Utilizing an Amino Acid Scaffold to Construct Heteroditopic Receptors Capable of Interacting with Salts under Interfacial Conditions
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Consideration
3.2. Synthetic Details
3.3. X-ray Measurements
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
- Wenzel, M.; Hiscock, J.R.; Gale, P.A. Anion receptor chemistry: Highlights from 2010. Chem. Soc. Rev. 2012, 41, 480–520. [Google Scholar] [CrossRef]
- Evans, N.H.; Beer, P.D. Advances in anion supramolecular chemistry: From recognition to chemical application. Angew. Chem. Int. Ed. 2014, 53, 11716–11754. [Google Scholar] [CrossRef] [Green Version]
- Busschaert, N.; Caltagirone, C.; Rossom, W.V.; Gale, P.A. Applications of supramolecular anion recognition. Chem. Rev. 2015, 115, 8038–8155. [Google Scholar] [CrossRef] [PubMed]
- Williams, G.T.; Haynes, C.J.E.; Fares, M.; Caltagirone, C.; Hiscock, J.R.; Gale, P.A. Advances in applied supramolecular technologies. Chem. Soc. Rev. 2021, 50, 2737–2763. [Google Scholar] [CrossRef] [PubMed]
- Gale, P.A.; Caltagirone, C. Anion sensing by small molecules and molecular ensembles. Chem. Soc. Rev. 2015, 44, 4212–4227. [Google Scholar] [CrossRef]
- Hein, R.; Berr, P.D.; Davis, J.J. Electrochemical anion sensing: Supramolecular approaches. Chem. Rev. 2020, 120, 1888–1935. [Google Scholar] [CrossRef]
- McNaughton, D.A.; Fares, M.; Picci, G.; Gale, P.A.; Caltagirone, C. Advances in fluorescent and colorimetric sensors for anionic species. Coord. Chem. Rev. 2021, 427, 213573. [Google Scholar] [CrossRef]
- Guo, C.; Sedgwick, A.C.; Hirao, T.; Sessler, J.L. Supramolecular fluorescent sensors: An historical overview and update. Coord. Chem. Rev. 2021, 427, 213560. [Google Scholar] [CrossRef]
- Manesiotis, P.; Riley, A.; Bollen, B. Polymerisable squaramide receptors for anion binding and sensing. J. Mater. Chem. C 2014, 2, 8990–8995. [Google Scholar] [CrossRef] [Green Version]
- Vargas-Zúňiga, G.I.; Sessler, J.L. Anion and Ion Pair Recognition Under Interfacial Aqueous Condition. In Comprehensive Supramolecular Chemistry II; Gokel, G.W., Atwood, J.L., Eds.; Elsevier: Amsterdam, The Netherlands, 2017; Volume 1, pp. 161–185. [Google Scholar]
- Chen, L.; Berry, S.N.; Wu, X.; Howe, E.N.W.; Gale, P.A. Advances in anion receptor chemistry. Chem 2020, 6, 61–141. [Google Scholar] [CrossRef]
- Wu, X.; Gilchrist, A.M.; Gale, P.A. Prospects and challenges in anion recognition and transport. Chem 2020, 6, 1296–1309. [Google Scholar] [CrossRef]
- Davis, J.T.; Gale, P.A.; Quesada, R. Advances in anion transport and supramolecular medicinal chemistry. Chem. Soc. Rev. 2020, 49, 6056–6086. [Google Scholar] [CrossRef]
- Li, Y.; Yang, G.-H.; Shen, Y.-Y.; Xue, X.-S.; Li, X.; Cheng, J.-P. N-tert-butyl sulfinyl squaramide receptors for anion recognition through assisted tert-butyl C-H hydrogen bonding. J. Org. Chem. 2017, 82, 8662–8667. [Google Scholar] [CrossRef]
- Alemàn, J.; Parra, A.; Jiang, H.; Jørgensen, K.A. Squaramides: Bridging from molecular recognition to bifunctional organocatalysis. Chem. Eur. J. 2011, 17, 6890–6899. [Google Scholar] [CrossRef] [PubMed]
