Self‐assembling nanocomposites for protein delivery: Supramolecular interactions between PEG‐cholane and rh‐G‐CSF

Salmaso, Stefano; Bersani, Sara; Mastrotto, Francesca; Tonon, Giancarlo; Schrepfer, Rodolfo; Genovese, Stefano; Caliceti, Paolo

doi:10.1016/j.jconrel.2012.06.018

Cited by 24 publications

(30 citation statements)

References 42 publications

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“…8). Although different conclusions were reported on the effect of PEG molecular weight on CMC [13], for vitamin E/PEG conjugates, an increase in the molecular weight of the PEG chain was reported to lead to smaller CMC values [14]. This may explain the lower CMC values observed in the current study when compared to vitamin E TPGS, which was reported to have a CMC value of 200 μg/mL [1].…”

Section: Resultsmentioning

confidence: 62%

Synthesis, physiochemical characterization, and in vitro antitumor activity of the amide and pH cleavable hydrazone conjugates of γ-tocotrienol isomer of vitamin E with methoxy-poly(ethylene) glycol

Abu-Fayyad

Nazzal

2017

International Journal of Pharmaceutics

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The anticancer activity of water soluble methoxy polyethylene glycol (mPEG) derivatives of tocotrienol (T3) isomers of vitamin E was previously found to be reduced when compared to the parent free isomers. This could be due to the ester bond formation between the mPEG and the 6-OH group on the chroman moiety of the T3 isomer. To further investigate, the objectives of the current study were to (1) synthesize and characterize stable amide and cleavable hydrazone conjugates between mPEG and carbon-5 on the chroman moiety of T3, and (2) examine the cytotoxicity of the newly synthesized mPEG conjugates against breast (MCF-7 and MDA-MB-231) and pancreatic (BxPC-3 and PANC-1) cancer cells. Conjugates were synthesized by direct conjugation of succinyl chloride derivatives of mPEG to the α-tocopherol and γ-tocotrienol isomers of vitamin E, and were characterized by 1H-NMR, FT-IR, and mass spectrometry. The micelles of the amide and hydrazone self-assembled conjugates were characterized for size, zeta, CMC, and stability at different pH media. The hydrolysis of the hydrazone conjugate was pH dependent with highest release at acidic (pH 5.5) conditions, whereas the amide conjugate was stable in all tested media. The amide conjugate nonetheless showed greater cytotoxicity than the hydrazone conjugate, which suggested that maintaining solubility and the presence of free 6-OH group are important for γ-T3 to exert anticancer activity in vitro. The results from the current study demonstrated the importance of considering the nature of the chemical bond between T3 and mPEG when designing functional ingredients for use in drug delivery.

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Section: Resultsmentioning

confidence: 62%

Synthesis, physiochemical characterization, and in vitro antitumor activity of the amide and pH cleavable hydrazone conjugates of γ-tocotrienol isomer of vitamin E with methoxy-poly(ethylene) glycol

Abu-Fayyad

Nazzal

2017

International Journal of Pharmaceutics

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“…Reports on these types of correlation studies are more difficult to find, presumably because they focus on such a specific relationship. One report characterized binding constants for non‐covalent PEG‐cholane/protein complexes by using two methods, ITC and gel filtration experiments, and in addition to considering biophysical parameters, such as binding constants, cargo intracellular function was also considered . The protein cargo, a cytokine, still maintained bioactivity in the cell post‐delivery.…”

Section: Correlating Binding With the Intracellular Activity Of Bioacmentioning

confidence: 75%

“…One report characterized binding constants for non-covalentP EG-cholane/ protein complexes by using two methods, ITC and gel filtration experiments, and in addition to considering biophysical parameters, such as binding constants, cargo intracellularf unction was also considered. [98] The protein cargo,acytokine, still maintained bioactivity in the cell post-delivery. Even though this report measured binding constants for as eries of PEGbased assemblies, they only selected one PEG-based assembly, with K d = 1.89 mm,f or their subsequent in vitro and in vivo work.…”

