The Versatility of Squaramides: From Supramolecular Chemistry to Chemical Biology

Marchetti, Luke A.; Kumawat, Lokesh Kumar; Mao, Nan; Stephens, John C.; Elmes, Robert B. P.

doi:10.1016/j.chempr.2019.02.027

Cited by 115 publications

(103 citation statements)

References 163 publications

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“…[13] Diamides (squaramides) have been used as ap hosphate surrogate in nucleotide [14] or oligonucleotide (ON) analogues. [13] Diamides (squaramides) have been used as ap hosphate surrogate in nucleotide [14] or oligonucleotide (ON) analogues.…”

Section: Protein-dnainteractions Are Of Crucial Importance Inmentioning

confidence: 99%

“…Mono-amides of squaric acid (squaramates) are often used for bioconjugations with Lysa nd other amines. [13] Diamides (squaramides) have been used as ap hosphate surrogate in nucleotide [14] or oligonucleotide (ON) analogues. [15] Ac hemically synthesized 2'-sugar-linked squaramate-RNAc onjugate,p repared through reaction of 2'amino-modified RNAwith diethyl squarate,w as reported to cross-link to aminoacyl-transferase FemX Wv , [16] as the only example of its use in nucleic-acid conjugation.…”

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Squaramate‐Modified Nucleotides and DNA for Specific Cross‐Linking with Lysine‐Containing Peptides and Proteins

et al. 2019

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Squaramate‐linked 2′‐deoxycytidine 5′‐O‐triphosphate was synthesized and found to be good substrate for KOD XL DNA polymerase in primer extension or PCR synthesis of modified DNA. The resulting squaramate‐linked DNA reacts with primary amines to form a stable diamide linkage. This reaction was used for bioconjugations of DNA with Cy5 and Lys‐containing peptides. Squaramate‐linked DNA formed covalent cross‐links with histone proteins. This reactive nucleotide has potential for other bioconjugations of nucleic acids with amines, peptides or proteins without need of any external reagent.

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Section: Protein-dnainteractions Are Of Crucial Importance Inmentioning

confidence: 99%

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confidence: 99%

Squaramate‐Modified Nucleotides and DNA for Specific Cross‐Linking with Lysine‐Containing Peptides and Proteins

et al. 2019

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“…This group of compounds comprises squaramides, which are a special class of monotopic anion receptors able to interact with anions more effectively than their urea or thiourea analogues. 2 However, monotopic receptors are capable of interacting with one type of ion (anions), which in the presence of strongly coordinating counterions (cations) may lose their effectivity in ion binding due to the formation of ion pairs out of the receptor’s binding site. 3 To eliminate this dysfunction, ion pair receptors, compounds capable of simultaneously binding anions and cations, have been proposed and recently intensively investigated.…”

Section: Introductionmentioning

confidence: 99%

Cooperative Transport and Selective Extraction of Sulfates by a Squaramide-Based Ion Pair Receptor: A Case of Adaptable Selectivity

et al. 2020

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The use of a squaramide-based ion pair receptor offers a solution to the very challenging problem of extraction and transport of extremely hydrated sulfate salt. Herein we demonstrate for the first time that a neutral receptor is able not only to selectively extract but also to transport sulfates in the form of an alkali metal salt across membranes and to do so in a cooperative manner while overcoming the Hofmeister bias. This was made possible by an enhancement in anion binding promoted by cation assistance and by diversifying the stoichiometry of receptor complexes with sulfates and other ions. The existence of a peculiar 4:1 complex of receptor 2 with sulfates in solution was confirmed by UV–vis and 1 H NMR titration experiments, DOSY and DLS measurements, and supported by solid-state X-ray measurements. By varying the separation technique and experimental conditions, it was possible to switch the depletion of the aqueous layer into extremely hydrophilic or less lipophilic salts, thus obtaining the desired selectivity.

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“…While myriads of tripodal anion receptors have been reported, to the best of our knowledge there is only one report on an ion-pair receptor built on TREN platform and utilizing amide and crown ether moieties to binds anions and cations, respectively [ 49 ]. On the other hand, currently there is increased interest in synthetic receptors containing a squaramide based anion binding domain [ 50 , 51 , 52 , 53 ]. Numerous studies by Costa have shown the versatility of squaramides, which have been utilized in the formation of self-assembly structures [ 54 , 55 ], hydrogel formation [ 56 ], binding and sensing an anions [ 38 ], peptidomimetic synthesis [ 57 , 58 ], and potential treatment of Chagas disease [ 59 ].…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient, Tripodal Ion-Pair Receptors for Switching Selectivity between Acetates and Sulfates Using Solid–Liquid and Liquid–Liquid Extractions

Zaleskaya

Romański

2020

IJMS

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A tripodal, squaramide-based ion-pair receptor 1 was synthesized in a modular fashion, and 1H NMR and UV-vis studies revealed its ability to interact more efficiently with anions with the assistance of cations. The reference tripodal anion receptor 2, lacking a crown ether unit, was found to lose the enhancement in anion binding induced by presence of cations. Besides the ability to bind anions in enhanced manner by the “single armed” ion-pair receptor 3, the lack of multiple and prearranged binding sites resulted in its much lower affinity towards anions than in the case of tripodal receptors. Unlike with receptors 2 or 3, the high affinity of 1 towards salts opens up the possibility of extracting extremely hydrophilic sulfate anions from aqueous to organic phase. The disparity in receptor 1 binding modes towards monovalent anions and divalent sulfates assures its selectivity towards sulfates over other lipophilic salts upon liquid–liquid extraction (LLE) and enables the Hofmeister bias to be overcome. By changing the extraction conditions from LLE to SLE (solid–liquid extraction), a switch of selectivity from sulfates to acetates was achieved. X-ray measurements support the ability of anion binding by cooperation of the arms of receptor 1 together with simultaneous binding of cations.

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The Versatility of Squaramides: From Supramolecular Chemistry to Chemical Biology

Cited by 115 publications

References 163 publications

Squaramate‐Modified Nucleotides and DNA for Specific Cross‐Linking with Lysine‐Containing Peptides and Proteins

Squaramate‐Modified Nucleotides and DNA for Specific Cross‐Linking with Lysine‐Containing Peptides and Proteins

Cooperative Transport and Selective Extraction of Sulfates by a Squaramide-Based Ion Pair Receptor: A Case of Adaptable Selectivity

Highly Efficient, Tripodal Ion-Pair Receptors for Switching Selectivity between Acetates and Sulfates Using Solid–Liquid and Liquid–Liquid Extractions

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