The effect of π-Conjugation on the self-assembly of micelles and controlled cargo release

Liang, Yan; Sun, Yongkun; Fu, Xiaoheng; Lin, Yang; Zhu, Meng; Meng, Yanan; Niu, Jiping; Lai, Yusi; Sun, Yong

doi:10.1080/21691401.2020.1725028

Cited by 13 publications

(7 citation statements)

References 44 publications

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“…The low signal intensity of the aromatic peaks for individual drugs can be attributed likely to the existence of drugs in a self-assembled form when incorporated on HA. This is consistent with previous reports of strong attenuations or complete disappearance of the drugs' aromatic signals, which remains buried within the core of self-assembled HA conjugate aggregates (20)(21)(22)(23). The presence of strong signals for HA and the low aromatic signals for the drugs during NMR analysis indicate the formation of HA self-assembled structures in the aqueous solution.…”

Section: Synthesis Of Ha-dox Ha-cpt and Doctorsupporting

confidence: 92%

Hyaluronic acid conjugates for topical treatment of skin cancer lesions

et al. 2021

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Skin cancer is one of the most common types of cancer in the United States and worldwide. Topical products are effective for treating cancerous skin lesions when surgery is not feasible. However, current topical products induce severe irritation, light-sensitivity, burning, scaling, and inflammation. Using hyaluronic acid (HA), we engineered clinically translatable polymer-drug conjugates of doxorubicin and camptothecin termed, DOxorubicin and Camptothecin Tailored at Optimal Ratios (DOCTOR) for topical treatment of skin cancers. When compared to the clinical standard, Efudex, DOCTOR exhibited high cancer-cell killing specificity with superior safety to healthy skin cells. In vivo studies confirmed its efficacy in treating cancerous lesions without irritation or systemic absorption. When tested on patient-derived primary cells and live-skin explants, DOCTOR killed the cancer with a selectivity as high as 21-fold over healthy skin tissue from the same donor. Collectively, DOCTOR provides a safe and potent option for treating skin cancer in the clinic.

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Section: Synthesis Of Ha-dox Ha-cpt and Doctorsupporting

confidence: 92%

Hyaluronic acid conjugates for topical treatment of skin cancer lesions

et al. 2021

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“…The concentration at the inflection point corresponds to the critical micellar concentration (CMC). Nile red molecules preferentially partition into the hydrophobic core of the micelles driven by the force of hydrophobic interactions due to the π–π interaction between benzene rings. , According to the results shown in Figure A, the CMC of mPEG 200 - g -OPhe NPs, mPEG 400 - g -OPhe NPs, and mPEG 1000 - g -OPhe NPs are 0.25 ± 0.02, 0.33 ± 0.02, and 0.85 ± 0.03 mg/mL, respectively.…”

Section: Resultsmentioning

confidence: 94%

“…Nile red molecules preferentially partition into the hydrophobic core of the micelles driven by the force of hydrophobic interactions due to the π−π interaction between benzene rings. 45,46 According to the results shown in Figure 7A, the CMC of mPEG 200 -g-OPhe NPs, mPEG 400 -g-OPhe NPs, and mPEG 1000 -g-OPhe NPs are 0.25 ± 0.02, 0.33 ± 0.02, and 0.85 ± 0.03 mg/mL, respectively. Considering that OPhe NPs are amphiphobic solid particles, we speculated about the possibility of the self-assembly of amphiphilic mPEG-g-OPhe NPs into reverse micelles in CyH driven by the interfacial free energy between the hydrophilic mPEG chain and CyH.…”

Section: ■ Results and Discussionmentioning

confidence: 95%

Amphiphilic mPEG-Modified Oligo-Phenylalanine Nanoparticles Chemoenzymatically Synthesized via Papain

