, Inbred C57BL
  • Quillaja / chemistry*
  • Saponins / chemical synthesis*
  • Saponins / immunology*
  • Saponins / isolation & purification
  • Vaccines / immunology*

Substances

  • Adjuvants, Immunologic
  • Saponins
  • Vaccines