Isobaric Labeling Reagents for Steroid Quantitation

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current methods for quantitating steroids, such as immunoassays and traditional mass spectrometry techniques, face challenges including low sensitivity, interference from cross-reacting substances, and the need for expensive isotopically enriched internal standards, which limits the accuracy and efficiency of steroid analysis.

Innovation Solution

The development of a set of labels comprising compounds with heavy atom isotopes, used for isobaric or mass differential labeling, allows for the absolute quantitation of steroids without the need for isotopically enriched standards, utilizing parent-daughter ion transition monitoring (PDITM) for analysis.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If traditional mass spectrometry techniques are used for steroid quantitation, then detection capability is provided, but sensitivity is low and interference from cross-reacting substances occurs

Engineering Contradiction:
Improvedetection capabilityVSAvoidsensitivity
Core Design Contradiction:
Measurement precisionVSReliability

Solution Approach 1:

The patent introduces isobaric labeling reagents as intermediaries that covalently attach to steroids to create differentially labeled analytes. These labels serve as mediators that enable mass spectrometric detection while the isobaric nature (same mass) of the labels prevents interference from cross-reacting substances, thereby improving both detection capability and sensitivity simultaneously

Inventive Principle:
Principle #24Intermediary (Mediator)

2Measurement precision

If isotopically enriched internal standards are used for absolute quantitation, then quantitation accuracy is improved, but costs increase and compatibility with tandem mass spectrometry is reduced

Engineering Contradiction:
Improvequantitation accuracyVSAvoidcost and method compatibility
Core Design Contradiction:
Measurement precisionVSDevice complexity

Solution Approach 1:

The patent creates isotopic copies of steroid analytes through chemical labeling with isobaric reagents rather than using expensive naturally occurring isotopically enriched standards. The labeling process generates analyte copies that have identical mass and chromatographic behavior but can be distinguished by MS/MS fragmentation patterns, achieving accurate quantitation without the need for costly isotopically enriched materials

Inventive Principle:
Principle #26Copying

Solution Approach 2:

The patent changes the mass-to-charge ratio parameter of the labeling reagents to be isobaric (same mass) rather than using traditional isotopically different masses. This parameter change enables the use of conventional mass spectrometry instruments without requiring expensive isotopically enriched standards while maintaining the ability to distinguish labeled from unlabeled analytes through fragmentation patterns

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If HPLC with derivatization is used for steroid analysis, then multiple steroids can be analyzed, but analysis time increases and sensitivity remains low

Engineering Contradiction:
Improvemultiplexing capabilityVSAvoidanalysis time
Core Design Contradiction:
Adaptability or versatilityVSLoss of time

Solution Approach 1:

The patent performs preliminary labeling of multiple steroids with isobaric tags before mass spectrometric analysis. This preliminary action enables all steroids to be prepared in advance with uniform labeling, eliminating the need for time-consuming individual derivatization steps during analysis and enabling rapid multiplexed detection

Inventive Principle:
Principle #10Preliminary action

4Ease of operation

If immunoassays are used for steroid quantitation, then ease of operation is maintained, but sensitivity is low and cross-reacting substances cause interference

Engineering Contradiction:
Improveoperational simplicityVSAvoidsensitivity and specificity
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent replaces the biological recognition mechanism of immunoassays (antibody-antigen binding) with a chemical labeling mechanism using isobaric reagents. This substitution maintains operational simplicity through automated labeling while eliminating cross-reactivity issues inherent in immunoassays, as the chemical labels provide specific mass spectral identification without biological interference

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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

This approach enhances the sensitivity and specificity of steroid analysis, enabling accurate quantitation and multiplexing capabilities, reducing costs and analytical time while minimizing interference.

Implementation Method 1

Mass spectrometry is one technique that can provide rapid sample analysis

Methodology Applied
Scientific EffectMass spectrometry:

Implementation Method 2

one or more of the compounds of the general formula (IV) of the set of labels is isotopically enriched with two or more heavy atoms

Methodology Applied
Scientific EffectIsotopic enrichment:

Data Source

PatentEP2054540B1Tagging reagents and methods for hydroxylated compounds
Publication Date: 2014.11.26 DH TECH DEVMENT PTE
  • EP2054540B1 patent drawingFigure 1
  • EP2054540B1 patent drawingFigure 2
  • EP2054540B1 patent drawingFigure 3A~3H

AI summary

In various aspects, the present teachings provide labeling reagents and sets of labeling reagents containing one or more heavy atom isotopes for the relative quantitation, absolute quantitation, or both, of hydroxylated compounds including, but not limited to, hydroxylated ring containing compounds, steroids and sterols. In various aspects, the present teachings also provide methods for the analysis hydroxylated compounds including, but not limited to, hydroxylated ring containing compounds, steroids and sterols my MS/MS methods, in particular using mass differential tags.