Correlating Molecular Character of NIR Imaging Agents with Tissue-Specific Uptake

Owens, Eric A.; Hyun, Hoon; Tawney, Joseph G.; Choi, Hak; Henary, Maged

doi:10.1021/acs.jmedchem.5b00475

Cited by 53 publications

(60 citation statements)

References 33 publications

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“…Our previous publications suggest that subtle variations in chemical structure result in large variations in the trafficking, biodistribution, and clearance of a contrast agent, which directly affect its targeting and imaging of the specific tissue and organ. 26–29 …”

Section: Nir Fluorescent Contrast Agents For Targeted Imagingmentioning

confidence: 99%

“…Hyun et al 26 and Owens et al 29 were two of the first suggestions in the literature that the molecular character may be modified and finely tuned to achieve selective uptake with high SBR in particular tissues using a structure-inherent approach that exploits chemical recognition to biological tissue for targeting and biodistribution. Selective modifications can direct the pharmacophore to distinct regions utilizing the structure-inherent chemical recognition to the targeted tissue.…”

Section: Nir Fluorescent Contrast Agents For Targeted Imagingmentioning

confidence: 99%

“…We observed that tuning the lipophilicity and noncharged structures of NIR fluorophores allows for high uptake in the endocrine system. 29 …”

Section: Nir Fluorescent Contrast Agents For Targeted Imagingmentioning

confidence: 99%

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Tissue-Specific Near-Infrared Fluorescence Imaging

et al. 2016

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CONSPECTUS Near-infrared (NIR) fluorescence light has been widely utilized in clinical imaging by providing surgeons highly specific images of target tissue. The “NIR window” from 650 to 900 nm is especially useful due to several special features such as minimal autofluorescence and absorption of biomolecules in tissue, as well as low light scattering. Compared with visible wavelengths, NIR fluorescence light is invisible, thus allowing highly sensitivity real-time image guidance in human surgery without changing the surgical field. The benefit of using NIR fluorescence light as a clinical imaging technology can be attributed to its molecular fluorescence as an exogenous contrast agent. Indeed, whole body preoperative imaging of single-photon emission computed tomography (SPECT) and positron emission tomography (PET) remains important in diagnostic utility, but they lack the efficacy of innocuous and targeted NIR fluorophores to simultaneously facilitate the real-time delineation of diseased tissue while preserving vital tissues. Admittedly, NIR imaging technology has been slow to enter clinical use mostly due to the late-coming development of truly breakthrough contrast agents for use with current imaging systems. Therefore, clearly defining the physical margins of tumorous tissue remains of paramount importance in bioimaging and targeted therapy. An equally noteworthy yet less researched goal is the ability to outline healthy vital tissues that should be carefully navigated without transection during the intraoperative surgery. Both of these paths require optimizing a gauntlet of design considerations to obtain not only an effective imaging agent in the NIR window but also high molecular brightness, water solubility, biocompatibility, and tissue-specific targetability. The imaging community recognizes three strategic approaches which include (1) passive targeting via the EPR effect, (2) active targeting using the innate overall biodistribution of known molecules, and (3) activatable targeting through an internal stimulus, which turns on fluorescence from an off state. Recent advances in nanomedicine and bioimaging offer much needed promise toward fulfilling these stringent requirements as we develop a successful catalog of targeted contrast agents for illuminating both tumors and vital tissues in the same surgical space by employing spectrally distinct fluorophores in real time. These tissue-specific contrast agents can be versatile arsenals to physicians for real-time intraoperative navigation as well as image-guided targeted therapy. There is a versatile library of tissue-specific fluorophores available in the literature, with many discussed herein, which offers clinicians an array of possibilities that will undoubtedly improve intraoperative success and long-term postoperation prognosis.

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Section: Nir Fluorescent Contrast Agents For Targeted Imagingmentioning

confidence: 99%

Section: Nir Fluorescent Contrast Agents For Targeted Imagingmentioning

confidence: 99%

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Tissue-Specific Near-Infrared Fluorescence Imaging

et al. 2016

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“…[6] The unique photophysical properties of cyanine dyes are used fort he photon upconversion in nanoparticles [7,8] or as contrasta gents in bioimaginga pplications. [9] Numerous examples of the utilization of cyanine fluorophores can be found in literature [2,[10][11][12][13][14][15] and their utilization is proven by thef luorescent contrasta gent indocyanine green (ICG, 1)a nd derivatives thereof (for example SIDAG [16] and cipate [17] ).…”

mentioning

confidence: 99%

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

Braun

Wehl

Schepers

et al. 2019

Chemistry A European J

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In this communication, the synthesis of three unknown polyfluorinated cyanine dyes and their application as selective markers for mitochondria are presented. By incorporating fluorous side chains into cyanine dyes, their remarkable photophysical properties were enhanced. To investigate their biological application, several different cell lines were incubated with the synthesized cyanine dyes. It was discovered that the presented dyes can be utilized for selective near‐infrared‐light (NIR) staining of mitochondria, with very low cytotoxicity determined by MTT assay. This is the first time that polyfluorinated cyanine fluorophores are presented as selective markers for mitochondria. Due to the versatile applications of polyfluorinated fluorophores in bioimaging and materials science, it is expected that the presented fluorophores will be stimulating for the scientific community.

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“…Alkylation of 1,1,2-trimethyl-1H-benzo[e]indole with various alkylating agents, such as iodomethane [1], iodoethane [2], 4-iodobutane [3], 1-iodo-3-phenylpropane [4], benzyl bromides [5,6] or 3-iodopropanoic acid [7] affords the corresponding N-quaternary 1,1,2-trimethyl-1H-benzo[e]indolium salts. The reactions are usually performed in aprotic solvents such as acetonitrile or toluene with conventional or microwave heating [8].…”

Section: Introductionmentioning

confidence: 99%

10a,11,11-Trimethyl-10a,11-dihydro-8H-benzo[e]imidazo[1,2-a]indol-9(10H)-one

Ščerbetkaitė¹,

Tamulienė²,

Bieliauskas³

et al. 2017

Preprint

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Abstract:The alkylation of 1,1,2-trimethyl-1H-benzo[e]indole with 2-chloroacetamide, followed by work-up of the reaction mixture with a base and the subsequent treatment of a crude product with acetic acid gives 10a,11,11-trimethyl-10a,11-dihydro-8H-benzo[e]imidazo[1,2-a]indol-9(10H)-one. The structure assignments were based on data from 1 H, 13 C and 15 N NMR spectroscopy. The optical properties of the obtained compound were studied by UV-vis and fluorescence spectroscopy.

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Correlating Molecular Character of NIR Imaging Agents with Tissue-Specific Uptake

Cited by 53 publications

References 33 publications

Tissue-Specific Near-Infrared Fluorescence Imaging

Tissue-Specific Near-Infrared Fluorescence Imaging

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

10a,11,11-Trimethyl-10a,11-dihydro-8<em>H</em>-benzo[<em>e</em>]imidazo[1,2-<em>a</em>]indol-9(10<em>H</em>)-one

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