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Chemiluminescent probes for imaging/detection of proteases

A compound and alkyl technology, applied in the field of dioxetane-based chemiluminescent probes

Active Publication Date: 2020-03-31
特拉维夫大学拉玛特有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these probes display remarkable signal-to-noise ratios, they prohibit live-cell imaging of proteases due to the two-step analysis required

Method used

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  • Chemiluminescent probes for imaging/detection of proteases
  • Chemiluminescent probes for imaging/detection of proteases
  • Chemiluminescent probes for imaging/detection of proteases

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Experimental program
Comparison scheme
Effect test

Embodiment

[0090] experiment

[0091] general method

[0092] All reactions requiring anhydrous conditions were performed under argon atmosphere. All reactions were performed at room temperature unless otherwise stated. Chemicals and solvents were of analytical reagent (A.R.) grade or purified by standard techniques. TLC: Silica gel plate Merck60F 254 : The compound is visualized by irradiation with UV light. Column chromatography (FC): silica gel Merck 60 (particle size 0.040-0.063 mm), eluents are given in brackets. RP-HPLC: C18 5u, 250 x 4.6 mm, eluents are given in brackets. Preparative RP-HPLC: C18 5u, 250 x 21 mm, eluents are given in brackets. Measured using a Bruker Avance operating at 400MHz 1 H-NMR spectrum. Measured with Bruker Avance operating at 100MHz 13 C-NMR spectrum. Chemical shifts are reported in ppm on the δ scale relative to residual solvent (CDCl 3 :for 1 H-NMR is δ=7.26 and for 13 C-NMR 77.16, DMSO-d 6 :for 1 H-NMR is δ=2.50 and for 13 C-NMR 39.52)....

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Abstract

The present invention provides turn-ON dioxetane-based chemiluminescence probes based on the Schapp's adamantylidene-dioxetane probe, which are capable of detecting or imaging, more specifically, determining the presence, or measuring the level, of proteases, as well as compositions and uses thereof.

Description

technical field [0001] The invention provides a dioxetane-based chemiluminescent probe capable of detecting protease, as well as its composition and use. [0002] Abbreviations: ACN, acetonitrile; DCM, dichloromethane; DIPEA, diisopropylethylamine; DMF, N,N'-dimethylformamide; EEDQ, N-ethoxycarbonyl-2-ethoxy-1 ,2-Dihydroquinoline; Et 2 O, diethyl ether; Et 3 N, triethylamine; EtOAc, ethyl acetate; HBTU, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; HPLC, high pressure Liquid chromatography; K 2 CO 3 , potassium carbonate; MeOH, methanol; Na 2 S 2 o 3 , sodium thiosulfate; Na 2 SO 4 , sodium sulfate; NH 4 Cl, ammonium chloride; PABA, p-aminobenzoic acid; PEG, polyethylene glycol; RLU, relative light unit; RP-HPLC, reversed-phase high-pressure liquid chromatography; TFA, trifluoroacetic acid; TIPS, triisopropylsilane ; TLC, thin layer chromatography; TMS-Cl, trimethylchlorosilane; 7HC, 7-hydroxycoumarin. Background technique [0003] Prot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D321/00C07D405/12C07D405/14C07D413/14C09K11/06C07K5/00C07K7/00A61K38/04A61K38/05
CPCC07D321/00C07D405/12C09K11/06C09K11/07C07K5/06052C07K7/06G01N33/573C07K2319/10G01N2333/96466C07K2319/50C09K2211/1007C09K2211/1011C09K2211/1018C12Q1/37G01N21/76
Inventor D·莎芭特M·E·罗斯-康福提
Owner 特拉维夫大学拉玛特有限公司
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