Facile synthesis and self-assembly of amphiphilic polydimethylsiloxane with poly(ethylene glycol) moieties via thiol-ene click reaction

Xia, Yafeng; Yao, Hongtao; Miao, Zhihui; Ma, Yan; Cui, Meifang; Yan, Liqiang; Ling, Huanhuan; Qi, Zhengjian

doi:10.1039/c5ra10150f

Cited by 10 publications

(5 citation statements)

References 39 publications

(36 reference statements)

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“…The CMC of P 2 and P 3 were also obtained by the same method and shown in Figure S4 . The CMC values of the three polymers increased as the proportion of polyether segment increased, which is consistent with the expected order (but it is different from polysiloxane system [ 54 ]). For polysiloxane system, because of the formation of vesicles and lamellae, the CMC values decreased as the proportion of polyether segment increased.…”

Section: Resultssupporting

confidence: 80%

Facile Synthesis and Self-Assembly of Amphiphilic Polyether-Octafunctionalized Polyhedral Oligomeric Silsesquioxane via Thiol-Ene Click Reaction

et al. 2017

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We demonstrated here a facile and efficient synthesis of polyhedral oligomeric silsesquioxane-based amphiphilic polymer by thiol-ene click chemistry. The properties of polyhedral oligomeric silsesquioxane (POSS)–PEG amphiphilic polymers were studied in detail by a combination of 1H NMR, 13C NMR, 29Si NMR FT-IR, GPC, and TG analysis. The newly-designed thiol-ene protocol obtains only anti-Markovnikov addition POSS-based amphiphilic polymers when compared with platinum-catalysed hydrosilylation method. The critical micelle concentration (CMC) of the resulting polymers are in the range of 0.011 to 0.050 mg/mL, and dynamic light scattering (DLS) results revealed that the obtained amphiphilic polymers can self-assemble into nanoparticles in aqueous solutions with a bimodal (two peaks) distribution. Furthermore, the specific polymer showed obvious thermo-sensitive behaviour at 45.5 °C.

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Section: Resultssupporting

confidence: 80%

Facile Synthesis and Self-Assembly of Amphiphilic Polyether-Octafunctionalized Polyhedral Oligomeric Silsesquioxane via Thiol-Ene Click Reaction

et al. 2017

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“…The BCM were prepared by the co-solvent evaporation method. The critical micelle concentration (CMC) value of TPE-(PEO- b -PCL) 2 before and after RhB conjugation was determined by fluorescence spectroscopy using pyrene as a hydrophobic probe , (Figure S3, Supporting Information). The CMC was measured to be 8.0 and 10.0 μg mL –1 for TPE-(PEO- b -PCL) 2 and TPE-(PEO- b -PCL-RhB) 2 , respectively.…”

Section: Resultsmentioning

confidence: 99%

Rhodamine B-Conjugated Fluorescent Block Copolymer Micelles for Efficient Chlorambucil Delivery and Intracellular Imaging

et al. 2023

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The clinical development of the anticancer drug chlorambucil (CHL) is limited by its low solubility in water, poor bioavailability, and offtarget toxicity. Besides, another constraint for monitoring intracellular drug delivery is the non-fluorescent nature of CHL. Nanocarriers based on block copolymers of poly(ethylene glycol)/poly(ethylene oxide) (PEG/PEO) and poly(ε-caprolactone) (PCL) are an elegant choice for drug delivery applications due to their high biocompatibility and inherent biodegradability properties. Here, we have designed and prepared block copolymer micelles (BCM) containing CHL (BCM-CHL) from a block copolymer having fluorescent probe rhodamine B (RhB) end-groups to achieve efficient drug delivery and intracellular imaging. For this purpose, the previously reported tetraphenylethylene (TPE)-containing poly(ethylene oxide)-b-poly(ε-caprolactone) [TPE-(PEO-b-PCL) 2 ] triblock copolymer was conjugated with RhB by a feasible and effective post-polymerization modification method. In addition, the block copolymer was obtained by a facile and efficient synthetic strategy of one-pot block copolymerization. The amphiphilicity of the resulting block copolymer TPE-(PEO-b-PCL-RhB) 2 led to the spontaneous formation of micelles (BCM) in aqueous media and successful encapsulation of the hydrophobic anticancer drug CHL (CHL-BCM). Dynamic light scattering and transmission electron microscopy analyses of BCM and CHL-BCM revealed a favorable size (10−100 nm) for passive targeting of tumor tissues via the enhanced permeability and retention effect. The fluorescence emission spectrum (λ ex 315 nm) of BCM demonstrated Forster resonance energy transfer between TPE aggregates (donor) and RhB (acceptor). On the other hand, CHL-BCM revealed TPE monomer emission, which may be attributed to the π−π stacking interaction between TPE and CHL molecules. The in vitro drug release profile showed that CHL-BCM exhibits drug release in a sustained manner over 48 h. A cytotoxicity study proved the biocompatibility of BCM, while CHL-BCM revealed significant toxicity to cervical (HeLa) cancer cells. The inherent fluorescence of RhB in the block copolymer offered an opportunity to directly monitor the cellular uptake of the micelles by confocal laser scanning microscopy imaging. These results demonstrate the potential of these block copolymers as drug nanocarriers and as bioimaging probes for theranostic applications.

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“…Although the Hy reaction is the most used, some authors have mentioned that Karstedt's catalyst shows drawbacks because despite giving a high number of catalytic cycles (TON), it exhibits low selectivity and is a more expensive transition metal than others such as iron, cobalt, and nickel, which showed good Hy yields. [32][33][34] In this sense, Yong Xia et al 35 coupled PDMS and PEG via thiol-ene click chemistry free of a metal catalyst. The synthesis was carried out in four stages.…”

Section: Introductionmentioning

confidence: 99%

One-step synthesis of amphiphilic copolymers PDMS-b-PEG using tris(pentafluorophenyl)borane and subsequent study of encapsulation and release of curcumin

Camacho-Ramírez,

Meléndez-Zamudio,

Cervantes

et al. 2024

J. Mater. Chem. B

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Facile synthesis and self-assembly of amphiphilic polydimethylsiloxane with poly(ethylene glycol) moieties via thiol-ene click reaction

Abstract: A facile and efficient synthesis of polysiloxane-based amphiphilic copolymer via thiol-ene click chemistry.

Cited by 10 publications

References 39 publications

Facile Synthesis and Self-Assembly of Amphiphilic Polyether-Octafunctionalized Polyhedral Oligomeric Silsesquioxane via Thiol-Ene Click Reaction

Facile Synthesis and Self-Assembly of Amphiphilic Polyether-Octafunctionalized Polyhedral Oligomeric Silsesquioxane via Thiol-Ene Click Reaction

Rhodamine B-Conjugated Fluorescent Block Copolymer Micelles for Efficient Chlorambucil Delivery and Intracellular Imaging

One-step synthesis of amphiphilic copolymers PDMS-b-PEG using tris(pentafluorophenyl)borane and subsequent study of encapsulation and release of curcumin

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