Biocompatible and bioreducible micelles fabricated from novel α-amino acid-based poly(disulfide urethane)s: design, synthesis and triggered doxorubicin release
Literature Information
Wentao Lu, Xiuxiu Wang, Ru Cheng, Chao Deng, Fenghua Meng, Zhiyuan Zhong
α-Amino acid-based functional biopolymers are highly appealing for various biomedical applications including controlled drug delivery. In this paper, we report the design and development of novel reductively biodegradable α-amino acid-based poly(disulfide urethane)s, denoted as AAPU(SS)s, as well as PEG-AAPU(SS)-PEG triblock copolymer micelles for triggered intracellular doxorubicin (DOX) release. AAPU(SS)s were synthesized with controlled Mn ranging from 4.6 to 35.7 kg mol−1via polycondensation reaction between two α-amino acid derivatives, disulfide-linked bis(ethyl L-serinate) (SS-BSER) and L-lysine ethyl ester diisocyanate (LDI). AAPU(SS)s are amorphous with a glass transition temperature (Tg) of 31.7–49.2 °C and were degraded into low molecular weight fragments under a reductive condition. PEG-AAPU(SS)-PEG copolymer could be readily obtained by treating AAPU(SS) with mPEG-NCO. PEG-AAPU(SS)-PEG formed micelles with a mean diameter of 155 nm. The in vitro release studies showed that drug release from DOX-loaded PEG-AAPU(SS)-PEG micelles was significantly accelerated in the presence of 10 mM glutathione (GSH). MTT assays revealed that DOX-loaded PEG-AAPU(SS)-PEG micelles caused effective growth inhibition of both RAW 264.7 and drug resistant MCF-7 cells (MCF-7/ADR) while the corresponding blank micelles were non-cytotoxic even at a high concentration of 1.0 mg mL−1. Confocal microscopy showed that PEG-AAPU(SS)-PEG micelles efficiently transported and released DOX into the perinuclear and nuclear regions of MCF-7/ADR cells. These biocompatible and bioreducible α-amino acid-based poly(disulfide urethane) micelles have appeared to be a particularly interesting platform for triggered intracellular anticancer drug delivery.
Related Literature
Synthesis of renewable alkylated decalins with p-quinone and 2-methyl-2,4-pentanediol
Yancheng Hu, Guangyi Li, Yu Cong, Xiaodong Wang
DOI: 10.1039/D1SE01684A
Green hydrogen and platform chemicals production from acidogenic conversion of brewery spent grains co-fermented with cheese whey wastewater: adding value to acidogenic CO2
Omprakash Sarkar, Ulrika Rova, Paul Christakopoulos, Leonidas Matsakas
DOI: 10.1039/D1SE01691A
Correction: Facile fluorene-based hole-transporting materials and their dual application toward inverted and regular perovskite solar cells
Rong-hao Cen, Xueping Zong, Yang Cheng, Mei Zhao, Ming Luo, Yantao Zhang, Song Xue
DOI: 10.1039/D1SE90080C
Harnessing the potential of lead-free Sn–Ge based perovskite solar cells by unlocking the recombination channels
Yulia Galagan, Hamid Ez-Zahraouy
DOI: 10.1039/D1SE00687H
Metal fuel production through the solar carbothermal reduction of magnesia: effect of the reducing agent
Youssef Berro, Damaris Kehrli, Jean-François Brilhac, Marianne Balat-Pichelin
DOI: 10.1039/D1SE01549D
How to go beyond C1 products with electrochemical reduction of CO2
Hao Zhang, Hang Xiang, Shahid Rasul, Alberto Roldan, Rebecca Taylor, Yujie Feng, Liam Banerji, Alexander Cowan, Jin Xuan
DOI: 10.1039/D1SE00861G
Nanoparticles of aromatic biopolymers catalyze CO2 cycloaddition to epoxides under atmospheric conditions
Wimalin Jaroonwatana, Tharinee Theerathanagorn, Man Theerasilp, Silvano Del Gobbo, Doungporn Yiamsawas, Valerio D'Elia, Daniel Crespy
DOI: 10.1039/D1SE01305J
NiOx-supported PtRh nanoalloy enables high-performance hydrogen evolution reaction under universal pH conditions
Dinesh Bhalothia, Yu-Min Yu, Yi-Ru Lin, Tzu- Hsi Huang, Che Yan, Jyh-Fu Lee, Kuan-Wen Wang
DOI: 10.1039/D1SE01331A
You might also like
What precautions should be taken when handling 2-Methyl-2-propanyl 5-amino-2-thiophenecarboxylate (CAS: 1498311-57-1)?
When handling 2-Methyl-2-propanyl 5-amino-2-thiophenecarboxylate (CAS: 1498311-5...
What are the physical and chemical properties of 5-Bromo-1,2-dichloro-3-fluorobenzene (CAS: 1000572-93-9)?
5-Bromo-1,2-dichloro-3-fluorobenzene (CAS: 1000572-93-9) is a crystalline solid ...
How should (2R)-2-Amino-2-(4-bromophenyl)ethanol (CAS: 354153-64-3) be stored?
(2R)-2-Amino-2-(4-bromophenyl)ethanol (CAS: 354153-64-3) should be stored in a c...
What regulatory guidelines apply to Methyl 4-(aminomethyl)tetrahydro-2H-pyran-4-carboxylate hydrochloride (CAS: 362707-24-2)?
Methyl 4-(aminomethyl)tetrahydro-2H-pyran-4-carboxylate hydrochloride (CAS: 3627...
What are the main uses of 1,4-dimethyl-1H-pyrazole-5-sulfonyl chloride (CAS: 1174834-52-6)?
1,4-Dimethyl-1H-pyrazole-5-sulfonyl chloride is primarily used as an intermediat...
Is Dinaphtho[1,2-b:2',1'-d]furan (CAS: 239-69-0) safe?
Dinaphtho[1,2-b:2',1'-d]furan is generally safe when handled with appropriate pe...
What is the market or research trend for 7-Methyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione (CAS: 612-37-3)?
The market for 7-Methyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione (CAS: 612-37-3) i...
What are the physical and chemical properties of 2-(4-Chlorophenyl)malonaldehyde (CAS: 205676-17-1)?
2-(4-Chlorophenyl)malonaldehyde (CAS: 205676-17-1) is a colorless or light yello...
How is 2-Methylchrysene (CAS: 3351-32-4) typically synthesized?
2-Methylchrysene (CAS: 3351-32-4) is typically synthesized via the reaction of c...
Is N-(6-aminopyrimidin-4-yl)acetamide (CAS: 89533-23-3) safe?
N-(6-aminopyrimidin-4-yl)acetamide (CAS: 89533-23-3) is generally considered saf...
Source Journal
Polymer Chemistry

Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.












methyl]-N,2-dimethyl-2-propanesulfinamide structure N-[(R)-[3-(Benzyloxy)-2-(dicyclohexylphosphino)phenyl](phenyl)methyl]-N,2-dimethyl-2-propanesulfinamide structure](https://static.chemtradehub.com/structs/256/2565792-50-7-8a26.webp)

![3-(benzotriazol-1-yl)-N-[[2-[(3-bromophenyl)methoxy]phenyl]methylideneamino]propanamide structure 3-(benzotriazol-1-yl)-N-[[2-[(3-bromophenyl)methoxy]phenyl]methylideneamino]propanamide structure](https://static.chemtradehub.com/structs/559/5595-78-8-0a32.webp)