Hyaluronic acid–lipid binding

Abstract

Background Phospholipid (PL)–hyaluronic acid (HA) interactions are relevant to aging-associated vitreous humor liquefaction, therapies for dry eye disease, skin-care products and synovial joint lubrication. Phosphatidyl choline–HA interactions have been well characterized. However, other major lipids found in tears, vitreous humor and synovial joints have not. The purpose of this study was to bridge this gap of knowledge. Methods HA (1600 kDa) at 5 mg/mL, was mixed with various lipids ranging in concentration from 0.1 to 10 mg/mL in D2O. HA–PL binding was measured from the decrease in HA proton resonance intensity with binding using a nuclear magnetic resonance spectrometer. Results Cholesterol weakly bound to HA, followed by monoglyceride and palmitoyl palmitate < phosphatidyl choline, phosphatidic acid and sphingomyelin. The maximum amount of PL bound was 14 ± 1 µmoles inferring a 1 to 1 molar ratio of bound PL to HA dimer. Monoglyceride and palmitoyl palmitate required two to three times more lipid to achieve 100% bound HA compared to PL. Conclusions Physiological levels of HA, phosphatidyl choline and sphingomyelin would result in only 4% of the hydrophobic hydrogens of HA to be bound. HA–PL binding interactions could be important for therapeutic use of HA in eye drops in future studies to treat dry eye and to trap PL entering the VH to keep them from forming light scattering micelles. HA–lipid binding may also be relevant to the therapeutic effects of topical skin-care products. Both head group and hydrocarbon chain moieties influence HA–lipid interactions.

Robust Synthesis of Targeting Glyco‐Nanoparticles for Surface Enhanced Resonance Raman Based Image‐Guided Tumor Surgery

“…It is known that HA can interact with phospholipids through hydrogen bonding and hydrophobic interactions with HA distributed in punctate patterns on lipid bilayer surface. [ 59,60 ] The sulfhydryl groups in thiolated HA may cluster HA around SERS‐NPs on the liposomes enhancing the avidity with CD44. Under the same experimental conditions, liposome‐SERS‐PEG exhibited no competition against HA in the competitive ELISA assay either, highlighting the important role of HA for SERS‐HA binding with CD44 (Figure 3h).…”

“…Higher loading percentage of HA determined from the competitive ELISA assay may be due to the enhanced multi‐valency effect after HA attachment to the SERS‐NPs, which may be through thiol‐gold interaction [ 51 ] and HA binding to liposome. [ 62 ]…”

Exploring Acne Treatments: From Pathophysiological Mechanisms to Emerging Therapies

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Smart Lipid–Polysaccharide Nanoparticles for Targeted Delivery of Doxorubicin to Breast Cancer Cells

“…The composition of PHYN nanoparticles was then verified by 1 H-NMR spectrum (Figure 2d), showing the resonances at about 0.81 ppm and in the region 1.01-1.58 ppm corresponding to the terminal methyl groups and methylene protons ((CH 2 ) n ) of the hydrocarbon chains of PDC moiety, respectively, as well as the signal at 1.82 ppm, assigned to the protons of the HA acetyl groups. The signals of protons related to HA disaccharide repeating units appeared at 3.01-3.80 ppm, while the signals at about 5.15 and 5.30 ppm corresponded to the methine hydrogen of glycerol backbone and to the olefinic protons of PDC, respectively [33,34].…”