Functionalization of benzo[<i>c,d</i>]indole system for the synthesis of visible and near‐infrared dyes

Henary, Maged; Say, Martial; Strękowski, Lucjan

doi:10.1002/jhet.39

Cited by 21 publications

(15 citation statements)

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“…Heptamethine cyanine was selected as a uorophore because of its NIR emission 13 and more importantly, tautomerism between its enol form and ketone form resulted from conjugated p-electron modulation. 22 As the pK a of hydroxy-cyanine is relatively low, 22 the ketone form is in the majority under physiological pH of 7.4. Therefore, when the hydroxyl is replaced by an analyte-sensitive group, the tautomerism can be readily triggered in the presence of analytes with the elimination of the sensitive group.…”

Section: Resultsmentioning

confidence: 99%

A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells

et al. 2013

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We describe the design and synthesis of a cyanine-based near-infrared ratiometric fluorescent probe, HS-Cy, for H 2 S detection, which features rapid response, high sensitivity, and mitochondria targeting. After a rapid quenching at 780 nm by initial nucleophilic addition on the aldehyde group, HS-Cy experienced a polymethine p-electron conjugation modulation triggered by a second nucleophilic addition on the ester, releasing the cyanine fluorophore which underwent tautomerism from enol form to ketone form. Therefore, gradual emergence of a new peak at 625 nm was observed, constructing a ratiometric signal for H 2 S with a detection limit of 5.0-10 nM, which is the most sensitive among the reported H 2 Ssensing fluorescent probes. HS-Cy was proven to selectively locate into mitochondria with faster trapping kinetics towards H 2 S. Based on this, the endogenously generated H 2 S in human A549 cells was ratiometrically detected and imaged by HS-Cy.

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Section: Resultsmentioning

confidence: 99%

A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells

et al. 2013

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“…Using readily available 1,8-naphtholactam as a substrate they were able to obtain both hydrophobic and water soluble fluorophores. These molecules are expected to be more stable and exhibit enhanced bathochromic shifts as compared to other benzoindolium-derived cyanine congeners [11]. …”

Section: Introductionmentioning

confidence: 99%

NIR dyes for bioimaging applications

Escobedo

Rusin

Lim

et al. 2010

Current Opinion in Chemical Biology

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Summary of recent advances Fluorescent dyes based on small organic molecules that function in the near infra red (NIR) region are of great current interest in chemical biology. They allow for imaging with minimal autofluorescence from biological samples, reduced light scattering and high tissue penetration. Herein, examples of ongoing NIR fluorophore design strategies as well as their properties and anticipated applications relevant to the bioimaging are presented.

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“…Notably, since the report of Flav7, similar strategies have been employed to utilize or design polymethine dyes for SWIR imaging. 40 , 41 , 42 , 43 , 44 Due to the ability to image both bright NIR-excitable dyes, such as ICG, as well as red-shifted SWIR-excitable polymethine dyes, such as Flav7, with an identical SWIR detection window, we envisioned that polymethine dyes with both well-separated and laser-line compatible absorption could enable efficient multicolor SWIR imaging via excitation-multiplexing. To realize this multiplexing strategy, structural modifications to Flav7 were necessary to tune the λ max,abs to match accessible laser wavelengths used for SWIR imaging.…”

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Shortwave infrared polymethine fluorophores matched to excitation lasers enable non-invasive, multicolour in vivo imaging in real time

et al. 2020

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High resolution, multiplexed experiments are a staple in cellular imaging. Analogous experiments in animals are challenging, however, due to significant scattering and autofluorescence in tissue at visible (VIS, 350–700 nm) and near-infrared (NIR, 700–1000 nm) wavelengths. Here, we enable real-time, non-invasive multicolor imaging experiments in animals through the design of optical contrast agents for the shortwave infrared (SWIR, 1000–2000 nm) region and complementary advances in imaging technologies. We developed tunable, SWIR-emissive flavylium polymethine dyes and established structure-photophysical property relationships for this class of bright SWIR contrast agents. In parallel, we designed an imaging system with variable NIR/SWIR excitation and single-channel detection, facilitating video-rate multicolor SWIR imaging for optically guided surgery and imaging of awake and moving mice with multiplexed detection. Optimized dyes matched to 980 nm and 1064 nm lasers, combined with the clinically approved indocyanine green, enabled real-time, three-color imaging with high temporal and spatial resolutions.

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Functionalization of benzo[c,d]indole system for the synthesis of visible and near‐infrared dyes

Abstract: A number of benzo[c,d]indolium derivatives have been synthesized. J. Heterocyclic Chem., 46, 84 (2009).

Cited by 21 publications

References 9 publications

A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells

A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells

NIR dyes for bioimaging applications

Shortwave infrared polymethine fluorophores matched to excitation lasers enable non-invasive, multicolour in vivo imaging in real time

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