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

Controlled modification of the carboxylic acid moieties of hyaluronic acid with mono- and polyfunctional hydrazides leads to biochemical probes, biopolymers with altered physical and chemical properties, tethered drugs for controlled release, and crosslinked hydrogels as biocompatible scaffoldings for tissue engineering. Methods for polyhydrazide synthesis, for prodrug preparation, for hydrogel crosslinking, and for monitoring biodegradation are described.

Biocompatible Materials↗

Hyaluronic acid and yeast extract do not oxidize DOPA.

Hyaluronic acid and yeast extract, separately and in combination, were tested for their ability to oxidize dopa to pigment. Two types of hyaluronic acid and yeast extract were used. The activities were assayed both spectrophotometrically and by oxygen-uptake determinations. The results were uniformly negative. The biological role of hyaluronic acid is discussed. Use of pigment formation from phenolic compounds as an identification test of another organism is pointed out.

Catechol Oxidase↗

Stimulatory effect of prostaglandins on the production of hexosamine-containing substances by cultured fibroblasts (3) induction of hyaluronic acid synthetase by prostaglandin F2alpha.

The mechanism of the stimulatory effect of prostaglandin(PG)F2alpha on the production of hexosamine-containing substances by cultured fibroblasts was studied. Treatment of the cells with 1 microgram/ml of PGF2alpha resulted in a doubled net synthesis of acidic glycosaminoglycans during 20 hrs measured with uronic acid as index, and also resulted in 300 per cent increase of 3H-glucosamine incorporation into hexosamine-containing substances during the first 6 hrs. Fractionation of the PGF2alpha-stimulated hexosamine-containing substances with double isotope technique revealed that hyaluronic acid was the most stimulated component. Prior to the increase of hyaluronic acid, hyaluronic acid synthetase activity was found to be augmented by PGF2alpha as high as 4 times over the control. The augmentation of hyaluronic acid synthetase activity by PGF2alpha did not take place if actinomycin D was simultaneously present in the culture medium, suggesting that PGF2alpha induced the enzyme.

Animals↗

Concentration of hyaluronic acid in primary open-angle glaucoma aqueous humor.

We compared the concentration of hyaluronic acid in the aqueous humor of primary open-angle glaucoma (POAG) patients and non-glaucomatous patients. Aqueous humor samples were obtained from 22 patients just before trabeculectomy for clinically uncontrolled POAG (POAG group). Aqueous humor (0.1 mL) was aspirated by inserting a 26-gauge needle into the anterior chamber. The same procedure was performed for 22 non-glaucomatous patients just before cataract surgery (control group). Immediately after collection, the aqueous humor was stored at -20 degrees C. The concentration of hyaluronic acid was determined by a sensitive, noncompetitive and nonisotopic fluoroassay. The median (range) concentrations of hyaluronic acid of the POAG and control groups were 298.4 microg L(-1) (99.0-743.7 microg L(-1)) and 545.1 microg L(-1) (145.0-2366.0 microg L(-1)), respectively. The difference in concentrations of hyaluronic acid between the groups was statistically significant (P<0.001). In conclusion, the concentration of hyaluronic acid in the aqueous humor in POAG patients is lower than in non-glaucomatous patients. Further studies are necessary to determine the role of hyaluronic acid in the pathophysiology of POAG.

Adult↗

Highly efficient syntheses of hyaluronic acid oligosaccharides.

Highly efficient syntheses of hyaluronic acid oligosaccharides have been accomplished through the pre-activation based iterative one-pot strategy. A series of oligosaccharides ranging from di- to hexasaccharides were rapidly assembled using only near stoichiometric amounts of the building blocks without aglycon adjustment or purifications of intermediate oligosaccharides. Deprotection and oxidation protocols were developed for protective group removal and oxidation-state adjustment. The availability of such structurally well defined synthetic hyaluronic acid oligosaccharides will greatly facilitate the establishment of detailed structure-function relationships.

Glycosaminoglycans↗

Hyaluronic acid is an endogenous inducer of interleukin-1 production by human monocytes and rabbit macrophages.

