Synthesis of Benz[e]indolium Heptamethine Cyanines Containing C‐Substituents at the Central Portion of the Heptamethine Moiety.

Saloň, Jozef; Wolińska, Ewa; Raszkiewicz, Aldona; Patonay, Gábor; Strękowski, Lucjan

doi:10.1002/chin.200547179

Cited by 3 publications

(3 citation statements)

References 9 publications

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“…Symmetric heptamethyne cyanine cores (cyclic or non-cyclic) were synthesized by following the literature methods reported elsewhere [73][74][75]. The chlorine atom in the cyclic cyanines was then substituted by SNAr reaction with appropriate phenolic nucleophiles under basic condition (Figure 1a).…”

Section: Design Of Dyes and Fluorescent Coatingsmentioning

confidence: 99%

Near-infrared fluorescent coatings of medical devices for image-guided surgery

et al. 2020

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Rapidly expanding field of image-guided surgery needs new materials for near-infrared imaging with deep tissue penetration. Here, we introduce near-infrared coating of equipment (NICE) for image-guided surgery based on a series of lipophilic cyanine-7.5 dyes with bulky hydrophobic counterions and a biocompatible polymer, poly(methyl methacrylate). The NICE material exhibits superior brightness (15-20-fold higher) and photostability compared to fluorescent coatings based on commonly used indocyanine green (ICG). It can be deposited on different surfaces and devices, such as steel and gold fiducials, silicone and PVC catheters, polymeric surgical sutures and gauzes. Such coated medical devices show excellent stability in air and buffer for 150 days. Accelerated ageing revealed their shelf-life of 3 years. They are also stable in serum-containing media, whereas ICG-based coating shows rapid dye leakage. NICE is compatible with standard sterilization protocols based on ethylene oxide and vapor. Moreover, our coating material is biocompatible, where cultured cells spread effectively without signs of cytotoxicity. Ex vivo studies suggest that NICE on fiducials can be visualized as deep as 0.5 cm, and NICE on catheters enables their visualization inside ureters and esophagus. Finally, NICE on different medical devices has been validated for image-guided surgery in porcine and human cadaver models. Thus, the developed NIR coating material emerges as a powerful tool for a variety of medical applications.

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Section: Design Of Dyes and Fluorescent Coatingsmentioning

confidence: 99%

Near-infrared fluorescent coatings of medical devices for image-guided surgery

et al. 2020

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“…However, this procedure gives moderate yields only for methyl-and phenyl-substituted cyclohexenes presumably because of harsh conditions employed in the synthesis. 41,42 Besides a cyclopentyl or cyclohexyl ring embedded within the heptamethine scaffold, no modifications at the C3′ and C5′ positions have been reported to date. Therefore, essentially only the C4′-position modifications are available for modification to date, imposing fundamental restrictions on the design of new Cy7 fluorophores.…”

Section: ■ Introductionmentioning

confidence: 99%

Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts

2019

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Cyanine dyes play an indispensable and central role in modern fluorescence-based biological techniques.Despite their importance and widespread use, the current synthesis methods of heptamethine chain modification are restricted to coupling reactions and nucleophilic substitution at the meso position in the chain. Herein, we report the direct transformation of Zincke salts to cyanine dyes under mild conditions, accompanied by the incorporation of a substituted pyridine residue into the heptamethine scaffold. This work represents the first general approach that allows the introduction of diverse substituents and different substitution patterns at the C3′−C5′ positions of the chain. High yields, functional tolerance, versatility toward the condensation partners, and scalability make this method a powerful tool for accessing a new generation of cyanine derivatives.

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“…The alternative route to meso-arylated dyes requires the preparation of meso-arylated pentamethine salts formed by Vilsmeier-Haack formylation of 1-arylcyclohexenes, 10 which are not readily available, especially with functional substitution (COOH, NH 2 , OH). IR-780 and their related dyes slowly decom- pose under Suzuki coupling conditions, since addition of basic nucleophiles to C@N bonds is not completely reversible.…”

Section: Introductionmentioning

confidence: 99%

New acyclic Pd–diaminocarbene catalyst for Suzuki arylation of meso-chlorosubstituted tricarboindocyanine dyes

Miltsov¹,

Karavan²,

Boyarsky³

et al. 2013

Tetrahedron Letters

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Synthesis of Benz[e]indolium Heptamethine Cyanines Containing C‐Substituents at the Central Portion of the Heptamethine Moiety.

Abstract: An efficient procedure for the synthesis of near-infrared dyes 5a-d is described.

Cited by 3 publications

References 9 publications

Near-infrared fluorescent coatings of medical devices for image-guided surgery

Near-infrared fluorescent coatings of medical devices for image-guided surgery

Approach to a Substituted Heptamethine Cyanine Chain by the Ring Opening of Zincke Salts

New acyclic Pd–diaminocarbene catalyst for Suzuki arylation of meso-chlorosubstituted tricarboindocyanine dyes

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