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Synthetic and Immunological Studies on Clustered Modes of Mucin-Related Tn and TF O-Linked Antigens:  The Preparation of a Glycopeptide-Based Vaccine for Clinical Trials against Prostate Cancer

Kuduk, Scott D ; Schwarz, Jacob B ; Chen, Xiao-Tao ; Glunz, Peter W ; Sames, Dalibor ; Ragupathi, Govindaswami ; Livingston, Philip O ; Danishefsky, Samuel J

Journal of the American Chemical Society, 1998-12, Vol.120 (48), p.12474-12485 [Peer Reviewed Journal]

American Chemical Society

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  • Title:
    Synthetic and Immunological Studies on Clustered Modes of Mucin-Related Tn and TF O-Linked Antigens:  The Preparation of a Glycopeptide-Based Vaccine for Clinical Trials against Prostate Cancer
  • Author: Kuduk, Scott D ; Schwarz, Jacob B ; Chen, Xiao-Tao ; Glunz, Peter W ; Sames, Dalibor ; Ragupathi, Govindaswami ; Livingston, Philip O ; Danishefsky, Samuel J
  • Is Part Of: Journal of the American Chemical Society, 1998-12, Vol.120 (48), p.12474-12485
  • Notes: ark:/67375/TPS-SN4ZHR9N-C
    istex:B5A8AC55A074B09ACA47C753940EC4540F222F21
    Abbreviations:  BSA, bovine serum albumin; DAST, diethylaminosulfurtrifluoride; DIEA, diisopropylethylamine; ELISA, enzyme-linked immunosorbent assay; FMOC, fluorenylmethoxycarbonyl; GalNAc, N-acetylgalactosamine; IIDQ, 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihryoquinoline; HATU, O-(7-azabenzotriazol-1-yl)-N,N,N‘,N‘-tetramethyluronium hexafluorophosphate; KLH, keyhole limpet hemacyanin; pam, palmitoylcysteine; MBS, m-maleimimidobenzoyl-N-hydroxysuccinimide ester; NHS, N-hydroxysuccinimide; SAMA−OPfp, S-acetylthioglycolic pentafluorophenyl ester; TFA, trifluoroacetic acid; Tn(c), Tn cluster.
  • Description: The syntheses of two tumor-associated carbohydrate antigens, Tn and TF, have been achieved using glycal assembly and cassette methodologies. These synthetic antigens were subsequently clustered (c) and immunoconjugated to a carrier protein (KLH or BSA) or a synthetic lipopeptide (pam) for immunological study. Three Tn conjugates were used to vaccinate groups of mice, and all preparations proved to be immunogenic. The Tn(c) covalently linked to KLH (27−KLH) plus the adjuvant QS-21 was the optimal vaccine, inducing high median IgM and IgG titers against Tn(c) by ELISA. These antibodies were strongly reactive with the Tn(c) positive human colon cancer cell line LS-C but not the Tn(c) negative colon cancer cell line LS-B by FACS. The antibodies' reactivities with natural antigens were inhibited with synthetic Tn(c) but not with structurally unrelated compounds. On the basis of these results, vaccines containing 27−KLH and 30−pam plus QS-21 are being tested in patients with prostate cancer.
  • Publisher: American Chemical Society
  • Language: English
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