When human peripheral monocytes and rabbit peritoneal macrophages were incubated with hyaluronic acid, the media were found to contain interleukin-1 (IL-1) activity and to stimulate collagenase production by rabbit fibroblasts. A digestion of hyaluronic acid by testicular hyaluronidase decreased the IL-1 inducing activity. Polymixin B, an inhibitor of endotoxin, did not exert any effect towards the action of hyaluronic acid. Hyaluronic acid also stimulated human polymorphonuclear leucocytes to produce IL-1 like activity. These results indicate that hyaluronic acid is an endogenous IL-1 inducer and may play important roles in the pathological and/or physiological changes of connective tissues.

Animals↗

[The change of hyaluronic acid of the vitreous humour by oxidation-reduction-systems (author's transl)].

Purified hyaluronic acid of ox vitreous humour was isolated treating the acetone precipitate of a vitreous humour homogenate with 1 M NaCl solution and thereafter with cetylpyridiniumchloride. Both disc-electrophoresis and hydroxyproline content proved the absence of collagen in the purified hyaluronic acid. FeSO4, ascorbate, and cysteine changed the hyaluronic acid molecule and lowered the viscosity of the hyaluronic acid solution, EDTA alone did not affect the viscosity but enhanced the effectiveness of iron ions or ascorbate on the viscosity of the solution. Catalase prevented the reduction of the viscosity by the above mentioned substances. Therefore, it is suggested that H2O2 and free radicals are generated during the reaction. The free radicals produced are responsible for the change of the hyaluronic acid molecule.

Animals↗

Interaction of fibronectin and its proteolytic fragments with hyaluronic acid.

The interaction of porcine plasma fibronectin and its proteolytic fragments with hyaluronic acid was investigated by affinity chromatography using hyaluronic acid-linked Sepharose 4B. Hyaluronic acid was found to interact with all major fragments including the gelatin-binding polypeptide which has no affinity for heparin. A difference between hyaluronic acid and heparin was also noted in the relative interaction with two larger fragments. This type of multiple interaction may account for the affinity for hyaluronic acid strong enough to prevent the elution of fibronectin from the hyaluronate-column with a buffer containing 2 M NaCl.

Amino Acids↗

The hydrodynamic resistance of hyaluronic acid: estimates from sedimentation studies.

The problem of estimating the permeability of hyaluronic acid as a function of concentration has been examined. A previously known method of obtaining permeability from sedimentation studies has been employed, and the results have been compared to those obtained from convection studies, in which solvent is forced through the hyaluronic acid. The two sets of results were seen to be at variance, which could be explained by a flow-induced polarization of the hyaluronic acid in the convection studies. The polarization phenomenon was described in terms of a convection-associated compaction balancing the hyaluronic acid's intrinsic resistance to compression. Based on these results and other arguments, it was suggested that data from sedimentation studies provide a more accurate estimate of hyaluronic acid permeability than do convection experiments. The implications of this finding in a physiological context were briefly discussed.

Gels↗

Preparation of alkylamine and 125I-radiolabeled derivatives of hyaluronic acid uniquely modified at the reducing end.

Present procedures to obtain radiolabeled hyaluronic acid derivatives are limited to low-specific-activity isotopes and small amounts of material, and often involve multiple points of chemical modification within the polymer. A synthesis has been developed which affords large quantities of a unique, chemically modified derivative of hyaluronic acid containing a single hydroxyphenyl group at the reducing end, which can be radioiodinated to high specific activity. Very little alteration in oligosaccharide structure is expected since only the terminal reducing sugar is modified. Oligosaccharides of hyaluronic acid, which have no free amino groups, were first converted to alkylamine derivatives to allow subsequent reaction with the Bolton-Hunter reagent, N-succinimidyl-3(4-hydroxyphenyl)propionate. Synthesis of the hyaluronate-amine was achieved by (i) reduction of the terminal reducing sugar with sodium borohydride, (ii) controlled sodium periodate oxidation to generate an aldehyde group only at the reduced end, and (iii) coupling this aldehyde to an alpha,omega- alkyldiamine (e.g., 1,6- hexanediamine ) in the presence of sodium cyanoborohydride. Purified hyaluronate-amine oligosaccharides were then reacted with the Bolton-Hunter reagent, and the hydroxyphenyl derivative thus obtained was radioiodinated with Na125I. Specific activities up to 8 X 10(9) cpm/nmol oligosaccharide can be obtained. This approach yields a uniquely modified, highly radioactive probe which will be useful in studies of cellular and extracellular matrix interactions with hyaluronic acid. In addition, the uniquely modified alkylamine derivative of hyaluronic acid has been used to prepare affinity chromatography media and synthetic cell culture surfaces.

