title: Form Matters: Stable Helical Foldamers Preferentially Target Human Monocytes and Granulocytes.
abstract: Some hybrid foldamers of various length, all containing the (4R,5S)-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 μm. 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.
authors.affiliation: Dipartimento di Chimica Ciamician, Alma Mater Studiorum Università di Bologna, Via Selmi 2, 40126, Bologna, Italy.
authors.forename: Benedetta
authors.initials: B
authors.lastname: Del Secco
authors.affiliation: Dipartimento di Scienze Biomediche, Università di Padova, Viale G. Colombo 3, 35121, Padova, Italy.
authors.forename: Giulia
authors.initials: G
authors.lastname: Malachin
authors.affiliation: Dipartimento di Chimica Ciamician, Alma Mater Studiorum Università di Bologna, Via Selmi 2, 40126, Bologna, Italy.
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Milli
authors.affiliation: Dipartimento di Chimica Ciamician, Alma Mater Studiorum Università di Bologna, Via Selmi 2, 40126, Bologna, Italy.
authors.forename: Nicola
authors.initials: N
authors.lastname: Zanna
authors.affiliation: Dipartimento di Scienze Biomediche, Università di Padova, Viale G. Colombo 3, 35121, Padova, Italy.
authors.forename: Emanuele
authors.initials: E
authors.lastname: Papini
authors.affiliation: Dipartimento di Scienze Chimiche e Geologiche, Università di Modena e Reggio Emilia & INSTM, Via G. Campi 103, 41125, Modena, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Cornia
authors.affiliation: Dipartimento di Scienze Biomediche, Università di Padova, Viale G. Colombo 3, 35121, Padova, Italy.
authors.forename: Regina
authors.initials: R
authors.lastname: Tavano
authors.affiliation: Dipartimento di Chimica Ciamician, Alma Mater Studiorum Università di Bologna, Via Selmi 2, 40126, Bologna, Italy.
authors.forename: Claudia
authors.identifier: 0000-0002-6310-2704
authors.initials: C
authors.lastname: Tomasini
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D006098:Granulocytes / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D018613:Microscopy, Confocal; D008968:Molecular Conformation; D009000:Monocytes / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism; D034444:Peptoids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000596:Amino Acids; D001672:Biocompatible Materials; D034444:Peptoids
keywords: bioconjugates; conformational analysis; foldamers; leukocytes; peptides