Controlled chemical modification of hyaluronic acid: synthesis, applications, and biodegradation of hydrazide derivatives

Prestwich, Glenn D.; Marecak, Dale M.; Marecek, James F.; Vercruysse, Koen; Ziebell, Michael R.

doi:10.1016/s0168-3659(97)00242-3

Cited by 376 publications

(220 citation statements)

References 15 publications

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“…As a drug delivery carrier, HA has numerous functional groups obtainable for conjugation. 22 On the other hand, the natural cationic polymer CHI has been shown to have absorption enhancer properties through mucosa, controlled drug release, and bioadhesion. 21 CHI has also been found to enhance the cytotoxicity and apoptotic induction of chemotherapeutic agent oxaliplatin via mitochondrial-associated pathways.…”

Section: Introductionmentioning

confidence: 99%

Improvement and enhancement of antibladder carcinoma cell effects of heteronemin by the nanosized hyaluronan aggregation

Huang

Kuo

et al. 2016

IJN

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The effects against tumors exerted by marine active compounds have been highlighted and investigated. Polymeric nanoparticles made from biodegradable and biocompatible molecules such as hyaluronan (HA) and chitosan (CHI) are able to aggregate the compounds to enhance their activities against tumor cells and reduce the toxicity on normal cells. Here, we extensively examined the antitumor activities and the mechanisms of HA/CHI nanoparticles-aggregated heteronemin (HET) extracted from the sponge Hippospongia sp. The half-maximal inhibitory concentration (IC 50 ) of pure HET toward T24 bladder carcinoma cells is ~0.28 µg/mL. Pure HET from 0.2 to 0.8 µg/mL and HA nanoparticles-aggregated HET at 0.1 and 0.2 µg/mL significantly reduced T24 cell viability. Compared to pure HET, HA nanoparticles/HET aggregates showed much weaker viability-inhibitory effects on L929 normal fibroblasts. HET dose-dependently suppressed cancer cell migration as HA/CHI nanoparticles-aggregated HET displayed stronger migration-inhibitory effects than pure HET. Flow cytometric analysis showed that pure HET increased early/total apoptosis and JC-1 monomer fluorescence, while HA/CHI nanoparticles-aggregated HET induced higher apoptosis and JC-1 monomer rates than pure HET, suggesting that aggregation of HA nanoparticles offers HET stronger apoptosis-inducing capacity through mitochondrial depolarization. Western blot analysis showed that HA nanoparticles-aggregated HET further increased mitochondrial-associated, caspase-dependent and caspase-independent, as well as endoplasmic reticulum stress-related factors in comparison with pure HET. These data indicated that pure HET possesses cytotoxic, antimigratory, and apoptosis-inducing effects on bladder cancer cells in vitro, and its induction of apoptosis in bladder carcinoma cells is mainly caspase dependent. Moreover, HA nanoparticle aggregation reinforced the cytotoxic, antimigratory, and apoptosis-inducing activities against bladder carcinoma cells and attenuated the viability-inhibitory effects on normal fibroblasts. This aggregation reinforces antibladder carcinoma effects of HET via diverse routes, including mitochondrial-related/caspase-dependent, caspase-independent, and endoplasmic reticulum stress-related pathways. The current data also strongly suggested that HA/CHI nanoparticles-aggregated HET would be a potential treatment for urothelial cancer in vivo.

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Section: Introductionmentioning

confidence: 99%

Improvement and enhancement of antibladder carcinoma cell effects of heteronemin by the nanosized hyaluronan aggregation

Huang

Kuo

et al. 2016

IJN

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“…Hyaluronan has not only peculiar physical properties in terms of hydration, viscosity and hydrogel formation but it becomes more and more investigated for its specific biological and bioactive properties and its implications in cell adhesion properties 5,6 and motility 7 . One of the main applications of hyaluronan concerns tissue engineering, where it has been mostly used to form a wide variety of hydrogels [8][9][10] . Several strategies have been developed to prepare these gels and rely usually on the introduction of chemically modified groups or on its complexation with cationic biopolymers (such as chitosan or collagen at acidic pHs) such as to form composite hydrogels 11,12 .…”

Section: Introductionmentioning

confidence: 99%

Layer-by-Layer Films from Hyaluronan and Amine-Modified Hyaluronan

et al. 2007

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Hyaluronan is a polysaccharide that is increasingly investigated for its role in cellular adhesion and for the preparation of biomimetic matrices for tissue engineering. Hyaluronan gels are prepared for application as space fillers whereas hyaluronan films are usually obtained by adsorbing or grafting a single hyaluronan layer onto a biomaterial surface. Here, we examine the possibility to employ the layer-by-layer technique to deposit thin films of cationic modified hyaluronan (HA + ) and hyaluronan (HA) of controlled thicknesses. The buildup conditions are investigated and growth is compared to that of other polyelectrolyte multilayer films containing either HA as polyanion or HA + as polycation. The films could be formed in a low ionic strength medium but required to be cross-linked prior to be put in contact with physiological medium. NIH3T3 fibroblasts were perfectly viable on selfassembled hyaluronan films with however a preference for hyaluronan ending films. These findings point out the possibility to tune the thickness of thin hyaluronan films at the nanometer scale. Such architectures could be employed for investigating cell/substrate interactions or for functionalizing biomaterial surfaces.

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“…This lack of immunogenicity makes HA an attractive building block for the design of novel biomaterials. [7][8][9][10] Another characteristic that makes HA an attractive candidate for engineering new biomaterials is its lubricity and nonadhesive nature. There is evidence that HA coats and separates most tissue surfaces that slide along each other; it is found in high concentrations in synovial fluid.…”

Section: Introductionmentioning

confidence: 99%

Attachment of hyaluronan to metallic surfaces

Pitt

Morris

Mason

et al. 2003

J Biomedical Materials Res

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Metal implants are in general not compatible with the tissues of the human body, and in particular, blood exhibits a severe hemostatic response. Herein we present results of a technique to mask the surface of metals with a natural biopolymer, hyaluronan (HA). HA has minimal adverse interactions with blood and other tissues, but attachment of bioactive peptides can promote specific biological interactions. In this study, stainless steel was cleaned and then surface-modified by covalent attachment of an epoxy silane. The epoxy was subsequently converted to an aldehyde functional group and reacted with hyaluronan through an adipic dihydrazide linkage, thus covalently immobilizing the HA onto the steel surface. Fluorescent labeling of the HA showed that the surface had a fairly uniform covering of HA. When human platelet rich plasma was placed on the HA-coated surface, there was no observable adhesion of platelets. HA derivatized with a peptide containing the RGD peptide sequence was also bound to the stainless steel. The RGD-containing peptide was bioactive as exemplified by the attachment and spreading of platelets on this surface. Furthermore, when the RGD peptide was replaced with the nonsense RDG sequence, minimal adhesion of platelets was observed. This type of controlled biological activity on a metal surface has potential for modulating cell growth and cellular interactions with metallic implants, such as vascular stents, orthopedic implants, heart valve cages, and more.

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Controlled chemical modification of hyaluronic acid: synthesis, applications, and biodegradation of hydrazide derivatives

Cited by 376 publications

References 15 publications

Improvement and enhancement of antibladder carcinoma cell effects of heteronemin by the nanosized hyaluronan aggregation

Improvement and enhancement of antibladder carcinoma cell effects of heteronemin by the nanosized hyaluronan aggregation

Layer-by-Layer Films from Hyaluronan and Amine-Modified Hyaluronan

Attachment of hyaluronan to metallic surfaces

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