HIP Probe Radiohalogen Protein Labeling for Tumor Retention

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Solution Overview

Problem

Current methods for labeling proteins with iodine radionuclides face challenges such as rapid diffusion of iodotyrosine from cells after endocytosis and lysosomal degradation, while radiometal-chelate complexes like 111In-DOTA have residualizing properties but are limited by short decay half-life and imaging quality issues.

Innovation Solution

A 4-hydroxy-3-iodophenyl (HIP) probe is synthesized using a Ugi multi-component reaction and conjugated to antibodies, offering superior tumor uptake and retention, combining the long decay half-life and low energy emissions of iodine with the tumor accumulation of radiometals.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If iodine radionuclides are used for labeling proteins, then long decay half-life and low energy emissions are achieved, but rapid diffusion of iodotyrosine from cells after endocytosis occurs

Engineering Contradiction:
Improvedecay half-lifeVSAvoidtumor retention
Core Design Contradiction:
Duration of action of stationary objectVSReliability

Solution Approach 1:

The patent introduces a tyrosine derivative as an intermediary carrier that binds the radioiodine label and presents it to the protein in a form that resists cellular efflux. The derivative acts as a mediator between the radioiodine and the protein, enabling the label to be retained within cells after endocytosis while maintaining the beneficial long half-life and low energy emission properties of iodine radionuclides

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention modifies the chemical structure by using a specific tyrosine derivative with altered properties compared to natural tyrosine. This structural parameter change in the amino acid derivative prevents the rapid diffusion that occurs with conventional iodotyrosine labeling, while preserving the radiochemical advantages of iodine labels

Inventive Principle:
Principle #35Parameter changes

2Reliability

If radiometal-chelate complexes are used for labeling, then residualizing properties are achieved, but short decay half-life and imaging quality issues occur

Engineering Contradiction:
Improvetumor retentionVSAvoiddecay half-life
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent merges the advantageous properties of two different labeling approaches: it combines the residualizing tumor retention特性 of radiometal-chelate complexes with the long decay half-life and low energy emissions of iodine radionuclides. The tyrosine derivative-based labeling method achieves both sustained intracellular retention and favorable radiochemical properties that neither approach alone can provide

Inventive Principle:
Principle #5Merging (Combining)

3Ease of manufacture

If conventional tyrosine-based radiohalogenation is used, then labeling is achieved, but cellular efflux of the radiolabel occurs

Engineering Contradiction:
Improvelabeling simplicityVSAvoidcellular retention
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The invention changes the chemical parameter of the amino acid from natural tyrosine to a modified tyrosine derivative. This parameter change in the substrate structure prevents the cellular efflux mechanism that operates on conventional iodotyrosine, while maintaining compatibility with standard radioiodination procedures, thus preserving ease of manufacture while improving cellular retention

Inventive Principle:
Principle #35Parameter changes

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 HIP probe provides enhanced tumor retention and imaging quality, potentially leading to improved radioimmunotherapy and diagnostic imaging by maintaining radioactivity within tumor cells and reducing radiation exposure.

Implementation Method 1

combining the long decay half-life and low energy emissions of iodine with the tumor accumulation of radiometals

Methodology Applied
Scientific EffectRadioactive decay: Radioactive Decay

Data Source

PatentEP2934602B1Methods and compositions for radiohalogen protein labeling
Publication Date: 2019.02.27 GENENTECH INC
  • EP2934602B1 patent drawingFigure 1A~1B
  • EP2934602B1 patent drawingFigure 2
  • EP2934602B1 patent drawingFigure 3

AI summary

Methods and compositions are provided for labeling proteins with radiohalogen-label reagents. Radiohalogen-labeled proteins may be used for imaging studies, as therapeutics and in diagnostic tests. The [125I] HIP-DOTA label reagent 6 is prepared by an efficient and convenient process.