Biodegradation of random co-polypeptide hydrogels consisting of N-hydroxypropyl l-glutamine as one component

Hayashi, Takanori; Kanai, Hiroyoshi; Yodoya, Shinya; Oka, M.; Hayashi, Toshio

doi:10.1016/s0014-3057(01)00137-9

Cited by 13 publications

(7 citation statements)

References 20 publications

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“…For the same alcohol amine and diamine, the larger the amount of crosslinking agent used, the larger the f C and the smaller the amount of M C obtained, the less Q were measured. Our results were similar to the properties of PHPG films using 1,8-diamino octane as a crosslinking agent by Hayashi [6,7,10].…”

Section: Atr-ir Spectra Analysissupporting

confidence: 89%

“…Polyhydroxyalkyl glutamine crosslinked films including polyhydroxyethyl glutamine (PHEG), polyhydroxyapropyl glutamine (PHPG) and polyhydroxypeptyl glutamine (PHPeG) were made from different aminolysis agents and crosslinking agents. An aminolysis reaction of PBLG films was carried out in the mixture of an alcohol amine (2-amino 1-ethanol or 3-amino-1-propanol) and a diamine (1,2-diamino ethane,1,6-diamino hexane or 1,8-diamino octane) at 60 AE 1 C for 48 h [6,7]. The products were washed with ethanol three times, then immersed in ethanol overnight and finally dried at 50 C, thus, colorless translucent PHEG or PHPG films were obtained.…”

Section: Aminolysis and Crosslinking Reactionmentioning

confidence: 99%

“…The products were washed with ethanol three times, then immersed in ethanol overnight and finally dried at 50 C, thus, colorless translucent PHEG or PHPG films were obtained. An aminolysis reaction of PMLG films was carried out in a mixture of 5-amino-1-pentanol/pentanol 1 : 1 by weight and 1,6-hexamethylene diamine by the same procedures as above [7] and translucent PHPeG films were obtained. The starting materials of PHAGs are listed in Table 1.…”

Section: Aminolysis and Crosslinking Reactionmentioning

confidence: 99%

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Preparation of Hydrophilic Polyhydroxyalkyl Glutamine Crosslinked Films and its Biodegradability

Pan

Wang

2006

J Biomater Appl

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Polybenzyl glutamate (PBLG) or polymethyl glutamate (PMLG) films have been aminolyzed with amino alcohol and crosslinked with aliphatic diamine at 60 degrees C for 48 h simultaneously which led to the formation of crosslinked films of polyhydroxyalkyl glutamine (PHAG). ATR-IR indicates that for the aminolysis of PBLG with 2-amino-1-ethanol or 3-amino-1-propanol, benzyl glutamate almost completely turned to hydroxyalkyl glutamine, however for the aminolysis of PMLG with 5-amino-1-pentanol, methyl glutamate partially turned to hydroxypentanyl glutamine. The water-swelling test shows that water-swelling ratio Q of PHAG films from amino alcohol with longer carbon chain was smaller, the PHAG films crosslinked by 1,2-diamino ethane have the higher water-swelling ratio Q, but the PHAG films crosslinked by 1,8-diamino octane have the lower water swelling ratio Q; and PHAG films with a greater amount of crosslinking agents have high crosslinking density or the low water swelling-ratio Q for same amino alcohol and diamine. It is obvious from in vitro enzymatic hydrolysis test that specimens with smaller swelling ratio Q displayed larger T(1/2), time for half weight digestion of PHAG film, that is, less biodegradability. Therefore, biodegradability of the crosslinked PHAG films can be controlled by changing amino alcohol and diamine.

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Section: Atr-ir Spectra Analysissupporting

confidence: 89%

Section: Aminolysis and Crosslinking Reactionmentioning

confidence: 99%

Section: Aminolysis and Crosslinking Reactionmentioning

confidence: 99%

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Preparation of Hydrophilic Polyhydroxyalkyl Glutamine Crosslinked Films and its Biodegradability

Pan

Wang

2006

J Biomater Appl

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“…Recently, the utilization of enzymatic degradation of polypeptide-based nanoparticles by proteolytic enzymes has been investigated as an additional advantage of such systems, offering a new stimulus for their drug release applications and establishing biodegradation as an important structural characteristic. − Cancer cells often secrete proteolytic enzymes that can act as an external stimulus for polypeptide-based materials to gradually release their loaded cargo. Due to the partial polypeptide nature of the NPs developed in the present study, we exploited their responsiveness toward this external stimulus in order to induce the release of their drug cargo.…”

