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.
Recommended Journals

Heteroatom Chemistry

Medicinal Chemistry Research

Bioorganic & Medicinal Chemistry Letters

Acta Metallurgica Sinica-English Letters

NDT & E International

Journal of the Indian Institute of Science

Main Group Chemistry

Bioorganic & Medicinal Chemistry

Cellulose

Critical Reviews in Solid State and Materials Sciences
Related Literature
Influence of the solvent on the crystal structure of PCBM and the efficiency of MDMO-PPV:PCBM ‘plastic’ solar cells
Minze T. Rispens, Auke Meetsma, Roman Rittberger, Christoph J. Brabec, N. Serdar Sariciftci, Jan C. Hummelen
DOI: 10.1039/B305988J
Using biofunctional magnetic nanoparticles to capture Gram-negative bacteria at an ultra-low concentration
Hongwei Gu, Pak-Leung Ho, Kenneth WT Tsang, Chun-Wing Yu, Bing Xu
DOI: 10.1039/B305421G
Inner C-cyanide addition and nucleophilic addition to Ni(ii) N-confused porphyrins
Ziwei Xiao, Brian O. Patrick, David Dolphin
DOI: 10.1039/B211990K
Ag8Cl2[Se2P(OEt)2]6: A rare example containing a combination of discrete clusters and chains
C. W. Liu, Chiu-Mine Hung, Hsien-Chung Haia, Ben-Jie Liaw, Lin-Shu Liou, Yi-Fang Tsai, Ju-Chun Wang
DOI: 10.1039/B300887H
A novel approach to carbon hollow spheres and vessels from CCl4 at low temperatures
Zhengquan Li, Changzheng Wu, Rong Zhang
DOI: 10.1039/B211996J
Selective synthesis of conformationally restricted mono-cyclopentadienyl titanium(iv) complexes of p-tBu-calix[6]arene
Antonella J. Petrella, Nicholas K. Roberts, Donald C. Craig, Colin L. Raston, Robert N. Lamb
DOI: 10.1039/B301075A
An (E)-selective synthesis of trisubstituted (E)-α,β-unsaturated acid derivatives
Fred J. P. Feuillet, Diane E. J. E. Robinson, Steven D. Bull
DOI: 10.1039/B304213H
A novel peptide synthesis using fluorous chemistry
Mamoru Mizuno, Kohtaro Goto, Tsuyoshi Miura, Daisuke Hosaka, Toshiyuki Inazu
DOI: 10.1039/B300682D
“The splice is right”: how protein splicing is opening new doors in protein science
Edmund C. Schwartz, Tom W. Muir, Amy B. Tyszkiewicz
DOI: 10.1039/B304989M
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.
![L-Lysine,N6-[2-[[(1,1-dimethylethoxy)carbonyl]amino]benzoyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]- structure L-Lysine,N6-[2-[[(1,1-dimethylethoxy)carbonyl]amino]benzoyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]- structure](https://static.chemtradehub.com/structs/159/159322-59-5-c046.webp)


![2-[2-(2-Methoxyethoxy)ethoxy]-2-methylpropane structure 2-[2-(2-Methoxyethoxy)ethoxy]-2-methylpropane structure](https://static.chemtradehub.com/structs/527/52788-79-1-71c1.webp)
