Binding of organic anions to a macrocyclic alkaloid d-tubocurarine

Alcántar, Carolina Godoy; Елисеев, А. В.; Yatsimirsky, Anatoly K.

doi:10.1016/0960-894x(95)00519-1

Cited by 3 publications

(9 citation statements)

References 16 publications

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“…Although all compounds examined also had an aromatic group (for detection purposes) within two or three atoms of the chiral center, this is probably not a strict requirement for optical resolution, as a difference in the binding constants between the enantiomers of a nonaromatic derivatized amino acid with d -tubocurarine has been reported. For example, the equilibrium constant for the interaction of d - N -acetylalanine was 80 M -1 , whereas it was <20 M -1 for l - N -acetylalanine …”

Section: Resultsmentioning

confidence: 98%

“…It is a neuromuscular blocking drug 20,21 and has been used in surgery and intensive care units in very small doses as a complement to anesthetics to produce skeletal muscle relaxation as well as in the treatment of various neuromuscular disorders. DTC has also been suggested as a potentially good model or mimetic agent for cyclophanes since it resembles that class of compounds in some respects …”

Section: Resultsmentioning

confidence: 99%

“…Thus, it should be possible to employ fluorescence detection schemes with this chiral selector. In fact, the presence of DTC is reported to elicit fluorescence enhancements for some aromatic compounds 2 UV−visible absorption spectrum of d -tubocurarine (1.0 × 10 -4 M) in water at 25 °C. …”

Section: Resultsmentioning

confidence: 99%

“…Results indicate that tubocurarine can function as an effective chiral additive for the CE separation of the optical isomers of compounds containing a carboxylate moiety in the vicinity of the stereogenic center. The selection of enantiomeric organic carboxylates as the general analyte class was made on the basis of a previous conductivity study, which indicated that tubocurarine selectively interacted with organic anions, including enantiospecific binding of some N -acetyl-α-amino acids …”

mentioning

confidence: 99%

“…The selection of enantiomeric organic carboxylates as the general analyte class was made on the basis of a previous conductivity study, which indicated that tubocurarine selectively interacted with organic anions, including enantiospecific binding of some N-acetyl-R-amino acids. 19…”

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confidence: 99%

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Characterization and Evaluation of d-(+)-Tubocurarine Chloride as a Chiral Selector for Capillary Electrophoretic Enantioseparations

1998

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A new macrocyclic of the bis(benzylisoquinoline) alkaloid family, d-(+)-tubocurarine chloride (DTC), has been evaluated as a chiral selector for the separation of optical isomers of organic carboxylates using capillary electrophoresis (CE). The pertinent physicochemical properties, such as absorption spectrum, isoionic point, and solution conformation, of DTC were determined. The effects of varying such experimental parameters as DTC concentration, pH, and methanol content in the running buffer were assessed. CE separation of the enantiomers of 18 different compounds was achieved using DTC as the chiral selector under optimized background electrolytic conditions.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Characterization and Evaluation of d-(+)-Tubocurarine Chloride as a Chiral Selector for Capillary Electrophoretic Enantioseparations

1998

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Complexation of dicarboxylates and phosphates by a semisynthetic alkaloid‐based cyclophane in water

Lara

Godoy‐Alcántar

Rivera

et al. 2001

J of Physical Organic Chem

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Dicationic N,N′‐dibenzylated cyclophane‐type derivative 1 of a bisisoquinoline macrocyclic alkaloid, S,S‐(+)‐tetrandrine, was prepared and characterized. In aqueous solution 1 undergoes dimerization, which was studied by the concentration dependence of its 1H NMR signals. The salt effect on the dimerization constant was analyzed by using different versions of Debye–Hückel‐type equations. 1H NMR titration of 1 by 10 dicarboxylate anions of different structures revealed strong peak binding selectivity for succinate in the series of α,ω‐dicarboxylates. Aromatic carboxylates have larger binding constants and for o‐phthalate the formation of both 1:1 and 1:2 host–guest complexes is observed. Binding of nucleotides (AMP, ADP and ATP) to 1 is surprisingly insensitive to the guest charge, indicating a major contribution of stacking interactions of the nucleobase with 1. Copyright © 2001 John Wiley & Sons, Ltd.

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Recognition of α-amino acid derivatives by N,N′-dibenzylated S,S-(+)-tetrandrine

et al. 2004

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Complexation of free and N-acetylated alpha-amino acid anions (Gly, Ala, Phe) and some structurally related guests by a dicationic cyclophane-type N,N'-dibenzylated chiral derivative of a bisisoquinoline macrocyclic alkaloid S,S-(+)-tetrandrine (DBT) has been studied by (1)H-NMR titrations in D(2)O. In contrast to other macrocyclic hosts like cyclodextrins and calixarenes, DBT shows highest affinity and large enantioselectivity (K(S)/K(R) >/=10) toward smaller N-acetylalanine and binds larger phenylalanine derivatives more weakly and non-selectively. With 1,2,3,4-tetrahydroisoquinoline-3-carboxylate, a rigid analog of phenylalanine, binding again becomes enantioselective with K(S)/K(R)= 3.8. The binding specificity of DBT is rationalized on the basis of molecular mechanics calculations.

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Binding of organic anions to a macrocyclic alkaloid d-tubocurarine

Cited by 3 publications

References 16 publications

Characterization and Evaluation of d-(+)-Tubocurarine Chloride as a Chiral Selector for Capillary Electrophoretic Enantioseparations

Characterization and Evaluation of d-(+)-Tubocurarine Chloride as a Chiral Selector for Capillary Electrophoretic Enantioseparations

Complexation of dicarboxylates and phosphates by a semisynthetic alkaloid‐based cyclophane in water

Recognition of α-amino acid derivatives by N,N′-dibenzylated S,S-(+)-tetrandrine

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