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Synthesis of Pt IV ‐Biomolecule Conjugates through Click Chemistry
Author(s) -
Gabano Elisabetta,
Ravera Mauro,
Tinello Stefano,
Osella Domenico
Publication year - 2015
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201501066
Subject(s) - chemistry , click chemistry , combinatorial chemistry , conjugate , azide , dipeptide , cycloaddition , biomolecule , alkyne , solid phase synthesis , stereochemistry , organic chemistry , amino acid , peptide , catalysis , biochemistry , mathematical analysis , mathematics
Abstract The azide‐functionalized Pt IV complex {( OC ‐6–34)‐chlorido(cyclobutane‐1,1′‐dicarboxylato)(cyclohexane‐1 R ,2 R ‐diamine)[2‐hydroxyethyl(2‐{2‐[2‐(2‐azidoethoxy)ethoxy]ethoxy}ethyl)carbamate]platinum(IV)} was synthesized and characterized to obtain a starting complex that was suitable for coupling with appropriate biological carriers in a drug targeting and delivery strategy. The following click reaction (Cu I ‐catalyzed Huisgen cycloaddition, CuAAC) was successfully applied for coupling with three different model biomolecules that can be exploited for selective targeting of the platinum conjugate toward tumor cells; i.e., the amino acid alanine and the dipeptide lysine‐alanine, both previously alkyne‐functionalized with pent‐4‐ynoic acid, and the hormone 17α‐ethynylestradiol. The title complex demonstrated very good compatibility with both CuAAC reaction and solid‐phase peptide synthesis conditions, making it a suitable antiproliferative fragment for the design of nanovectors.