- Visco, M.D.; Attard, J.; Guan, Y.; Mattson, A.E. Anion-binding catalyst designs for enantioselective synthesis. Tetrahedron Lett. 2017, 58, 2623–2628. [Google Scholar] [CrossRef]
- Breugst, M.; von der Helden, D.; Schmauck, J. Novel noncovalent interactions in catalysis: A focus on halogen, chalcogen, and anion-π bonding. Synthesis 2017, 49, 3224–3236. [Google Scholar] [CrossRef] [Green Version]
- Shukla, R.; Kida, T.; Smith, B.D. Effect of competing alkali metal cations on neutral host’s anion binding ability. Org. Lett. 2000, 2, 3099–3102. [Google Scholar] [CrossRef]
- Böhmer, V.; Cort, A.D.; Mandolini, L. Counteranion effect on complexation of quats by a neutral calix [5] arene receptor. J. Org. Chem. 2001, 66, 1900–1902. [Google Scholar] [CrossRef]
- Kim, S.K.; Sessler, J.L. Ion pair receptors. Chem. Soc. Rev. 2010, 39, 3784–3809. [Google Scholar] [CrossRef]
- McConnelll, A.J.; Beer, P.D. Heteroditopic receptors for ion-pair recognition. Angew. Chem. Int. Ed. 2012, 51, 2–12. [Google Scholar] [CrossRef] [PubMed]
- McConnell, A.J.; Docker, A.; Beer, P.D. From heteroditopic to multitopic receptors for ion-pair recognition: Advances in receptor design and applications. ChemPlusChem 2020, 85, 1824–1841. [Google Scholar] [CrossRef]
- He, Q.; Vargas-Zúňiga, I.; Kim, S.H.; Kim, S.K.; Sessler, J.L. Macrocycles as ion pair receptors. Chem. Rev. 2019, 119, 9753–9835. [Google Scholar] [CrossRef] [PubMed]
- Jagleniec, D.; Ziach, K.; Dąbrowa, K.; Romański, J. The effect of substitution pattern on binding ability in regioisomeric ion pair receptors based on an aminobenzoic platform. Molecules 2019, 24, 2990. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Qiao, B.; Sengupta, A.; Liu, Y.; McDonald, K.P.; Pink, M.; Anderson, J.R.; Raghavachari, K.; Flodd, A.H. Electrostatic and allosteric cooperativity in ion-pair binding: A quantitative and coupled experiment-theory study with aryl-triazole-ether macrocycles. J. Am. Chem. Soc. 2015, 137, 9746–9757. [Google Scholar] [CrossRef]
- Von Krbek, L.K.S.; Schalley, C.A.; Thordarson, P. Assessing cooperativity in supramolecular systems. Chem. Soc. Rev. 2017, 46, 2622–2637. [Google Scholar] [CrossRef]
- Zaleskaya, M.; Jagleniec, D.; Romański, J. Macrocyclic squaramides as ion pair receptors and fluorescent sensors selective towards sulfates. Dalton Trans. 2021, 50, 3904–3915. [Google Scholar] [CrossRef]
- Kubik, S. Amino acid containing anion receptors. Chem. Soc. Rev. 2009, 38, 585–605. [Google Scholar] [CrossRef]
- Kubik, S.; Mungalpara, D. Amino Acid-Based Receptors. In Comprehensive Supramolecular Chemistry II; Gokel, G.W., Atwood, J.L., Eds.; Elsevier: Amsterdam, The Netherlands, 2017; Volume 1, pp. 293–308. [Google Scholar]
- Elmes, R.B.P.; Jolliffe, K.A. Anion recognition by cyclic peptides. Chem. Commun. 2015, 51, 4951–4968. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Kubik, S. Anion recognition in aqueous media by cyclopeptides and other synthetic receptors. Acc. Chem. Res. 2017, 50, 2870–2878. [Google Scholar] [CrossRef]
- Sommer, F.; Marcus, Y.; Kubik, S. Effects of solvent properties on the anion binding of neutral water-soluble bis(cyclopeptides) in water and aqueous solvent mixtures. ACS Omega 2017, 2, 3669–3680. [Google Scholar] [CrossRef]
