Synthesis of an Octa‐<i>tert</i>‐butylphthalocyanine: A Low‐Aggregating and Photochemically Stable Photosensitizer

a Chlorin-e6 (chl-e6) and a hydrogenated derivative (chl-e6H) were semi-synthesized, and their photophysical properties and photodynamic activity against Escherichia coli, Staphylococcus aureus and Candida albicans evaluated. Methyl pheophorbide-a (Mepheo-a) was obtained from S. maxima using methanolic extraction with acid catalysis (CH 3 OH-H 2 SO 4 ). Chlorin-e6 was prepared from Mepheo-a by basic hydrolysis with H 2 O-acetone and NaOH. Hydrogenated Chlorin-e6 was synthesized by a similar procedure starting from the hydrogenated methyl pheophorbide-a (Mepheo-aH). Photophysical studies were performed in order to determine the singlet oxygen quantum yield of chl-e6H which is higher than that of chl-e6. The microorganism inactivation of chl-e6 and chl-e6H was investigated at two concentrations and three fluence levels. Both chl-e6 and chl-e6H showed microorganism inactivation against Gram-positive bacteria and a fungus.

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“…The absorbance spectra were monitored after each irradiation interval. 45,46 These protocols were performed in triplicate.…”

Section: Methodsmentioning

confidence: 99%

Photobiological characteristics of chlorophyll a derivatives as microbial PDT agents

Uliana

Pires

Pratavieira

et al. 2014

Photochem Photobiol Sci

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“…Furthermore, phthalocyanines show promising absorption properties in the near-infrared region of the solar spectrum and are known to be efficient triplet sensitizers for the production of singlet oxygen. − As the maximum of the solar photon emission is centered around 880 nm, increasing interest was devoted to applying this relatively low-energy radiation in chemical reactions, , which led to various chemical modifications of phthalocyanine derivatives for reaching even more efficient photophysical properties, especially in the infrared region. ,,, After having explored the harvesting of infrared photons by surface-modified TiO 2 nanoparticles for the oxidative α-cyanation of tertiary amines, we became interested in using direct infrared photochemistry in a homogeneous solution for the same purpose. The products, α-aminonitriles, show a unique reactivity pattern and are synthetically useful compounds , ( e.g.…”

Section: Introductionmentioning

confidence: 99%

Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts

et al. 2022

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While photochemical transformations with sunlight almost exclusively utilize the UV–vis part of the solar spectrum, the majority of the photons emitted by the sun have frequencies in the near-infrared region. Phthalocyanines show high structural similarity to the naturally occurring light-harvesting porphyrins, chlorins, and mainly bacteriochlorins and are also known for being efficient and affordable near-infrared light absorbers as well as triplet sensitizers for the production of singlet oxygen. Although having been neglected for a long time in synthetic organic chemistry due to their low solubility and high tendency toward aggregation, their unique photophysical properties and chemical robustness make phthalocyanines attractive photocatalysts for the application in near-infrared-light-driven synthesis strategies. Herein, we report a cheap, simple, and efficient photocatalytic protocol, which is easily scalable under continuous-flow conditions. Various phthalocyanines were studied as near-infrared photosensitizers in oxidative cyanations of tertiary amines to generate α-aminonitriles, a synthetically versatile compound class.

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“…Photosensitizers and photothermal conversion agents are the main factors affecting phototherapy. Most photosensitizers are hydrophobic under physiological conditions; thus, they are easy to aggregate in solution, and their transports are affected in vivo [132,133]. Meanwhile, photosensitizers often exhibit short half life and non-targeting, so they have certain limitations in practical applications [134].…”

Section: Phototherapymentioning

confidence: 99%

Design and Application of Hybrid Polymer-Protein Systems in Cancer Therapy

Sun

Yang

2023

Polymers

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Polymer-protein systems have excellent characteristics, such as non-toxic, non-irritating, good water solubility and biocompatibility, which makes them very appealing as cancer therapeutics agents. Inspiringly, they can achieve sustained release and targeted delivery of drugs, greatly improving the effect of cancer therapy and reducing side effects. However, many challenges, such as reducing the toxicity of materials, protecting the activities of proteins and controlling the release of proteins, still need to be overcome. In this review, the design of hybrid polymer–protein systems, including the selection of polymers and the bonding forms of polymer–protein systems, is presented. Meanwhile, vital considerations, including reaction conditions and the release of proteins in the design process, are addressed. Then, hybrid polymer–protein systems developed in the past decades for cancer therapy, including targeted therapy, gene therapy, phototherapy, immunotherapy and vaccine therapy, are summarized. Furthermore, challenges for the hybrid polymer–protein systems in cancer therapy are exemplified, and the perspectives of the field are covered.

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Synthesis of an Octa‐tert‐butylphthalocyanine: A Low‐Aggregating and Photochemically Stable Photosensitizer

Cited by 10 publications

References 35 publications

Photobiological characteristics of chlorophyll a derivatives as microbial PDT agents

Photobiological characteristics of chlorophyll a derivatives as microbial PDT agents

Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts

Design and Application of Hybrid Polymer-Protein Systems in Cancer Therapy

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