Enzyme activatable photodynamic therapy agents targeting melanoma

Verirsen, Imran; Uyar, Busra; Ozsamur, Nezahat Gokce; Demirok, Naime; Erbaş-Çakmak, Sündüs

doi:10.1039/d2ob01937j

Cited by 10 publications

(4 citation statements)

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“…13 Self-immolated elimination of 4-amino benzyl or 4-hydroxy benzyl groups is taking place spontaneously under physiological conditions, as reported by us and others. 14 In the design, methyl groups located at the 1 and 7 positions of core BODIPY are expected to force bulky substituents at the meso position to adopt out-of-plane orientation, as shown in Fig. 1, which is also reported in the literature with BODIPY molecules.…”

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confidence: 62%

Downregulation of gene expression in hypoxic cancer cells by an activatable G-quadruplex stabiliser

et al. 2023

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confidence: 62%

Downregulation of gene expression in hypoxic cancer cells by an activatable G-quadruplex stabiliser

et al. 2023

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“…Indeed, the heteroatom‐substitution approach is intensively used to readily convert conventional O‐xanthene dyes into superior fluorophores and/or photosensitizers [39] . The flexibility of pyridine caging/decaging strategy proposed by the Ge group, [21] is obvious because its implementation to a wide range of different reactive biomarkers will only require a minor structural alteration, namely the replacement of recognition moiety introduced onto the self‐immolative benzyl‐pyridinium linker [40] …”

Section: Discussionmentioning

confidence: 99%

Valkyrie Probes: A Novel Class of Enzyme‐Activatable Photosensitizers based on Sulfur‐ and Seleno‐Rosamines with Pyridinium Unit**

Lioret,

Renault,

Maury

et al. 2023

Chemistry An Asian Journal

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The rational design of activatable photosensitizers (aPSs) uncaged by specific disease biomarkers is currently booming due to their positive attributes to achieve targeted photodynamic therapy (PDT). In this context, we present here the synthesis and detailed photophysical characterization of a novel class of hetero‐rosamine dyes bearing sulfur or selenium as bridging heavy atom and 4‐pyridyl meso‐substituent as optically tunable group. The main feature of such photoactive platforms is the spectacular change of their spectral properties depending on the caging/decaging status of their 4‐pyridyl moiety (cationic pyridinium vs. neutral pyridine). The preparation of two alkaline phosphatase (ALP)‐responsive probes (named Valkyrie probes) was achieved through formal N‐quaternarization with 4‐phosphoryloxybenzyl, the traditional recognition moiety for this important diagnostic enzyme. Bio‐analytical validations including fluorescence/singlet oxygen phosphorescence enzyme assays and RP‐HPLC‐fluorescence/‐MS analyses have enabled us to demonstrate the viability and effectiveness of this novel photosensitizer activation strategy. Since sulfur‐containing Valkyrie probe also retains high fluorogenicity in the orange‐red spectral range, this study highlights meso‐pyridyl‐substituted S‐pyronin scaffolds as valuable candidates for the rapid construction of molecular phototheranostic platforms suitable for combined fluorescence diagnosis and PDT.

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“…407 Sundus Erbas-Cakmak and co-workers developed the first tyrosinase-activatable BODIPY-based PDT agent (Figure 73). 408 In this work, an iodine-substituted BODIPY was cyclometalated Pt(II) complex (as the PSs core). 409 As depicted in Figure 74, after reacting with tyrosinase, 136tyro was converted into 136-OH through rapid rearrangement and elimination, leading to an obvious fluorescence off-on response at 530 nm.…”

Section: Tyrosinase-activatable Theranostic Probes In Pdtmentioning

confidence: 99%

“…Sundus Erbas-Cakmak and co-workers developed the first tyrosinase-activatable BODIPY-based PDT agent ( Figure 73 ). 408 In this work, an iodine-substituted BODIPY was chosen as the PS scaffold, and 3-hydroxy benzyl was used as a tyrosinase substrate motif. Meanwhile, an acetyl group was introduced to improve cellular internalization and tyrosinase-catalyzed oxidation.…”

Section: Theranostic Fluorescence Probes In Cancer Therapymentioning

confidence: 99%

Theranostic Fluorescent Probes

Sharma,

Verwilst,

et al. 2024

Chem. Rev.

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The ability to gain spatiotemporal information, and in some cases achieve spatiotemporal control, in the context of drug delivery makes theranostic fluorescent probes an attractive and intensely investigated research topic. This interest is reflected in the steep rise in publications on the topic that have appeared over the past decade. Theranostic fluorescent probes, in their various incarnations, generally comprise a fluorophore linked to a masked drug, in which the drug is released as the result of certain stimuli, with both intrinsic and extrinsic stimuli being reported. This release is then signaled by the emergence of a fluorescent signal. Importantly, the use of appropriate fluorophores has enabled not only this emerging fluorescence as a spatiotemporal marker for drug delivery but also has provided modalities useful in photodynamic, photothermal, and sonodynamic therapeutic applications. In this review we highlight recent work on theranostic fluorescent probes with a particular focus on probes that are activated in tumor microenvironments. We also summarize efforts to develop probes for other applications, such as neurodegenerative diseases and antibacterials. This review celebrates the diversity of designs reported to date, from discrete small-molecule systems to nanomaterials. Our aim is to provide insights into the potential clinical impact of this stillemerging research direction.

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Enzyme activatable photodynamic therapy agents targeting melanoma

Abstract: Cell-selective activity regulation of therapeutics are necessary for efficient personalized treatments with minimal off-target effect. Here, the first example of structurally simple, pyridinium BODIPY-based, tyrosinase activatable photosensitizer is developed and...

Cited by 10 publications

References 50 publications

Downregulation of gene expression in hypoxic cancer cells by an activatable G-quadruplex stabiliser

Downregulation of gene expression in hypoxic cancer cells by an activatable G-quadruplex stabiliser

Valkyrie Probes: A Novel Class of Enzyme‐Activatable Photosensitizers based on Sulfur‐ and Seleno‐Rosamines with Pyridinium Unit**

Theranostic Fluorescent Probes

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