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SWIR emissive RosIndolizine dyes with nanoencapsulation in water soluble dendrimers.

ABSTRACT: Shortwave infrared (SWIR) emission has great potential for deep-tissue in vivo biological imaging with high resolution. In this article, the synthesis and characterization of two new xanthene-based RosIndolizine dyes coded ^PhRosIndz and ^tolRosIndz is presented. The dyes are characterized via femtosecond transient absorption spectroscopy as well as steady-state absorption and emission spectroscopies. The emission of these dyes is shown in the SWIR region with peak emission at 1097 nm. ^TolRosIndz was encapsulated with an amphiphilic linear dendritic block co-polymer (LDBC) coded 10-PhPCL-G3 with high uptake yield. Further, cellular toxicity was examined in vitro using HEK (human embryonic kidney) cells where a >90% cell viability was observed at practical concentrations of the encapsulated dye which indicates low toxicity and reasonable biocompatibility.

SUBMITTER: Chatterjee S

PROVIDER: S-EPMC9037842 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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SWIR emissive RosIndolizine dyes with nanoencapsulation in water soluble dendrimers.

Chatterjee Satadru S Meador William E WE Smith Cameron C Chandrasiri Indika I Zia Mohammad Farid MF Nguyen Jay J Dorris Austin A Flynt Alex A Watkins Davita L DL Hammer Nathan I NI Delcamp Jared H JH

RSC advances 20210816 45

Shortwave infrared (SWIR) emission has great potential for deep-tissue in vivo biological imaging with high resolution. In this article, the synthesis and characterization of two new xanthene-based RosIndolizine dyes coded PhRosIndz and tolRosIndz is presented. The dyes are characterized via femtosecond transient absorption spectroscopy as well as steady-state absorption and emission spectroscopies. The emission of these dyes is shown in the SWIR region with p ...[more]

PMID: 35480767

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Project description:Dual or multimodal imaging probes have become potent tools for enhancing detection sensitivity and accuracy in disease diagnosis. In this context, we present a bimodal imaging dendrimer-based structure that integrates magnetic and fluorescent imaging probes for potential applications in magnetic resonance imaging and fluorescence imaging. It stands out as one of the rare examples where bimodal imaging probes use organic radicals as the magnetic source, despite their tendency to entirely quench fluorophore fluorescence. Opting for organic radicals over metal-based contrast agents like gadolinium (Gd3+)-chelates is crucial to mitigate associated toxicity concerns. We utilized an amino-terminated polyamide dendrimer containing a 1,8-naphthalimide (Naft) fluorescent group, amino acid derivatives as linkers to enhance water solubility, and TEMPO organic radicals as terminal groups. The same dendrimer structure, featuring an equivalent number of branches but lacking the fluorophore group, was also functionalized with amino acid and terminal radicals to serve as a reference. Remarkably, we achieved a fully water-soluble dendrimer-based structure exhibiting both magnetic and fluorescent properties simultaneously. The fluorescence of the Naft group in the final structure is somewhat quenched by the organic radicals, likely due to photoinduced electron transfer with the nitroxyl radical acting as an electron acceptor, which has been supported by density functional theory calculations. Molecular dynamics simulations are employed to investigate how the dendrimers' structure influences the electron paramagnetic resonance characteristics, relaxivity, and fluorescence. In summary, despite the influence of the radicals-fluorophore interactions on fluorescence, this bimodal dendrimer demonstrates significant fluorescent properties and effective r1 relaxivity of 1.3 mM-1 s-1. These properties have proven effective in staining the live mesenchymal stem cells without affecting the cell nucleus.

Dataset Information

SWIR emissive RosIndolizine dyes with nanoencapsulation in water soluble dendrimers.

Publications

SWIR emissive RosIndolizine dyes with nanoencapsulation in water soluble dendrimers.

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