Synthesis and Characterization of BODIPY-α-Tocopherol: A Fluorescent Form of Vitamin E

West, Ryan; Panagabko, Candace; Atkinson, Jeffrey

doi:10.1021/jo100095n

Cited by 50 publications

(24 citation statements)

References 67 publications

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“…In this manner, both styryl-and acrylate-substituted fluorophores could be obtained (9g and 9h, respectively). Contrary to a recent report by Atkinson et al [20] and attesting to the generality of this procedure, the Heck reaction (Table 1, entry 9i) also proceeded cleanly and in good yield for the meso-unsubstituted dye 4a under these conditions.…”

Section: Synthesis Of 3-chloro-bodipy Dyescontrasting

confidence: 81%

2‐ and 3‐Monohalogenated BODIPY Dyes and Their Functionalized Analogues: Synthesis and Spectroscopy

et al. 2011

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Starting from appropriately halogenated acylpyrroles, a wide range of reactive 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) derivatives can be obtained. The fluorescent dyes display excellent reactivity in nucleophilic aromatic substitution, transition‐metal‐catalyzed cross‐coupling and copper‐catalyzed cycloaddition to azides (click chemistry). The spectral properties of the starting and final difluoroboron dipyrromethenes are discussed as a function of their structure.

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Section: Synthesis Of 3-chloro-bodipy Dyescontrasting

confidence: 81%

2‐ and 3‐Monohalogenated BODIPY Dyes and Their Functionalized Analogues: Synthesis and Spectroscopy

et al. 2011

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“…BDP α-tocopherol was synthesized as described previously (19). Propidium iodide (PI), cell culture media, and reagents for cell culture were purchased from Life Technologies.…”

Section: Methodsmentioning

confidence: 99%

Vitamin E sequestration by liver fat in humans

et al. 2020

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BACKGROUND. We hypothesized that obesity-associated hepatosteatosis is a pathophysiological chemical depot for fat-soluble vitamins and altered normal physiology. Using α-tocopherol (vitamin E) as a model vitamin, pharmacokinetics and kinetics principles were used to determine whether excess liver fat sequestered α-tocopherol in women with obesity-associated hepatosteatosis versus healthy controls. METHODS. Custom-synthesized deuterated α-tocopherols (d 3-and d 6-α-tocopherols) were administered to hospitalized healthy women and women with hepatosteatosis under investigational new drug guidelines. Fluorescently labeled α-tocopherol was custom-synthesized for cell studies. RESULTS. In healthy subjects, 85% of intravenous d 6-α-tocopherol disappeared from the circulation within 20 minutes but reappeared within minutes and peaked at 3-4 hours; d 3-and d 6-α-tocopherols localized to lipoproteins. Lipoprotein redistribution occurred only in vivo within 1 hour, indicating a key role of the liver in uptake and re-release. Compared with healthy subjects who received 2 mg, subjects with hepatosteatosis had similar d 6-α-tocopherol entry rates into liver but reduced initial release rates (P < 0.001). Similarly, pharmacokinetics parameters were reduced in hepatosteatosis subjects, indicating reduced hepatic d 6-α-tocopherol output. Reductions in kinetics and pharmacokinetics parameters in hepatosteatosis subjects who received 2 mg were echoed by similar reductions in healthy subjects when comparing 5-and 2-mg doses. In vitro, fluorescentlabeled α-tocopherol localized to lipid in fat-loaded hepatocytes, indicating sequestration. CONCLUSIONS. The unique role of the liver in vitamin E physiology is dysregulated by excess liver fat. Obesity-associated hepatosteatosis may produce unrecognized hepatic vitamin E sequestration, which might subsequently drive liver disease. Our findings raise the possibility that hepatosteatosis may similarly alter hepatic physiology of other fat-soluble vitamins. TRIAL REGISTRATION. ClinicalTrials.gov, NCT00862433.

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“…Their emission wavelength is tunable by increasing the resonance within the BODIPY core [35]. The BODIPY dyes have been used in a variety of applications such as biological labels and probes [36][37][38], fluorescent probes [39], laser dyes [40,41], light emitting diodes [42], solar cells [43,44], and potential sensitizers in photodynamic therapy [45,46]. Although BODIPYs are versatile compounds with good optical properties, their use in developing bimodal contrast agents remain scarce [47][48][49][50][51][52].…”

Section: Introductionmentioning

confidence: 99%

Gadolinium(III)-DOTA Complex Functionalized with BODIPY as a Potential Bimodal Contrast Agent for MRI and Optical Imaging

et al. 2015

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The synthesis and characterization of a novel gadolinium(III) DOTA complex functionalized with a boron-dipyrromethene derivative (BODIPY) is described. The assembly of the complex relies on azide diazotransfer chemistry in a copper tube flow reactor. The azide thus formed is coupled directly with an alkyne via click chemistry, resulting into a paramagnetic and luminescent gadolinium(III) complex. Luminescent data and relaxometric properties of the complex have been evaluated, suggesting the potential applicability of the complexes as a bimodal contrast agent for magnetic resonance and optical imaging. The complex displays a bright emission at 523 nm with an absorption maximum of 507 nm and high quantum yields of up to 83% in water. The proton relaxivity of the complex measured at 310 K and at frequencies of 20 and 60 MHz had the values of 3.9 and 3.6 s −1 •mM −1 , respectively.

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Synthesis and Characterization of BODIPY-α-Tocopherol: A Fluorescent Form of Vitamin E

Cited by 50 publications

References 67 publications

2‐ and 3‐Monohalogenated BODIPY Dyes and Their Functionalized Analogues: Synthesis and Spectroscopy

2‐ and 3‐Monohalogenated BODIPY Dyes and Their Functionalized Analogues: Synthesis and Spectroscopy

Vitamin E sequestration by liver fat in humans

Gadolinium(III)-DOTA Complex Functionalized with BODIPY as a Potential Bimodal Contrast Agent for MRI and Optical Imaging

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