Spectroscopic study on the inclusion complexes of β-cyclodextrin with selected metabolites of catecholamines

Korytkowska‐Wałach, Anna; Dubrawska, Beata; Śmiga-Matuszowicz, Monika; Bieg, Tadeusz

doi:10.1016/j.molstruc.2016.08.010

Cited by 5 publications

(6 citation statements)

References 21 publications

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“…Two other groups carried out 1 H NMR titration, similarly to the present Job plot, to obtain K βCD/Val = 74−172 M −1 . 38,45 Their values are at most 3 times larger than ours, but we do not know the reason for this discrepancy. On the other hand, Karathanos et al 37 obtained K βCD/Val = 5.3 M −1 using the solubility method, which is much smaller than our values.…”

Section: ■ Discussioncontrasting

confidence: 84%

“…This is consistent with the previous discussion as well as other studies. 37,38 βCDNP 0.9 −Val shows the correlation between βCDNP and all phenyl ring protons including H-1, but it was difficult to distinguish the interaction between CD in CDNP and Val from that of Val and the polymerized ECH matrix. Therefore, there is a possibility that Val may be trapped by the polymerized ECH matrix instead of the host−guest interaction between CD in CDNP and Val.…”

Section: −43mentioning

confidence: 99%

“…Vanillin was chosen instead of MGS because the solubility of vanillin in water is quite suitable for NMR experiments, whereas that of MGS is too small to allow accurate NMR experiments. Additionally, the interaction between vanillin and CDs has been studied by various groups and it is now well-established that (1) vanillin forms a stable 1:1 complex with βCD, − (2) the binding constant between them in water at ambient temperate ranges from 10 to 2 × 10 2 M –1 , depending on the method and reseachers, ,, and (3) vanillin is oriented with the phenolic end nearer to the narrower end (or lower rim) and the aldehyde end near to the wider end (upper rim) of βCD . By use of such well-studied vanillin, we should be able to clarify the molecular mechanism of the CDNP–vanillin interaction by two-dimensional (2D) ROESY and NOESY and examine the binding constant for various types of CDNPs using DOSY.…”

Section: Introductionmentioning

confidence: 99%

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Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY)

Doan

Katsuki

et al. 2022

ACS Omega

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We report that the polymerization of cyclodextrin (CD) with epichlorohydrin (ECH) dramatically increases the binding constant of CD to vanillin, from 55 to 8.4 × 10 3 M –1 , by approximately 100 times, as determined by diffusion ordered spectroscopy (DOSY)– 1 H NMR. The binding constant increased with an increase of the ECH content of the polymer, although ECH polymers without CDs showed no affinity at all, suggesting that the hydrophobicity of the ECH network outside of CDs helps to enhance the binding. This increased binding constant allows CD–ECH polymers to increase the drug loading ratio, which may be one of the most critical issues for drug delivery systems.

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Section: ■ Discussioncontrasting

confidence: 84%

Section: −43mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY)

Doan

Katsuki

et al. 2022

ACS Omega

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“…An aqueous solution of 3-(trimethylsilyl)propionic-2,2,3,3-d 4 acid sodium salt (TSP) was used as an external reference to avoid errors in the determination of association constants [ 37 ].…”

Section: Resultsmentioning

confidence: 99%

β-Cyclodextrin Derivative Grafted on Silica Gel Represents a New Polymeric Sorbent for Extracting Nitisinone from Model Physiological Fluids

2021

Self Cite

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Nitisinone (NTBC) is used in the treatment of disorders affecting the tyrosine pathway, including hereditary tyrosinemia type I, alkaptonuria, and neuroblastoma. An inappropriate dosage of this therapeutic drug causes side effects; therefore, it is necessary to develop a rapid and sensitive method to monitor the content of NTBC in patients’ blood. This study aimed to develop anew polymeric sorbent containing β-cyclodextrin (β-CD) derivatives grafted on silica gel to effectively extract NTBC from model physiological fluids. The inclusion complex formed between β-CD and NTBC was examined by proton nuclear magnetic resonance spectroscopy. The novel sorbents with derivatives of β-CD were prepared on modified silica gel using styrene as a comonomer, ethylene glycol dimethacrylate as a crosslinking agent, and 2,2′-azo-bis-isobutyronitrile as a polymerization initiator. The obtained products were characterized via Fourier transform infrared spectroscopy and then used as sorbents as part of a solid phase extraction technique. High NTBC recovery (70%indicated that the developed polymeric sorbent may be suitable for extracting this compound from patients’ blood samples.

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“…Ion-Pair Cyclodextrin Complex Stoichiometry: A continuous variation method was employed to determine the ion-pair CD complex stoichiometry following the previous studies, using 1 H-NMR. [34,35] The total concentration of CD and the theophylline-spermine ion-pair in the solutions was kept constant at 5 × 10 −3 m. The molar fraction (r) of [CD]/[CD mixture] varied in the range of 0.1-0.9. The final pH of all mixtures was kept at 9.6 ± 0.1.…”

Section: Methodsmentioning

confidence: 99%

A Cyclodextrin‐Stabilized Spermine‐Tagged Drug Triplex that Targets Theophylline to the Lungs Selectively in Respiratory Emergency

Sofian

Benaouda

Wang

et al. 2020

Advanced Therapeutics

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Ion‐pairing a lifesaving drug such as theophylline with a targeting moiety could have a significant impact on medical emergencies such as status asthmaticus or COVID‐19 induced pneumomediastinum. However, to achieve rapid drug targeting in vivo the ion‐pair must be protected against breakdown before the entry into the target tissue. This study aims to investigate if inserting theophylline, when ion‐paired to the polyamine transporter substrate spermine, into a cyclodextrin (CD), to form a triplex, could direct the bronchodilator to the lungs selectively after intravenous administration. NMR demonstrates that upon the formation of the triplex spermine protruded from the CD cavity and this results in energy‐dependent uptake in A549 cells (1.8‐fold enhancement), which persists for more than 20 min. In vivo, the triplex produces a 2.4‐fold and 2.2‐fold increase in theophylline in the lungs 20 min after injection in rats and mice, respectively ( p < 0.05). The lung targeting is selective with no increase in uptake into the brain or the heart where the side‐effects of theophylline are treatment‐limiting. Selectively doubling the concentration of theophylline in the lungs could improve the benefit‐risk ratio of this narrow therapeutic index medicine, which continues to be important in critical care.

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Spectroscopic study on the inclusion complexes of β-cyclodextrin with selected metabolites of catecholamines

Cited by 5 publications

References 21 publications

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY)

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY)

β-Cyclodextrin Derivative Grafted on Silica Gel Represents a New Polymeric Sorbent for Extracting Nitisinone from Model Physiological Fluids

A Cyclodextrin‐Stabilized Spermine‐Tagged Drug Triplex that Targets Theophylline to the Lungs Selectively in Respiratory Emergency

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