Amines↗

Characterization of chemisorbed hyaluronic acid directly immobilized on solid substrates.

Hyaluronic acid (HA) has a number of potential biomedical applications in drug delivery and tissue engineering. For these applications, a prerequisite is to understand the characteristic of HA films directly immobilized to solid substrates. Here, we demonstrate that high molecular weight HA can be directly immobilized onto hydrophilic substrates without any chemical manipulation, allowing for the formation of an ultrathin chemisorbed layer. Hyaluronic acid is stabilized on these surfaces through hydrogen bonding between the hydrophilic moieties in HA [such as carboxylic acid (-COOH) or hydroxyl (-OH) groups] with silanol (-SiOH), carboxylic acid or hydroxyl groups on the hydrophilic substrates. Despite the water solubility, the chemisorbed HA layer remained stable on glass or silicon oxide substrates for at least 7 days in phosphate-buffered saline. Furthermore, HA immobilized on silicon and other dioxide surfaces in much higher quantities than other polysaccharides including dextran sulfate, heparin, heparin sulfate, chondroitin sulfate, dermatan sulfate, and alginic acid. This behavior is related to the molecular entanglement and intrinsic stiffness of HA as a result of strong internal and external hydrogen bonding as well as high molecular weight. These results demonstrate that HA can be used to coat surfaces through direct immobilization.

Absorption↗

Low molecular weight hyaluronic acid prevents oxygen free radical damage to granulation tissue during wound healing.

Hyaluronic acid protects granulation tissue from oxygen free radical damage and stimulates wound healing, but its molecular weight prevents it from permeating the epidermal barrier A low molecular weight hyaluronic acid preparation is able to permeate the skin, but it is unknown whether or not it retains the scavenging effects of oxygen free radicals in granulation tissue. Our experiments were conducted in rats with excisional or incisional wounds. Wound contraction over 11 days and breaking strength on the fifth day were measured. Oxygen free radical production was induced by intraperitoneal administration of two different xenobiotics: phenazine methosulfate and zymosan. The wounds were treated topically with low molecular weight hyaluronic acid (0.2%) cream or placebo. In the incisional wound group, the effects of superoxide dismutase were also determined. Absolute controls received wounds and placebo but no xenobiotics. Wound healing was significantly slower in the xenobiotic group than in the control groups. These effects were strongly reduced by topical administration of low molecular weight hyaluronic acid (0.2%) cream and in incisional wounds by topically injected superoxide dismutase. Low molecular weight hyaluronic acid is effective as the native compound against oxygen free radicals. Its pharmacological effects through transdermal administration should be tested in appropriate models.

Granulation Tissue↗

The composition and physicochemical properties of hyaluronic acids prepared from ox synovial fluid and from a case of mesothelioma.

