A Simple and Efficient Method for Preparation of Monomethoxypolyethylene Glycol Activated with p-Nitrophenylchloroformate and Its Application to Modification of L-Asparaginase.

Kito, Mariko; Miron, Talia; Wilchek, Meir; Kojima, Nakao; Ohishi, Nobuko; Yagi, Kazuichi

doi:10.3164/jcbn.21.101

Cited by 4 publications

(2 citation statements)

References 19 publications

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“…A single-step method for activation of PEG using 4-nitrophenyl chloroformate (4-NPCl) can produce a series of reactive PEG-phenylcarbonate derivatives. The PEG intermediates are stable for storage, and reaction with amino groups proceeds rapidly at near-neutral pH [ 21 , 22 ].…”

Section: Methodsmentioning

confidence: 99%

Delicate Hybrid Laponite–Cyclic Poly(ethylene glycol) Nanoparticles as a Potential Drug Delivery System

Tang,

Chen,

Cannon

et al. 2023

Pharmaceutics

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The objective of the study was to explore the feasibility of a new drug delivery system using laponite (LAP) and cyclic poly(ethylene glycol) (cPEG). Variously shaped and flexible hybrid nanocrystals were made by both the covalent and physical attachment of chemically homogeneous cyclized PEG to laponite nanodisc plates. The size of the resulting, nearly spherical particles ranged from 1 to 1.5 µm, while PEGylation with linear methoxy poly (ethylene glycol) (mPEG) resulted in fragile sheets of different shapes and sizes. When infused with 10% doxorubicin (DOX), a drug commonly used in the treatment of various cancers, the LAP-cPEG/DOX formulation was transparent and maintained liquid-like homogeneity without delamination, and the drug loading efficiency of the LAP-cPEG nano system was found to be higher than that of the laponite-poly(ethylene glycol) LAP-mPEG system. Furthermore, the LAP-cPEG/DOX formulation showed relative stability in phosphate-buffered saline (PBS) with only 15% of the drug released. However, in the presence of human plasma, about 90% of the drug was released continuously over a period of 24 h for the LAP-cPEG/DOX, while the LAP-mPEG/DOX formulation released 90% of DOX in a 6 h burst. The results of the cell viability assay indicated that the LAP-cPEG/DOX formulation could effectively inhibit the proliferation of A549 lung carcinoma epithelial cells. With the DOX concentration in the range of 1–2 µM in the LAP-cPEG/DOX formulation, enhanced drug effects in both A549 lung carcinoma epithelial cells and primary lung epithelial cells were observed compared to LAP-mPEG/DOX. The unique properties and effects of cPEG nanoparticles provide a potentially better drug delivery system and generate interest for further targeting studies and applications.

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Section: Methodsmentioning

confidence: 99%

Delicate Hybrid Laponite–Cyclic Poly(ethylene glycol) Nanoparticles as a Potential Drug Delivery System

Tang,

Chen,

Cannon

et al. 2023

Pharmaceutics

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“…Although useful, it has been indicated that these methods afford an unknown mPEG-amine as impurity. It was suggested that pure 19 can be prepared upon reaction of mPEG with 4-nitrophenylchloroformate in toluene with tripentylamine [92] or with 4-dimethylaminopyridine in dioxane [93].…”

Section: Pegmentioning

confidence: 99%

Evolution of Reactive mPEG Polymers for the Conjugation of Peptides and Proteins

Gonzalez¹,

Vaillard²

2013

COC

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The covalent attachment of methoxy-poly(ethylene glycol) (mPEG) is a well established strategy used to improve the pharmaceutical properties of several biomolecules. Since the pioneering work of Abuchovsky, PEGylation has emerged as a powerful technology of significant relevance, not only for the development of new and better drugs, but also for application in material science. Peptides and proteins are the most traditional targets for PEGylation due to their intense and diverse biotechnological applications. The terminal amino group, as well as the -amino group of lysine and the thiol group of cysteine, are all well known nucleophilic sites that have traditionally been used to couple peptides and proteins to mPEG derivatives. Advances in the methods for preparation of the mPEG starting materials, together with a careful selection of new mPEG functional end-groups have allowed new reactive mPEGs to emerge, which show narrow polydispersity and controlled reactivity, providing more homogeneous conjugates. In the last few years the trend has moved towards site-selective, reversible and enzymatic PEGylation using a new generation of tailor-made reagents and strategies. The main goal of this article is to present some of the most relevant achievements obtained in the PEGylation of peptides and proteins. The chemistry underlying the current methods used for the preparation of mPEG reagents, as well as the chemistry involved in the PEGylation reactions are presented in detail, in order of stimulating the synthetic and polymer chemist to turn their attention in this fascinating multi and interdisciplinary field of research.

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Reagents for the Covalent Attachment of mPEG to Peptides and Proteins

Gonzalez

Vaillard

2015

Handbook of Polymers for Pharmaceutical Technologies

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A Simple and Efficient Method for Preparation of Monomethoxypolyethylene Glycol Activated with p-Nitrophenylchloroformate and Its Application to Modification of L-Asparaginase.

Cited by 4 publications

References 19 publications

Delicate Hybrid Laponite–Cyclic Poly(ethylene glycol) Nanoparticles as a Potential Drug Delivery System

Delicate Hybrid Laponite–Cyclic Poly(ethylene glycol) Nanoparticles as a Potential Drug Delivery System

Evolution of Reactive mPEG Polymers for the Conjugation of Peptides and Proteins

Reagents for the Covalent Attachment of mPEG to Peptides and Proteins

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