Xanthene dyes for cancer imaging and treatment: A material odyssey

Karaman, Osman; Alkan, Gizem Atakan; Kizilenis, Caglayan; Akgul, Cevahir Ceren; Günbaş, Görkem

doi:10.1016/j.ccr.2022.214841

Cited by 22 publications

(10 citation statements)

References 133 publications

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“…As researchers continue to study xanthene‐based PSs, very promising results have been obtained. The promising properties of xanthene‐based PSs, such as water solubility, photostability, and ease of modification, motivated researchers to investigate improvements on classical dyes, such as fluorescein and rhodamine B, toward realizing NIR absorption with highly cancer‐selective activation for phototheranostics opportunities [98]. RB is a well‐known derivative of fluorescein with a heavy atom, which absorbs at 549 nm with a high molar extinction coefficient (~100,000 M −1 cm −1 ).…”

Section: The Acq‐to‐aie Transformation Of Xanthene‐pssmentioning

confidence: 99%

Reviewing the evolutive ACQ‐to‐AIE transformation of photosensitizers for phototheranostics

Zhu,

Huang,

et al. 2023

Luminescence

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Photodynamic therapy (PDT) represents an emerging noninvasive treatment technique for cancers and various nonmalignant diseases, including infections. During the process of PDT, the physical and chemical properties of photosensitizers (PSs) critically determine the effectiveness of PDT. Traditional PSs have made great progress in clinical applications. One of the challenges is that traditional PSs suffer from aggregation‐caused quenching (ACQ) due to their discotic structures. Recently, aggregation‐induced emission PSs (AIE‐PSs) with a twisted propeller‐shaped conformation have been widely concerned because of high reactive oxygen species (ROS) generation efficiency, strong fluorescence efficiency, and resistance to photobleaching. However, AIE‐PSs also have some disadvantages, such as short absorption wavelengths and insufficient molar absorption coefficient. When the advantages and disadvantages of AIE‐PSs and ACQ‐PSs are complementary, combining ACQ‐PSs and AIE‐PSs is a “win‐to‐win” strategy. As far as we know, the conversion of traditional representative ACQ‐PSs to AIE‐PSs for phototheranostics has not been reviewed. In the review, we summarize the recent progress on the ACQ‐to‐AIE transformation of PSs and the strategies to achieve desirable theranostic applications. The review would be helpful to design more efficient ACQ‐AIE‐PSs in the future and to accelerate the development and clinical application of PDT.

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Section: The Acq‐to‐aie Transformation Of Xanthene‐pssmentioning

confidence: 99%

Reviewing the evolutive ACQ‐to‐AIE transformation of photosensitizers for phototheranostics

Zhu,

Huang,

et al. 2023

Luminescence

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“…In the 19th century, people found that some substances absorb light energy to emit fluorescence, belonging to a photoluminescence phenomenon. [ 47 ] Since then, people have used fluorescent materials for lighting, [ 48 ] bioimaging, [ 49 ] anti‐counterfeiting encryption, [ 50 ] solar energy storage [ 51 ] and conversion, etc . More and more fluorescent materials were developed, including semiconductor quantum dots, [ 52 ] carbon dots, [ 53 ] complexes, [ 54 ] etc .…”

Section: Fluorescent Materialsmentioning

confidence: 99%

Fluorescent Silk Obtained by Feeding Silkworms with Fluorescent Materials^†

Sun

Xiong

2023

Chin. J. Chem.

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Comprehensive Summary Fluorescent silk has potential application in many fields such as bioimaging, tissue engineering scaffolds, luminescent marks, and dazzling fabrics. Among the methods to endow natural silk with fluorescent properties, feeding silkworms with fluorescent additives is facile, low‐cost and environment friendly, which has the prospect of large‐scale production. In this paper, we reviewed the research progress for this aim in the past ten years, and summarized the unified characteristics for the substances that can enter the silk gland by digestive tract of silkworms. The advantages and disadvantages of various fluorescent materials for this application are compared in detail. And the future research directions are suggested to overcome the shortcomings of the present research.

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“…This popular transformation has furnished a variety of xanthene dye derivatives, including red-shifted fluorophores with heteroatom exchange [35][36][37][38][39] and has been incorporated in many fluorescent probes for advanced bioimaging and biosensing. [40][41][42] Inspired by these successes, we have noticed the structural similarity between the xanthone substrate in xanthene dye synthesis and the ketoform of heptamethine dyes, the S RN 1 hydrolysis product of common 4'-chloro heptamethine fluorophores, and discovered that such lithium addition reaction can be used to construct 4'-aryl modified heptamethine dyes (Figure 1). Using this strategy, we show our successful preparation of a panel of 4'-aryl substituted heptamethine fluorophores starting from the 4'-chloro precursor.…”

Section: Introductionmentioning

confidence: 99%

Engineering Central Substitutions in Heptamethine Dyes via Aryl-lithium Addition for Improved Fluorophore Performance

Guo,

Yang,

Dong

et al. 2024

Preprint

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As a major family of red-shifted fluorophores that operate beyond the visible light, polymethine dyes are pivotal in light-based biological techniques. However, the methods for tuning this kind of fluorophores by structural modification remain restricted to bottom-up synthesis and modification using coupling or nucleophilic substitutions. In this study, we introduce a two-step, late-stage functionalization process for heptamethine dyes. This process enables the substitution of the central chloride atom in the commonly used 4'-chloro heptamethine scaffold with various aryl groups using aryllithium reagents. This method borrows the building block and designs from the xanthene dye community, and offers a mild and convenient way for the diversification of heptamethine fluorophores. Notably, this efficient conversion allows for the synthesis of heptamethine-X, the heptamethine scaffold with two ortho-substituents on the 4’-aryl modification, which brings enhanced stability and reduced aggregation to the fluorophore. We showcase the utility of this synthesis by a facile synthesis of a fluorogenic, membrane-localizing fluorophore that outperforms the commercial counterparts with higher brightness and contrast. Overall, this method establishes the synthetic similarities between polymethine and xanthene fluorophores, and provides reference for future optimizing heptamethine fluorophores for their biological applications.

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Xanthene dyes for cancer imaging and treatment: A material odyssey

Cited by 22 publications

References 133 publications

Reviewing the evolutive ACQ‐to‐AIE transformation of photosensitizers for phototheranostics

Reviewing the evolutive ACQ‐to‐AIE transformation of photosensitizers for phototheranostics

Fluorescent Silk Obtained by Feeding Silkworms with Fluorescent Materials^†

Engineering Central Substitutions in Heptamethine Dyes via Aryl-lithium Addition for Improved Fluorophore Performance

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Xanthene dyes for cancer imaging and treatment: A material odyssey

Cited by 22 publications

References 133 publications

Reviewing the evolutive ACQ‐to‐AIE transformation of photosensitizers for phototheranostics

Reviewing the evolutive ACQ‐to‐AIE transformation of photosensitizers for phototheranostics

Fluorescent Silk Obtained by Feeding Silkworms with Fluorescent Materials†

Engineering Central Substitutions in Heptamethine Dyes via Aryl-lithium Addition for Improved Fluorophore Performance

Contact Info

Product

Resources

About

Fluorescent Silk Obtained by Feeding Silkworms with Fluorescent Materials^†