Complexation of pillar[5]arene-based Schiff bases with methylene blue: Formation of binary complexes with improved anticancer activity

Zhou, Youjun; Wang, Qing; Ma, Longtao; Fan, Jingwen; Han, Ying; Yan, Chao‐Guo

doi:10.1016/j.molstruc.2022.132588

Cited by 12 publications

(3 citation statements)

References 42 publications

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“…Zhou et al (128) have reported a host-guest complex of methylene blue (MB) and pillar [5]arene covalently functionalized with salicylic hydrazide (P5SB) through an imide bond (Schiff base) which self-assembled into pH-responsive vesicles (P5SB-MB). These vesicles, then, were loaded with doxorubicin (DOX).…”

Section: Host-guest Complexes Of Photosensitizersmentioning

confidence: 99%

Recent Photosensitizer Developments, Delivery Strategies and Combination‐based Approaches for Photodynamic Therapy^†

Mariño-Ocampo¹,

Dibona‐Villanueva

Álvarez

et al. 2022

Photochem & Photobiology

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Photodynamic therapy of cancer (PDT) is a therapeutic technique, minimally invasive, which is currently used to treat cancerous lesions and tumors that have been in the spotlight for its potential over the recent decades. Nonetheless, PDT still needs further development to become a first-option treatment for patients. This review compiles recent progress in several aspects of the current research in the constantly growing area of PDT to overcome the main challenges as an attempt to serve as a guide and reference for newcomers into this research area. This review has been prepared to highlight the use of chemical modifications on photosensitizers to improve their solubility, photostability, selectivity and phototoxicity. Additionally, the use of liposomes and cavitands as drug delivery systems to aid in the biodistribution and bioaccumulation of photosensitizers is presented. Also, the combination of PDT with chemotherapy or immunotherapy as an option to boost and improve treatment outcomes is discussed. Finally, the inhibition of antioxidant enzymes as a strategy for a synergistic effect to ameliorate the performance of the photosensitizers in PDT is presented as an alternative for future researchers.

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Section: Host-guest Complexes Of Photosensitizersmentioning

confidence: 99%

Recent Photosensitizer Developments, Delivery Strategies and Combination‐based Approaches for Photodynamic Therapy^†

Mariño-Ocampo¹,

Dibona‐Villanueva

Álvarez

et al. 2022

Photochem & Photobiology

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“…[32] Furthermore, when combined with other treatments such as DOX-based chemotherapy, MB photodynamic therapy has resulted in a synergistic effect, providing enhanced therapeutic efficacy. [33] Zhou et al [34] recently reported an improved anti-cancer efficiency of DOX encapsulated within a delivery system composed of pillar [5]arene-based Schiff base and methylene blue. As shown in Figure 1(f), the molecular structure of MB contains a charged site and aromatic groups, which provides an opportunity for diverse interactions such as ionic, aromatic, and hydrophobic interactions, as well as hydrogen bonding.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, when combined with other treatments such as DOX‐based chemotherapy, MB photodynamic therapy has resulted in a synergistic effect, providing enhanced therapeutic efficacy [33] . Zhou et al [34] . recently reported an improved anti‐cancer efficiency of DOX encapsulated within a delivery system composed of pillar[5]arene‐based Schiff base and methylene blue.…”

Section: Introductionmentioning

confidence: 99%

Drug Encapsulation via Peptide‐Based Polyelectrolyte Complexes

Tabandeh,

Ateeq,

Leon

2023

ChemBioChem

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Peptide‐based polyelectrolyte complexes are biocompatible materials that can encapsulate molecules with different polarities due to their ability to be precisely designed. Here we use UV‐Vis spectroscopy, fluorescence microscopy, and infrared spectroscopy to investigate the encapsulation of model drugs, doxorubicin (DOX) and methylene blue (MB) using a series of rationally designed polypeptides. For both drugs, we find an overall higher encapsulation efficiency with sequences that have higher charge density, highlighting the importance of ionic interactions between the small molecules and the peptides. However, comparing molecules with the same charge density, illustrated that the most hydrophobic sequence pairs had the highest encapsulation of both DOX and MB molecules. The phase behavior and stability of DOX‐containing complexes did not change compared to the complexes without drugs. However, MB encapsulation caused changes in the stabilities of the complexes. The sequence pair with the highest charge density and hydrophobicity had the most dramatic increase in stability, which coincided with a phase change from liquid to solid. This study illustrates how multiple types of molecular interactions are required for efficient encapsulation of poorly soluble drugs and provides insights into the molecular design of delivery carriers.

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Chalcogen Bond‐Driven Alkylations: Selenoxide‐Pillar[5]arene as a Recyclable Catalyst for Displacement Reactions in Water

Cordeiro,

Menezes,

Ángel

et al. 2024

Chemistry An Asian Journal

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A novel strategy to catalyze alkylation reactions through chalcogen bond interaction using a supramolecular structure is presented herein. Utilizing just 1.0 mol% of selenoxide‐pillar[5]arene (P[5]SeO) as the catalyst we achieved efficient catalysis in the cyanation of benzyl bromide in water. Our approach demonstrated high efficiency and effectiveness, with the results supported by designed control experiments and theoretical models, highlighting the catalytic effect of the pillar[5]arene through noncovalent interactions. Quantum‐chemical calculations (ωB97X‐D/def2‐TZVP@SMD) pointed out that the catalyzed cyanation reaction followed an SN2‐like mechanism, with energy barriers (ΔH‡) ranging from 16.7 to 18.2 kcal mol–1, exhibiting dissociative character depending on the para‐substituent. 1H NMR analysis revealed that P[5]SeO acted as a catalyst through inclusion complex formation, facilitating the transfer of the electrophilic substrate to the aqueous solution for nucleophilic displacement. Our reaction protocol proved applicable to various substrates, including aromatic and alpha‐carbonyl derivatives. The use of sodium azide as the nucleophile was also feasible. Importantly, our method allowed scalability, and the catalyst P[5]SeO could be recovered and reused effectively for multiple reaction cycles, showcasing sustainability.

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Complexation of pillar[5]arene-based Schiff bases with methylene blue: Formation of binary complexes with improved anticancer activity

Cited by 12 publications

References 42 publications

Recent Photosensitizer Developments, Delivery Strategies and Combination‐based Approaches for Photodynamic Therapy^†

Recent Photosensitizer Developments, Delivery Strategies and Combination‐based Approaches for Photodynamic Therapy^†

Drug Encapsulation via Peptide‐Based Polyelectrolyte Complexes

Chalcogen Bond‐Driven Alkylations: Selenoxide‐Pillar[5]arene as a Recyclable Catalyst for Displacement Reactions in Water

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Complexation of pillar[5]arene-based Schiff bases with methylene blue: Formation of binary complexes with improved anticancer activity

Cited by 12 publications

References 42 publications

Recent Photosensitizer Developments, Delivery Strategies and Combination‐based Approaches for Photodynamic Therapy†

Recent Photosensitizer Developments, Delivery Strategies and Combination‐based Approaches for Photodynamic Therapy†

Drug Encapsulation via Peptide‐Based Polyelectrolyte Complexes

Chalcogen Bond‐Driven Alkylations: Selenoxide‐Pillar[5]arene as a Recyclable Catalyst for Displacement Reactions in Water

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Product

Resources

About

Recent Photosensitizer Developments, Delivery Strategies and Combination‐based Approaches for Photodynamic Therapy^†

Recent Photosensitizer Developments, Delivery Strategies and Combination‐based Approaches for Photodynamic Therapy^†