Section: Examples Of Polymer-protein Bindingc Orrelating With Intracementioning

confidence: 99%

Associative and Dissociative Processes in Non‐Covalent Polymer‐Mediated Intracellular Protein Delivery

Posey

Tew

2018

Chemistry An Asian Journal

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Functional protein delivery has created new opportunities for studying intracellular processes and discovering new therapeutics. To that end, researchers have pursued intracellular protein delivery by using an increasing number of methods. This focus review will highlight polymeric carriers that non-covalently bind and deliver protein cargo in vitro. The correlation between polymer-protein binding and delivery as well as the correlation between complex-membrane binding and delivery is reviewed. Finally, binding and its relation to the intracellular function of the protein post-delivery is considered. The purpose of this review is to evaluate the role that binding interactions play in the non-covalent protein-delivery landscape. Presently, the literature does not adequately resolve how binding throughout the process ultimately affects delivery. The field does contain preliminary insights that are expected to impact future delivery applications when developed further.

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“…Salmaso, Caliceti and coworkers developed non-covalent supramolecular protein/PEG delivery systems using the synthesized PEG-cholane derivatives with PEG of different molecular weights. 51 Their results showed an apparently large hydrophilic size of the protein/PEG associations, which enhanced the protein solubility and stability. The changes in PEG molecular weight and protein/PEG ratio resulted in significant changes in the physicochemical, pharmacokinetic, and pharmacodynamic profiles of the loaded protein.…”

Section: Peg Derivativesmentioning

confidence: 98%

“…Camptothecin (CPT) conjugated PEG could self-assemble into nanomicelles, with CPT released at a tumor relevant condition. 51 Tang, Shen and coworkers conjugated curcumin with two short oligo(ethylene glycol) (Curc-OEG) chains via b-thioester bonds that are labile in the presence of intracellular glutathione and esterase. Curc-OEG based nanoparticles under aqueous conditions can serve as an anticancer prodrug and a drug carrier.…”

Section: Peg Derivativesmentioning

confidence: 99%

Polymeric Nanosystems for Targeted Theranostics

Li¹,

Wen²,

Dong³

et al. 2016

Nanomaterials for Tumor Targeting Theranostics

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Past several years have seen extensive developments of a variety of theranostic nanosystems. Significant advances on polymeric theranostic nanosystem have been made in image-guided drug delivery taking advantage of the versatility, adaptability and biocompatibility of the rationally designed polymers. In this chapter, the critical issues confronted in the design, synthesis, and characterization of polymeric nanosystem are addressed. An overview is further given on the applications of polymeric nanosystem in biomedicine. In particular, the discussions are focused on some of the key elements of theranostics in terms of fluorescent imaging, drug storage, and controlled delivery. Some novel drug release behavior based on intelligent triggering mechanisms is also discussed. IntroductionThe cure of the cancer critically depends on the early detection and timely medical treatment. The survival rate of patients with breast cancer is approximately 90 %, if it can be diagnosed at an early stage before occurrence of metastasis to distant tissues, organs or lymph nodes. In contrast, the survival rate significantly decreases to 20%, if discovered at a later stage.

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Self‐assembling nanocomposites for protein delivery: Supramolecular interactions between PEG‐cholane and rh‐G‐CSF

Cited by 24 publications

References 42 publications

Synthesis, physiochemical characterization, and in vitro antitumor activity of the amide and pH cleavable hydrazone conjugates of γ-tocotrienol isomer of vitamin E with methoxy-poly(ethylene) glycol

Synthesis, physiochemical characterization, and in vitro antitumor activity of the amide and pH cleavable hydrazone conjugates of γ-tocotrienol isomer of vitamin E with methoxy-poly(ethylene) glycol

Associative and Dissociative Processes in Non‐Covalent Polymer‐Mediated Intracellular Protein Delivery

Polymeric Nanosystems for Targeted Theranostics

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