Synthesis and characterization of novel multi-hydroxy polyaspartamide derivative and its crosslinked hydrogels

Dang, Quoc Dat; Park, Jung Hwan; Bhang, Suk Ho; Kim, Ji‐Heung

doi:10.1016/j.reactfunctpolym.2019.104455

Cited by 8 publications

(7 citation statements)

References 23 publications

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“…After ring-opening reaction with side chains containing amine groups, the resulting polyaspartamide degrades to non-toxic byproducts. Second, PSI can be easily coupled with versatile graft chains and therapeutics. − The facile coupling chemistry makes the polymer an ideal platform to construct nanoparticles incorporated with targeting, imaging, and therapeutic functions.…”

Section: Discussionmentioning

confidence: 99%

Combining Doxorubicin-Conjugated Polymeric Nanoparticles and 5-Aminolevulinic Acid for Enhancing Radiotherapy against Lung Cancer

Han

Yang

et al. 2022

Bioconjugate Chem.

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Radiation therapy (RT) concurrent with chemotherapy improves local lung cancer control but may cause systemic toxicity. There is an unmet clinical need of treatments that can selectively sensitize cancer cells to RT. Herein, we explored a radiosensitizing strategy that combines doxorubicin (DOX)-encapsulated polyaspartamide nanoparticles and 5-aminolevulinic acid (5-ALA). The DOX-polyaspartamide nanoparticles were coupled with NTSmut, a ligand specific to neurotensin receptor type 1 (NTSR1), for lung cancer targeting. DOX was coupled to the polymer backbone through a pH-sensitive hydrazone linker, which allows for controlled release of the drug in an acidic tumor micromovement. Meanwhile, 5-ALA accumulates in the cancer cell’s mitochondria, forming protoporphyrin (PpIX) that amplifies RT-induced oxidative stress. When tested in vitro in H1299 cells, DOX-encapsulated nanoparticles in conjugation with 5-ALA enhanced cancer cell killing owing to the complementary radiosensitizing effects of DOX and 5-ALA. In vivo studies confirmed that the combination improved tumor suppression relative to RT alone without causing toxicity to normal tissues. Overall, our study suggests an effective and selective radiosensitizing approach.

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Section: Discussionmentioning

confidence: 99%

Combining Doxorubicin-Conjugated Polymeric Nanoparticles and 5-Aminolevulinic Acid for Enhancing Radiotherapy against Lung Cancer

Han

Yang

et al. 2022

Bioconjugate Chem.

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“…The disappearance of the imide ring peak (1707 cm −1 ) and the appearance of two amide bond peaks (1637 and 1526 cm −1 ) in the FTIR spectrum of PDHPA indicated the conversion of PSI to PDHPA (Figure 2b). [16] The structure of PDHPA was confirmed using 1 H NMR spectroscopy (Figure 2c) revealing the dihydroxypropyl group of pendant and the amide group of peptide backbone. [16] Complete conversion was verified by the absence of a succinimide ring peak at around 5.3 ppm in the NMR spectrum of PDHPA (Figure S1a,b, Supporting Information).…”

Section: Synthesis Of Pdhpa Polymer and Preparation Of Pdhpa-ba Hydrogelmentioning

confidence: 93%

“…[16] The structure of PDHPA was confirmed using 1 H NMR spectroscopy (Figure 2c) revealing the dihydroxypropyl group of pendant and the amide group of peptide backbone. [16] Complete conversion was verified by the absence of a succinimide ring peak at around 5.3 ppm in the NMR spectrum of PDHPA (Figure S1a,b, Supporting Information). [16] Molecular weight of PSI and PDHPA determined using Mark-Houwink equation were 75 and 146 kDa, respectively (Figure S1c, Supporting Information).…”

