A new long-wavelength fluorigenic substrate for alkaline phosphatase: synthesis and characterisation

Sarpara, G. Hussain; Hu, Si Jung; Miller, James N.; Palmer, Diane; French, Martin T.; Evans, Mark

doi:10.1039/a809018a

Cited by 8 publications

(2 citation statements)

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“…40 Naphthofluorescein (ex/em: 595/660 nm) contains two resonant active hydroxyl groups and has been shown previously to have reduced fluorescence upon conjugation. 41 These two hydroxyls are available for esterification, allowing for the synthesis of a diarachidonate probe. 7-Hydroxy-9H-(1,3-dichloro-9,9-dimethylacridin-2-one) (DDAO) (ex/em: 600/660 nm) is an ortho- dichlorinated resorufin derivative that results in red-shifted fluorescence.…”

Section: Resultsmentioning

confidence: 99%

“…Resorufin has been shown to have ablated fluorescence upon conjugation to a photoremovable protecting group . Naphthofluorescein (ex/em: 595/660 nm) contains two resonant active hydroxyl groups and has been shown previously to have reduced fluorescence upon conjugation . These two hydroxyls are available for esterification, allowing for the synthesis of a diarachidonate probe.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Evaluation of Cytosolic Phospholipase A₂ Activatable Fluorophores for Cancer Imaging

et al. 2015

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Activatable fluorophores selective to cytosolic phospholipase A2 (cPLA2) were synthesized and evaluated for their ability to image triple negative breast cancer cells. The activatable constructs were synthesized by esterification of a small molecule fluorophore with a fatty acid resulting in ablated fluorescence. Selectivity for cPLA2 was generated through the choice of fluorophore and fatty acid. Esterification with arachidonic acid was sufficient to impart specificity to cPLA2 when compared to esterification with palmitic acid. In vitro analysis of probes incorporated into phosphatidylcholine liposomes demonstrated that a non-selective phospholipase (sPLA2 group IB) was able to hydrolyze both arachidonate and palmitate coupled fluorophores resulting in the generation of fluorescence. Of the four fluorophores tested, DDAO (7-hydroxy-9H-(1,3-dichloro-9,9-dimethylacridin-2-one)) was observed to perform optimally in vitro and was analyzed further in 4175-Luc+ cells, a metastatic triple negative human breast cancer cell line expressing high levels of cPLA2. In contrast to the in vitro analysis, DDAO arachidonate was shown to activate selectively in 4175-Luc+ cells compared to the control DDAO palmitate as measured by fluorescence microscopy and quantitated with fluorescence spectroscopy. The addition of two agents known to activate cPLA2 enhanced DDAO arachidonate fluorescence without inducing any change to DDAO palmitate. Inhibition of cPLA2 resulted in reduced fluorescence of DDAO arachidonate but not DDAO palmitate. Together, we report the synthesis of a cPLA2 selective activatable fluorophore capable of detecting cPLA2 in triple negative breast cancer cells.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Cytosolic Phospholipase A₂ Activatable Fluorophores for Cancer Imaging

et al. 2015

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Advances in Fluorescence Enzyme Detection Methods

Miller

Springer Series on Fluorescence

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Flow injection system for potentiometric determination of alkaline phosphatase inhibitors

Koncki

Rudnicka

Tymecki

2006

Analytica Chimica Acta

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A new long-wavelength fluorigenic substrate for alkaline phosphatase: synthesis and characterisation

Abstract: A new long-wavelength fluorigenic substrate for alkaline phosphatase: synthesis and characterisation C o m m u n i c a t i o n

Cited by 8 publications

References 11 publications

Synthesis and Evaluation of Cytosolic Phospholipase A₂ Activatable Fluorophores for Cancer Imaging

Synthesis and Evaluation of Cytosolic Phospholipase A₂ Activatable Fluorophores for Cancer Imaging

Advances in Fluorescence Enzyme Detection Methods

Flow injection system for potentiometric determination of alkaline phosphatase inhibitors

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A new long-wavelength fluorigenic substrate for alkaline phosphatase: synthesis and characterisation

Abstract: A new long-wavelength fluorigenic substrate for alkaline phosphatase: synthesis and characterisation C o m m u n i c a t i o n

Cited by 8 publications

References 11 publications

Synthesis and Evaluation of Cytosolic Phospholipase A2 Activatable Fluorophores for Cancer Imaging

Synthesis and Evaluation of Cytosolic Phospholipase A2 Activatable Fluorophores for Cancer Imaging

Advances in Fluorescence Enzyme Detection Methods

Flow injection system for potentiometric determination of alkaline phosphatase inhibitors

Contact Info

Product

Resources

About

Synthesis and Evaluation of Cytosolic Phospholipase A₂ Activatable Fluorophores for Cancer Imaging

Synthesis and Evaluation of Cytosolic Phospholipase A₂ Activatable Fluorophores for Cancer Imaging