Recent advances in the transmembrane transport of anions

Davis, Jeffery T.; Okunola, Oluyomi A.; Quesada, Roberto

doi:10.1039/b926164h

Cited by 346 publications

(210 citation statements)

References 148 publications

(180 reference statements)

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“…[85][86][87][88][89] Prodiginines are small natural products that represent the most widely studied transmembrane chloride transporters due to their alleged anticancer activity.…”

Section: Transmembrane Anion Transportmentioning

confidence: 99%

Anion receptor chemistry: highlights from 2008 and 2009

2010

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“…[85][86][87][88][89] Prodiginines are small natural products that represent the most widely studied transmembrane chloride transporters due to their alleged anticancer activity.…”

Section: Transmembrane Anion Transportmentioning

confidence: 99%

Anion receptor chemistry: highlights from 2008 and 2009

2010

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confidence: 99%

Efficient, non-toxic anion transport by synthetic carriers in cells and epithelia

Valkenier

Judd³

et al. 2015

Nature Chem

155

160

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The transport of anions across cell membranes has become an important goal for supramolecular chemistry [1][2][3][4] . It is well-known that cation carriers (cationophores) can serve as antibiotics and toxins 5,6 , and it seems likely that anion carriers might also show useful biological activity. However, suitable anionophores have only recently become available 7-10 , and the nature of their biological effects is still in question. A particular hope is that anionophores might be used to replace the activity of endogenous anion channels which are missing or defective 11,2 . Such deficiencies underlie a number of medical conditions including Best disease, Startle disease, Bartter's syndrome and, most notably, the widespread lifeshortening genetic disease cystic fibrosis (CF) 12,13 .If anionophores are to be used to treat these "channelopathies", it must be shown that they can be delivered to cells in sufficient quantities to produce substantial effects, of the same order of magnitude as endogenous anion channels, and that these quantities are not toxic to the cells. However, while a wide variety of anionophores have been studied in synthetic membranes (principally large unilamellar vesicles, or LUVs), the range of systems subjected to biological investigations is still quite limited. Moreover, from the point of view of CF treatment, the results thus far have been mixed. On the positive side, a few systems have been tested in whole cells, epithelia or (in one case) genetically modified mice 14 , using electrophysiological methods such as patch-clamp and Ussing chamber, and shown to induce anion conduction without obvious toxic effects. These anionophores include synthetic 3 peptides conceptually related to natural anion channels 11,[15][16][17] , as well as the steroid-based system 1 from the authors' laboratory 18 , and other small organic molecules 14,19,20 .Less encouragingly, a number of molecules showing anion transport in LUVs have tested positive for anti-cancer cytotoxicity (potentially valuable, but incompatible with CF treatment) 8,[21][22][23][24][25] . Many of these systems, including the well-studied prodigiosin 2 26 , transport protons as well as anions 8,[21][22][23] . Intracellular acidification can lead to apoptosis 26 , so in these cases proton transport could underlie toxicity. On the other hand, a recent study on calixpyrroles 3 suggested that anion transport as such could be cytotoxic 25 . As the transport activity of 3 was only weak, this raises the concern that powerful anionophores might be highly toxic and thus unsuitable for CF treatment. Thus far the only biological testing of these "1,5-diaxial" systems has been the early study on 1, referred to above 18 . The assay involved the application of 1 to the apical membrane of oriented Madin Darby canine kidney cell (MDCK) epithelia, mounted in an Ussing chamber, and measurement of the resulting electrical current caused by Cl − transport. The methodology is well-established, but not so convenient for screening large numbers of compounds.Mor...

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“…1 The structures of the compounds were elucidated by single crystal X-ray diffraction. Figure 6 shows that in the solid state the receptors adopt a conformation in which the NH hydrogen bond donors are nearly parallel.…”

Section: Resultsmentioning

confidence: 99%

Anion transport and binding properties of N N′-(phenylmethylene)dibenzamide based receptors

Clarke

Rossom

Light

et al. 2015

Supramolecular Chemistry

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Dedicated to friend and mentor Professor Jonathan L. Sessler on the occasion of his 60th birthday.The anion transport and binding properties of a series of bis-amide based compounds have been studied in POPC lipid bilayers. The compounds display evidence of aggregation in solution with single crystal X-ray crystallographic analysis showing hydrogen bonding between the amide substituents of adjacent receptors in the solid state.

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Recent advances in the transmembrane transport of anions

Cited by 346 publications

References 148 publications

Anion receptor chemistry: highlights from 2008 and 2009

Anion receptor chemistry: highlights from 2008 and 2009

Efficient, non-toxic anion transport by synthetic carriers in cells and epithelia

Anion transport and binding properties of N N′-(phenylmethylene)dibenzamide based receptors

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