Section: Resultsmentioning

confidence: 99%

Marcromolecular Architecture and Encapsulation of the Anticancer Drug Everolimus Control the Self-Assembly of Amphiphilic Polypeptide-Containing Hybrids

et al. 2019

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Macromolecular architecture plays an important role in the self-assembly process of block copolymer amphiphiles. Herein, two series of stimuli-responsive amphiphilic 3-miktoarm star hybrid terpolypeptides and their corresponding linear analogues were synthesized exhibiting the same overall composition and molecular weight but different macromolecular architecture. The macromolecular architecture was found to be a key parameter in defining the morphology of the nanostructures formed in aqueous solutions as well as to alter the self-assembly behavior of the polymers independently of their composition. In addition, it was found that the assemblies prepared from the star-shaped polymers showed superior tolerance against enzymatic degradation due to the increased corona block density on the outer surface of the nanoparticles. Encapsulation of the hydrophobic anticancer drug Everolimus resulted in the formation of intriguing non-spherical and non-symmetric pH-responsive nanostructures, such as “stomatocytes” and “multi-compartmentalized suprapolymersomes”, while the pH-triggered release of the drug was also investigated. Owing to the similarities of the developed “stomatocytes” with red blood cells, in combination with their pH-responsiveness and superior stability over enzymatic degradation, they are expected to present advanced drug delivery properties and have the ability to bypass several extra- and intracellular barriers to reach and effectively treat cancer cells.

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“…Recently, the utilization of enzymes as a stimuli has received a great deal of attention for drug delivery by vesicles . Advances in the field of synthetic biomaterials have added the enzymatic degradation of the polypeptide-based hydrogels as a further advantage of those systems, offering a new stimulus for their drug release applications and establishing biodegradation as an important property. − However, the evaluation of the sensitivity of these hydrogels to proteases has not yet been reported. Cancer cells often secrete proteolytic enzymes that can act as a stimulus for polypeptidic materials to release their cargo.…”

Section: Resultsmentioning

confidence: 99%

Self-Healing pH- and Enzyme Stimuli-Responsive Hydrogels for Targeted Delivery of Gemcitabine To Treat Pancreatic Cancer

et al. 2018

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A novel, multifunctional hydrogel that exhibits a unique set of properties for the effective treatment of pancreatic cancer (PC) is presented. The material is composed of a pentablock terpolypeptide of the type PLys- b-(PHIS- co-PBLG)-PLys- b-(PHIS- co-PBLG)- b-PLys, which is a noncytotoxic polypeptide. It can be implanted via the least invasive route and selectively delivers gemcitabine to efficiently treat PC. Simply mixing the novel terpolypeptide with an aqueous solution of gemcitabine within a syringe results in the facile formation of a hydrogel that has the ability to become liquid under the shear rate of the plunger. Upon injection in the vicinity of cancer tissue, it immediately reforms into a hydrogel due to the unique combination of its macromolecular architecture and secondary structure. Because of its pH responsiveness, the hydrogel only melts close to PC; thus, the drug can be delivered directionally toward the cancerous rather than healthy tissues in a targeted, controlled, and sustained manner. The efficacy of the hydrogel was tested in vivo on human to mouse xenografts using the drug gemcitabine. It was found that the efficacy of the hydrogel loaded with only 40% of the drug delivered in one dose was equal to or slightly better than the peritumoral injection of 100% of the free drug delivered in two doses, the typical chemotherapy used in clinics so far. This result suggests that the hydrogel can direct the delivery of the encapsulated drug effectively in the tumor tissue. Enzymes lead to its biodegradation, avoiding removal by resection of the polypeptidic carrier after cargo delivery. The unique properties of the hydrogel formed can be predetermined through its molecular characteristics, rendering it a promising modular material for many biological applications.

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Biodegradation of random co-polypeptide hydrogels consisting of N-hydroxypropyl l-glutamine as one component

Cited by 13 publications

References 20 publications

Preparation of Hydrophilic Polyhydroxyalkyl Glutamine Crosslinked Films and its Biodegradability

Preparation of Hydrophilic Polyhydroxyalkyl Glutamine Crosslinked Films and its Biodegradability

Marcromolecular Architecture and Encapsulation of the Anticancer Drug Everolimus Control the Self-Assembly of Amphiphilic Polypeptide-Containing Hybrids

Self-Healing pH- and Enzyme Stimuli-Responsive Hydrogels for Targeted Delivery of Gemcitabine To Treat Pancreatic Cancer

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