ArticleJournal of the American Chemical Society2016
Cell-Penetrating, Guanidinium-Rich Oligophosphoesters: Effective and Versatile Molecular Transporters for Drug and Probe Delivery.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 114 citations in OpenAlex.
- Dual-Functional Polyphosphoesters for Gene Delivery: Synergistic Effects of Guanidinium and Hydrophobic Side Chains in Degradable Polymers.Advanced healthcare materials · 2026Article
- Fine-Tuning Side Chain Substitutions: Impacts on the Lipophilicity-Solubility-Permeability Interplay in Macrocyclic Peptides.Marine drugs · 2025Article
- Ionizable guanidine-based lipid nanoparticle for targeted mRNA delivery and cancer immunotherapy.Science advances · 2025Article
- Synergistic Effects of Polycationic and Polyfluorinated Functionalities for Efficient Intracellular Protein Delivery.Biomacromolecules · 2025Article
- Bioactive fatty acid analog-derived hybrid nanoparticles confer antibody-independent chemo-immunotherapy against carcinoma.Journal of nanobiotechnology · 2023Article
- Intracellular delivery of therapeutic proteins. New advancements and future directions.Frontiers in bioengineering and biotechnology · 2023Review
- Accelerating the end-to-end production of cyclic phosphate monomers with modular flow chemistry.Chemical science · 2022Article
- Unraveling the Pivotal Role of Atropisomerism for Cellular Internalization.Journal of the American Chemical Society · 2022Article
- Covalent Labeling-Mass Spectrometry Provides a Molecular Understanding of Noncovalent Polymer-Protein Complexation.ACS biomaterials science & engineering · 2022Article
- Article
- Bioorthogonal Turn-On BODIPY-Peptide Photosensitizers for Tailored Photodynamic Therapy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Osteogenic Differentiation of Human Adipose Tissue-Derived MSCs by Non-Toxic Calcium Poly(ethylene phosphate)s.International journal of molecular sciences · 2019Article
- Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks.Angewandte Chemie (International ed. in English) · 2019Article
- Oligo(serine ester) Charge-Altering Releasable Transporters: Organocatalytic Ring-Opening Polymerization and their Use for in Vitro and in Vivo mRNA Delivery.Journal of the American Chemical Society · 2019Article
- Emerging transporter-targeted nanoparticulate drug delivery systems.Acta pharmaceutica Sinica. B · 2019Review
- Delivery of Inorganic Polyphosphate into Cells Using Amphipathic Oligocarbonate Transporters.ACS central science · 2018Article
- Cell Penetration, Herbicidal Activity, andHelvetica chimica acta · 2018Article
- Inhibit or Evade Multidrug Resistance P-Glycoprotein in Cancer Treatment.Journal of medicinal chemistry · 2018Review
- New tetrahydroisoquinoline-based P-glycoprotein modulators: decoration of the biphenyl core gives selective ligands.MedChemComm · 2018Article
- Efficient Delivery of Quantum Dots into the Cytosol of Cells Using Cell-Penetrating Poly(disulfide)s.Journal of the American Chemical Society · 2017Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The design, synthesis, and biological evaluation of a new family of highly effective cell-penetrating molecular transporters, guanidinium-rich oligophosphoesters, are described. These unique transporters are synthesized in two steps, irrespective of oligomer length, by the organocatalytic ring-opening polymerization (OROP) of 5-membered cyclic phospholane monomers followed by oligomer deprotection. Varying the initiating alcohol results in a wide variety of cargo attachment strategies for releasable or nonreleasable transporter applications. Initiation of oligomerization with a fluorescent probe produces, upon deprotection, a transporter-probe conjugate that is shown to readily enter multiple cell lines in a dose-dependent manner. These new transporters are superior in cell uptake to previously studied guanidinium-rich oligocarbonates and oligoarginines, showing over 2-fold higher uptake than the former and 6-fold higher uptake than the latter. Initiation with a protected thiol gives, upon deprotection, thiol-terminated transporters which can be thiol-click conjugated to a variety of probes, drugs and other cargos as exemplified by the conjugation and delivery of the model probe fluorescein-maleimide and the medicinal agent paclitaxel (PTX) into cells. Of particular significance given that drug resistance is a major cause of chemotherapy failure, the PTX-transporter conjugate, designed to evade Pgp export and release free PTX after cell entry, shows efficacy against PTX-resistant ovarian cancer cells. Collectively this study introduces a new and highly effective class of guanidinium-rich cell-penetrating transporters and methodology for their single-step conjugation to drugs and probes, and demonstrates that the resulting drug/probe-conjugates readily enter cells, outperforming previously reported guanidinium-rich oligocarbonates and peptide transporters.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.