Cellular Phosphate Sensing and Anion Binding by an Azacrown‐Calixpyrrole Hybrid

Ray, Debmalya; Sartori, Austin R.; Radujević, Aco; George, Sandra M.; Postema, Rick; Tan, Xiaohong; Bryantsev, Vyacheslav S.; Anzenbacher, Jr., Pavel

doi:10.1002/chem.202401872

Title: Cellular Phosphate Sensing and Anion Binding by an Azacrown‐Calixpyrrole Hybrid

Journal Article · 16 October 2024 · Chemistry - A European Journal

DOI: https://doi.org/10.1002/chem.202401872 · OSTI ID:2472482

Ray, Debmalya ^[1]; Sartori, Austin R. ^[2]; Radujević, Aco ^[2]; George, Sandra M. ^[2]; Postema, Rick ^[2]; Tan, Xiaohong ^[2]; Bryantsev, Vyacheslav S. ^[1];

^[2]

Chemical Separations Group Oak Ridge National Laboratory Oak Ridge Tennessee USA
Chemistry Department Bowling Green State University Bowling Green Ohio USA

Abstract A hybrid receptor‐sensor for anions originating from the merging of positively charged ammonium moieties for electrostatic attraction/stronger binding of azacrowns with directionality of calixpyrrole hydrogen bond donors for selectivity is investigated. As demonstrated this hybrid receptor‐sensor shows a remarkable selectivity for orthophosphate even in the presence of other phosphates and anions found in cellular materials (K _assoc H ₂ PO ₄ ⁻ >H ₂ P ₂ O ₇ ²⁻ >AMP ⁻ ≫ADP ²⁻ or ATP ³⁻ over halides, nitrate, or hydrogen sulfate; all Na ⁺ salts in water) but also cellular polyphosphate or phospholipids. This selectivity is harnessed in a real‐time monitoring of cell lysis by lysozyme, which releases orthophosphate and other phosphates and anions from the cells. This sensitive (LOD 0.4 μM) fluorescence‐based microscale method compares favorably with the state‐of‐the‐art techniques but can easily be practiced in a high‐throughput screening (HTS) manner. The anion binding and selectivity in aqueous solutions were investigated by NMR and put in context with phosphate binding of the parent calix[4]pyrrole. The microscopic understanding of anion binding by the hybrid receptor was then obtained from a combination of density functional theory (DFT), classical molecular dynamics (MD) with explicit water solvation, and ab initio MD (AIMD) simulations. Correlating the NMR and fluorescence binding data with studies of solvation of the receptor, phosphate anion, and the resulting complex confirms the binding is largely driven by entropic component (TΔS) associated with receptor and anion desolvation.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 2472482

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 61 Vol. 30; ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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