1H NMR studies on the hydrogen-bonding network in mono-altro-β-cyclodextrin and its complex with adamantane-1-carboxylic acid

Hakkarainen, Birgit; Fujita, Kahee; Immel, Stefan; Kenne, Lennart; Sandström, Corine

doi:10.1016/j.carres.2005.03.016

Cited by 44 publications

(27 citation statements)

References 24 publications

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“…[21] Spectra were also obtained at a higher temperature (323 K), and d(NH) shifted to a lower frequency, as hydrogen bonding was disrupted by the increase in temperature. Three NMR samples of 3A5AF with different concentrations were prepared.…”

Section: Detection Of Hydrogen Bonding In 3a5af Molecules With Infrarmentioning

confidence: 99%

Combined Experimental and Computational Studies on the Physical and Chemical Properties of the Renewable Amide, 3‐Acetamido‐5‐acetylfuran

2014

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The pK(a) of 3-acetamido-5-acetylfuran (3A5AF) was predicted to be in the range 18.5-21.5 by using the B3LYP/6-311+G(2d,p) method and several amides as references. The experimental pK(a) value, 20.7, was determined through UV/Vis titrations. Its solubility was measured in methanol-modified supercritical CO2 (mole fraction, 3.23×10(-4), cloud points 40-80 °C) and it was shown to be less soluble than 5-hydroxymethylfurfural (5-HMF). Dimerization energies were calculated for 3A5AF and 5-HMF to compare hydrogen bonding, as such interactions will affect their solubility. Infrared and (1) H nuclear magnetic resonance spectra of 3A5AF samples support the existence of intermolecular hydrogen bonding. The highest occupied molecular orbital, lowest unoccupied molecular orbital, and electrostatic potential of 3A5AF were determined through molecular orbital calculations using B3LYP/6-311+G(2d,p). The π-π* transition energy (time-dependent density functional theory study) was compared with UV/Vis data. Calculated atomic charges were used in an attempt to predict the reactivity of 3A5AF. A reaction between 3A5AF and CH3MgBr was conducted. As 3A5AF is a recently developed renewable compound that has previously not been studied extensively, these studies will be helpful in designing future reactions and processes involving this molecule.

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Section: Detection Of Hydrogen Bonding In 3a5af Molecules With Infrarmentioning

confidence: 99%

Combined Experimental and Computational Studies on the Physical and Chemical Properties of the Renewable Amide, 3‐Acetamido‐5‐acetylfuran

2014

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“…Skewboat forms may also be of relevance for some systems. 48,[54][55][56][57][58][59][60][61][62][63][64][65] For a given monosaccharide stereochemistry, the relative free energies of the different pyranose ring conformations in aqueous solution may be estimated using empirical additive schemes (e.g., HasselOttar, 66 Reeves-Kelly, 38,41 Angyal 18,67 and CoreyFeiner 68,69 schemes). These schemes were derived from experimental complexation 38,39,41,70,71 and NMR 18,67,72 measurements on model six-membered ring compounds.…”

Section: Introductionmentioning

confidence: 99%

Conformation, dynamics, solvation and relative stabilities of selected β-hexopyranoses in water: a molecular dynamics study with the gromos 45A4 force field

Kräutler

Müller

Hünenberger

2007

Carbohydrate Research

139

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“…Since both adamantyl27–31 and naphthyl32–36 groups are known to serve as guest molecules for β-CD, it was reasoned that β-CD could bind to CD437 in a 2:1 stoichiometry. A convenient way to test this hypothesis is through proton NMR titrations since the aromatic naphthyl protons and aliphatic adamantyl protons appear in distinct regions of the NMR spectrum.…”

mentioning

confidence: 99%

Molecular recognition and enhancement of aqueous solubility and bioactivity of CD437 by β-cyclodextrin

Mishur

Griffin

Battle

et al. 2011

Bioorganic & Medicinal Chemistry Letters

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CD437 (6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid) is a novel synthetic retinoic acid derivative that has been shown to selectively induce apoptosis in human lung cancer cells. This compound, however, is limited in its application due to its low solubility in aqueous solutions. One technique for increasing the solubility and bioavailability of a cytotoxic agent is the formation of inclusion complexes with cyclodextrins. Herein, we report the formation and characterization of a 2:1 complex between β-cyclodextrin (β-CD) and CD437. It is shown that CD437 is a tight binder of β-CD with an overall association constant of 2.6 ± 0.6 ×10 7 M −2 . In addition, we demonstrate (a) that β-CD-derived complexation enhances the aqueous solubility of CD437, and (b) that a significant increase in the toxicity of CD437 against a human lung adenocarcinoma cell line can be achieved by co-treatment with β-CD. Keywordscyclodextrin; inclusion complex formation; supramolecular chemistry; anticancer agent CD437 (6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid) is a synthetic retinoic acid (RA) derivative which is known to have antineoplastic properties across a variety of cancer cell lines, including lung, 1 prostate, 2 ovarian, 3-4 cervical, 5 and head and neck. 6 Typically, the molecular action of retinoids depends on the binding to and activation of a subset of the nuclear hormone receptor superfamily which contains both retinoic acid receptors (RARs) and retinoid X receptors (RXRs), each of which is encoded by three genes, α, β, and γ. CD437, like RA, can bind directly to a heterodimer formed between retinoic acid receptor γ (RARγ) and a retinoid X receptor (RXR). Growth arrest and cell differentiation then occur when the activated RARγ/RXR dimer binds to a RA response element on DNA. 7 In contrast to RA, however, CD437 also displays strong apoptotic properties. In addition to the RARγ-dependent pathway, CD437 is also able to exert its * Corresponding Author: J. Jayawickramarajah, Tel.: +01-504-862-3580, Fax: +01-504-865-5596, jananj@tulane.edu. † Department of Medicine ‡ Department of Chemistry Supplementary data Supplementary data associated with this article can be found, in the online version, at xxx Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. NIH Public Access NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author Manuscript apoptotic effects through an RARγ-independent pathway. 8 Thus CD437 has been shown to induce apoptosis in both RA-resistant cell lines [8][9] and RARγ-negative cell lines. 8,10 Despite the significant anti...

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1H NMR studies on the hydrogen-bonding network in mono-altro-β-cyclodextrin and its complex with adamantane-1-carboxylic acid

Cited by 44 publications

References 24 publications

Combined Experimental and Computational Studies on the Physical and Chemical Properties of the Renewable Amide, 3‐Acetamido‐5‐acetylfuran

Combined Experimental and Computational Studies on the Physical and Chemical Properties of the Renewable Amide, 3‐Acetamido‐5‐acetylfuran

Conformation, dynamics, solvation and relative stabilities of selected β-hexopyranoses in water: a molecular dynamics study with the gromos 45A4 force field

Molecular recognition and enhancement of aqueous solubility and bioactivity of CD437 by β-cyclodextrin

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