Secreted protein profile from HepG2 cells incubated by S(−) and R(+) enantiomers of chiral drug warfarin – An analysis in cell‐based system and clinical samples

Bai, Jing; Ching, Chi Bun; Chowbay, Balram; Chen, Wei Ning

doi:10.1002/prca.201000027

Cited by 2 publications

(1 citation statement)

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“…Molecular chirality frequently plays an important role in many important areas, including the pharmaceutical, food and beverage and agrochemical industries, as well as the environment (Bai et al ., ; Kasprzyk‐Hordern, ). With the exception of glycine, the remaining 19 proteinogenic amino acids contain at least one chiral carbon atom, with isoleucine (Ile) and threonine also containing a second chiral carbon atom.…”

Section: Introductionmentioning

confidence: 99%

Structure‐guided RP‐HPLC chromatography of diastereomeric α‐helical peptide analogs substituted with single amino acid stereoisomers

Huang

Pan

Zhao

et al. 2013

Biomedical Chromatography

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An α-helical model peptide (Ac-EAEKAAKE-X-EKAAKEAEK-amide) was used as a template to examine the efficacy of conventional reversed-phase high-performance liquid chromatography (RP-HPLC) in separating peptide analogs with single substitutions (at position X) of diasteromeric amino acids Ile, allo-Ile, D-Ile and D-allo-Ile. We compared differences of peptide retention behavior on a C8 column and a C18 column at different temperatures. We demonstrated how subtle differences in peptide secondary structure affected by the different substitutions of amino acids with identical overall hydrophobicity enabled effective resolution of these peptide analogs. We also demonstrated the ability of RP-HPLC to separate Ile- and allo-Ile-substituted analogs of a 26-residue α-helical antimicrobial peptide (AMP), with the substitution site towards the C-terminus of the α-helix. These peptides show different values of antibacterial activity and hemolytic activity, and different selectivity against bacteria and human cells. Our results underline the ability of RP-HPLC to resolve even difficult diasteromeric peptide mixtures as well as its value in monitoring very subtle hydrophobicity changes in de novo-designed AMP.

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Section: Introductionmentioning

confidence: 99%