Facile Fabrication of 10-Hydroxycamptothecin-Backboned Amphiphilic Polyprodrug with Precisely Tailored Drug Loading Content for Controlled Release

Bioconjugate Chemistry
Xiaolong ZhangHua Wei

Abstract

Polymeric prodrugs with precisely controlled drug loading content (DLC) and rapid intracellular destabilization generally require complicated chemistry that hinders large-scale manufacture. For this purpose, we reported in this study a facile construction of reduction-sensitive amphiphilic polyprodrugs with an anticancer drug, 10-hydroxycamptothecin (HCPT), and a hydrophilic poly(ethylene oxide) (PEG) moiety as the alternating building blocks of the multiblock copolymer using Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAc) click coupling between azide-SS-HCPT-SS-azide and alkyne-PEG-alkyne. Adoption of PEGs with two different molecular weights (MWs) of 400 and 1450 Da (PEG400 and PEG1450) afforded two polyprodrugs with different DLCs. Both formulations can self-assemble into spherical micelles with hydrodynamic diameter smaller than 200 nm, and exhibit glutathione (GSH)-triggered degradation for promoted drug release. A further comparison study revealed that the PEG1450-based polyprodrug is a better formulation than the analogue constructed from PEG400 in terms of in vitro drug release behaviors, and cytotoxicity. This work thus provides a facile yet efficient strategy toward polymeric prodrugs with precisely controlled DLC ...Continue Reading

References

Aug 26, 2000·The Journal of Organic Chemistry·H ZhaoR B Greenwald
Mar 4, 2003·Nature Reviews. Drug Discovery·J Milton Harris, Robert B Chess
Jul 13, 2004·Bioorganic & Medicinal Chemistry·Xungui HeJian Ding
Oct 26, 2005·Drug Discovery Today·Francesco M Veronese, Gianfranco Pasut
Nov 30, 2005·Journal of Biomedical Materials Research. Part a·Kenya Whitaker-Brothers, Kathryn Uhrich
Aug 11, 2006·Nature Reviews. Cancer·Ruth Duncan
Mar 5, 2008·Clinical Cancer Research : an Official Journal of the American Association for Cancer Research·Kwangjae ChoDong M Shin
Mar 29, 2008·Bioconjugate Chemistry·Hong ZhaoIvan D Horak
Apr 1, 2008·Advanced Drug Delivery Reviews·Chun Li, Sidney Wallace
Oct 23, 2008·Journal of Medicinal Chemistry·Sung-Ju MoonDavid M Goldenberg
Dec 31, 2008·International Journal of Pharmaceutics·Xingguo YangYebang Tan
Feb 22, 2011·Advanced Drug Delivery Reviews·Rubi MahatoKun Cheng
Sep 6, 2011·Annual Review of Medicine·Andrew Z WangOmid C Farokhzad
Aug 11, 2012·Journal of Controlled Release : Official Journal of the Controlled Release Society·Roselin Rosario-MeléndezKathryn E Uhrich
Dec 25, 2012·Journal of Controlled Release : Official Journal of the Controlled Release Society·Rui ZhangJindřich Kopeček
Mar 30, 2013·Biomaterials·Kai HanXian-Zheng Zhang
May 8, 2013·Angewandte Chemie·Yanfeng ZhangJianjun Cheng
May 14, 2014·Advanced Drug Delivery Reviews·Mathumai KanapathipillaiDonald E Ingber
Aug 1, 2014·Journal of the American Chemical Society·Ping HuangDeyue Yan
Aug 6, 2014·Proceedings of the National Academy of Sciences of the United States of America·Rui ZhangJindřich Kopeček
Mar 6, 2015·Journal of the American Chemical Society·Kaimin CaiJianjun Cheng
Sep 28, 2015·Journal of Controlled Release : Official Journal of the Controlled Release Society·Jiyuan YangJindřich Kopeček
Oct 25, 2017·Nature Chemistry·Mikiembo KukwikilaAli Tavassoli
Mar 21, 2017·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Zhiyun ZhangYubin Huang
Jun 21, 2017·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Xufeng ZhouHua Wei

❮ Previous
Next ❯

Citations

Aug 28, 2019·Wiley Interdisciplinary Reviews. Nanomedicine and Nanobiotechnology·Debabrata DuttaZhishen Ge
Nov 30, 2018·Bioconjugate Chemistry·Chuang GaoZhifei Dai
Jan 20, 2021·ACS Biomaterials Science & Engineering·Yuping LiuHua Wei
Oct 26, 2021·Advanced Materials·Kuikun YangXiaoyuan Chen
Jan 27, 2022·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Shuying LiZhaowei Chen

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.