Design, synthesis and evaluation of near-infrared fluorescent pH indicators in a physiologically relevant range

Zhang, Zongren; Achilefu, Samuel

doi:10.1039/b512315a

Cited by 118 publications

(54 citation statements)

References 18 publications

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“…This fluorophore platform possesses near-IR absorption and emission profiles to maximize tissue penetration of the fluorescent signal from the dye while minimizing native tissue autofluorescence, in addition to being biologically inert, nontoxic, and compatible with aqueous media (42,43). Moreover, related probes for nitric oxide and pH show that the fluorescence properties of Cy7-type dyes can be modulated by PET (44)(45)(46)(47)(48)(49). As such, we reasoned that installing an electron-rich 9-aza-2,6,13-trithiapentadecane receptor in appropriate proximity to a Cy7 scaffold would produce a sensor that is responsive to Cu þ , the dominant oxidation state for this metal in cells.…”

Section: Resultsmentioning

confidence: 99%

Near-infrared fluorescent sensor for in vivo copper imaging in a murine Wilson disease model

Hirayama¹,

Bittner²,

Gray

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

199

138

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Copper is an essential metal nutrient that is tightly regulated in the body because loss of its homeostasis is connected to severe diseases such as Menkes and Wilson diseases, Alzheimer’s disease, prion disorders, and amyotrophic lateral sclerosis. The complex relationships between copper status and various stages of health and disease remain challenging to elucidate, in part due to a lack of methods for monitoring dynamic changes in copper pools in whole living organisms. Here we present the synthesis, spectroscopy, and in vivo imaging applications of Coppersensor 790, a first-generation fluorescent sensor for visualizing labile copper pools in living animals. Coppersensor 790 combines a near-infrared emitting cyanine dye with a sulfur-rich receptor to provide a selective and sensitive turn-on response to copper. This probe is capable of monitoring fluctuations in exchangeable copper stores in living cells and mice under basal conditions, as well as in situations of copper overload or deficiency. Moreover, we demonstrate the utility of this unique chemical tool to detect aberrant increases in labile copper levels in a murine model of Wilson disease, a genetic disorder that is characterized by accumulation of excess copper. The ability to monitor real-time copper fluxes in living animals offers potentially rich opportunities to examine copper physiology in health and disease.

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Section: Resultsmentioning

confidence: 99%

Near-infrared fluorescent sensor for in vivo copper imaging in a murine Wilson disease model

Hirayama¹,

Bittner²,

Gray

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

199

138

View full text Add to dashboard Cite

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“…H-ICG is an example of such NIR dye which is sensitive to pH changes at a physiologically relevant range. A hydroxyl-sulfonylbutyl arm from the commercially available ICG dye was removed to produce a non-specific pH indicator that is useful at physiological range [73]. Recently, the same group developed a highly selective NIR-pH activatable probe which specifically targets an integrin overexpressed in endothelial cells during tumor angiogenesis.…”

Section: Organic Fluorophoresmentioning

confidence: 99%

FLIM-FRET for Cancer Applications

Rajoria

Zhao

Intes

et al. 2015

CMI

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Optical imaging assays, especially fluorescence molecular assays, are minimally invasive if not completely noninvasive, and thus an ideal technique to be applied to live specimens. These fluorescence imaging assays are a powerful tool in biomedical sciences as they allow the study of a wide range of molecular and physiological events occurring in biological systems. Furthermore, optical imaging assays bridge the gap between the in vitro cell-based analysis of subcellular processes and in vivo study of disease mechanisms in small animal models. In particular, the application of Förster resonance energy transfer (FRET) and fluorescence lifetime imaging (FLIM), well-known techniques widely used in microscopy, to the optical imaging assay toolbox, will have a significant impact in the molecular study of protein-protein interactions during cancer progression. This review article describes the application of FLIM-FRET to the field of optical imaging and addresses their various applications, both current and potential, to anti-cancer drug delivery and cancer research.

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“…These probes can be used as powerful detection or treatment tools in biological systems [1,2,3,4,5,6,7,8,9], such as tools allowing detection of DNA and RNA in gel by flow cytometry or microscopy. Embedded fluorescent dyes such as Thiazole Orange (TO) and Oxazole Yellow (YO) are of particular interest because they have lower quantum yields and weaker fluorescence in solution, while larger fluorescence enhancements are observed when bound to DNA or RNA partners [10].…”

Section: Introductionmentioning

confidence: 99%

Targeted Thiazole Orange Derivative with Folate: Synthesis, Fluorescence and in Vivo Fluorescence Imaging

Fei

Wang

et al. 2010

Molecules

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A Thiazole Orange conjugated with folate derivative was synthesized in two steps. Firstly, folate was coupled with 1-(3-aminopropyl)-4-methylquinolinium bromide to afford folate-methylquinolinium bromide, which then reacted with benzothiazolium to obtain the title folate-conjugated compound. The compound was evaluated by 1H-NMR MS, TG/DTA and fluorescence spectroscopic methods. The title compound could selectively target folate receptor expressing tumors according to the in vivo fluorescence imaging preliminarily performed on nude mice with breast tumors.

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Design, synthesis and evaluation of near-infrared fluorescent pH indicators in a physiologically relevant range

Abstract: Removal of a hydroxylsulfonylbutyl arm from indocyanine green dye produced a pH-sensitive near-infrared (NIR) fluorescent indicator that is useful at physiological range.

Cited by 118 publications

References 18 publications

Near-infrared fluorescent sensor for in vivo copper imaging in a murine Wilson disease model

Near-infrared fluorescent sensor for in vivo copper imaging in a murine Wilson disease model

FLIM-FRET for Cancer Applications

Targeted Thiazole Orange Derivative with Folate: Synthesis, Fluorescence and in Vivo Fluorescence Imaging

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