Fluorescent amino acid initiated de novo cyclic peptides for the label‐free assessment of cell permeability
| Autor: | James Rowley, Dhira Joshi, M. Teresa Bertran, Louise J. Walport, Ewen D. D. Calder, Yuteng Wu |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Fluorescence-lifetime imaging microscopy
Gene Expression Peptide Chemistry Medicinal RaPID Biochemistry 0305 Organic Chemistry chemistry.chemical_compound Drug Discovery Pharmacology & Pharmacy General Pharmacology Toxicology and Pharmaceutics Chemical Biology & High Throughput chemistry.chemical_classification Alanine Molecular Structure Chemistry Communication Optical Imaging Tryptophan cell permeability Fluorescence Cyclic peptide Amino acid Molecular Medicine 1115 Pharmacology and Pharmaceutical Sciences Sesquiterpenes Life Sciences & Biomedicine Intracellular Fluorophore Medicinal & Biomolecular Chemistry Immunology Biochemistry & Proteomics Peptides Cyclic label-free Azulenes Permeability fluorescence imaging Cell Line Tumor Humans Fluorescent Dyes Pharmacology Science & Technology 0304 Medicinal and Biomolecular Chemistry FOS: Clinical medicine Organic Chemistry Cell Biology Communications In vitro Biophysics peptides Structural Biology & Biophysics |
| Zdroj: | Chemmedchem |
| Popis: | The major obstacle in applying peptides to intracellular targets is their low inherent cell permeability. Standard approaches to attach a fluorophore (e. g. FITC, TAMRA) can change the physicochemical properties of the parent peptide and influence their ability to penetrate and localize in cells. We report a label‐free strategy for evaluating the cell permeability of cyclic peptide leads. Fluorescent tryptophan analogues 4‐cyanotryptophan (4CNW) and β‐(1‐azulenyl)‐L‐alanine (AzAla) were incorporated into in vitro translated macrocyclic peptides by initiator reprogramming. We then demonstrate these efficient blue fluorescent emitters are good tools for monitoring peptide penetration into cells. Without a trace: Fluorescent amino acids ClAc−4CNW, ClAc−AzAla were incorporated into in vitro translated macrocyclic peptides by genetic code reprogramming. The minimally perturbing dyes were found to be good tools for tracking peptide penetration into cells by fluorescence imaging and flow cytometry. |
| Databáze: | OpenAIRE |
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