A soft supramolecular carrier with enhanced singlet oxygen photosensitizing properties

Voskuhl, Jens; Kauscher, Ulrike; Gruener, Malte; Frisch, Hendrik; Wibbeling, Birgit; Strassert, Cristian A.; Ravoo, Bart Jan

doi:10.1039/c2sm27353e

Cited by 60 publications

(68 citation statements)

References 30 publications

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“…Considering their enhanced structural stability and diversity in potential applications of other emerging areas such as electrocatalysis, photocatalysis, lithium ion battery, etc., endeavors should be made to achieve macrocycle‐based COFs. The difficulty in their synthesis may lie in several aspects: 1) some macrocycles such as cucurbiturils are difficult to functionalize and thus cannot react with other simple organic linkages to give frameworks; 2) some macrocycles that are easily modified with functional groups are too soft to construct robust COFs that retain their frameworks upon desolvation; (3) incorporation of large macrocycles into COFs may lead to an increase in the structural complexity, which on the other hand will likely destroy the crystallinity and generate amorphous frameworks . However, considering the huge progress in macrocycle‐based MOFs, improvement of macrocycle‐based COFs will be definitely achieved in the near future by overcoming these barriers.…”

Section: Resultsmentioning

confidence: 99%

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

et al. 2019

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macrocycles. They have been also employed to modify the surface properties of metal nanoparticles via noncovalent host−guest interactions, [31] covering their applications in drug delivery, [32] highly sensitive sensors, [33] selective catalysis, [34] and so on.In addition to their intensive applications based on their host−guest chemistry, macrocycles have also been used as building blocks to construct solid materials including porous organic polymers (POPs), [35,36] metal-organic frameworks (MOFs), [37][38][39][40][41][42][43] and crystalline organic materials (COMs). [44][45][46][47][48][49][50][51][52][53][54][55][56][57] Particular attention should be paid to COMs, a class of organic materials featuring facile preparation, high crystallinity, structural diversity, chemical stability, solution-processability, etc. [58][59][60][61][62][63][64][65][66][67][68][69][70] Different from MOFs that are composed of both inorganic (metal ions) and organic species (organic ligands) through coordination, COMs refer to a kind of crystalline materials composed of pure organics connected by either covalent or noncovalent bonds. [71][72][73] For COMs connected by noncovalent bonds, the typical materials are organic molecular crystals with intriguing properties such as semiconductor, [53] porosity, [68] etc. Owing to the inefficient packing of organic building blocks in the crystal state, some molecular crystals display extrinsic porosity, which are often termed as hydrogen-bonded organic frameworks (HOFs) [74,75] or supramolecular organic frameworks (SOFs). [76][77][78][79][80] For COMs connected by covalent bonds, typical materials are crystalline covalent organic frameworks (COFs), which were firstly reported in 2005 by Yaghi and co-workers [44] Benefitting from rigid chemical bonds and building blocks, COFs show permanent and well-ordered porosity. [45][46][47][48] Supramolecular-macrocycle-based COMs, a class of COMs with macrocycles as the main building blocks, have drawn particular attention in recent years. According to their components, supramolecular-macrocycle-based COMs can be classified into two main categories, the ones composed of pure macrocycles and the others consisting of macrocycles and other simple organic building blocks. Owing to their prefabricated cavities of a certain type, some of macrocycle-based COMs exhibit intrinsic microporosity for guest adsorption in the solid state. On the other hand, the extrinsic porosity of some macrocyclebased COMs may form due to the inefficient packing of these rigid macrocyclic molecules in the crystalline state. In certain circumstances, both intrinsic and extrinsic microporosity can be created in a single lattice of a certain COM, thus leading to Supramolecular macrocycles are well known as guest receptors in supramolecular chemistry, especially host−guest chemistry. In addition to their wide applications in host−guest chemistry and related areas, macrocycles have also been employed to construct crystalline organic materials (COMs) owing to their particular structur...

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Section: Resultsmentioning

confidence: 99%

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

et al. 2019

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“…developed an amphiphilic CD12 to realize their proposed strategy to prevents the forming inactive aggregates of photosensitizer. They synthesized a water soluble zinc(II) phthalocyanine bearing adamantane moieties (ZnPcA) . Vesicles formed by CD12 complexed with ZnPcA through host‐guest interactions in aqueous solution, hindering the forming inactive aggregates of ZnPcA and enhancing its photosensitizing ability (Figure ).…”

Section: Amphiphilic Cds For Drug Deliverymentioning

confidence: 99%

Macrocyclic Amphiphiles for Drug Delivery

Zheng

Geng

et al. 2019

Israel Journal of Chemistry

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Nanoparticles are the most crucial part of nanomedicine and various kinds of nanoparticles have been developed for drug delivery. As a new kind of nanoparticles, macrocyclic amphiphiles are gaining more and more attention in the field of nanomedicine due to their intrinsic features of molecular recognition and robust assembly. In this review, we summarized the reported works of drug delivery using macrocyclic amphiphiles, including cyclodextrin, calixarene, cucurbituril and pillararene species. These macrocyclic amphiphiles, serving as a new matrix of nanomedicine, can enhance drug solubility, improve drug stability, selectively deliver drugs to disease both in vitro and in vivo.

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“…As complementary information and concerning the elaboration of the nanoassemblies of amphiphilic CDs and porphyrinoid PSs, we can mention also an article published in 2013 by Voskuhl et al [ 174 ]. The authors investigated the self-assembly of a supramolecular 1 O 2 photosensitizing system based on host–guest interactions between an adamantane-functionalized ZnPc (Ada-ZnPc) and β-CD vesicles (β-CDVs).…”

Section: Cyclodextrins For Anticancer Photodynamic Therapymentioning

confidence: 99%

Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

et al. 2018

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Photodynamic therapy (PDT) is mainly used to destroy cancerous cells; it combines the action of three components: a photoactivatable molecule or photosensitizer (PS), the light of an appropriate wavelength, and naturally occurring molecular oxygen. After light excitation of the PS, the excited PS then reacts with molecular oxygen to produce reactive oxygen species (ROS), leading to cellular damage. One of the drawbacks of PSs is their lack of solubility in water and body tissue fluids, thereby causing low bioavailability, drug-delivery efficiency, therapeutic efficacy, and ROS production. To improve the water-solubility and/or drug delivery of PSs, using cyclodextrins (CDs) is an interesting strategy. This review describes the in vitro or/and in vivo use of natural and derived CDs to improve antitumoral PDT efficiency in aqueous media. To achieve these goals, three types of binding modes of PSs with CDs are developed: non-covalent CD–PS inclusion complexes, covalent CD–PS conjugates, and CD–PS nanoassemblies. This review is divided into three parts: (1) non-covalent CD-PS inclusion complexes, covalent CD–PS conjugates, and CD–PS nanoassemblies, (2) incorporating CD–PS systems into hybrid nanoparticles (NPs) using up-converting or other types of NPs, and (3) CDs with fullerenes as PSs.

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A soft supramolecular carrier with enhanced singlet oxygen photosensitizing properties

Cited by 60 publications

References 30 publications

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

Macrocyclic Amphiphiles for Drug Delivery

Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

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