Self-assembled nanoparticles formed <i>via</i> complementary nucleobase pair interactions between drugs and nanocarriers for highly efficient tumor-selective chemotherapy

Ilhami, Fasih Bintang; Chung, Ai; Alemayehu, Yihalem Abebe; Lee, Ai-Wei; Chen, Jem-Kun; Lai, Juin‐Yih; Cheng, Chih‐Chia

doi:10.1039/d1qm00428j

Cited by 6 publications

(12 citation statements)

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“…In addition, BU-PEG is a white, semi-crystalline powder and can easily dissolve in water at 25 • C, even at concentrations as high as 50 mg/mL. Due to the formation of A-U base-pairings between BU-PEG and adenine-functionalized molecules, a strong cooperative hydrogen bonding partner drug, A-R6G, was synthesized according to our previous report [31]. After the introduction of an adenine moiety into the R6G structure, the drug exhibited extremely poor solubility in water, buffer and biological media, demonstrated unique green-fluorescent behavior, and exerted strong cytotoxic effects in various normal and cancer cell lines [31,[35][36][37].…”

Section: Resultsmentioning

confidence: 99%

“…Due to the formation of A-U base-pairings between BU-PEG and adenine-functionalized molecules, a strong cooperative hydrogen bonding partner drug, A-R6G, was synthesized according to our previous report [31]. After the introduction of an adenine moiety into the R6G structure, the drug exhibited extremely poor solubility in water, buffer and biological media, demonstrated unique green-fluorescent behavior, and exerted strong cytotoxic effects in various normal and cancer cell lines [31,[35][36][37]. Due to the significant differences in the water solubility between the BU-PEG polymer and A-R6G drug, these intriguing findings motivated our interest in exploring the co-assembly behavior of BU-PEG/A-R6G complexes in water.…”

Section: Resultsmentioning

confidence: 99%

“…All chemicals and reagents were employed as received. Adenine-functionalized rhodamine derivative (A-R6G) and PEG diacrylate (PEGDA, number average molecular weight (M n ) = ~2000) were synthesized and characterized according to procedures that have been described previously [31][32][33].…”

Section: Chemicals and Materialsmentioning

confidence: 99%

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Complementary Nucleobase Interactions Drive Co-Assembly of Drugs and Nanocarriers for Selective Cancer Chemotherapy

2021

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A new concept in cooperative adenine–uracil (A–U) hydrogen bonding interactions between anticancer drugs and nanocarrier complexes was successfully demonstrated by invoking the co-assembly of water soluble, uracil end-capped polyethylene glycol polymer (BU-PEG) upon association with the hydrophobic drug adenine-modified rhodamine (A-R6G). This concept holds promise as a smart and versatile drug delivery system for the achievement of targeted, more efficient cancer chemotherapy. Due to A–U base pairing between BU-PEG and A-R6G, BU-PEG has high tendency to interact with A-R6G, which leads to the formation of self-assembled A-R6G/BU-PEG nanogels in aqueous solution. The resulting nanogels exhibit a number of unique physical properties, including extremely high A-R6G-loading capacity, well-controlled, pH-triggered A-R6G release behavior, and excellent structural stability in biological media. Importantly, a series of in vitro cellular experiments clearly demonstrated that A-R6G/BU-PEG nanogels improved the selective uptake of A-R6G by cancer cells via endocytosis and promoted the intracellular release of A-R6G to subsequently induce apoptotic cell death, while control rhodamine/BU-PEG nanogels did not exert selective toxicity in cancer or normal cell lines. Overall, these results indicate that cooperative A–U base pairing within nanogels is a critical factor that improves selective drug uptake and effectively promotes apoptotic programmed cell death in cancer cells.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Complementary Nucleobase Interactions Drive Co-Assembly of Drugs and Nanocarriers for Selective Cancer Chemotherapy

2021

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“…Another interesting strategy has been explored in the development of drug delivery systems by the use of a nucleobase-conjugated drug along with a complementary-nucleobase-conjugated polymer chain. For instance, Cheng and co-workers recently reported a coassembled system using uracil end-capped poly(propylene glycol) (U-PPG-U) and adenine-modified rhodamine 6G (A-R6G) featuring an extremely high A-R6G loading and excellent structural stability in biological media along with pH-triggered release of A-R6G . A similar concept was also explored by Lee and co-workers using uracil-functionalized PPG and an adenine-connected model drug.…”

