Efficient Synthesis of an Aldehyde Functionalized Hyaluronic Acid and Its Application in the Preparation of Hyaluronan−Lipid Conjugates

Ruhela, Dipali; Riviere, Kareen; Szoka, Francis C.

doi:10.1021/bc0600721

Cited by 48 publications

(49 citation statements)

References 16 publications

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“…Aldehyde hyaluronic acid (A-HA) was synthesized according to an already reported procedure slightly modified 44, 45 . Briefly, 1 g HA (2.5 mmol) was dissolved in 100 mL double distilled water at a concentration of 10 mg/ml.…”

Section: Methodsmentioning

confidence: 99%

Injectable in situ cross-linking chitosan-hyaluronic acid based hydrogels for abdominal tissue regeneration

Deng

Ren

Chen

et al. 2017

Sci Rep

130

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Abdominal wall defect caused by open abdomen (OA) or abdominal trauma is a serious issue since it induces several clinical problems. Although a variety of prosthetic materials are commonly employed, complications occur including host soft tissue response, fistula formation and chronic patient discomfort. Recently, abundant natural polymers have been used for injectable hydrogel synthesis in tissue regeneration. In this study, we produced the chitosan - hyaluronic acid (CS/HA) hydrogel and investigated its effects on abdominal tissue regeneration. The physical and biological properties of the hydrogel were demonstrated to be suitable for application in abdominal wounds. In a rat model simulating open abdomen and large abdominal wall defect, rapid cellular response, sufficient ECM deposition and marked neovascularization were found after the application of the hydrogel, compared to the control group and fibrin gel group. Further, the possible mechanism of these findings was studied. Cytokines involved in angiogenesis and cellular response were increased and the skew toward M2 macrophages credited with the functions of anti-inflammation and tissue repair was showed in CS/HA hydrogel group. These findings suggested that CS/HA hydrogel could prevent the complications and was promising for abdominal tissue regeneration.

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Section: Methodsmentioning

confidence: 99%

Injectable in situ cross-linking chitosan-hyaluronic acid based hydrogels for abdominal tissue regeneration

Deng

Ren

Chen

et al. 2017

Sci Rep

130

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“…Hyaluronated conjugates were synthesized as described by Ruhela et al [28] with minor modifications. Briefly, 0.060 mmol of HA (HA4800 0.3 g; HA12000 0.72 g) was quite completely dissolved in 20 ml of methanol and dimethyl sulfoxide (1:1 v/v) and stirred at 60 °C.…”

Section: Synthesis and Characterization Of Hyaluronated Conjugatesmentioning

confidence: 99%

“…Then the Schiff base or imine, which is formed initially in situ and is unstable, is reduced in presence of NaBH(OAc)3 to a secondary amine leading to the formation of the conjugate. The high reaction yield was obtained using a mixture of solvents as previously reported by Ruhela [28]: methanol and dimethylsulfoxyde for the HA, methanol and chloroform for the phospholipid and for NaBH(OAc)3.…”

Section: Synthesis Of Hyaluronated Conjugatesmentioning

confidence: 99%

Hyaluronic acid-coated liposomes for active targeting of gemcitabine

Berlier

Lerda

Pozza

et al. 2013

European Journal of Pharmaceutics and Biopharmaceutics

129

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The aim of this work was the preparation, characterization and preliminary evaluation of the targeting ability towards pancreatic adenocarcinoma cells of liposomes containing the gemcitabine lipophilic prodrug [4-(N)-lauroyl-gemcitabine, C12GEM]. Hyaluronic acid (HA) was selected as targeting agent since it is biodegradable, biocompatible, can be chemically modified and its cell surface receptor CD44 is overexpressed on various tumors.For this purpose, conjugates between a phospholipid, the 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE), and HA of two different low molecular weights 4800 Da (12 disaccharidic units) and 12000 Da (32 disaccharidic units), were prepared, characterized and introduced in the liposomes during the preparation.Different liposomal formulations were prepared and their characteristics were analyzed: size, Z potential and TEM analyses underline a difference of the HA-liposomes from the non-HA ones. In order to better understand the HA-liposome cellular localization and to evaluate their interaction with CD44 receptor, confocal microscopy studies were performed. The results demonstrate that HA facilitates the recognition of liposomes by MiaPaCa2 cells (CD44 + ) and that the uptake increases with increasing of the polymer molecular weight.Finally, the cytotoxicity of the different preparations was evaluated and data show that incorporation of C12GEM increases their cytotoxic activity and that HA-liposomes inhibit cell growth more than plain liposomes.Altogether the results demonstrate the specificity of C12GEM targeting towards CD44-overexpressing pancreatic adenocarcinoma cell line using HA as a ligand.

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“…For targeting of the anticancer drugs to the tumors, there must be some form of prolonged association between the HA and drug/s which could simply be the result of normal blood flow and cardiac output dynamics, while the increased retention of tumoral drug could be a result of abnormal flow dynamics within the microvasculature of the tumors. Ruhela et al (2006) synthesized HA oligosaccharide lipid conjugates as described previously. This strategy was based on the introduction of a double bond in the glucuronic acid of the HA, by the biodegradation of HA with hyaluronate lyase, followed by the generation of a free aldehyde group at the nonreducing end of HA via ozonolysis and the subsequent reduction of the generated ozonide.…”

Section: Applications Of Ha In Dosage Form In the Drug Delivery Systemmentioning

confidence: 99%

An insight on hyaluronic acid in drug targeting and drug delivery

Yadav

Mishra

Agrawal

2008

Journal of Drug Targeting

111

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Hyaluronic acid (HA) has recently been studied for its use in drug delivery applications. Medically, HA is used as a surgical aid in ophthalmology. It also possesses therapeutic potential in the treatment of arthritis and wound healing. HA-binding receptors, CD44 and receptor for hyaluronan-mediated motility have attracted much enthusiasm, mainly because they are believed to be involved in cancer metastasis. This review unravels the role of HA in drug delivery and targeting. Designing of various novel drug delivery systems using HA as a biopolymer will also be reviewed in the present article.

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Efficient Synthesis of an Aldehyde Functionalized Hyaluronic Acid and Its Application in the Preparation of Hyaluronan−Lipid Conjugates

Cited by 48 publications

References 16 publications

Injectable in situ cross-linking chitosan-hyaluronic acid based hydrogels for abdominal tissue regeneration

Injectable in situ cross-linking chitosan-hyaluronic acid based hydrogels for abdominal tissue regeneration

Hyaluronic acid-coated liposomes for active targeting of gemcitabine

An insight on hyaluronic acid in drug targeting and drug delivery

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