Efficient energy transfer between coronene-modified permethyl-β-cyclodextrins and porphyrin for light induced DNA cleavage

Abstract

A novel supramolecular assembly was constructed by the noncovalent complexation of hexa-cata-hexabenzocoronene modified permethyl-β-cyclodextrins with tetrasodium tetraphenylporphyrintetrasulfonate in water, exhibiting highly efficient excited energy transfer behaviors and a promising DNA photocleavage ability.

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

“…Besides application in transistor, cata ‐HBC systems were also used in organic solar cells [221] and biological applications. For example, cata ‐HBC fused with β‐cyclodextrins was used in fluorescence imaging toward anticancer activity [222] and showed promise in DNA photocleavage [223] …”

Visible Light Photochemical Reactions for Nucleic Acid-Based Technologies

“…Types of photosensitizers for nucleic acid strand photocleavage and their properties are summarized in Table 1. Other compounds, such as naphthalimides, coronene, 2-quinolinium dicarbocyanine, and Fe(II)N4Py, were introduced to visible light-induced photocleavage of DNA strands [41][42][43][44][45][46]. Table 1.…”

Long‐Range Chiral Induction by a Fully Noncovalent Approach in Supramolecular Porphyrin–Calixarene Assemblies

“…Charged porphyrins as such are water soluble; however, because of their hydrophobic skeleton, they tend to undergo uncontrolled self‐aggregation in water. Several templates, including polyelectrolytes, inorganic molecules and macrocycles have been employed to control the self‐assembly processes.…”

“…[11,[14][15][16][17] In otherw ords, by mixingt ogether ac hiral template and achiralm olecules,e xploiting intermolecular forces, such as hydrogen bonding, p-p,van der Waals and electrostatic interactions, [18,19] transmission of chirality occurs and an induced circular dichroisms ignal appears in the absorption region of the achiral molecules.Amongt he wide variety of building blocks available, watersoluble porphyrins have been shown to act as promising molecular tools for gaining an insight into the process of intermo-lecular transfer of chirality in supramolecular aggregates in aqueouss olution. [20][21][22][23][24][25][26][27][28][29] Charged porphyrins as such are water soluble;h owever,b ecause of their hydrophobic skeleton, they tend to undergo uncontrolleds elf-aggregation in water.S everal templates,i ncluding polyelectrolytes, [30][31][32][33] inorganic molecules [34][35][36] and macrocycles [36][37][38][39][40][41][42] have been employed to control the self-assembly processes.Charged water-soluble calix[n]arene derivatives, [43][44][45][46][47][48][49] owing to the cooperative effect of electrostatic forces and the intrinsic solvophobic nature of their cavities, show robust binding interactions towards species with oppositely charged moieties. [50]…”

“…Amongt he wide variety of building blocks available, watersoluble porphyrins have been shown to act as promising molecular tools for gaining an insight into the process of intermo-lecular transfer of chirality in supramolecular aggregates in aqueouss olution. [20][21][22][23][24][25][26][27][28][29] Charged porphyrins as such are water soluble;h owever,b ecause of their hydrophobic skeleton, they tend to undergo uncontrolleds elf-aggregation in water.S everal templates,i ncluding polyelectrolytes, [30][31][32][33] inorganic molecules [34][35][36] and macrocycles [36][37][38][39][40][41][42] have been employed to control the self-assembly processes.…”