Syntheses and Immunological Evaluation of Self-Adjuvanting Clustered N-Acetyl and N-Propionyl Sialyl-Tn Combined with a T-helper Cell Epitope as Antitumor Vaccine Candidates

Tsung Che Chang, Yoshiyuki Manabe, Yukari Fujimoto, Shino Ohshima, Yoshie Kametani, Kazuya Kabayama, Yuka Nimura, Chun Cheng Lin, Koichi Fukase

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Sialyl-Tn (STn) is a tumor-associated carbohydrate antigen (TACA) rarely observed on healthy tissues. We synthesized two fully synthetic N-acetyl and N-propionyl STn trimer (triSTn) vaccines possessing a T-helper epitope and a TLR2 agonist, since the clustered STn antigens are highly expressed on many cancer cells. Immunization of both vaccines in mice induced the anti-triSTn IgG antibodies, which recognized triSTn-expressing cell lines PANC-1 and HepG2. The N-propionyl triSTn vaccine induced the triSTn-specific IgGs, while IgGs induced by the N-acetyl triSTn vaccine were less specific. These results illustrated that N-propionyl triSTn is a valuable unnatural TACA for anticancer vaccines.

Original languageEnglish
Pages (from-to)8219-8224
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number27
DOIs
Publication statusPublished - 2018 Jul 2

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Epitopes
Vaccines
Antigens
Tumor-Associated Carbohydrate Antigens
Carbohydrates
Tumors
Cells
Immunization
Antibodies
Tissue

Keywords

  • adjuvants
  • antigens
  • cancer vaccines
  • carbohydrates
  • sialyl-Tn

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Syntheses and Immunological Evaluation of Self-Adjuvanting Clustered N-Acetyl and N-Propionyl Sialyl-Tn Combined with a T-helper Cell Epitope as Antitumor Vaccine Candidates. / Chang, Tsung Che; Manabe, Yoshiyuki; Fujimoto, Yukari; Ohshima, Shino; Kametani, Yoshie; Kabayama, Kazuya; Nimura, Yuka; Lin, Chun Cheng; Fukase, Koichi.

In: Angewandte Chemie - International Edition, Vol. 57, No. 27, 02.07.2018, p. 8219-8224.

Research output: Contribution to journalArticle

Chang, Tsung Che ; Manabe, Yoshiyuki ; Fujimoto, Yukari ; Ohshima, Shino ; Kametani, Yoshie ; Kabayama, Kazuya ; Nimura, Yuka ; Lin, Chun Cheng ; Fukase, Koichi. / Syntheses and Immunological Evaluation of Self-Adjuvanting Clustered N-Acetyl and N-Propionyl Sialyl-Tn Combined with a T-helper Cell Epitope as Antitumor Vaccine Candidates. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 27. pp. 8219-8224.
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