Octafluorocalix[4]pyrrole: a Chloride/bicarbonate Antiport Agent

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2010 Feb 19

PMID 20163121

Citations 14

Authors

Philip A Gale

Christine C Tong

Cally J E Haynes

Olubukunola Adeosun

Dustin E Gross

Elizabeth Karnas

Elaine M Sedenberg

Roberto Quesada

Jonathan L Sessler

Affiliations

Soon will be listed here.

Abstract

meso-Octamethyloctafluorocalixpyrrole, a simple tetrapyrrolic macrocycle, has been shown to function as both a chloride/nitrate and a chloride/bicarbonate antiport agent for lipid bilayer transmembrane anion transport. This is the first example of a synthetic macrocyclic pyrrole-based receptor capable of transmembrane bicarbonate transport.

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References

Sessler J, Eller L, Cho W, Nicolaou S, Aguilar A, Lee J . Synthesis, anion-binding properties, and in vitro anticancer activity of prodigiosin analogues. Angew Chem Int Ed Engl. 2005; 44(37):5989-92. DOI: 10.1002/anie.200501740. View

Mareda J, Matile S . Anion-pi slides for transmembrane transport. Chemistry. 2008; 15(1):28-37. DOI: 10.1002/chem.200801643. View

Seganish J, Santacroce P, Salimian K, Fettinger J, Zavalij P, Davis J . Regulating supramolecular function in membranes: calixarenes that enable or inhibit transmembrane Cl- transport. Angew Chem Int Ed Engl. 2006; 45(20):3334-8. DOI: 10.1002/anie.200504489. View

Koulov A, Lambert T, Shukla R, Jain M, Boon J, Smith B . Chloride transport across vesicle and cell membranes by steroid-based receptors. Angew Chem Int Ed Engl. 2003; 42(40):4931-3. DOI: 10.1002/anie.200351957. View

Sidorov V, Kotch F, Abdrakhmanova G, Mizani R, Fettinger J, Davis J . Ion channel formation from a calix[4]arene amide that binds HCl. J Am Chem Soc. 2002; 124(10):2267-78. DOI: 10.1021/ja012338e. View

Fyles T . Synthetic ion channels in bilayer membranes. Chem Soc Rev. 2007; 36(2):335-47. DOI: 10.1039/b603256g. View

Fowler C, Haverlock T, Moyer B, Shriver J, Gross D, Marquez M . Enhanced anion exchange for selective sulfate extraction: overcoming the Hofmeister bias. J Am Chem Soc. 2008; 130(44):14386-7. PMC: 2650011. DOI: 10.1021/ja806511b. View

Perez-Velasco A, Gorteau V, Matile S . Rigid oligoperylenediimide rods: anion-pi slides with photosynthetic activity. Angew Chem Int Ed Engl. 2008; 47(5):921-3. DOI: 10.1002/anie.200703749. View

McNally B, Koulov A, Lambert T, Smith B, Joos J, Sisson A . Structure-activity relationships in cholapod anion carriers: enhanced transmembrane chloride transport through substituent tuning. Chemistry. 2008; 14(31):9599-606. PMC: 2849112. DOI: 10.1002/chem.200801163. View

10.

Santacroce P, Davis J, Light M, Gale P, Iglesias-Sanchez J, Prados P . Conformational control of transmembrane Cl(-) transport. J Am Chem Soc. 2007; 129(7):1886-7. DOI: 10.1021/ja068067v. View

11.

Sidorov V, Kotch F, Kuebler J, Lam Y, Davis J . Chloride transport across lipid bilayers and transmembrane potential induction by an oligophenoxyacetamide. J Am Chem Soc. 2003; 125(10):2840-1. DOI: 10.1021/ja029372t. View

12.

Gale P, Garric J, Light M, McNally B, Smith B . Conformational control of HCl co-transporter: imidazole functionalised isophthalamide vs. 2,6-dicarboxamidopyridine. Chem Commun (Camb). 2007; (17):1736-8. PMC: 2864111. DOI: 10.1039/b703259e. View

13.

Davis J, Spada G . Supramolecular architectures generated by self-assembly of guanosine derivatives. Chem Soc Rev. 2007; 36(2):296-313. DOI: 10.1039/b600282j. View

14.

Gale P, Light M, McNally B, Navakhun K, Sliwinski K, Smith B . Co-transport of H+/Cl- by a synthetic prodigiosin mimic. Chem Commun (Camb). 2005; (30):3773-5. DOI: 10.1039/b503906a. View

15.

Davis A, Sheppard D, Smith B . Development of synthetic membrane transporters for anions. Chem Soc Rev. 2007; 36(2):348-57. PMC: 2854546. DOI: 10.1039/b512651g. View

16.

Davis J, Gale P, Okunola O, Prados P, Iglesias-Sanchez J, Torroba T . Using small molecules to facilitate exchange of bicarbonate and chloride anions across liposomal membranes. Nat Chem. 2011; 1(2):138-44. DOI: 10.1038/nchem.178. View

17.

Fisher M, Gale P, Hiscock J, Hursthouse M, Light M, Schmidtchen F . 1,2,3-triazole-strapped calix[4]pyrrole: a new membrane transporter for chloride. Chem Commun (Camb). 2009; (21):3017-9. DOI: 10.1039/b904089g. View

18.

Tong C, Quesada R, Sessler J, Gale P . meso-octamethylcalix[4]pyrrole: an old yet new transmembrane ion-pair transporter. Chem Commun (Camb). 2008; (47):6321-3. PMC: 2866091. DOI: 10.1039/b814988g. View

19.

Smith B, Lambert T . Molecular ferries: membrane carriers that promote phospholipid flip-flop and chloride transport. Chem Commun (Camb). 2003; (18):2261-8. DOI: 10.1039/b303359g. View