Utilizing an Amino Acid Scaffold to Construct Heteroditopic Receptors Capable of Interacting with Salts Under Interfacial Conditions

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2021 Oct 13

PMID 34639095

Authors

Damian Jagleniec

Natalia Walczak

Lukasz Dobrzycki

Jan Romanski

Affiliations

Soon will be listed here.

Abstract

A 4-nitro-L-phenylalanine scaffold was used to construct effective ion pair receptors capable of binding anions in an enhanced manner with the assistance of alkali metal cations. A benzocrown ether was linked to a receptor platform the amide function so as to support the squaramide function in anion binding and to allow all three NHs to act simultaneously. The binding properties of the receptors were determined using UV-vis, H NMR, 2D NMR, and DOSY spectroscopy in MeCN and in the solid state by X-ray measurements. Ion pair receptor was found to interact with the most strongly with salts, and the removal of its key structural elements was shown to hinder the receptor action. The amide proton was recognized to switch from having involvement in an intramolecular hydrogen bond to interacting with anions upon complexation. Apart from carboxylates, which promote deprotonation, and other monovalent salts creating 1:1 complexes with the receptor, more complex equilibria were established upon the complexation of with sulfates. Receptor was shown to be capable of the extraction of ion pairs from the aqueous to organic phase and of the cation-enhanced transport chloride and sulfate anions across a bulk chloroform membrane. These features may open the door for its use in regulating ion concertation under interfacial conditions and acting as a potential drug to treat channelopathies.

References

Zaleskaya M, Karbarz M, Wilczek M, Dobrzycki L, Romanski J . Cooperative Transport and Selective Extraction of Sulfates by a Squaramide-Based Ion Pair Receptor: A Case of Adaptable Selectivity. Inorg Chem. 2020; 59(18):13749-13759. PMC: 7509838. DOI: 10.1021/acs.inorgchem.0c02114. View

Zwicker V, Yuen K, Smith D, Ho J, Qin L, Turner P . Deltamides and Croconamides: Expanding the Range of Dual H-bond Donors for Selective Anion Recognition. Chemistry. 2017; 24(5):1140-1150. DOI: 10.1002/chem.201704388. View

Davis J, Gale P, Quesada R . Advances in anion transport and supramolecular medicinal chemistry. Chem Soc Rev. 2020; . DOI: 10.1039/c9cs00662a. View

Mungalpara D, Valkonen A, Rissanen K, Kubik S . Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties. Chem Sci. 2017; 8(9):6005-6013. PMC: 5621005. DOI: 10.1039/c7sc02700a. View

Powers F . The role of chloride in acid-base balance. J Intraven Nurs. 2000; 22(5):286-91. View

Kubik S . Anion Recognition in Aqueous Media by Cyclopeptides and Other Synthetic Receptors. Acc Chem Res. 2017; 50(11):2870-2878. DOI: 10.1021/acs.accounts.7b00458. View

Dungan V, Ngo H, Young P, Jolliffe K . High affinity sulfate binding in aqueous media by cyclic peptides with thiourea arms. Chem Commun (Camb). 2012; 49(3):264-6. DOI: 10.1039/c2cc37686e. View

Guo C, Sedgwick A, Hirao T, Sessler J . Supramolecular Fluorescent Sensors: An Historical Overview and Update. Coord Chem Rev. 2021; 427. PMC: 8184024. DOI: 10.1016/j.ccr.2020.213560. View

Marti I, Rubio J, Bolte M, Isabel Burguete M, Vicent C, Quesada R . Tuning chloride binding, encapsulation, and transport by peripheral substitution of pseudopeptidic tripodal small cages. Chemistry. 2012; 18(52):16728-41. DOI: 10.1002/chem.201202182. View

10.

Bartl J, Reinke L, Koch M, Kubik S . Selective sensing of sulfate anions in water with cyclopeptide-decorated gold nanoparticles. Chem Commun (Camb). 2020; 56(72):10457-10460. DOI: 10.1039/d0cc04796a. View

11.

Elmes R, Jolliffe K . Anion recognition by cyclic peptides. Chem Commun (Camb). 2015; 51(24):4951-68. DOI: 10.1039/c4cc10095f. View

12.

Yunos N, Bellomo R, Story D, Kellum J . Bench-to-bedside review: Chloride in critical illness. Crit Care. 2010; 14(4):226. PMC: 2945073. DOI: 10.1186/cc9052. View

13.

von Krbek L, Roberts D, Pilgrim B, Schalley C, Nitschke J . Multivalent Crown Ether Receptors Enable Allosteric Regulation of Anion Exchange in an Fe L Tetrahedron. Angew Chem Int Ed Engl. 2018; 57(43):14121-14124. DOI: 10.1002/anie.201808534. View

14.

Elmes R, Yuen K, Jolliffe K . Sulfate-selective recognition by using neutral dipeptide anion receptors in aqueous solution. Chemistry. 2014; 20(24):7373-80. DOI: 10.1002/chem.201400292. View

15.

He Q, Vargas-Zuniga G, Kim S, Kuk Kim S, Sessler J . Macrocycles as Ion Pair Receptors. Chem Rev. 2019; 119(17):9753-9835. DOI: 10.1021/acs.chemrev.8b00734. View

16.

Wenzel M, Hiscock J, Gale P . Anion receptor chemistry: highlights from 2010. Chem Soc Rev. 2011; 41(1):480-520. DOI: 10.1039/c1cs15257b. View

17.

Evans N, Beer P . Advances in anion supramolecular chemistry: from recognition to chemical applications. Angew Chem Int Ed Engl. 2014; 53(44):11716-54. DOI: 10.1002/anie.201309937. View

18.

Kubik S . Amino acid containing anion receptors. Chem Soc Rev. 2009; 38(2):585-605. DOI: 10.1039/b810531f. View

19.

Bartl J, Kubik S . Anion Binding of a Cyclopeptide-Derived Molecular Cage in Aqueous Solvent Mixtures. Chempluschem. 2020; 85(5):963-969. DOI: 10.1002/cplu.202000255. View

20.

McConnell A, Docker A, Beer P . From Heteroditopic to Multitopic Receptors for Ion-Pair Recognition: Advances in Receptor Design and Applications. Chempluschem. 2020; 85(8):1824-1841. DOI: 10.1002/cplu.202000484. View