1. Materials containing hyaluronic acid have been prepared by filtration (Ogston & Stanier, 1950) from ox synovial fluid and from a protein-rich human mesothelioma fluid. The ox material has been deproteinized by treatment with chloroform and pentanol and by gradient elution on DEAE-Sephadex; several fractions were obtained by the latter method. These materials can be stored in solution at -20 degrees without change of properties. The ox material contained 21% of protein; all other preparations contained less than 6% of protein. 2. The two materials have been compared by sedimentation and viscosity and shown to be closely similar. Treatment of the ox material with neuraminidase caused no change in its viscosity behaviour. 3. Information about the molecular configuration of the ox material has been obtained from measurements of light-scattering and viscosity. The results, though consistent with a highly extended configuration, are not consistent with a linear random-coil configuration. It is tentatively suggested that the structure may have some degree of branching and of cross-linking, which give it a rigidity with respect to expansion of the molecular domain that would not be possessed by a random coil. 4. The deproteinized material recovered from DEAE-Sephadex, though polydisperse, showed unchanged average molecular weight; however, the average radius of gyration was greater than before this treatment. 5. Acidification to approx. pH3 resulted in a contraction of the structure, with only a slight degree of expansion when the pH was restored to 6.8-7.0. 6. Measurements of optical rotatory dispersion qualitatively support a structure less simple than a linear random coil. 7. Colloid osmotic pressures of mixed solutions of bovine serum albumin and of hyaluronic acid prepared by filtration from ox synovial fluid have been measured. The results agree approximately with those of Laurent & Ogston (1963) but are in quantitative disagreement with the partition measurements of Ogston & Phelps (1960). The relationships between thermodynamic quantities in a quaternary system of electrolytes are discussed in Appendix 2. 8. Refractometric measurements have been made in connexion with light-scattering measurements, as the basis for a convenient method of determining the concentrations of solutions of hyaluronic acids, and to measure the partition of sodium chloride in dialysis experiments. The theory of the last use is discussed in Appendix 1. 9. Sedimentation measurements on the ox preparation have been made up to a concentration of 1.4x10(-2)g./ml. The form of the sedimentation coefficient-concentration relationship is discussed. The value of the sedimentation coefficient at higher concentration is the basis of an illustration of the likely effect of hyaluronic acid on the flow of water through narrow channels in connective tissue. 10. Available colorimetric methods have been shown to give low estimates for glucuronic acid when applied to highly polymerized materials, as compared with estimates by decarboxylation. A spectrophotometric titration with cetylpyridinium bromide has been shown to give estimates of carboxyl groups that agree well with those of decarboxylation when applied to preparations of hyaluronic acid under suitable conditions; the results are not affected by the presence of protein. 11. Estimates of glucosamine (Ogston, 1964) have been found to be low compared with those of total acetyl, independently of the presence of protein. The magnitude of the discrepancy is characteristically different for preparations from ox synovial fluid and from mesothelioma. 12. Sialic acid was estimated in several preparations. It is likely that this forms part of the protein. 13. Analyses of preparations for total nitrogen, amino acids, total acetyl, glucuronic acid (by decarboxylation) and ash account for at least 95.7% of the dry weight in terms of N-acetylglucosaminyl, glucuronyl, protein and metal ions. Previously published analyses of hyaluronic acids are reviewed. 14. The estimated molar ratios of glucuronic acid to glucosamine were all significantly greater than unity. 15. The analytical results are interpreted as agreeing with the physicochemical measurements in suggesting a more complex structure, for at least some hyaluronic acids, than that of an alternate linear copolymer in random-coil configuration.

Animals↗

Chemical alterations of hyaluronic acid and dermatan sulfate detected in aging human skin by infrared spectroscopy.

Age-mediated deacetylation of hyaluronic acid and dermatan sulfate, and shift of sulfate ester configuration were indicated by infrared spectroscopy. Hyaluronic acid and the three dermatan sulfates (DS18, DS28 and DS35), sequentially precipitated from adult skin with 18%, 28% and 35% ethanol, were analyzed at varying ages. At age 75 years, loss of infrared bands in the 1,650-1,600 cm-1 region, at 1,380 cm-1 and 1,320 cm-1 and appearance of a band at 1,560 cm-1 were characteristic of hyaluronic acid and DS35; moreover, in DS28 and DS35 the intensities of the bands at 840 cm-1 and 860 cm-1 were, respectively, decreased and increased. A low intensity band in the 805-785 cm-1 region was observed in the spectra of DS18 (19-35 years), DS28 (70-80 years) and DS35 (all ages). It intensified in DS28 of the 80-year-olds. In the 75 +/- 5-year-old group, ninhydrin-positive material of hyaluronic acid and DS35 increased, while reducing GlcNAc of hyaluronic acid decreased. The data demonstrated hyaluronic acid and DS35 deacetylation and suggested a decrease of equatorial sulfates with infrared band at 840 cm-1 and an increase of axial sulfates with band at 860 cm-1 in DS28 and DS35 of the 75 +/- 5-year-old set. Equatorial Equatorial sulfates with band in the 805 +/- 785 cm-1 region apparently decreased in DS18 after 35 years and increased in DS28 of the oldest group.

