Synthesis of a novel zwitterionic biodegradable poly (α,β-l-aspartic acid) derivative with some l-histidine side-residues and its resistance to non-specific protein adsorption

Wang, Xiaojuan; Wu, Guolin; Lu, Caicai; Wang, Yinong; Fan, Yunge; Gao, Hui; Ma, Jianbiao

doi:10.1016/j.colsurfb.2011.04.010

Cited by 29 publications

(25 citation statements)

References 35 publications

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“…Poly(succinimide) (PSI) (PDI = 1.30, M n = 21.0 kDa, determined by GPC using DMF as eluent) was synthesized in our laboratory, according to the Refs. . Sodium periodate (NaIO 4 ) and hydrazine hydrate aqueous solution (80%) were purchased from Tianjin Chemical Reagent; 3‐amino‐1,2‐propanediol was purchased from J&K chemical Ltd. Doxorubicin hydrochloride (DOX·HCl) was obtained from Beijing Huafeng United Technology Co., Ltd and was used as received.…”

Section: Methodsmentioning

confidence: 99%

An injectable and biodegradable hydrogel based on poly(α,β‐aspartic acid) derivatives for localized drug delivery

Wang

et al. 2013

J Biomedical Materials Res

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An injectable hydrogel via hydrazone cross-linking was prepared under mild conditions without addition of cross-linker or catalyst. Hydrazine and aldehyde modified poly(aspartic acid)s were used as two gel precursors. Both of them are water-soluble and biodegradable polymers with a protein-like structure, and obtained by aminolysis reaction of polysuccinimide. The latter can be prepared by thermal polycondensation of aspartic acid. Hydrogels were prepared in PBS solution and characterized by different methods including gel content and swelling, Fourier transformed-infrared spectroscopy, and in vitro degradation experiment. A scanning electron microscope viewed the interior morphology of the obtained hydrogels, which showed porous three-dimensional structures. Different porous sizes were present, which could be well controlled by the degree of aldehyde substitution in precursor poly(aspartic acid) derivatives. The doxorubicin-loaded hydrogels were prepared and showed a pH-sensitive release profile. The release rate can be accelerated by decreasing the environmental pH from a physiological to a weak acidic condition. Moreover, the cell adhesion and growth behaviors on the hydrogel were studied and the polymeric hydrogel showed good biocompatibility.

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Section: Methodsmentioning

confidence: 99%

An injectable and biodegradable hydrogel based on poly(α,β‐aspartic acid) derivatives for localized drug delivery

Wang

et al. 2013

J Biomedical Materials Res

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“…11,18,24,25 In addition to this, poly(sulfobetaine) with tunable UCST has been extensively reported by several researchers. 26−29 Chang et al have also studied reversible pH-and salt-responsive soluble−insoluble phase transition in detail for the zwitterionic poly(sulfobetaine methacrylate)s. 30,31 Recently, Agarwal and co-workers published an excellent review focused on detailed discussion on polymers with UCST-type transition in aqueous solution.…”

Section: ■ Introductionmentioning

confidence: 98%

Dual-Stimuli-Responsive l-Serine-Based Zwitterionic UCST-Type Polymer with Tunable Thermosensitivity

et al. 2015

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The synthesis of L-serine-based zwitterionic polymers, poly(L-serinyl acrylate)s (PSAs), of controllable molecular weights and low polydispersities via reversible addition−fragmentation chain transfer (RAFT) polymerization in water at 70°C is described. The obtained homopolymer PSA exhibits dual responsiveness toward pH and temperature in aqueous solution. The PSA exhibits an isoelectric point near pH 2.85 where the PSA molecules exist in its zwitterionic form. In the pH range of 2.3−3.5, the aqueous PSA solution appears as a two-phase system due to the formation of insoluble aggregates through the intra-and intermolecular electrostatic interaction between the pendent ammonium and carboxylate groups of the neighboring zwitterionic PSA molecules. Furthermore, in this pH range, the two-phase PSA solution becomes one-phase upon heating, exhibiting distinct reversible upper critical solution temperature (UCST)-type phase transition. The cloud point (T p ) is found to increase with increasing molecular weights of PSAs. It is also observed that the T p changes with changing the solution pH, exhibiting highest T p near the isoelectric point of PSA. Addition of an electrolyte such as brine solution also affects the T p of PSA solution following the antipolyelectrolyte effect. Finally, fluorescein isothiocyanate (FITC) tagged PSA with dual-responsiveness is prepared by the postmodification of pendent amino groups of PSA for futuristic applications in biosensors and bioimaging.

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“…Biodegradable zwitterionic polymers based on poly(amino acid)s, polysaccharides (such as chitosan and starch), and polycarbonates have been prepared [39–42]. These biodegradable zwitterionic polymers may possess either mixed oppositely charged moieties [39, 40], or integrated zwitterions [42, 43]. Noticeable efforts in incorporating zwitterions with aliphatic polyesters have also been made [44–47], but zwitterionic polymers with well-defined aliphatic polymer-based backbones carrying pendant zwitterions have not been obtained.…”

Section: Introductionmentioning

confidence: 99%

Biodegradable zwitterionic sulfobetaine polymer and its conjugate with paclitaxel for sustained drug delivery

et al. 2017

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A fully biodegradable zwitterionic polymer and the corresponding conjugate with paclitaxel (PTX) were synthesized as promising biomaterials. Allyl-functionalized polylactide (PLA) was employed as the precursor of polymer backbones. UV-induced thiol-ene reaction was conducted to conjugate thiol-functionalized sulfobetaine (SB) with the PLA-based backbone. The resulting zwitterionic polymer did not exhibit considerable cytotoxicity. A polymer-drug conjugate was also obtained by thiol-ene reaction of both thiol-functionalized SB and PTX with allyl-functionalized PLA. The conjugate could readily form narrowly-dispersed nanoparticles in aqueous solutions with a volume-average hydrodynamic diameter (Dh,V) of 19.3 ± 0.2 nm. Such a polymer-drug conjugate-based drug delivery system showed full degradability, well-suppressed non-specific interaction with biomolecules, and sustained drug release. In vitro assessments also confirmed the significant anti-cancer efficacy of the conjugate. After 72 h incubation with PLA-SB/PTX containing 10 μg/mL of PTX, the cell viabilities of A549, MCF7, and PaCa-2 cells were as low as 20.0 ± 2.5 %, 1.7 ± 1.7 %, and 14.8 ± 0.9 %, respectively. Both flow cytometry and confocal microscopy suggested that the conjugates could be easily uptaken by A549 cells before the major release of PTX moieties. Overall, this work elucidates promising potentials of biodegradable zwitterionic polymer-based materials in biomedical applications.

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Synthesis of a novel zwitterionic biodegradable poly (α,β-l-aspartic acid) derivative with some l-histidine side-residues and its resistance to non-specific protein adsorption

Cited by 29 publications

References 35 publications

An injectable and biodegradable hydrogel based on poly(α,β‐aspartic acid) derivatives for localized drug delivery

An injectable and biodegradable hydrogel based on poly(α,β‐aspartic acid) derivatives for localized drug delivery

Dual-Stimuli-Responsive l-Serine-Based Zwitterionic UCST-Type Polymer with Tunable Thermosensitivity

Biodegradable zwitterionic sulfobetaine polymer and its conjugate with paclitaxel for sustained drug delivery

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