Section: Nucleobase-interaction-assisted Therapeutic Agent Loadingmentioning

confidence: 99%

“…For instance, Cheng and co-workers recently reported a coassembled system using uracil end-capped poly(propylene glycol) (U-PPG-U) and adenine-modified rhodamine 6G (A-R6G) featuring an extremely high A-R6G loading and excellent structural stability in biological media along with pH-triggered release of A-R6G. 49 A similar concept was also explored by Lee and co-workers 50 using uracil-functionalized PPG and an adenine-connected model drug. In that study, the formation of supramolecular micelles by U:A interactions followed by irradiation-mediated photo-cross-linking of the U units resulted in long-term structural stability of the micelles in serum solution.…”

Section: Nucleobase-interaction-assisted Therapeutic Agent Loadingmentioning

confidence: 99%

Nucleobase-Interaction-Directed Biomimetic Supramolecular Self-Assembly

2022

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Conspectus The design and fabrication of synthetic self-assembled systems that can mimic some biological features require exquisitely sophisticated components that make use of supramolecular interactions to attain enhanced structural and functional complexity. In nature, nucleobase interactions play a key role in biological functions in living organisms, including transcription and translation processes. Inspired by nature, scientists are progressively exploring nucleobase synthons to create a diverse range of functional systems with a plethora of nanostructures by virtue of molecular-recognition-directed assembly and flexible programmability of the base-pairing interactions. To that end, nucleobase-functionalized molecules and macromolecules are attracting great attention because of their versatile structures with smart and adaptive material properties such as stimuli responsiveness, interaction with external agents, and ability to repair structural defects. In this regard, a range of nucleobase-interaction-mediated hierarchical self-assembled systems have been developed to obtain biomimetic materials with unique properties. For example, a new “grafting to” strategy utilizing complementary nucleobase interactions has been demonstrated to temporarily control the functional group display on micellar surfaces. In a different approach, complementary nucleobase interactions have been explored to enable morphological transitions in functionalized diblock copolymer assembly. It has been demonstrated that complementary nucleobase interactions can drive the morphological transformation to produce highly anisotropic nanoparticles by controlling the assembly processes at multiple length scales. Furthermore, nucleobase-functionalized bottle brush polymers have been employed to generate stimuli-responsive hierarchical assembly. Finally, such interactions have been exploited to induce biomimetic segregation in polymer self-assembly, which has been employed as a template to synthesize polymers with narrow polydispersity. It is evident from these examples that the optimal design of molecular building blocks and precise positioning of the nucleobase functionality are essential for fabrication of complex supramolecular assemblies. While a considerable amount of research remains to be explored, our studies have demonstrated the potential of nucleobase-interaction-mediated supramolecular assembly to be a promising field of research enabling the development of biomimetic materials. This Account summarizes recent examples that employ nucleobase interactions to generate functional biomaterials by judicious design of the building blocks. We begin by discussing the molecular recognition properties of different nucleobases, followed by different strategies to employ nucleobase interactions in polymeric systems in order to achieve self-assembled nanomaterials with versatile properties. Moreover, some of their prospective biological/material applications such as enhanced drug encapsulation, superior adhesion,...

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Hybrid perylene-cored poly(amidoamine) dendrimer with coumarin and calcozine red 6G end groups: From photophysical properties to cell imaging

Golshan

Salami‐Kalajahi

Roghani‐Mamaqani

2022

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Self-assembled nanoparticles formed via complementary nucleobase pair interactions between drugs and nanocarriers for highly efficient tumor-selective chemotherapy

Abstract: We report a significant breakthrough in the development of complementary hydrogen-bonded drug-carrier systems, namely the construction of self-assembled nanoparticles with desirable functionalities conferred by the presence of stable complementary uracil–adenine...

Cited by 6 publications

References 52 publications

Complementary Nucleobase Interactions Drive Co-Assembly of Drugs and Nanocarriers for Selective Cancer Chemotherapy

Complementary Nucleobase Interactions Drive Co-Assembly of Drugs and Nanocarriers for Selective Cancer Chemotherapy

Nucleobase-Interaction-Directed Biomimetic Supramolecular Self-Assembly

Hybrid perylene-cored poly(amidoamine) dendrimer with coumarin and calcozine red 6G end groups: From photophysical properties to cell imaging

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