- Mungalpara, D.; Valkonen, A.; Rissanen, K.; Kubik, S. Efficient stabilization 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, 6005–6013. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Bartl, J.; Kubik, S. Anion binding of a cyclopeptide-derived molecular cage in aqueous solvent mixtures. ChemPlusChem 2020, 85, 963–969. [Google Scholar] [CrossRef] [PubMed]
- Bartl, J.; Reinke, L.; Koch, M.; Kubik, S. Selective sensing of sulfate anions in water with cyclopeptide-decorated gold nanoparticles. Chem. Commun. 2020, 56, 10457–10460. [Google Scholar] [CrossRef]
- Dungan, V.J.; Ngo, H.T.; Young, P.G.; Jolliffe, K.A. High affinity sulfate binding in aqueous media by cyclic peptides with thiourea arms. Chem. Commun. 2013, 49, 264–266. [Google Scholar] [CrossRef] [PubMed]
- Elmes, R.B.P.; Yuen, K.K.Y.; Jolliffe, K.A. Sulfate-selective recognition by using neutral dipeptide anion receptors in aqueous solution. Chem. Eur. J. 2014, 20, 7373–7380. [Google Scholar] [CrossRef]
- Elmes, R.B.P.; Jolliffe, K.A. Amino acid-based squaramides for anion recognition. Supramol. Chem. 2015, 27, 321–328. [Google Scholar] [CrossRef]
- Zakrzewski, M.; Kwietniewska, N.; Walczak, W.; Piątek, P. A non-multimacrocyclic heteroditopic receptor that cooperatively binds and effectively extracts KAcO salt. Chem. Commun. 2018, 54, 7018–7021. [Google Scholar] [CrossRef]
- Marti, I.; Rubio, J.; Bolte, M.; Burguete, M.I.; Vicent, C.; Quesada, R.; Alfonos, I.; Luis, S.V. Tuning chloride binding, encapsulation, and transport by peripheral substitution of pseudopeptidic tripodal small cages. Chem. Eur. J. 2012, 18, 16728–16741. [Google Scholar] [CrossRef]
- Marti, I.; Burguete, I.; Gale, P.A.; Luis, S.V. Acyclic pseudopeptidic hosts as molecular receptors and transporters for anions. Eur. J. Org. Chem. 2015, 23, 5150–5158. [Google Scholar] [CrossRef]
- Gonzàlez-Mendoza, L.; Altava, B.; Burguete, M.I.; Escorihuela, J.; Hernando, E.; Lusi, S.V.; Quesada, R.; Vicent, C. Bis(imidazolium) salts derived from amino acids as receptors and transport agents for chloride anions. RSC Adv. 2015, 5, 34415–34423. [Google Scholar] [CrossRef] [Green Version]
- Xin, P.; Tan, S.; Wang, Y.; Sun, Y.; Wang, Y.; Xu, Y.; Chen, C.-P. Functionalized hydrazide macrocycle ion channels showing pH-sensitive ion selectivities. Chem. Commun. 2017, 53, 625–628. [Google Scholar] [CrossRef]
- Fuertes, A.; Amorín, M.; Granja, J.R. Versatile symport transporters based on cyclic peptide dimers. Chem. Commun. 2020, 56, 46–49. [Google Scholar] [CrossRef] [PubMed]
- Busschaert, N.; Kariagiannidis, L.E.; Wenzel, M.; Haynes, C.J.; Wells, N.J.; Young, P.G.; Makuc, D.; Plavec, J.; Jolliffe, K.A.; Gale, P.A. Synthetic transporters for sulfate: A new method for the direct detection of lipid bilayer sulfate transport. Chem. Sci. 2014, 5, 1118–1127. [Google Scholar] [CrossRef] [Green Version]
- Zaleskaya, M.; Karbarz, M.; Wilczek, M.; Dobrzycki, Ł.; Romański, J. Cooperative transport and selective extraction of sulfates by a squaramide-based ion pair receptor: A case of adaptable selectivity. Inorg. Chem. 2020, 59, 13749–13759. [Google Scholar] [CrossRef]
