Nitric Oxide Detection Compounds Using Sulfonamide Luminescence Probes

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Solution Overview

Problem

Current methods for detecting nitric oxide (NO) suffer from low specificity and generate false positives due to reactions with other molecules, necessitating the development of quantitative and specific assays.

Innovation Solution

The use of caged aminoluciferin and aminocyanobenzothiazole compounds that selectively react with nitric oxide, forming stable reporter products for luminescence detection through luciferin-utilizing luciferase enzymes, allowing for homogeneous 'add and read' plate-based assays.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If o-phenylene diamine based reactive moieties are used for NO detection, then detection capability is achieved, but false positives occur due to reaction with bis electrophiles such as dehydroascorbic acid

Engineering Contradiction:
Improvedetection specificityVSAvoidfalse positive rate
Core Design Contradiction:
Measurement precisionVSReliability

Solution Approach 1:

The patent extracts the problematic o-phenylene diamine reactive moiety from the detection system and replaces it with a sulfonamide-based reactive moiety. This extraction of the harmful component eliminates the false positive reactions with bis electrophiles while retaining the ability to detect nitric oxide through the luciferin-luciferase luminescence pathway.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the chemical parameter of the reactive moiety from o-phenylene diamine to sulfonamide group. This parameter change in the chemical structure fundamentally alters the reactivity profile, making the probe selective for nitric oxide while avoiding cross-reactions with other bis electrophiles present in biological samples.

Inventive Principle:
Principle #35Parameter changes

2Measurement precision

If indirect colorimetric measurement through Griess reaction is used, then NO detection is achieved, but the method measures terminal products rather than direct NO

Engineering Contradiction:
Improvedetection capabilityVSAvoiddirect NO measurement
Core Design Contradiction:
Measurement precisionVSLoss of information

Solution Approach 1:

The patent introduces a direct NO-reactive probe containing a sulfonamide reactive moiety that directly reacts with nitric oxide to form a stable intermediate that can be detected by luciferin-utilizing luciferase. This intermediary probe enables direct measurement of NO rather than measuring downstream terminal products, preserving information about actual NO levels.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If caged aminoluciferin compounds are used for direct NO detection, then specificity is improved, but the assay requires luciferin-utilizing luciferase addition

Engineering Contradiction:
Improvedetection specificityVSAvoidassay procedure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent designs the caged aminoluciferin compound with a sulfonamide reactive moiety that self-reacts with nitric oxide in the sample to form the detectable luminescent product. The compound essentially services its own detection function by directly converting NO signal into luminescence output, reducing the need for complex additional reagents or steps.

Inventive Principle:
Principle #25Self-service

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The compounds provide high specificity for nitric oxide detection, reducing false positives and enabling quantitative measurement of NO levels in various samples, including live cells, with stable reporter products that allow for continuous monitoring of NO production.

Implementation Method 1

detecting luminescence in the sample

Methodology Applied
Scientific EffectLuminescence: Luminescence

Implementation Method 2

luciferin-utilizing luciferase enzymes, allowing for homogeneous 'add and read' plate-based assays

Methodology Applied
Scientific EffectBioluminescence: Bioluminescence

Data Source

PatentEP4408829B1Compounds and methods for detection of nitric oxide
Publication Date: 2025.11.05 PROMEGA CORP
  • EP4408829B1 patent drawingFigure 1
  • EP4408829B1 patent drawingFigure 2
  • EP4408829B1 patent drawingFigure 3~4

AI summary

Disclosed herein are compounds that can be used to selectively detect nitric oxide in samples. Also disclosed herein are compositions comprising the compounds and methods of detecting nitric oxide using the compounds.