Preparation and spectroscopic studies of an inclusion complex of adenine with β-cyclodextrin in solution and in the solid state

Xu, Hao; Liang, Chen; Chao, Jianbin

doi:10.1039/b200594h

Cited by 15 publications

(7 citation statements)

References 18 publications

(20 reference statements)

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“…However, the nicotinamide moiety of NADH, which is responsible for redox and spectrophotometric properties of the whole molecule of NADH, cannot form inclusion complexes with CDs as was confirmed by the studies presented in [24]. Another literature report [25] shows that adenine, which is a less important moiety in the NADH molecule than the nicotinamide one, is able to form complexes with ␤-CD. The above-reported experimental findings could explain our observations connected with the unchanged absorption coefficient (within the limits of experimental error) of NADH in the presence and in the absence of CDs.…”

Section: Introductionsupporting

confidence: 62%

Enhanced enzymatic activity of phenylalanine dehydrogenase caused by cyclodextrins

Gubica

Pałka

Szeleszczuk

et al. 2015

Journal of Molecular Catalysis B: Enzymatic

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Section: Introductionsupporting

confidence: 62%

Enhanced enzymatic activity of phenylalanine dehydrogenase caused by cyclodextrins

Gubica

Pałka

Szeleszczuk

et al. 2015

Journal of Molecular Catalysis B: Enzymatic

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“…19 Hao et al reported that the adenine molecule in solution prefers to be included in the more hydrophobic environment inside the β-CD cavity based on enhancement of the fluorescence intensity of adenine in the presence of β-CD. 20 Kondo and Nishikawa reported that adenine and β-CD forms an inclusion complex based on the results of an ultrasonic relaxation study. 8 Other evidence indicating that hydrophobic interactions play important roles comes from the crystal structure of cAMP bound in the binding pocket of PDE.…”

Section: Discussionmentioning

confidence: 99%

Complex Formation of Adenosine 3',5'-Cyclic Monophosphate with β-Cyclodextrin: Kinetics and Mechanism by Ultrasonic Relaxation

Bae¹,

Kim²,

Lee

2010

Bulletin of the Korean Chemical Society

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Adenosine 3',5'-cyclic monophosphate (cAMP) is a second messenger responsible for a multitude of cellular responses. In this study, we utilized β-cyclodextrin (β-CD) as an artificial receptor with a hydrophobic cavity to elucidate the inclusion kinetics of cAMP in a hydrophobic environment using the ultrasonic relaxation method. The results revealed that the interaction of cAMP with β-CD followed a single relaxation curve as a result of host-guest interactions. The inclusion of cAMP into the β-CD cavity was found to be a diffusion-controlled reaction. The dissociation of cAMP from the β-CD cavity was slower than that of adenosine 5'-monophosphate (AMP). The syn and anti glycosyl conformations of adenine nucleotides are considered to play an important role in formation of the inclusion complex. Taken together, our findings indicate that hydrophobic interactions are involved in the inclusion complex formation of cAMP with β-CD and provide insight into the interactions of cAMP with cAMP-binding proteins.

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“…This contrasts with the ability of lactones to form inclusion complexes with cyclodextrins, such as the ε-caprolactone/β-CD inclusion complex [ 24 ]. However, the inclusion of nitrogenous heterocyclic bases such as, e.g., adenine [ 25 ], bipyridines [ 26 ] or α-aminopyridine [ 27 ] into β-CD has been reported in the literature. As far as we know, inclusion complexes between DMAP and β-cyclodextrin have never been reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

Cyclodextrins Initiated Ring-Opening Polymerization of Lactide Using 4-Dimethylaminopyridine (DMAP) as Catalyst: Study of DMAP/β-CD Inclusion Complex and Access to New Structures

Meimoun¹,

Phuphuak

Miyamachi³

et al. 2022

Molecules

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Cyclodextrins (CDs) are cyclic oligosaccharides used in many fields. Grafting polymers onto CDs enables new structures and applications to be obtained. Polylactide (PLA) is a biobased, biocompatible aliphatic polyester that can be grafted onto CDs by -OH-initiated ring-opening polymerization. Using 4-dimethylaminopyridine (DMAP) as an organocatalyst, a quantitative functionalization is reached on native α-, β-, γ- and 2,3-dimethyl- β-cyclodextrins. Narrow molecular weight distributions are obtained with the native CDs (dispersity < 1.1). The DMAP/β-CD combination is used as a case study, and the formation of an inclusion complex (1/1) is shown for the first time in the literature, which is fully characterized by NMR. The inclusion of DMAP into the cavity occurs via the secondary rim of the β-CD and the association constant (Ka) is estimated to be 88.2 M−1. Its use as an initiator for ring-opening polymerization leads to a partial functionalization efficiency, and thus a more hydrophilic β-CD-PLA conjugate than that obtained starting from native β-CD. Polymerization results including also the use of the adamantane/β-CD inclusion complex as an initiator suggest that inclusion of the DMAP catalyst into the CD may not occur during polymerization reactions. Rac-lactide does not form an inclusion complex with β-CD.

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Preparation and spectroscopic studies of an inclusion complex of adenine with β-cyclodextrin in solution and in the solid state

Cited by 15 publications

References 18 publications

Enhanced enzymatic activity of phenylalanine dehydrogenase caused by cyclodextrins

Enhanced enzymatic activity of phenylalanine dehydrogenase caused by cyclodextrins

Complex Formation of Adenosine 3',5'-Cyclic Monophosphate with β-Cyclodextrin: Kinetics and Mechanism by Ultrasonic Relaxation

Cyclodextrins Initiated Ring-Opening Polymerization of Lactide Using 4-Dimethylaminopyridine (DMAP) as Catalyst: Study of DMAP/β-CD Inclusion Complex and Access to New Structures

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