Wang

et al. 2020

ACS Omega

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Amphiphilic mPEG-modified peptide nanoparticles were developed from oligo-phenylalanine (OPhe) nanoparticles (NPs) synthesized via papain. Tyndall effects indicate that OPhe NPs are amphiphobic. Addition of protein perturbants, sodium dodecyl sulfate (SDS), and urea, in the dispersion solution of OPhe NPs can significantly reduce the R h,m value of NPs, from approximately 749.2 nm to about 200 nm. Therefore, the hydrophobic interaction and hydrogen bonding play major roles in maintaining the aggregation of OPhe NPs. Using the “grafting to” method, the methoxypolyethylene-modified OPhe NPs (mPEG-g-OPhe NPs) were synthesized and characterized by Fourier transform infrared spectroscopy (FTIR), 1H NMR, electrospray ionization mass spectrometry (ESI-MS), and dynamic light scattering (DLS). The attenuated total reflectance (ATR) spectrum of OPhe NPs and mPEG-g-OPhe NPs demonstrate that the secondary structures of these NPs are mainly β-type. mPEG-g-OPhe NPs can self-aggregate into spherical micelles both in water and cyclohexane. Increasing the chain length of the mPEG moiety, the critical micellar concentrations of mPEG-g-OPhe NPs increased in water but decreased in cyclohexane. The light stability, thermal stability, hydrolysis stability, and encapsulation stability of curcumin were significantly promoted by encapsulation in the micelles formed by mPEG-g-OPhe NPs. The protective effects regularly varied with the variations in the mPEG chain length of mPEG-g-OPhe NPs.

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“…Moreover, if the general principle that an increase in solvent polarity leads to a deshielding effect in the fully soluble parts, which results in downfield-shifting, is taken into account, the NMR investigations confirmed the known character of ACN as a poor/non-solvent for PCLs [ 61 , 62 ]. Meanwhile, the upfield-shifting of a and b aromatic protons in Chl is striking evidence of the EDOT-PCL intermolecular π–π stacking of the aromatic segment of the molecule [ 63 ] in this solvent, thus suggesting the formation of associated supramolecular structures.…”

Section: Resultsmentioning

confidence: 99%

3,4-Ethylenedioxythiophene (EDOT) End-Group Functionalized Poly-ε-caprolactone (PCL): Self-Assembly in Organic Solvents and Its Coincidentally Observed Peculiar Behavior in Thin Film and Protonated Media

Bendrea¹,

Cianga²,

Ailiesei³

et al. 2021

Polymers

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End-group functionalization of homopolymers is a valuable way to produce high-fidelity nanostructured and functional soft materials when the structures obtained have the capacity for self-assembly (SA) encoded in their structural details. Herein, an end-functionalized PCL with a π-conjugated EDOT moiety, (EDOT-PCL), designed exclusively from hydrophobic domains, as a functional “hydrophobic amphiphile”, was synthesized in the bulk ROP of ε-caprolactone. The experimental results obtained by spectroscopic methods, including NMR, UV-vis, and fluorescence, using DLS and by AFM, confirm that in solvents with extremely different polarities (chloroform and acetonitrile), EDOT-PCL presents an interaction- and structure-based bias, which is strong and selective enough to exert control over supramolecular packing, both in dispersions and in the film state. This leads to the diversity of SA structures, including spheroidal, straight, and helical rods, as well as orthorhombic single crystals, with solvent-dependent shapes and sizes, confirming that EDOT-PCL behaves as a “block-molecule”. According to the results from AFM imaging, an unexpected transformation of micelle-type nanostructures into single 2D lamellar crystals, through breakout crystallization, took place by simple acetonitrile evaporation during the formation of the film on the mica support at room temperature. Moreover, EDOT-PCL’s propensity for spontaneous oxidant-free oligomerization in acidic media was proposed as a presumptive answer for the unexpected appearance of blue color during its dissolution in CDCl3 at a high concentration. FT-IR, UV-vis, and fluorescence techniques were used to support this claim. Besides being intriguing and unforeseen, the experimental findings concerning EDOT-PCL have raised new and interesting questions that deserve to be addressed in future research.

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The effect of π-Conjugation on the self-assembly of micelles and controlled cargo release

Cited by 13 publications

References 44 publications

Hyaluronic acid conjugates for topical treatment of skin cancer lesions

Hyaluronic acid conjugates for topical treatment of skin cancer lesions

Amphiphilic mPEG-Modified Oligo-Phenylalanine Nanoparticles Chemoenzymatically Synthesized via Papain

3,4-Ethylenedioxythiophene (EDOT) End-Group Functionalized Poly-ε-caprolactone (PCL): Self-Assembly in Organic Solvents and Its Coincidentally Observed Peculiar Behavior in Thin Film and Protonated Media

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