Phthalaldehyde-Amine Capture Reactions for Bioconjugation and Immobilization of Phthalocyanines

Wong, Chi‐Ming; Chu, Jacky; Ha, Summer Y.Y.; Wong, Roy C. H.; Dai, Guang; Kwong, Tsz Tung; Wong, Chi Hang; Ng, Dennis K. P.

doi:10.1021/acs.orglett.0c02398

Cited by 14 publications

(10 citation statements)

References 29 publications

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“…406 Recently, Ng et al designed a phthalaldehydesubstituted Zn(II) phthalocyanine (212) (Φ Δ = 0.70) that can conjugate to various biomolecules, such as lipids, monosaccharides, peptides, and DNAs, and be immobilized on the surface of BSA nanoparticles for enhanced PDT treatment against cancer cells and bacteria (Figure 93b). 407 The conjugation of PSs with biochemical motifs can enhance their PDT efficiency because they not only improve their water solubility but also act as carriers that are able to deliver them into tumor cells. Tome et al developed several amphiphilic Zn(II) phthalocyanine conjugates bearing α-, β-, and γ-cyclodextrins (213a−213c) for PDT treatment against human bladder cancer cells (Figure 94a).…”

Section: Phthalocyanine Derivativesmentioning

confidence: 97%

“…In 2013, Dumoulin reported chalcone–Zn(II) phthalocyanine conjugates via a PEG linker combining the vascular disrupting agent of chalcones and the PDT effect of phthalocyanine for the treatment of solid tumors . Recently, Ng et al designed a phthalaldehyde-substituted Zn(II) phthalocyanine ( 212 ) (Φ Δ = 0.70) that can conjugate to various biomolecules, such as lipids, monosaccharides, peptides, and DNAs, and be immobilized on the surface of BSA nanoparticles for enhanced PDT treatment against cancer cells and bacteria (Figure b) …”

Section: Representative Strategies For Conventional Photosensitizersmentioning

confidence: 99%

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Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy

et al. 2021

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This review presents a robust strategy to design photosensitizers (PSs) for various species. Photodynamic therapy (PDT) is a photochemical-based treatment approach that involves the use of light combined with a light-activated chemical, referred to as a PS. Attractively, PDT is one of the alternatives to conventional cancer treatment due to its noninvasive nature, high cure rates, and low side effects. PSs play an important factor in photoinduced reactive oxygen species (ROS) generation. Although the concept of photosensitizer-based photodynamic therapy has been widely adopted for clinical trials and bioimaging, until now, to our surprise, there has been no relevant review article on rational designs of organic PSs for PDT. Furthermore, most of published review articles in PDT focused on nanomaterials and nanotechnology based on traditional PSs. Therefore, this review aimed at reporting recent strategies to develop innovative organic photosensitizers for enhanced photodynamic therapy, with each example described in detail instead of providing only a general overview, as is typically done in previous reviews of PDT, to provide intuitive, vivid, and specific insights to the readers.

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Section: Phthalocyanine Derivativesmentioning

confidence: 97%

Section: Representative Strategies For Conventional Photosensitizersmentioning

confidence: 99%

Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy

et al. 2021

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“…Because of these reasons, we believed β-Gal is an ideal candidate for extrinsic enzymes. To selectively deliver this enzyme into the cancer cells, it was modified with cyclic RGD peptide moieties that can target the α v β 3 integrin upregulated on most cancer cells, using our previously reported peptide cyclization strategy − and phthalaldehyde-amine capture (PAC) reaction. , It is worth mentioning that proteins are generally impermeable to the cells due to their high molecular weight. Various carriers, such as nanoparticles, polymers, and liposomes, have been utilized to assist the trafficking across the plasma membrane. − Cell-penetrating peptides have also been introduced for this purpose through protein expression, , covalent conjugation, or host–guest interactions .…”

