Near‐infrared bis(indolium heptamethine cyanine) dyes with a spacer derived from oligo(ethylene glycol)

Wolińska, Ewa; Henary, Maged; Paliakov, Ekaterina; Strękowski, Lucjan

doi:10.1002/jhet.171

Cited by 6 publications

(4 citation statements)

References 16 publications

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“…We hypothesized that under stringent conditions, cyanine 4 could lose its Fischer’s base by a retro-Knoevenagel reaction to give a putative half cyanine enol intermediate L . This hypothesis is based on the chemistry of cyanine dye formation that a half cyanine enol intermediate could condensate with Fischer’s base to yield a cyanine dye, and the Knoevenagel-type condensation reaction is reversible. The enol intermediate L could then undergo cyclization and dehydration reactions to furnish a much more stable product 1a .…”

Section: Resultsmentioning

confidence: 99%

A Unique Approach to Development of Near-Infrared Fluorescent Sensors for in Vivo Imaging

et al. 2012

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Near-infrared (NIR) fluorescent sensors have emerged as promising molecular tools for imaging biomolecules in living systems. However, NIR fluorescent sensors are very challenging to be developed. Herein, we describe the discovery of a new class of NIR fluorescent dyes represented by 1a/1c/1e, which are superior to the traditional 7-hydroxycoumarin and fluorescein with both absorption and emission in the NIR region while retaining an optically tunable hydroxyl group. Quantum chemical calculations with the B3LYP exchange functional employing 6-31G(d) basis sets provide insights into the optical property distinctions between 1a/1c/1e and their alkoxy derivatives. The unique optical properties of the new type of fluorescent dyes can be exploited as a useful strategy for development of NIR fluorescent sensors. Employing this strategy, two different types of NIR fluorescent sensors, NIR-H(2)O(2) and NIR-thiol, for H(2)O(2) and thiols, respectively, were constructed. These novel sensors respond to H(2)O(2) or thiols with a large turn-on NIR fluorescence signal upon excitation in the NIR region. Furthermore, NIR-H(2)O(2) and NIR-thiol are capable of imaging endogenously produced H(2)O(2) and thiols, respectively, not only in living cells but also in living mice, demonstrating the value of the new NIR fluorescent sensor design strategy. The new type of NIR dyes presented herein may open up new opportunities for the development of NIR fluorescent sensors based on the hydroxyl functionalized reactive sites for biological imaging applications in living animals.

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Section: Resultsmentioning

confidence: 99%

A Unique Approach to Development of Near-Infrared Fluorescent Sensors for in Vivo Imaging

et al. 2012

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Section: Synthesis Of Heptamethine Cyanine Dyesmentioning

confidence: 99%

“…Synthetic routes for obtaining unsymmetrical heptamethine cyanine dyes generally require the synthesis of intermediate compounds called hemicyanines, which include compounds such as 29 a-d (Scheme 6). [36] In this particular case, these compounds can be obtained from the cyclic bis-aldehyde 16, which acts as a precursor for the production of unsymmetrical bis-heptamethine cyanine dyes 32 a-i using a two-step method. Furthermore, nucleophilic species involved in condensation reactions (heterocyclic compounds) should always be present in equal or lesser quantities than the polymethine chains to avoid the formation of symmetrical cyanines.…”

Section: Unsymmetrical Heptamethine Cyanine Dyesmentioning

confidence: 99%

“…This mixture was heated under reflux in Ac 2 O for 10 min (Scheme 8). Hemicyanine (36) was obtained by filtration (71% yield) because the compound crystallized within the reaction medium. Subsequently, compound 38 was obtained by condensing 36 with compound 37 under reflux using a methanol/acetic acid mixture as the solvent and catalytic amounts of piperidine acetate.…”

Section: Unsymmetrical Heptamethine Cyanine Dyesmentioning

confidence: 99%

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Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

et al. 2022

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This review summarizes diverse synthetic methodologies to prepare a wide range of heptamethine cyanine dyes, including symmetrical, unsymmetrical, and meso‐substituted derivatives, and their photophysical properties and uses. Their sensing applications are also discussed, considering the nature of their electronic structures and photophysical properties. The optical sensing applications of these compounds can be potentially expanded via structural modification, broadening their absorption amplitude and spectral emission range from the ultraviolet to near‐infrared (NIR) region. In this review, several recent practical applications of the heptamethine cyanine dyes for ion and small molecule sensing, as well as bioimaging, are covered and discussed.

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Tumor‐Targeting Near‐Infrared Dimeric Heptamethine Cyanine Photosensitizers with an Aromatic Diphenol Linker for Imaging‐Guided Cancer Phototherapy

et al. 2023

Adv Healthcare Materials

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Phototherapy is considered a promising alternative to conventional tumor treatments due to its noninvasive modality and effective therapeutic effect. However, designing a photosensitizer with satisfactory therapeutic effect and high security remains a considerable challenge. Herein, a series of dimeric heptamethine cyanine photosensitizers with an aromatic diphenol linker at the meso position is developed to improve the photothermal conversion efficiency (PCE). Thanks to the extended conjugate system and high steric hindrance, the screened 26NA-NIR and 44BP-NIR exhibit high PCE (≈35%), bright near-infrared (NIR) fluorescence, excellent reactive oxygen species (ROS) generation capability, and improved photostability. Furthermore, their outstanding performance on imaging-guided PDT-PTT synergistic therapy is demonstrated by in vivo and in vitro experiments. In conclusion, this study designs a series of dimeric heptamethine cyanine photosensitizers and presents two compounds for potential clinical applications. The strategy provides a new method to design NIR photosensitizers for imaging-guided cancer treatment.

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Near‐infrared bis(indolium heptamethine cyanine) dyes with a spacer derived from oligo(ethylene glycol)

Abstract: magnified imageSynthesis of a series of near‐infrared dimeric dyes is presented. The intramolecular dimers contain two chromophores linked with a conformationally flexible ether or oligoether bridge. Optical properties of the dyes are discussed. J. Heterocyclic Chem., (2009).

Cited by 6 publications

References 16 publications

A Unique Approach to Development of Near-Infrared Fluorescent Sensors for in Vivo Imaging

A Unique Approach to Development of Near-Infrared Fluorescent Sensors for in Vivo Imaging

Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

Tumor‐Targeting Near‐Infrared Dimeric Heptamethine Cyanine Photosensitizers with an Aromatic Diphenol Linker for Imaging‐Guided Cancer Phototherapy

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