Crystal structure of 2-O-[(S)-2-hydroxypropyl]cyclomaltoheptaose

Harata, Kazuaki; Rao, C. Trinadha; Pitha, Josef; Fukunaga, Kazuhiro; Uekama, Kaneto

doi:10.1016/0008-6215(91)89004-y

Cited by 25 publications

(22 citation statements)

References 10 publications

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“…All calculations were performed using GaussView 6.0 and Gaussian 16 software packages [ 12 ]. The crystal structure of plumbagin, BCD, MBCD, and HPBCD molecules were downloaded from Cambridge Crystallographic Data Centre [ 13 ] with the Cambridge Structural Database (CSD) Entry: PVVAQS01 [ 14 ], BCDEXD03 [ 15 ], BOYFOK04 [ 16 ], and KOYYUS [ 17 ], respectively ( Figure 1 and Figure 2 ). Hydrogen atoms were added into the structures, and then fully optimized by the semi-empirical quantum mechanical PM6 and PM7 methods.…”

Section: Methodsmentioning

confidence: 99%

Host-Guest Interactions of Plumbagin with β-Cyclodextrin, Dimethyl-β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin: Semi-Empirical Quantum Mechanical PM6 and PM7 Methods

et al. 2018

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Molecular interactions of plumbagin inclusion complexes with β-cyclodextrin (BCD), dimethyl-β-cyclodextrin (MBCD), and hydroxypropyl-β-cyclodextrin (HPBCD) were investigated by semi-empirical, Parameterization Method 6 and 7 (PM6, and PM7) in the aqueous phase using polarizable continuum calculations. The results revealed two different binding modes of the plumbagin molecule inside the BCD cavity with a negative value of the complexation energy. In conformation-I, the hydroxyl phenolic group of plumbagin was placed in the BCD cavity near the narrow-side of the host molecule. In the other model, conformation-II, the methyl quinone group of plumbagin was placed in the cavity of BCD near the narrow-side of the host molecule. The higher the negative value of the complexation energy, the more favorable is the pathway of inclusion-complex formation.

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Section: Methodsmentioning

confidence: 99%

Host-Guest Interactions of Plumbagin with β-Cyclodextrin, Dimethyl-β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin: Semi-Empirical Quantum Mechanical PM6 and PM7 Methods

et al. 2018

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“…Some substituting groups have the tendency to incorporate in the core of CDs, so they compete with active drug molecules for inclusion complexation. Therefore, it is mandatory to select those substituents that are unable to fit in the cavity of CDs [58].…”

Section: Guidelines Regarding Synthesis Of CD Derivativesmentioning

confidence: 99%

Effect of Cyclodextrin Derivatization on Solubility and Efficacy of Drugs

Khalid¹,

Bashir²,

Asghar³

et al. 2020

Colloid Science in Pharmaceutical Nanotechnology

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Cyclodextrins (CDs) possess cyclic structure having (α-1,4)-linked glucopyranose units making them less vulnerable to enzymatic degradation as than the linear dextrins. Commonly used natural CDs are α-CD, β-CD, and ɣ-CD with truncated cone-like appearance having lipophilic central cavity and hydrophilic exterior surface. The problem of low aqueous solubility of natural CDs can be addressed by reacting them with various reagents to produce water-soluble derivatives. CD derivatives can be categorized in many ways depending upon their substituents, biological activity, polarity, and size. The derivatization of natural CDs produces noncrystalline and amorphous forms with higher water solubility that are physically and microbiologically stable for prolonged time period. Variety of methods can be used to determine average degree of substitution for a modified CD. Dissociation by dilution is considered as major release mechanism of drugs from complex. It is essential to optimize the amount of CDs for a given preparation because they can either retard or promote drug delivery through biological membrane.

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“…As compared to the abundance of cyclodextrin (CD) inclusion compounds which have been determined by X-ray crystallography (Saenger, 1984;Harata, 1996), relatively few structures of substituted CD's other than O-methylated derivatives have been elucidated (Harata, 1998). In the case of β-CD's monosubstituted at the primary carbon (C-6), the tethered substituent of one β-CD unit, such as t-butylthio (Hirotsu et al, 1982;Fujita et al, 1985), phenylthio and phenylsulfinyl (Kamitori et al, 1987), azido (Charpin et al, 1990), 2-hydroxypropyloxy (Harata et al, 1991) and (6-aminohexyl)amino (Mentzafos et al, 1996), is included in the cavity of another substituted β-CD. This simultaneous functioning of a molecule as host and guest provides unique three-dimensional self-assemblies, most notably helical polymers (Hirotsu et al, 1982;Kamitori et al, 1987).…”

Section: Figurementioning

confidence: 99%