Spectroscopic insight into supramolecular assemblies of boric acid derivatives and β-cyclodextrin

被引：25

作者：

Kasprzak, Artur ^{[1
]}

Borys, Krzysztof M. ^{[1
]}

Molchanov, Sergey ^{[1
]}

Adamczyk-Wozniak, Agnieszka ^{[1
]}

机构：

[1] Warsaw Univ Technol, Fac Chem, Noakowskiego 3, PL-00664 Warsaw, Poland

来源：

CARBOHYDRATE POLYMERS | 2018年 / 198卷

关键词：

beta-Cyclodextrin; Ferroceneboronic; Phenylboronic; Organoboron; Boric; INCLUSION COMPLEXES; ALPHA-CYCLODEXTRIN; HYDROXY PROTONS; METHYL-ORANGE; NMR; MECHANOCHEMISTRY; DISSOLUTION; RECOGNITION; BEHAVIOR; H-1-NMR;

D O I：

10.1016/j.carbpol.2018.06.085

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Interactions of select boric acid derivatives with beta-cyclodextrin were investigated. All products were obtained employing the grinding-induced mechanochemical approach. It was found that phenylboronic acid, benzoxaborole and boric acid form non-covalent, hydrogen bonding-based systems with beta-cyclodextrin, whereas catechol and pinacol esters of phenylboronic acid as well as ferroceneboronic acid form host-guest inclusion complexes. The interactions were probed using spectroscopic methods: H-1 NMR, H-1-H-1 ROESY NMR, H-1 DOSY NMR, FT-IR. Association constant values were evaluated by H-1 DOSY NMR. The highest association constant was found for boric acid (117.5 +/- 2.5 M-1), whilst the lowest for benzoxaborole (14.8 +/- 0.3 M-1). The study shows the influence of boron compound structure on the nature of the assembly formed with beta-cyclodextrin, laying up the basis for future work with such supramolecular systems.

引用

页码：294 / 301

页数：8

共 58 条

[1] Intramolecular interactions in ortho-methoxyalkylphenylboronic acids and their catechol esters [J].

Adamczyk-Wozniak, Agnieszka ;

Borys, Krzysztof M. ;

Czerwinska, Karolina ;

Gierczyk, Blazej ;

Jakubczyk, Michal ;

Madura, Izabela D. ;

Sporzynski, Andrzej ;

Tomecka, Ewelina .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2013, 116 :616-621

[2] Influence of the Substituents on the Structure and Properties of Benzoxaboroles [J].

Adamczyk-Wozniak, Agnieszka ;

Cyranski, Michal K. ;

Jakubczyk, Michal ;

Klimentowska, Paulina ;

Koll, Aleksander ;

Kolodziejczak, Jerzy ;

Pojmaj, Grzegorz ;

Zubrowska, Anna ;

Zukowska, Grazyna Z. ;

Sporzynski, Andrzej .

JOURNAL OF PHYSICAL CHEMISTRY A, 2010, 114 (06) :2324-2330

[3] Resolving natural product epimer spectra by matrix-assisted DOSY [J].

Adams, Ralph W. ;

Aguilar, Juan A. ;

Cassani, Julia ;

Morris, Gareth A. ;

Nilsson, Mathias .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) :7062-7064

[4] COMPLEX-FORMATION OF NITRAZEPAM IN COPRECIPITATING AND IN CO-GRINDING WITH METHYLATED BETA-CYCLODEXTRINS [J].

AHMED, MO ;

NAKAI, Y ;

ABOUTALEB, AE ;

YAMAMOTO, K ;

RAHMAN, AAZA ;

SALEH, SI .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) :3423-3427

[5] Linking Phenotype to Kinase: Identification of a Novel Benzoxaborole Hinge-Binding Motif for Kinase Inhibition and Development of High-Potency Rho Kinase Inhibitors [J].

Akama, Tsutomu ;

Dong, Chen ;

Virtucio, Charlotte ;

Sullivan, David ;

Zhou, Yasheen ;

Zhang, Yong-Kang ;

Rock, Fernando ;

Freund, Yvonne ;

Liu, Liang ;

Bu, Wei ;

Wu, Anne ;

Fan, Xiao-Qing ;

Jarnagin, Kurt .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2013, 347 (03) :615-625

[6] The effect of mechanical grinding on the formation, crystalline changes and dissolution behaviour of the inclusion complex of telmisartan and β-cyclodextrins [J].

Amarante Borba, Paola Aline ;

Pinotti, Mariha ;

Santana Andrade, George Ricardo ;

da Costa, Nivan Bezerra, Jr. ;

Olchanheski Junior, Luiz Renato ;

Fernandes, Daniel ;

Maduro de Campos, Carlos Eduardo ;

Stulzer, Hellen Karine .

CARBOHYDRATE POLYMERS, 2015, 133 :373-383

[7] Formation of cyclodextrin inclusion complexes with doxycyclin-hyclate: NMR investigation of their characterisation and stability [J].

Bakkour, Y ;

Vermeersch, G ;

Morcellet, M ;

Boschin, F ;

Martel, B ;

Azaroual, N .

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2006, 54 (1-2) :109-114

[8] Water-soluble calix[n]arenes as receptor molecules for non-polar substrates and inverse phase transfer catalysts [J].

Baur, M ;

Frank, M ;

Schatz, J ;

Schildbach, F .

TETRAHEDRON, 2001, 57 (32) :6985-6991

[9] 1H NMR studies of maltose, maltoheptaose, α-, β-, and γ-cyclodextrins, and complexes in aqueous solutions with hydroxy protons as structural probes [J].

Bekiroglu, S ;

Kenne, L ;

Sandström, C .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1671-1678

[10] 1H-NMR studies of the inclusion complexes between α-cyclodextrin and adamantane derivatives using both exchangeable hydroxy protons and non-exchangeable aliphatic protons [J].

Bendeby, B ;

Kenne, L ;

Sandström, C .

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2004, 50 (3-4) :173-181

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