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Form Matters: Stable Helical Foldamers Preferentially Target Human Monocytes and Granulocytes
Author(s) -
Del Secco Benedetta,
Malachin Giulia,
Milli Lorenzo,
Zanicola,
Papini Emanuele,
Cornia Andrea,
Tavano Regina,
Tomasini Claudia
Publication year - 2017
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201600597
Subject(s) - chemistry , cell sorting , hela , fluorescence , stereochemistry , moiety , biocompatibility , amino acid , rhodamine , cell , biophysics , biochemistry , biology , organic chemistry , physics , quantum mechanics
Some hybrid foldamers of various length, all containing the (4 R ,5 S )‐4‐carboxy‐5‐methyloxazolidin‐2‐one ( d ‐Oxd) moiety alternating with an l ‐amino acid ( l ‐Val, l ‐Lys, or l ‐Ala), were prepared in order to study their preferred conformations and to evaluate their biological activity. Surprisingly, only the longer oligomers containing l ‐Ala fold into well‐established helices, whereas all the other oligomers give partially unfolded turn structures. Nevertheless, they all show good biocompatibility, with no detrimental effects up to 64 μ m . After equipping some selected foldamers with the fluorescent tag rhodamine B, a quantitative analysis was performed by dose– and time–response fluorescence‐activated cell sorting (FACS) assays with human HeLa cells and primary blood lymphocytes, granulocytes, and monocytes. Among the cell types analyzed, the oligomers associated with monocytes and granulocytes with greatest efficacy, still visible after 24 h incubation. This effect is even more pronounced for foldamers that are able to form stable helices.