Molecular recognition and indicator-displacement assays for phosphoesters

Zhang, Tianzhi; Anslyn, Eric V.

doi:10.1016/j.tet.2004.08.059

Cited by 43 publications

(18 citation statements)

References 36 publications

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“…In Table 1 we show the binding constants and thermodynamic experimental results obtained by isothermal calorimetry (ITC; for details see the Supporting Information) for complexation between receptors 1a-b and 2a-b and dicarboxylate folate-related guests 3a, 3b, 4, 5, pteroic acid (6), and the glutamate anion (7). All host-guest complexes were studied in water at 293 K. To regulate the pH, a 0.25 m Tris-HCl buffer system was used, which provided the pH of 9.0 required to ensure the existence of the anionic form of the assayed guests.…”

Section: Synthesis Of the Receptorsmentioning

confidence: 99%

“…[3] Generally, the study of real analytical problems -complex mixtures of bioanalytes [4] (urine, blood, saliva) environmental analytes (industrial wastes), [5] cellular imaging, and quality control -concerning anionic species are carried out in water media and at a specific pH value, for example, phosphate [6] only exists in a particular pH range. One important part of anion coordination chemistry is the selective complexation of carboxylate anions by synthetic hosts.…”

Section: Introductionmentioning

confidence: 99%

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Synthetic Tripodal Squaramido‐Based Receptors for the Complexation of Antineoplastic Folates in Water

Quiñonero¹,

López²,

Deyà³

et al. 2011

Eur J Org Chem

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Three suitably oriented squaramido ammonium groups form the basis of the first abiotic receptor that employs the noncovalent ammonium–carboxylate electrostatic interaction and a hydrogen bond to achieve high‐affinity molecular recognition in water. These interacctions have been studied experimentally by isothermal calorimetry (ITC), NMR spectroscopy, and MS. Also, we have proposed a model for coordination from DFT calculations and NMR spectroscopy studies. Finally, a fluorimetric ensemble of the receptor with 5‐carboxyfluorescein was useful for the quantitative fluorimetric determination of folate and methotrexate in commercial samples using competition assays.

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Section: Synthesis Of the Receptorsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthetic Tripodal Squaramido‐Based Receptors for the Complexation of Antineoplastic Folates in Water

Quiñonero¹,

López²,

Deyà³

et al. 2011

Eur J Org Chem

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show abstract

“…42 After purification by passing through a pad of silica gel, compound 52 was converted to azide 53 by heating with sodium azide in DMF. Compound 53 was reacted with tosyl chloride and sodium hydroxide to give intermediate 54 , which was used to alkylate the secondary amines 55 – 60 yielding the tertiary amines 61–66 .…”

Section: Introductionmentioning

confidence: 99%

Largazole Analogues Embodying Radical Changes in the Depsipeptide Ring: Development of a More Selective and Highly Potent Analogue

et al. 2016

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A number of analogues of the marine-derived histone deacetylase inhibitor largazole incorporating major structural changes in the depsipeptide ring were synthesized. Replacing the thiazole-thiazoline fragment of largazole with a bipyridine group gave analogue 7 with potent cell growth inhibitory activity and an activity profile similar to that of largazole, suggesting that conformational change accompanying switching hybridization from sp3 to sp2at C-7 is well tolerated. Analogue 7 was more class I selective compared to largazole, with at least 464-fold selectivity for class I HDAC proteins over class II HDAC6 compared to a 22-fold selectivity observed with largazole. To our knowledge 7 represents the first example of a potent and highly cytotoxic largazole analogue not containing a thiazoline ring. The elimination of a chiral center derived from the unnatural amino acid R-α-methylcysteine makes the molecule more amenable to chemical synthesis and, coupled with its increased class I selectivity, 7 could serve as a new lead compound for developing selective largazole analogues.

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“…154,155 As [G] t increases, more indicator will be displaced, leading to a larger spectroscopic change. The use of IDAs has been popularized by our group, [156][157][158][159][160] as well as many other groups. [161][162][163][164][165][166][167][168][169] Our group has also introduced the use of IDAs for enantioselective discrimination, called enantioselective indicator displacement assays (eIDAs), where a chiral host/ receptor (H*) is used.…”

Section: Indicator Displacement Assaysmentioning

confidence: 99%

Rapid determination of enantiomeric excess: a focus on optical approaches

2012

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High-throughput screening (HTS) methods are becoming increasingly essential in discovering chiral catalysts or auxiliaries for asymmetric transformations due to the advent of parallel synthesis and combinatorial chemistry. Both parallel synthesis and combinatorial chemistry can lead to the exploration of a range of structural candidates and reaction conditions as a means to obtain the highest enantiomeric excess (ee) of a desired transformation. One current bottleneck in these approaches to asymmetric reactions is the determination of ee, which has led researchers to explore a wide range of HTS techniques. To be truly high-throughput, it has been proposed that a technique that can analyse a thousand or more samples per day is needed. Many of the current approaches to this goal are based on optical methods because they allow for a rapid determination of ee due to quick data collection and their parallel analysis capabilities. In this critical review these techniques are reviewed with a discussion of their respective advantages and drawbacks, and with a contrast to chromatographic methods (180 references).

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Molecular recognition and indicator-displacement assays for phosphoesters

Cited by 43 publications

References 36 publications

Synthetic Tripodal Squaramido‐Based Receptors for the Complexation of Antineoplastic Folates in Water

Synthetic Tripodal Squaramido‐Based Receptors for the Complexation of Antineoplastic Folates in Water

Largazole Analogues Embodying Radical Changes in the Depsipeptide Ring: Development of a More Selective and Highly Potent Analogue

Rapid determination of enantiomeric excess: a focus on optical approaches

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