Promising near-infrared non-targeted probes: benzothiazole heptamethine cyanine dyes

Okoh, Okoh Adeyi; Bisby, Roger H.; Lawrence, Clare; Rolph, Carole E.

doi:10.1080/17415993.2013.778258

Cited by 18 publications

(17 citation statements)

References 30 publications

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“…In general, the published procedures start with the synthesis of the terminal heterocycle. In most cases, indole derivatives are used to generate cyanine fluorophores, but other heterocycles have been also used . These indole derivatives are later derivatized, for example by alkylation of the nitrogen atom.…”

Section: Figurementioning

confidence: 99%

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

Braun

Wehl

Schepers

et al. 2019

Chemistry A European J

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In this communication, the synthesis of three unknown polyfluorinated cyanine dyes and their application as selective markers for mitochondria are presented. By incorporating fluorous side chains into cyanine dyes, their remarkable photophysical properties were enhanced. To investigate their biological application, several different cell lines were incubated with the synthesized cyanine dyes. It was discovered that the presented dyes can be utilized for selective near‐infrared‐light (NIR) staining of mitochondria, with very low cytotoxicity determined by MTT assay. This is the first time that polyfluorinated cyanine fluorophores are presented as selective markers for mitochondria. Due to the versatile applications of polyfluorinated fluorophores in bioimaging and materials science, it is expected that the presented fluorophores will be stimulating for the scientific community.

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Section: Figurementioning

confidence: 99%

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

Braun

Wehl

Schepers

et al. 2019

Chemistry A European J

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“…Being heterocyclic compounds, BTA derivatives find use in various branches of chemical research, for instance, in polymer chemistry [27,28], dyes [29,30], drugs [31] etc. BTA salts have been used in silver photography, essentially as sensitizing dyes [32].…”

Section: Introductionmentioning

confidence: 99%

A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry

Keri

Patil

et al. 2015

European Journal of Medicinal Chemistry

481

238

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“…The yield was reported as 55% when the equivalent ratio of pyran derivative and 15 NH 4 Cl was used. In a similar manner, 4‐methylpyridine was obtained from 2‐ethoxy‐4‐methyl‐3,4‐dihydro‐2 H ‐pyran . The main limitation of this synthetic approach is the use of substituted pyridine derivatives, which can be complex in the context of future SABRE biomedical applications …”

Section: Resultsmentioning

confidence: 99%

“…An initial quantity of N ‐(2,4‐dinitrophenyl)pyridinium chloride was prepared by interaction of pyridine with 1‐chloro‐2,4‐dinitrobenzene in acetone . This salt was used in the reaction with a methanol solution of 15 NH 4 Cl (Figure ).…”

Section: Resultsmentioning

confidence: 99%

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A versatile synthetic route to the preparation of ¹⁵N heterocycles

Чуканов

Kidd

Kovtunova

et al. 2019

Labelled Comp Radiopharmac

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A robust medium‐scale (approximately 3 g) synthetic method for 15N labeling of pyridine (15N‐Py) is reported based on the Zincke reaction. 15N enrichment in excess of 81% was achieved with approximately 33% yield. 15N‐Py serves as a standard substrate in a wide range of studies employing a hyperpolarization technique for efficient polarization transfer from parahydrogen to heteronuclei; this technique, called SABRE (signal amplification by reversible exchange), employs a simultaneous chemical exchange of parahydrogen and a to‐be‐hyperpolarized substrate (e.g., pyridine) on metal centers. In studies aimed at the development of hyperpolarized contrast agents for in vivo molecular imaging, pyridine is often employed either as a model substrate (for hyperpolarization technique development, quality assurance, and phantom imaging studies) or as a co‐substrate to facilitate more efficient hyperpolarization of a wide range of emerging contrast agents (e.g., nicotinamide). Here, the produced 15N‐Py was used for the feasibility study of spontaneous 15N hyperpolarization at high magnetic (HF) fields (7 T and 9.4 T) of an NMR spectrometer and an MRI scanner. SABRE hyperpolarization enabled acquisition of 2D MRI imaging of catalyst‐bound 15N‐pyridine with 75 × 75 mm2 field of view (FOV), 32 × 32 matrix size, demonstrating the feasibility of 15N HF‐SABRE molecular imaging with 2.4 × 2.4 mm2 spatial resolution.

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Promising near-infrared non-targeted probes: benzothiazole heptamethine cyanine dyes

Cited by 18 publications

References 30 publications

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry

A versatile synthetic route to the preparation of ¹⁵N heterocycles

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Promising near-infrared non-targeted probes: benzothiazole heptamethine cyanine dyes

Cited by 18 publications

References 30 publications

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry

A versatile synthetic route to the preparation of 15N heterocycles

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A versatile synthetic route to the preparation of ¹⁵N heterocycles