- Markovich, D. Physiological roles and regulation of mammalian sulfate transporters. Physiol. Rev. 2001, 81, 1499–1533. [Google Scholar] [CrossRef] [PubMed]
- Dawson, P.A.; Petersen, S.; Rodwell, R.; Johnson, P.; Gibbons, K.; McWhinney, A.; Bowling, F.G.; McIntyre, H.D. Reference intervals for plasma sulfate and urinary sulfate excretion in pregnancy. BMC Pregnancy Childbirth 2015, 15, 96. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Powers, F. The role of chloride in acid-base balance. J. Intraven. Nurs. 1999, 22, 286–291. [Google Scholar] [PubMed]
- Yunos, N.M.; Bellomo, R.; Story, D.; Kellum, J. Bench-to-bedside review: Chloride in critical illness. Crit. Care. 2010, 14, 226. [Google Scholar] [CrossRef] [Green Version]
- Busschaert, N.; Park, S.-H.; Baek, K.-H.; Choi, Y.P.; Park, J.; Howe, E.N.W.; Hiscock, J.R.; Karagiannidis, L.E.; Marques, I.; Félix, V.; et al. A synthetic ion transporter that disrupts autophagy and induces apoptosis by perturbing cellular chloride concentrations. Nat. Chem. 2017, 9, 667–675. [Google Scholar] [CrossRef]
- Romański, J.; Piątek, P. Tuning the binding properties of a new heteroditopic salt receptor through embedding in polymeric system. Chem. Commun. 2012, 48, 11346–11348. [Google Scholar] [CrossRef]
- Ziach, K.; Karbarz, M.; Romański, J. Cooperative binding and extraction of sodium nitrite by a ditopic receptor incorporated into a polymeric resin. Dalton Trans. 2016, 45, 11639–11643. [Google Scholar] [CrossRef] [PubMed]
- Zdanowski, S.; Piątek, P.; Romański, J. An ion pair receptor facilitating the extraction of chloride salt from the aqueous to the organic phase. New J. Chem. 2016, 40, 7190–7196. [Google Scholar] [CrossRef]
- Zwicker, V.E.; Yuen, K.K.Y.; Smith, D.G.; Ho, J.; Qin, L.; Turner, P.; Jolliffe, K.A. Deltamides and croconamides: Expanding the range of dual H-bond donors for selective anion recognition. Chem. Eur. J. 2018, 24, 1140–1150. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Amendola, V.; Bergamaschi, G.; Boiocchi, M.; Fabbrizzi, L.; Milani, M. The squaramide versus urea contest for anion recognition. Chem. Eur. J. 2010, 16, 4368–4380. [Google Scholar] [CrossRef] [PubMed]
- Marchetti, L.A.; Kumawat, L.K.; Mao, N.; Stephens, J.C.; Elmes, R.B.P. The versatility of squaramides: From supramolecular chemistry to chemical biology. Chem 2019, 5, 1–88. [Google Scholar] [CrossRef]
- Von Krbek, L.K.S.; Roberts, D.A.; Pilgrim, B.S.; Schalley, C.A.; Nitschke, J.R. Multivalent crown ether receptors enable allosteric regulation of anion exchange in an Fe4L4 tetrahedron. Angew. Chem. Int. Ed. 2018, 57, 14121–14124. [Google Scholar] [CrossRef]
- Jagleniec, D.; Siennicka, S.; Dobrzycki, Ł.; Karbarz, M.; Romański, J. Recognition and extraction of sodium chloride by a squaramide-based ion pair receptor. Inorg. Chem. 2018, 57, 12941–12952. [Google Scholar] [CrossRef]
- Jagleniec, D.; Dobrzycki, Ł.; Karbarz, M.; Romański, J. Ion-pair induced supramolecular assembly formation for selective extraction and sensing of potassium sulfate. Chem. Sci. 2019, 10, 9542–9547. [Google Scholar] [CrossRef]
- APEX3 V2019; Bruker Nano, Inc.: Madison, WI, USA, 2019.
- SAINT V8.40A; Bruker Nano, Inc.: Madison, WI, USA, 2019.
- SADABS V2016/2; Bruker Nano, Inc.: Madison, WI, USA, 2019.
