Hydrophobic ?-? stacking interactions and hydrogen bonds drive self-aggregation of luteolin in water

被引：14

作者：

Deogratias, Geradius ^{[1
]}

Shadrack, Daniel M. ^{[2
]}

Munissi, Joan J. E. ^{[1
]}

Kinunda, Grace A. ^{[1
]}

Jacob, Fortunatus R. ^{[1
]}

Mtei, Regina P. ^{[1
]}

Masalu, Rose J. ^{[3
]}

Mwakyula, Issakwisa ^{[4
]}

Kiruri, Lucy W. ^{[5
]}

Nyandoro, Stephen S. ^{[1
]}

机构：

[1] Univ Dar es Salaam, Coll Nat & Appl Sci, Chem Dept, POB 35061, Dar Es Salaam, Tanzania

[2] St Johns Univ Tanzania, Fac Nat & Appl Sci, Dept Chem, POB 47, Dodoma, Tanzania

[3] Univ Dar es Salaam, Coll Nat & Appl Sci, Dept Mol Biol & Biotechnol, POB 25179, Dar Es Salaam, Tanzania

[4] Univ Dar es Salaam, Mbeya Coll Hlth & Allied Sci, POB 608, Mbeya, Tanzania

[5] Kenyatta Univ, Dept Chem, POB 43844, Nairobi 00100, Kenya

来源：

JOURNAL OF MOLECULAR GRAPHICS & MODELLING | 2022年 / 116卷

关键词：

Luteolin; Hydrophobic; Hydrogen bonding; Interactions; Solubility; COPOLYMER MICELLES; DYNAMICS; SOLUBILIZATION; COCRYSTALS; BIOAVAILABILITY; NICLOSAMIDE; SYSTEMS;

D O I：

10.1016/j.jmgm.2022.108243

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

Luteolin is a flavonoid obtained from different plant species. It is known for its versatile biological activities. However, the beneficial effects of luteolin have been limited to small concentrations as a result of poor water solubility. This study aimed at investigating the hydrophobic interaction and hydration of luteolin towards the improvement of its solubility when used as a drug. We report the aggregation properties of luteolin in water by varying the number of monomers using atomistic molecular dynamics simulation. Results show that the equilibrium structure of luteolin occurs in an aggregated state with different structural arrangements. As the monomers size increase, the antiparallel flipped conformation dominates over T-shaped antiparallel, T-shaped parallel, and antiparallel conformations. The formation of intramolecular hydrogen bonding of 0.19 nm between the keto-enol groups results in hydrophobic characteristics. A larger cluster exhibits slow hydrogen bond dynamics for luteolin-luteolin than luteolin-water interaction. Water structure at large cluster size exhibited slow dynamics and low self-diffusion of luteolin. The existence of hydrophobic pi-pi and hydrogen bonds between luteolin molecules drives strong self-aggregation resulting in poor water solubility. Breakage of these established interactions would result in increased solubility of luteolin in water.

引用

页数：10

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[1] Enhanced Dissolution of Luteolin by Solid Dispersion Prepared by Different Methods: Physicochemical Characterization and Antioxidant Activity [J].