Shortwave Infrared Absorptive and Emissive Pentamethine-Bridged Indolizine Cyanine Dyes

Ndaleh, David; Smith, Cameron L. C.; Yaddehige, Mahesh Loku; Shaik, Abdul Kalam; Watkins, Davita L.; Hammer, Nathan I.; Delcamp, Jared H.

doi:10.1021/acs.joc.1c01908

Cited by 19 publications

(18 citation statements)

References 49 publications

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“…Exposure to POCl 3 followed by EtOH led to Me2-RI in a 59% yield after anion exchange. 7-DMA-RI was synthesized beginning from known lactone 8 and known indolizine 9 via palladium-catalyzed C–H activation to give lactone 10 . Lactone opening via POCl 3 and exposure to EtOH led to the formation of 7-DMA-RI after anion exchange.…”

Section: Resultsmentioning

confidence: 99%

“…Benchmark materials RI, tol RosIndz, and Ph RosIndz have been previously reported. 11,25 Compounds 1, 25 3, 36 6, 38 8, 37 and 9 38 have been previously reported. All reactions were heated in oil baths.…”

Section: ■ Conclusionmentioning

confidence: 85%

“…All of the reagents and solvents used in this study were purchased from Sigma-Aldrich, Acros Organics, and Thermo Fischer Scientific. Benchmark materials RI, tol RosIndz, and Ph RosIndz have been previously reported. , Compounds 1 , 3 , 6 , 8 , and 9 have been previously reported. All reactions were heated in oil baths.…”

Section: Methodsmentioning

confidence: 98%

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Design and Synthesis of RhodIndolizine Dyes with Improved Stability and Shortwave Infrared Emission up to 1250 nm

et al. 2022

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The design of shortwave infrared (SWIR) emissive small molecules with good stability in water remains an important challenge for fluorescence biological imaging applications. A series of four SWIR emissive rhodindolizine (RI) dyes were rationally designed and synthesized to probe the effects of nonconjugated substituents, conjugated donor groups, and nanoencapsulation in a water-soluble polymer on the stability and optical properties of the dyes. Steric protecting groups were added at the site of a significant LUMO presence to probe the effects on stability. Indolizine donor groups with added dimethylaniline groups were added to reduce the electrophilicity of the dyes toward nucleophiles such as water. All of the dyes were found to absorb (920–1096 nm peak values) and emit (1082–1256 nm peak values) within the SWIR region. Among xanthene-based emissive dyes, emission values >1200 nm are exceptional with 1256 nm peak emission being a longer emission than the recent record setting VIX-4 xanthene-based dye. Half-lives were improved from ∼5 to >24 h through the incorporation of either steric-based core protection groups or donors with increased donation strength. Importantly, the nanoencapsulation of the dyes in a water-soluble surfactant (Triton-X) allows for the use of these dyes in biological imaging applications.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 85%

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Design and Synthesis of RhodIndolizine Dyes with Improved Stability and Shortwave Infrared Emission up to 1250 nm

et al. 2022

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“…Among these dyes, those capable of absorbing in the second NIR window (NIR-II; 1000 to 1700 nm) are more attractive because of their low phototoxicity and deep-tissue penetration (3)(4)(5)(6)(7). However, the design of NIR-II-absorbing organic dyes for biophotonics is mainly limited to cyanine dyes (6)(7)(8)(9)(10)(11)(12)(13)(14), and their development remains an immense challenge.…”

Section: Introductionmentioning

confidence: 99%

Discovery of BODIPY J-aggregates with absorption maxima beyond 1200 nm for biophotonics

et al. 2022

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Organic dyes with absorption maxima in the second near-infrared window (NIR-II; 1000 to 1700 nm) are of great interest in biophotonics. However, because of the lack of appropriate molecular scaffolds, current research in this field is limited to cyanine dyes, and developing NIR-II–absorbing organic dyes for biophotonics remains an immense challenge. Here, we rationally designed an ethenylene-bridged BODIPY scaffold featuring excellent J-aggregation capabilities and revealed that the bridging ethylene unit is crucial for intermolecular J-coupling regulation. By integrating the electron-donating groups into the scaffold, we obtained a BODIPY dye, BisBDP2, with a J-aggregate absorption maximum of around 1300 nm. BisBDP2 J-aggregates show excellent photothermal performance, including intense photoacoustic response, and a high photothermal conversion efficiency value of 63%. In vivo results demonstrate the potential of J-aggregates for photoacoustic imaging and photothermal ablation of deep-seated tumors. This study will speed up the exploration of NIR-II–absorbing J-aggregates for future biophotonic applications.

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“…[18][19][20][21] Among them, smallmolecular organic NIR-II dyes with favorable excretion pharmacokinetics and minimal cellular toxicity are one of the most attractive candidates. 29,30 A series of small-molecular NIR-II probes with a benzobisthiadiazole (BBTD), 28 polymethine cyanine, [22][23][24] or xanthene 25,26 core have been intensively reported for in vivo imaging and image-guided therapeutic procedures. However, the studies on NIR-II Ru(II) polypyridyl fluorophores for precise cancer therapy are still scarce.…”

mentioning

confidence: 99%

A single-molecular ruthenium(ii) complex-based NIR-II fluorophore for enhanced chemo-photothermal therapy

Liu

Zhao

et al. 2022

Chem. Commun.

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Shortwave Infrared Absorptive and Emissive Pentamethine-Bridged Indolizine Cyanine Dyes

Cited by 19 publications

References 49 publications

Design and Synthesis of RhodIndolizine Dyes with Improved Stability and Shortwave Infrared Emission up to 1250 nm

Design and Synthesis of RhodIndolizine Dyes with Improved Stability and Shortwave Infrared Emission up to 1250 nm

Discovery of BODIPY J-aggregates with absorption maxima beyond 1200 nm for biophotonics

A single-molecular ruthenium(ii) complex-based NIR-II fluorophore for enhanced chemo-photothermal therapy

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