141743-15-9Relevant articles and documents
Peptide/peptoid hybrid oligomers: The influence of hydrophobicity and relative side-chain length on antibacterial activity and cell selectivity
Frederiksen, Nicki,Hansen, Paul R.,Bj?rkling, Fredrik,Franzyk, Henrik
, (2019/12/26)
Previous optimisation studies of peptide/peptoid hybrids typically comprise comparison of structurally related analogues displaying different oligomer length and diverse side chains. The present work concerns a systematically constructed series of 16 closely related 12-mer oligomers with an alternating cationic/hydrophobic design, representing a wide range of hydrophobicity and differences in relative side-chain lengths. The aim was to explore and rationalise the structure-activity relationships within a subclass of oligomers displaying variation of three structural features: (i) cationic side-chain length, (ii) hydrophobic side-chain length, and (iii) type of residue that is of a flexible peptoid nature. Increased side-chain length of cationic residues led to reduced hydrophobicity till the side chains became more extended than the aromatic/hydrophobic side chains, at which point hydrophobicity increased slightly. Evaluation of antibacterial activity revealed that analogues with lowest hydrophobicity exhibited reduced activity against E. coli, while oligomers with the shortest cationic side chains were most potent against P. aeruginosa. Thus, membrane-disruptive interaction with P. aeruginosa appears to be promoted by a hydrophobic surface of the oligomers (comprised of the aromatic groups shielding the cationic side chains). Peptidomimetics with short cationic side chains exhibit increased hemolytic properties as well as give rise to decreased HepG2 (hepatoblastoma G2 cell line) cell viability. An optimal hydrophobicity window could be defined by a threshold of minimal hydrophobicity conferring activity toward E. coli and a threshold for maximal hydrophobicity, beyond which cell selectivity was lost.
Convergent strategies for the attachment of fluorescing reporter groups to peptide nucleic acids in solution and on solid phase
Seitz, Oliver,Koehler, Olaf
, p. 3911 - 3925 (2007/10/03)
The site-selective conjugation of peptide nucleic acids (PNA) with fluorescent reporter groups is essential for the construction of hybridisation probes that can report the presence of a particular DNA sequence. This paper describes convergent methods for
Liquid-phase synthesis of polyamide nucleic acids (PNA)
Di Giorgio, Christophe,Pairot, Sandrine,Schwergold, Caroline,Patino, Nadia,Condom, Roger,Farese-Di Giorgio, Audrey,Guedj, Roger
, p. 1937 - 1958 (2007/10/03)
Three liquid-phase processes for the elaboration of short orthogonally protected PNA have been devised. Two of these methods are similar to the convergent and divergent approaches in peptide synthesis. The third process consists in building a fully protected polyamide backbone, by using as many different and orthogonal protecting groups as there are different types of nucleic bases in the targeted polyPNA. Simultaneous and selective cleavage of one kind of protecting group allows the simultaneous attachment of several identical nucleobase units.