Section: Introductionmentioning

confidence: 99%

Specific Activation of Photosensitizer with Extrinsic Enzyme for Precisive Photodynamic Therapy

et al. 2022

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Delivery of functional proteins into the intracellular space has been a challenging task that could lead to a myriad of therapeutic applications. We report herein a novel bioconjugation strategy for enzyme modification and selective delivery into cancer cells for lock-and-key-type activation of photosensitizers. Using a bifunctional linker containing a bis(bromomethyl)phenyl group and an o-phthalaldehyde moiety, it could induce cyclization of the peptide sequence Ac-NH-CRGDfC-CONH2 through site-specific dibenzylation with the two cysteine residues and further coupling with β-galactosidase via the phthalaldehyde-amine capture reaction. This facile two-step one-pot procedure enabled the preparation of cyclic RGD-modified β-galactosidase readily, which could be internalized selectively into αvβ3 integrin-overexpressed cancer cells. Upon encountering an intrinsically quenched distyryl boron dipyrromethene-based photosensitizer conjugated with a galactose moiety through a self-immolative linker inside the cells, the extrinsic enzyme induced specific cleavage of the β-galactosidic bond followed by self-immolation to release an activated derivative, thereby restoring the photodynamic activities and causing cell death effectively. The high specificity of this extrinsic enzyme-activated photosensitizing system was also demonstrated in vivo using nude mice bearing an αvβ3 integrin-positive U87-MG tumor. The specific activation at the tumor site resulted in lighting up and complete eradication of the tumor upon laser irradiation, while by using the native β-galactosidase, the effects were largely reduced. In contrast to the conventional activation using intrinsic enzymes, this extrinsic enzyme activatable approach can further minimize the nonspecific activation toward precisive photodynamic therapy.

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“…Phthalocyanine (Pc) compounds are blue-green functional materials that have been extensively synthesized and intensively studied, [1][2][3][4] since they were first identified in 1907; 5 such compounds are useful many applications, including pigments, [6][7][8] chemical sensors, 9,10 catalysts, 11,12 and photosensitizers applied in photodynamic therapy. [13][14][15][16] Classically, almost all of these compounds have been prepared by fusion of phthalic anhydride or its derivatives at temperatures over 170 °C, 17 or by condensation of phthalonitriles in systems above 130 °C or under reflux conditions. 18 However, the high temperatures rendered the reactions not only energy-consuming but also prone to the formation of byproducts, which complicated the purification of products, and was especially challenging for the synthesis from phthalonitriles with thermal-sensitive substituents.…”

mentioning

confidence: 99%

“…Phthalocyanine (Pc) compounds as a kind of blue-green functional materials have been extensively synthesized and intensively studied, [1][2][3][4] since it is first found in 1907, 5 for them useful in pigments, [6][7][8] chemical sensors, 9,10 catalysts, 11,12 photosensitizers applied in photodynamic therapy, [13][14][15][16] etc. Classically, almost of them were prepared by fusion of phthalic anhydride or its derivatives over 170 ℃, 17 or by condensation of phthalonitriles in systems above 130 ℃ or under reflux condition.…”

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confidence: 99%

Facile, Mild-Temperature Synthesis of Metal-Free Phthalocyanines

Cong

Jiang

et al. 2021

Synthesis

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It is important for the synthesis and research of phthalocyanine compounds for these compounds to be easily obtained at low temperature. We observed that metal-free phthalocyanine was sometimes found in a simple system used to synthesize phthalocyanine precursors at room temperature, and further studies showed that the key to the effective formation of phthalocyanines at low temperature lay in the presence of equal volumes of alcohol and amine, in addition to substrate phthalonitriles and solvents, in the reaction system. A synthetic mechanism was proposed and facile syntheses have been realized, such as the synthesis of tetra-α(β)-nitrophthalocyanines and tetra-α(β)-(4-tert-butylphenoxy)phthalocyanines from the corresponding substituted phthalonitriles at mild temperature (37 °C). The results are significant for the design and synthesis of new phthalocyanine derivatives, and the method is convenient and easy to adopt for general use in standard laboratories.

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Phthalaldehyde-Amine Capture Reactions for Bioconjugation and Immobilization of Phthalocyanines

Cited by 14 publications

References 29 publications

Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy

Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy

Specific Activation of Photosensitizer with Extrinsic Enzyme for Precisive Photodynamic Therapy

Facile, Mild-Temperature Synthesis of Metal-Free Phthalocyanines

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