Section: Synthesis Of Pdhpa Polymer and Preparation Of Pdhpa-ba Hydrogelmentioning

confidence: 93%

“…[15] Polyaspartamide derivatives have excellent biocompatibility and biodegradability owing to their peptide backbone. [15][16][17] The functionalization of diverse pendants makes polyaspartamide derivatives promising materials in various fields, such as metal ion adsorption, [17] drug delivery, [18,19] and bone adhesion. [20] Furthermore, owing to their versatility, they are frequently used to make various hydrogels, including photocrosslinkable, [18] and dual-crosslinked hydrogels.…”

Section: Introductionmentioning

confidence: 99%

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Adhesive Composite Hydrogel Patch Based on a Polyaspartamide Derivative to Treat Atopic Dermatitis

Park

Kim

et al. 2023

Advanced Therapeutics

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Transdermal patches offer significant advantages as a drug delivery system due to their ability to bypass first‐pass metabolism, sustain drug release, and provide predetermined dose and application area. However, to be effective, transdermal patches must have optimal adhesion and drug‐loading capacity. In this study, an adhesive composite hydrogel patch consisting of poly(N‐2,3‐dihydroxypropyl aspartamide) (PDHPA), a polyaspartamide derivative, and mesoporous silica nanoparticles (MSNs) are developed. To prepare the hydrogel, boric acid (BA) is utilized as a crosslinker to form reversible bonds between multiple hydroxyl groups in the polymer and BA. The PDHPA‐BA hydrogel exhibits dynamic reversibility, self‐healing properties, and a pH‐dependent sol–gel transition. The addition of MSNs with abundant hydroxyl groups improves the mechanical performance, adhesion properties, and self‐healing rate of the PDHPA‐BA hydrogel. In addition, MSNs enable the loading of hydrophobic drugs, such as dexamethasone (Dex), onto the hydrogel. Using the Dex‐loaded adhesive composite hydrogel as a transdermal patch, the severity of atopic dermatitis in a mouse model indicated by suppression of dermatitis score, epidermal thickness, number of mast cells, and serum interleukin‐4 levels is successfully reduced. These results suggest that the composite hydrogel patch is a highly promising transdermal drug delivery system for effectively treating inflammatory skin diseases.

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“…Cross-linking is a well-known strategy for preparing drug-loaded hydrogels or nanogels. The cross-linking reaction can occur between two polymers containing reactive functional groups [13,69,81], or between polymer and small molecule cross-linker [98][99][100][101]. Of course, enzymes can also be used as cross-linker to promote the cross-linking reaction of PASPAm derivatives for the preparation of nanogels [102].…”

Section: Drug Loadingmentioning

confidence: 99%

Stimuli-Responsive Poly(aspartamide) Derivatives and Their Applications as Drug Carriers

Zhang

Bao

2021

IJMS

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Poly(aspartamide) derivatives, one kind of amino acid-based polymers with excellent biocompatibility and biodegradability, meet the key requirements for application in various areas of biomedicine. Poly(aspartamide) derivatives with stimuli-responsiveness can usually respond to external stimuli to change their chemical or physical properties. Using external stimuli such as temperature and pH as switches, these smart poly(aspartamide) derivatives can be used for convenient drug loading and controlled release. Here, we review the synthesis strategies for preparing these stimuli-responsive poly(aspartamide) derivatives and the latest developments in their applications as drug carriers.

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Synthesis and characterization of novel multi-hydroxy polyaspartamide derivative and its crosslinked hydrogels

Cited by 8 publications

References 23 publications

Combining Doxorubicin-Conjugated Polymeric Nanoparticles and 5-Aminolevulinic Acid for Enhancing Radiotherapy against Lung Cancer

Combining Doxorubicin-Conjugated Polymeric Nanoparticles and 5-Aminolevulinic Acid for Enhancing Radiotherapy against Lung Cancer

Adhesive Composite Hydrogel Patch Based on a Polyaspartamide Derivative to Treat Atopic Dermatitis

Stimuli-Responsive Poly(aspartamide) Derivatives and Their Applications as Drug Carriers

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