Precise cell elimination within intricate cellular populations is hampered by issues arising from the multifaceted biological properties of cells and the expansive reactivity of chemical agents. Current chemical platforms are often limited by their complexity, toxicity, and poor physical/chemical properties. Here, we report on the synthesis of a structurally versatile library of chemically tunable bisacylphosphane oxides (BAPOs), which harnesses the spatiotemporal precision of light delivery, thereby establishing a universal strategy for on-demand, precise cellular ablation and .
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Tailored Bisacylphosphane Oxides for Precise Induction of Oxidative Stress-Mediated Cell Death in Biological Systems.
ACS Chem Biol
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Max Planck Institute for the Science of Light, Staudtstr. 2, 91058 Erlangen, Germany.
Precise cell elimination within intricate cellular populations is hampered by issues arising from the multifaceted biological properties of cells and the expansive reactivity of chemical agents. Current chemical platforms are often limited by their complexity, toxicity, and poor physical/chemical properties. Here, we report on the synthesis of a structurally versatile library of chemically tunable bisacylphosphane oxides (BAPOs), which harnesses the spatiotemporal precision of light delivery, thereby establishing a universal strategy for on-demand, precise cellular ablation and .
View Article and Find Full Text PDFA General Strategy for Sustainable 3D Printing Based on A Multifunctional Photoinitiator.
Angew Chem Int Ed Engl
July 2024
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology (NJUST), Nanjing, 210094, China.
A multifunctional photoinitiator is presented, offering precise control over light-induced polymerization initiation at 450 nm and material degradation at 365 nm. This is accomplished by covalently linking photoactive bis(acyl)phosphane oxide and photocleavable o-nitrobenzyl ether moieties onto the surface of γ-cyclodextrin. Upon degradation, the resulting linear polymers can be easily re-dissolved in their corresponding monomer and re-cured, exhibiting superior mechanical properties compared to the pristine material.
View Article and Find Full Text PDFACTIVE-BAPO - A Versatile Transfer Agent for Photoactive Bis(acyl)phosphane Oxide Units.
Chemistry
May 2023
Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1-5/10, 8093, Zürich, Switzerland.
A N-hydroxy succinimide (NHS) ester substituted bis(acyl)phosphane oxide (ACTIVE-BAPO) was prepared by phospha-Michael addition and used for an easy one-step BAPO ligation with substrates containing primary amino groups, such as amino acids, proteins, and poly(amidoamine) (PAMAM) dendrimers. Thereby, a range of new molecular and polymeric photoinitators was obtained. Real-time photo-rheology experiments demonstrated the outstanding efficiency of the PAMAM BAPOs as photoinitiators for free radical polymerization.
View Article and Find Full Text PDFOrganocatalyzed Phospha-Michael Addition: A Highly Efficient Synthesis of Customized Bis(acyl)phosphane Oxide Photoinitiators.
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Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1-5/10, 8093, Zürich, Switzerland.
Addition of the P-H bond in bis(mesitoyl)phosphine, HP(COMes) (BAPH), to a wide variety of activated carbon-carbon double bonds as acceptors was investigated. While this phospha-Michael addition does not proceed in the absence of an additive or catalyst, excellent results were obtained with stoichiometric basic potassium or caesium salts. Simple amine bases can be employed in catalytic amounts, and tetramethylguanidine (TMG) in particular is an outstanding catalyst that allows the preparation of bis(acyl)phosphines, R-P(COMes) , under very mild conditions in excellent yields after only a short time.
View Article and Find Full Text PDFSynthesis of γ-cyclodextrin substituted bis(acyl)phosphane oxide derivative (BAPO-γ-CyD) serving as multiple photoinitiator and crosslinking agent.
Chem Commun (Camb)
April 2020
DISAT, Politecnico di Torino, Corso Duca degli Abruzzi 21, 10129 Torino, Italy.
A new multi-photoactive γ-cyclodextrin substituted bis(acyl)phosphane oxide derivative (BAPO-γ-CyD) was successfully prepared via a convergent synthesis using a phospha-Michael-addition, as confirmed by 1H-, 13C-, 31P-NMR and IR spectroscopy and mass spectrometry. Kinetic studies carried out by photo-DSC and photo-rheology demonstrated its outstanding efficiency as a photoinitiator for free-radical polymerization. Remarkably, it is found that BAPO-γ-CyD also acts as a crosslinking agent to convert monofunctional methacrylate monomers into self-standing thermosetting networks with extensive swelling capability in water.
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