New amphiphilic hyaluronan derivatives based on modification with alkenyl and aryl succinic anhydrides

Tømmeraas, Kristoffer; Mellergaard, Martin; Malle, Birgitte M.; Skagerlind, Peter

doi:10.1016/j.carbpol.2011.02.011

Cited by 33 publications

(16 citation statements)

References 37 publications

(43 reference statements)

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“…A polydisperse pullulan sample (PUL) and octenyl succinic anhydride (OSA) used in this study were purchased from TCI (Tokyo Chemical Industry Co., Ltd., Tokyo, Japan). Amphiphilic copolymer samples PUL-OSA with four different degrees of substitution ( DS ) were synthesized in the same procedure as previous reported [ 10 , 11 ] according to Eenschooten et al [ 12 , 13 , 14 , 15 , 16 ]. That is, the PUL sample was firstly dissolved in Milli-Q water, and the pH of this PUL solution was adjusted to 8.5–9.0.…”

Section: Methodsmentioning

confidence: 99%

Characterization of the Micelle Formed by a Hydrophobically Modified Pullulan in Aqueous Solution: Size Exclusion Chromatography

Yang

Sato

2021

Polymers

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Size exclusion chromatography equipped with a multi-angle, light-scattering online detector (SEC-MALS) measurements were carried out on a hydrophobically modified pullulan (PUL-OSA) with degrees of substitution (DS) of 0.14, 0.2, and 0.3 in 0.01 M aqueous NaCl to obtain the degree of polymerization (N0) dependence of the radius of gyration (⟨S2⟩1/2) for PUL-OSA in the aqueous NaCl. The result was consistent with the loose flower necklace model proposed in a previous study, and the increase in the chain size with introducing OSA groups was explained by the backbone stiffness of the loose flower necklace formed by PUL-OSA. For PUL-OSA samples with DS = 0.2 and 0.3, ⟨S2⟩1/2 obtained by SEC-MALS in a high N0 region deviated downward from ⟨S2⟩1/2 expected by the loose flower necklace model. This deviation came from a tiny amount of the aggregating component of PUL-OSA, taking a branched architecture composed of loose flower necklaces. Although the aggregating component of PUL-OSA was also detected by previous small angle X-ray scattering measurements, its conformation was revealed in this study by SEC-MALS.

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Section: Methodsmentioning

confidence: 99%

Characterization of the Micelle Formed by a Hydrophobically Modified Pullulan in Aqueous Solution: Size Exclusion Chromatography

Yang

Sato

2021

Polymers

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“…The grafting of aryl and alkenyl succinic anhydrides, the smallest being phenyl succinic anhydride, to HA was also reported, resulting in a large family of amphiphilic hyaluronan derivatives (Tommeraas, Mellergaard, Malle & Skagerlind, 2011).…”

Section: Introductionmentioning

confidence: 96%

Enhancing hyaluronan pseudoplasticity via 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-mediated conjugation with short alkyl moieties

Petta

Eglin

Grijpma

et al. 2016

Carbohydrate Polymers

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“…To illustrate the importance of the mobile phase in SEC method development, the HA samples were first analyzed using the generally accepted standard procedure, that is, an aqueous NaCl mobile phase, where pure HA assumes a random coil conformation . From the solubility studies, this solvent system completely dissolved samples with a DS of less than 2.5.…”

Section: Resultsmentioning

confidence: 99%

“…HA can be modified at the hydroxyl and carboxyl groups using various reactions including amidation, esterification, etherification, and oxidation . In most cases, modification only targets the four hydroxyl groups since modification of the carboxyl group can affect HA’s biological properties .…”

Section: Introductionmentioning

confidence: 99%

Molar Mass Analysis of Hydrophobically Modified Hyaluronic Acid by SEC‐MALLS: Facing the Challenges of Amphiphilic Biomacromolecules

Botha

Kuntz

Moire

et al. 2018

Macro Chemistry & Physics

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A size exclusion chromatography–multiangle laser light scattering (SEC‐MALLS) method is developed for determining the molar masses of amphiphilic hyaluronan (HA), consisting of a hydrophilic polymer backbone modified to varying extents with hydrophobic, polymerizable acrylate groups. The polymers are prepared via the base‐catalyzed esterification of HA with acrylic anhydride. Various parameters are investigated including mobile phase composition, temperature, pH, salt type, and concentration in order to find the most suitable conditions for completely dissolving the modified polymers irrespective of the degree of substitution (DS), and for suppressing secondary polymer interactions. The hydrolytic and the thermal stability of the different materials at various experimental conditions are also extensively investigated. HAs with DS varying from 0 to 3.4 are subsequently analyzed at the optimized experimental conditions for the mobile phase being DMSO/H2O 60/40(v/v) with 0.05 M LiBr and an operating temperature of 40 °C. The refractive index increments (dn/dc) of the HAs are determined and the results show a dependence of dn/dc on DS.

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New amphiphilic hyaluronan derivatives based on modification with alkenyl and aryl succinic anhydrides

Cited by 33 publications

References 37 publications

Characterization of the Micelle Formed by a Hydrophobically Modified Pullulan in Aqueous Solution: Size Exclusion Chromatography

Characterization of the Micelle Formed by a Hydrophobically Modified Pullulan in Aqueous Solution: Size Exclusion Chromatography

Enhancing hyaluronan pseudoplasticity via 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-mediated conjugation with short alkyl moieties

Molar Mass Analysis of Hydrophobically Modified Hyaluronic Acid by SEC‐MALLS: Facing the Challenges of Amphiphilic Biomacromolecules

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