Synthesis and Biological Evaluation of Hapten‐Clicked Analogues of The Antigenic Peptide Melan‐A/MART‐1_26(27L)‐35

Abstract

Supporting information for this article is given via a link at the end of the document.

Peptide Vaccines in Melanoma: Chemical Approaches towards Improved Immunotherapeutic Efficacy

“…A derivative with an indole acetic acid sidechain resulted in an increased T cell response. In another study, a different side chain was introduced into this unit of ELA mimicking peptide using copper(I)-catalyzed azide-alkyne Huisgen 1,3-dipolar cycloaddition [ 89 ]. When the HLA-A2 binding activity and antigenicity of these new derivatives were compared, there was no correlation: the compound with weak binding ability was better recognized by T cells.…”

“…When the HLA-A2 binding activity and antigenicity of these new derivatives were compared, there was no correlation: the compound with weak binding ability was better recognized by T cells. These results demonstrate that the binding affinity to MHC I proteins does not predict the immunogenic potency [ 89 ].…”

Allylic and Retro‐Allylic Rearrangements upon Bromination of 8,9‐Substituted 4,4,6‐Trimethyl‐4H‐Pyrrolo[3,2,1‐ij]Quinoline‐1,2‐Diones. New Aspects and Synthetic Applications

“…One way to combine pharmacophoric elements is the functionalization of methyl groups associated with the heterocycle accompanied by the formation (or introduction) of reactive substituents and their subsequent interaction with the reaction centres of the second pharmacophore. This approach is used, in particular, in the selective bromination of various methylazaheterocycles (pyridine, pyrimidine, quinoline, and quinazoline) followed by the introduction of these bromomethyl derivatives into reactions with various N ‐, O ‐, S ‐, and C ‐nucleophiles [2a–j] …”

Fluorescence labeling of anchor‐modified Mart‐1 peptide for increasing its affinity for HLA‐A*0201: Hit two targets with one arrow

“…13 Since its discovery, many modifications have been made to it to obtain an analogous sequence that can effectively activate the immune system. [14][15][16] These researches led to anchor-modified decamer ELAGIGILTV (peptide 1 in Figure 2) that could bind to HLA-A*0201 molecules utmost strongly 17 and also vehemently stimulate the immune response by activating some T cells. 14 Peptide modification for increasing their binding strength to the HLA of interest and, consequently, creating immunogenicity is still a robust approach in developing peptide-based cancer vaccines.…”

“…Mart‐1 peptide (AAGIGILTV) was one of the first discovered epitope peptides related to melanoma cancer 13 . Since its discovery, many modifications have been made to it to obtain an analogous sequence that can effectively activate the immune system 14–16 . These researches led to anchor‐modified decamer ELAGIGILTV (peptide 1 in Figure 2) that could bind to HLA‐A*0201 molecules utmost strongly 17 and also vehemently stimulate the immune response by activating some T cells 14 .…”