Adult↗

Evaluation of hyaluronic acid binding ability of hepatic sinusoidal endothelial cells in rats with liver cirrhosis.

BACKGROUND & AIMS: In liver cirrhosis, the binding and degradation of hyaluronic acid in the hepatic sinusoidal endothelial cells are considered to be reduced by development of hepatic sinusoidal capillarization, resulting in high serum hyaluronic acid concentration. The aim of this study is to clarify the cause of high blood hyaluronic acid concentration in liver cirrhosis. METHODS: Liver cirrhosis was induced in rats by thioacetamide administration. In vivo observation of sinusoidal capillarization, in vitro immunolocalization of factor VIII-related antigen and CD44, and [14C]hyaluronic acid binding in cultured sinusoidal endothelial cells were determined. RESULTS: Basement membranes were observed on the basal side of sinusoidal endothelial cells. The fenestrae and fluorescent intensity of anti-CD44 bound to the cells decreased with progression of hepatic fibrosis. Immunofluorescent reactive products of factor VIII-related antigen were more abundant in the cirrhotic rats compared with the controls. Amount of [14C]hyaluronic acid binding was significantly decreased in the cirrhotic group compared with the controls. CONCLUSIONS: One reason that the blood hyaluronic acid concentration increases markedly in liver cirrhosis is considered to be the reduction in hyaluronic acid receptors of hepatic sinusoidal endothelial cells and in the amount of hyaluronic acid binding to the cells.

Animals↗

Histochemical studies on hyaluronic acid in the developing human retina.

Changes in the distribution of hyaluronic acid in the developing human retina were investigated histochemically with alcian blue staining and the Streptomyces hyaluronidase digestion method using 56 human embryos and fetuses ranging from 5 to 41 weeks of gestational age. Hyaluronic acid was first detected in the inner layer of the retina at 12 weeks. The site of accumulation extended towards the outer layer by 20 weeks. At the neonatal stage, longitudinal fibers, possibly the processes of Müller cells, were proved to contain hyaluronic acid. These findings suggest that Müller cells produce hyaluronic acid transiently from 12 weeks' gestation to the neonatal stage.

Aged↗

Circulating hyaluronic acid in nonpregnant, pregnant, and postpartum guinea pigs: elevated levels observed at parturition.

OBJECTIVE: Dilatation of the uterine cervix at parturition is associated with an increase in cervical hyaluronic acid content. The objective is to test the hypothesis that circulating hyaluronic acid is increased at parturition. STUDY DESIGN: Serum hyaluronic acid levels from nonpregnant (n = 5), pregnant (n = 13), and postpartum (n = 4) adult Hartley guinea pigs were determined with a radiometric assay that utilizes iodine 125-labeled hyaluronic acid-binding protein. Results were analyzed for statistical significance with Student's paired t test and regression analysis. RESULTS: The serum hyaluronic acid level in nonpregnant animals was 238 +/- 88 ng/ml (mean +/- SEM). During pregnancy, serum hyaluronic acid levels were 127 +/- 12 and 126 +/- 34 ng/ml at 25 and 50 to 63 days' gestation, respectively. At parturition, hyaluronic acid levels increased fivefold to 765 +/- 111 ng/ml (p less than 0.001). Hyaluronic acid levels returned to antepartum values 2 days post partum (153 +/- 27 ng/ml). There was no significant difference between arterial and venous levels. CONCLUSION: Circulating hyaluronic acid levels increase significantly at parturition in the guinea pig.

Animals↗