Cucurbit[7]uril-Anchored Porphyrin-Based Multifunctional Molecular Platform for Photodynamic Antimicrobial and Cancer Therapy

Özkan, Melis; Kumar, Yogesh; Keser, Yağmur; Hadi, Seyed Ehsan; Tuncel, Dönüş

doi:10.1021/acsabm.9b00763

Cited by 26 publications

(29 citation statements)

References 31 publications

(37 reference statements)

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“…Another CB [ n ]-porphyrin conjugation was then reported by our group in 2019 in which the monohydroxyl- CB [7] was conjugated to 4(TEG-OH)-TPP core. The as-prepared assembly was employed for electrophotocatalytic hydrogen generation from water splitting as well as photodynamic antibacterial and cancer therapy. , In the present paper, we report a CB[6] and porphyrin-based covalent organic framework. We first synthesized CB6(O–P) n by direct functionalization of CB[6] and then it was covalently attached to porphyrin core ( TPP-Zn-4N 3 ) through Cu-AAC click reaction to construct TPP-CB[6] covalent organic framework.…”

Section: Introductionmentioning

confidence: 99%

Covalent Organic Framework Constructed by Clicking Azido Porphyrin with Perpropargyloxy-Cucurbit[6]uril for Electrocatalytic Hydrogen Generation from Water Splitting

Khaligh

Sheidaei

Tuncel

2021

ACS Appl. Energy Mater.

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In the present study, we describe the synthesis and characterization of a new covalent organic framework (COF-TPP-CB [6]) which was assembled together by clicking perpropargyloxy cucurbit[6]uril (CB[6]) to the azidofunctionalized tetraphenylporphyrin (TPP-4N 3 ) through a copper-catalyzed azide−alkyne cycloaddition reaction (CuAAC). Perpropargyloxy CB[6] was synthesized through the direct oxidation of CB[6] to afford perhydroxy CB[6] followed by subsequent O-propargylation using NaH. We also demonstrated that the resulting framework (COF-TPP-CB[6]) can be employed as an efficient and stable electrocatalyst for hydrogen evolution reaction (HER) in alkaline medium upon loading it with a nickel cocatalyst. The effect of TiO 2 and different loadings of Ni on the HER performance of TPP-CB[6] was also studied. Herein, 12%Ni@ TPP-CB[6] as the optimum catalyst showed an impressive H 2 production rate of 18.7 mmol h −1 g −1 with a low onset potential of −250 mV.

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Section: Introductionmentioning

confidence: 99%

Covalent Organic Framework Constructed by Clicking Azido Porphyrin with Perpropargyloxy-Cucurbit[6]uril for Electrocatalytic Hydrogen Generation from Water Splitting

Khaligh

Sheidaei

Tuncel

2021

ACS Appl. Energy Mater.

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“…To further potentiate the antibacterial activity, the system could be loaded effectively with drug molecules. As illustrated in Figure 5 , the system was synthesized by conjugation of cucurbit ( Omolo et al, 2018 ) uril shell, which acted as host for loaded drugs, to a free-base porphyrin core via suitable linkers ( Kumar et al, 2019 ; Özkan et al, 2019 ). While the resulting system exhibited no dark activity towards E. coli (gram-negative bacteria), it showed relatively high cytotoxicity on B. subtilis (gram-positive bacteria).…”

Section: Advancement Of Porphyrin-based Photosensitizers For Targetedmentioning

confidence: 99%

“…This reaction resulted in a self-assembling amphiphilic system. Adapted with permission from Özkan et al (2019) .…”

Section: Advancement Of Porphyrin-based Photosensitizers For Targetedmentioning

confidence: 99%

Photodynamic Antimicrobial Chemotherapy: Advancements in Porphyrin-Based Photosensitize Development

2021

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The reduction of available drugs with effectiveness against microbes is worsening with the current global crisis of antimicrobial resistance. This calls for innovative strategies for combating antimicrobial resistance. Photodynamic Antimicrobial Chemotherapy (PACT) is a relatively new method that utilizes the combined action of light, oxygen, and a photosensitizer to bring about the destruction of microorganisms. This technique has been found to be effective against a wide spectrum of microorganisms, including bacteria, viruses, and fungi. Of greater interest is their ability to destroy resistant strains of microorganisms and in effect help in combating the emergence of antimicrobial resistance. This manuscript reviews porphyrins and porphyrin-type photosensitizers that have been studied in the recent past with a focus on their structure-activity relationship.

