Steroid-based head-to-tail amphiphiles as effective iono- and protonophores

Avallone, Elvira; Cressina, Elena; Fregonese, Massimo; Tecilla, Paolo; Izzo, Irene; Riccardis, Francesco De

doi:10.1016/j.tet.2005.08.085

Cited by 10 publications

(11 citation statements)

References 21 publications

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“…[29,30] Besides, numerous reports have also showed the main chain BAP synthesis by initiation of polymer growth from two of its functional sites; the carboxylic acid group end and the hydroxyl group at its farthest end. [31,32] Also, BAs can be functionalized at the polymeric chain end to make end-capped BAPs, [33,34] where one site initiation or postpolymerization tailoration of polymer chain is required from the carboxyl end of BAs. [35] Apart from this, core functionalized BAP craft is also possible where several derivatizations of macromolecular architecture produce polymers with star-shaped molecular orientation, [36] BA core confined macromolecular pocket, [37] and umbrella-like dendritic polymer formation.…”

Section: Various Bile Acid-based Polymeric Architectures: An Overviewmentioning

confidence: 99%

Recent Progress in Macromolecular Design and Synthesis of Bile Acid‐Based Polymeric Architectures

Sahoo

Ghosh

Khan

et al. 2021

Macro Chemistry & Physics

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Macromolecular engineering presents a pleasant tactic for planning the construction of desired molecular architectures from nano to macro configurations. The mechanistic pathways and synthetic features of macromolecular designs mostly rely on the precursor composition, topology, functionality, and complexity in architectures. Specifically, macromolecular design with biomolecular conjugation has attracted remarkable attention due to its typical biochemical and physiological affirmative traits. In this review article, it is intended to highlight the major progress on the macromolecular designs and synthesis of polymers comprising bile acid (BA) as the biomolecular colleague. BAs are steroidal biocomposites, produced through cholesterol metabolism in the bile of mammals and vertebrates. They are low priced, biocompatible, abundant, trivially toxic, and structurally unique for facewise amphiphilicity, which make them suitable for designing BA-based polymers (BAPs) to be utilized in biomedical fields. The major aim of this review article is to summarize the recent progress (2015-present) on the requisite necessity of BA in BAPs toward design and synthetic avenues. In particular, the design of various polymers with primary and secondary BAs at side chain, main chain, chain end, crosslinking zone, and core confined area are illustrated in this review article via numerous reported methods.

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Section: Various Bile Acid-based Polymeric Architectures: An Overviewmentioning

confidence: 99%

Recent Progress in Macromolecular Design and Synthesis of Bile Acid‐Based Polymeric Architectures

Sahoo

Ghosh

Khan

et al. 2021

Macro Chemistry & Physics

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“…Methylation of the cholic acid hydroxyl groups produced a channel with almost 17-fold cation selectivity, but with numerous conductance states between 5-20 pS. In addition, De Riccardis and co-workers have demonstrated that a C2symmetric sterol-oligo(ethylene glycol) (28) [40] is capable of spanning a liposome membrane and promoting Na + transport at a similar rate as its monomer unit (29) [41]. However, the C2-symmetric compound did have much higher proton transport rates compared to its monomeric derivative, which was attributed to the stability of the proposed self-assembled pore.…”

Section: Self-assembled Poresmentioning

confidence: 99%

Recent Advances in Synthetic Membrane Transporters

Smith

2007

Supramolecular Chemistry

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It is 25 years since the first report of a synthetic ion channel transporter. Today, dozens of molecular and supramolecular designs have been developed to facilitate ion and small molecule transport across a bilayer membrane. Presented here is a concise summary of the advances made over the past four years. The transporters are grouped into three mechanistic classes: mobile carrier, monomeric channel, and self-assembled pore. Common building blocks are crown ethers, steroids, cyclodextrins, peptides, curcubiturils, and calixarenes. The eventual goal is to produce functional supramolecular devices such as sensors, enzyme assays, and lead candidates for pharmaceutical development.

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“…The affinity of crown ethers for cations has been exploited to enhance the cation‐selectivity of these synthetic channels. Acyclic oligoether chains appended to steroids or a simple β‐ diketo scaffold have also been shown to enhance cation transport . Our group has developed dimeric ion channels from a picolinic acid and alanine derived tetrapeptide amphiphile 1 with a dangling diethylene glycol unit that shows Na + selectivity (Figure a) .…”

Section: Introductionmentioning

confidence: 99%

“…Acyclic oligoether chains appended to steroids or a simple βdiketo scaffold have also been shown to enhance cation transport. [28][29][30][31] Our group has developed dimeric ion channels from a picolinic acid and alanine derived tetrapeptide amphiphile 1 with a dangling diethylene glycol unit that shows Na + selectivity (Figure 1a). [32] The pendent oligoether chain was found to enhance the cation-selectivity of these channels.…”

Section: Introductionmentioning

confidence: 99%

Basic Design Elements for Tunable Cation Transport Using Picolinic‐Acid‐Incorporated Tetrapeptides

2018

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Selective transport of cations across cell membranes is essential for various biological functions in the body. Synthetic pores that mimic the selectivity of natural ion channels are attractive for development of drugs and materials. Peptides are now emerging as attractive therapeutic agents due to their biocompatibility and ready accessibility. Herein, we report a systematic study that identifies key elements to design cation‐selective channels using tetrapeptide scaffolds. The scaffolds are derived from picolinic acid and alanine. Their ion transport activity is enhanced by hydrophobic long alkyl chains at the N‐terminus. These scaffolds are exciting as cation‐selectivity can be induced as well as switched by varying the oligoether groups at the C‐terminus.

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Steroid-based head-to-tail amphiphiles as effective iono- and protonophores

Cited by 10 publications

References 21 publications

Recent Progress in Macromolecular Design and Synthesis of Bile Acid‐Based Polymeric Architectures

Recent Progress in Macromolecular Design and Synthesis of Bile Acid‐Based Polymeric Architectures

Recent Advances in Synthetic Membrane Transporters

Basic Design Elements for Tunable Cation Transport Using Picolinic‐Acid‐Incorporated Tetrapeptides

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