Diarylsulphide Linker Visible Light Cleavage

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Solution Overview

Problem

Current photocleavable compounds require near UV light for cleavage, which is costly, has limited luminous power, and can damage biomolecules due to broad spectral emission, leading to experimental inaccuracies and safety concerns.

Innovation Solution

Development of a photocleavable compound that can be cleaved using visible light in the range of 375 nm to 420 nm, specifically using phenylcarboxylic amide derivatives with functional groups like 4,4'-dimethoxytrityl-oxy-alkyl-, trifluoracetyl-amino-alkyl-, and alkylamido-biotin, which are linked to biomolecules, allowing for safer and more cost-effective light sources.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If near UV light (365 nm or shorter) is used for cleavage of photocleavable compounds, then the covalent bonds can be effectively cleaved, but the light sources become costly, have limited luminous power, short life-time, and can damage biomolecules

Engineering Contradiction:
Improvecleavage effectivenessVSAvoidbiomolecule damage and operational costs
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the wavelength parameter from near UV (365 nm or shorter) to visible light range (375-420 nm). This parameter change allows the use of safer, more cost-effective light sources while maintaining cleavage effectiveness and reducing biomolecule damage through the specific molecular structure design

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite molecular structure consisting of a diarylsulphide backbone combined with specific functional groups (4,4'-dimethoxytrityl-oxy-alkyl, trifluoracetyl-amino-alkyl, or alkylamido-biotin). This composite structure enables the material to respond to visible light while maintaining photocleavable functionality, resolving the contradiction between effectiveness and safety

Inventive Principle:
Principle #40Composite materials

2Reliability

If mercury arc lamps or UV-LEDs are used to generate UV wavelengths for photocleavage, then the cleavage reaction can proceed, but hazardous substances are involved requiring special safety measures and disposal procedures

Engineering Contradiction:
Improvephotocleavage capabilityVSAvoidoccupational safety risks and disposal costs
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent replaces expensive, hazardous UV light sources with inexpensive, safe visible light sources. The new photocleavable compounds can be used with simple LED or fluorescent light sources that are widely available, have long lifetimes, and pose no safety hazards, eliminating the need for special safety measures and disposal procedures

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent converts the previously harmful UV radiation requirement into a beneficial visible light response. The diarylsulphide backbone with specific functional groups is designed to absorb visible light (375-420 nm) and undergo photocleavage, transforming a harmful requirement into a safe and advantageous feature

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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

Enables efficient and precise cleavage of biomolecules using visible light, reducing damage and operational costs, while providing a safer experimental environment compared to UV-based methods.

Implementation Method 1

Photocleavable compounds play an important role as protecting groups in blocking functional groups present in nucleosides, nucleotides, sugars and amino acids, which are used for the synthesis of biomolecules. Upon radiation with visible light, the linker is cleaved, thereby releasing the two biomolecules.

Methodology Applied
Scientific EffectPhotocleavage: Photodissociation

Data Source

PatentEP2914607B1Photocleavable linker molecules with diarylsulphid backbone for transient bioconjugate synthesis
Publication Date: 2017.11.29 VENTANA MEDICAL SYSTEMS INC
  • EP2914607B1 patent drawingFigure 1
  • EP2914607B1 patent drawingFigure 2
  • EP2914607B1 patent drawingFigure 3

AI summary

The present description refers to photocleavable compounds which can be used as a photocleavable linker in order to link two biomolecules, such as oligonucleotides and peptides. The present description further refers to a method for the synthesis of said photocleavable compounds.