New muramyl dipeptide (MDP) mimics without the carbohydrate moiety as potential adjuvant candidates for a therapeutic hepatitis B vaccine (HBV)

A series of new muramyl dipeptide (MDP) mimics were designed and synthesized via a solid-phase synthetic route. Their adjuvant activities were evaluated ex vivo for investigation of the synergism of the S 28–39 peptide, which is an MHC class I binding epitope of recombinant hepatitis B surface antig...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2011-07, Vol.21 (14), p.4292-4295
Hauptverfasser:	Zhao, Nan, Ma, Yao, Zhang, Shengmei, Fang, Xin, Liang, Zhenglun, Liu, Gang
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetylmuramyl-Alanyl-Isoglutamine - chemical synthesis Acetylmuramyl-Alanyl-Isoglutamine - chemistry Acetylmuramyl-Alanyl-Isoglutamine - immunology Adjuvanticity Adjuvants Adjuvants, Immunologic Amino Acid Sequence Animals Carbohydrates Carbohydrates - chemistry chemistry Epitopes HBV hepatitis B hepatitis B antigens Hepatitis B surface antigen Hepatitis B Surface Antigens - chemistry Hepatitis B Surface Antigens - genetics Hepatitis B Surface Antigens - metabolism Hepatitis B Vaccines - immunology Hepatitis B virus humans Major histocompatibility complex MDP mimics Mice Mice, Inbred BALB C muramyl dipeptide Recombinant Proteins - chemistry Recombinant Proteins - genetics Recombinant Proteins - metabolism screening Solid-phase synthesis Structure-Activity Relationship synergism Vaccines
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Beschreibung
Zusammenfassung:	A series of new muramyl dipeptide (MDP) mimics were designed and synthesized via a solid-phase synthetic route. Their adjuvant activities were evaluated ex vivo for investigation of the synergism of the S 28–39 peptide, which is an MHC class I binding epitope of recombinant hepatitis B surface antigen (HBsAg) for both humans and mice. Several compounds without the carbohydrate moiety exerted better adjuvanticity than the MDP-C that has been reported by our laboratory previously. A primary screening test revealed that compounds 6, 14 and 16 exhibited stronger adjuvanticity compared with other MDP mimics.
ISSN:	0960-894X 1464-3405 1464-3405
DOI:	10.1016/j.bmcl.2011.05.056