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“…Finally, we evaluated the influence of the coating features (i.e., thickness, type of layer, polyelectrolyte functionalisation) on the antimicrobial activity of the prepared microcarriers against the Gram-positive (Staphylococcus aureus) and Gram-negative (Serratia marcescens) bacterial strains. The acquired beneficial physicochemical and biological properties of the fabricated microparticles could allow designing systems to deliver pharmaceuticals (e.g., CUR) by oral or intravesical administration in various ways of treatments, including antimicrobial and cancer therapies [28,29].…”

Section: Introductionmentioning

confidence: 99%

Multilayered Curcumin-loaded Hydrogel Microcarriers With Antimicrobial Function

Szczęsna¹,

Tsirigotis-Maniecka²,

Lamch³

et al. 2022

Preprint

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The design of multifunctional microcarriers has attracted significant attention because they combine various functions within a single system. In this study, we developed a set of multi-layered hydrogel microcarriers, which were first loaded with chemotherapeutic curcumin (CUR), then using the layer-by-layer (LbL) technique, coated through a polyelectrolyte shell consisting of chitosan (CHIT) or poly(allylamine hydrochloride) (PAH). As an outer layer with antimicrobial function, newly synthesised alkylene quaternary ammonium salt functionalised polyelectrolytes (A-QAS-PEs) were applied. For this purpose, poly(acrylic acid) (PAA) was decorated with dif-ferent hydrophobic side chains (n-hexane and n-dodecane side entities) and different degrees of substitution (m) of quaternary ammonium groups (abbreviated as PAA-C(O)O-(CH2)n-N+(CH3)3(m); n=6,12; m=8-14%). The grafting approach of PAA with the al-kylene quaternary ammonium salt moiety was performed under mild reaction conditions using Steglich esterification followed by quaternisation. The structure of antimicrobial decorated PAA was confirmed by 1H NMR and FTIR, and the mean diameter of all multifunctional microparticles was characterised by SEM. The viscoelastic properties of the functional layers were studied using QCM-D. The release of CUR from the microcarriers was described using a hybrid model, i.e., a combination of first-order kinetics and the Korsmeyer-Peppas model. The antimicrobial activity of functionalised PAA and multilayered CUR-loaded hydrogel microcarriers with quaternary am-monium function was assessed against Staphylococcus aureus and Serratia marcescens by the agar diffusion assay method. Only a limited inhibition zone of PAA was observed, but in the case of both antimicrobial decorated PAA and the corresponding multilayered nanocarriers, the inhibi-tory activity increase was achieved against both strains of bacteria.

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Cucurbit[7]uril-Anchored Porphyrin-Based Multifunctional Molecular Platform for Photodynamic Antimicrobial and Cancer Therapy

Cited by 26 publications

References 31 publications

Covalent Organic Framework Constructed by Clicking Azido Porphyrin with Perpropargyloxy-Cucurbit[6]uril for Electrocatalytic Hydrogen Generation from Water Splitting

Covalent Organic Framework Constructed by Clicking Azido Porphyrin with Perpropargyloxy-Cucurbit[6]uril for Electrocatalytic Hydrogen Generation from Water Splitting

Photodynamic Antimicrobial Chemotherapy: Advancements in Porphyrin-Based Photosensitize Development

Multilayered Curcumin-loaded Hydrogel Microcarriers With Antimicrobial Function

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