- Sheldrick, G.M. SHELXT-Integrated space-group and crystal-structure determination. Acta Cryst. Sect. A Found. Adv. 2015, 71, 3–8. [Google Scholar] [CrossRef] [Green Version]
- Sheldrick, G.M. Crystal structure refinement with SHELXL. Acta Cryst. Sect. C. Struct. Chem. 2015, 71, 3–8. [Google Scholar] [CrossRef]
- Cowley, J.M. International Tables for Crystallography; Wilson, A.J.C., Ed.; Kluwer: Dordrecht, The Netherlands, 1992; Volume C, pp. 223–245. [Google Scholar]
- Macrae, C.F.; Bruno, I.J.; Chisholm, J.A.; Edington, P.R.; McCabe, P.; Pidcock, E.; Rodriguez-Monege, L.; Taylor, R.; van de Streek, J.; Wood, P.A. Mercury CSD 2.0–new features for the visualization and investigation of crystal structures. J. Appl. Cryst. 2008, 41, 466–470. [Google Scholar] [CrossRef]
TBACl | TBACl + 1 eq. NaClO4 | TBACl + 1 eq. KPF6 | KNa+/KTBA+ | KK+/KTBA+ | |
---|---|---|---|---|---|
1 | 2.71 × 105 | 3.25 × 105 | - | 1.20 | - |
2 | 2.75 × 105 | 3.49 × 105 | 5.68 × 105 | 1.27 | 2.13 |
3 | 1.98 × 105 | 1.83 × 105 | 1.67 × 105 | 0.92 | 0.84 |
S2 | 3.40 × 103 | 5.70 × 103 | 6.80 × 103 | 1.68 | 2.00 |
TBACl | TBACl + 1 eq. NaClO4 | TBACl + 1 eq. KPF6 | |
---|---|---|---|
Cl− | 2.75 × 105 | 3.49 × 105 | 5.68 × 105 |
Br− | 2.52 × 104 | 4.11 × 104 | 4.40 × 104 |
NO2− | 1.33 × 105 | 1.67 × 105 | 1.75 × 105 |
NO3− | 5.73 × 103 | 6.30 × 103 | 6.50 × 103 |
SO42− | b | b | b |
PhCOO− | c | c | c |
CH3COO− | c | c | c |
Formula | C78H81.47Br2F12K0.27N10Na1.73O23.73, corresponding to: 2 × 2 + 1.73 × NaBr + 0.27 × KBr + 2.00 × acetonitrile + 1.73 × H2O |
Mx/g∙mol−1 | 1976.83 |
T/K | 130.0(5) |
λ/Å | 1.54178 |
Crystal size | 0.023 × 0.122 × 0.213 mm |
Space group | P |
Unit cell dimensions | a = 9.1517(3) Å α = 66.9565(14)° b = 14.9141(4) Å β = 83.4708(16)° c = 17.4557(5) Å γ = 87.1685(15)° |
V/Å3, Z | 2178.16(11), 1 |
Dx/g∙cm−3 | 1.507 |
μ/mm−1 | 2.300 |
F(000) | 1011 |
θmin, θmax | 2.77°, 66.48° |
Index ranges (merged data) | -10 ≤ h ≤ 10, −17 ≤ k ≤ 17, −20 ≤ l ≤ 20 |
Reflections collected/independent | 34181/7656, Rint = 0.0436 |
Completeness | 99.7% |
Absorption correction | Multi-Scan |
Tmax, Tmin | 0.949, 0.640 |
Refinement method | Full-matrix LSQ on F2 |
Data/restraints/parameters | 7656/181/782 |
GOF on F2 | 1.051 |
Final R indices | 6766 data; I > 2σ(I) R1 = 0.0517, wR2 = 0.1390 all data R1 = 0.0589, wR2 = 0.1465 |
Δρmax, Δρmin | 0.763, −0.675 e∙Å−3 |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Jagleniec, D.; Walczak, N.; Dobrzycki, Ł.; Romański, J. Utilizing an Amino Acid Scaffold to Construct Heteroditopic Receptors Capable of Interacting with Salts under Interfacial Conditions. Int. J. Mol. Sci. 2021, 22, 10754. https://doi.org/10.3390/ijms221910754
Jagleniec D, Walczak N, Dobrzycki Ł, Romański J. Utilizing an Amino Acid Scaffold to Construct Heteroditopic Receptors Capable of Interacting with Salts under Interfacial Conditions. International Journal of Molecular Sciences. 2021; 22(19):10754. https://doi.org/10.3390/ijms221910754
Chicago/Turabian StyleJagleniec, Damian, Natalia Walczak, Łukasz Dobrzycki, and Jan Romański. 2021. "Utilizing an Amino Acid Scaffold to Construct Heteroditopic Receptors Capable of Interacting with Salts under Interfacial Conditions" International Journal of Molecular Sciences 22, no. 19: 10754. https://doi.org/10.3390/ijms221910754