PSMA-Targeting Multivalent Scaffold for Enhanced Binding Affinity

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Solution Overview

Problem

Current methods for creating multivalent scaffolds for prostate-specific membrane antigen (PSMA) targeting are complex and have not successfully imaged PSMA in vivo, lacking efficient methods for multimeric presentation of PSMA and other targeting species.

Innovation Solution

Development of compounds with a lysine-based multimeric urea dendron structure, utilizing a DOTA chelating agent for radiometal incorporation, enabling the generation of bivalent and higher valent forms for improved PSMA targeting, which can be used with various radiometals and imaging isotopes for both imaging and therapy.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If multivalent scaffolds are constructed using various approaches, then binding affinity to PSMA is improved, but the chemistry used to produce them becomes complicated

Engineering Contradiction:
Improvebinding affinityVSAvoidchemistry complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The multivalent scaffold is constructed by segmenting the molecule into distinct functional modules: a dendron core structure, multiple PSMA-targeting ligand arms, and a radionuclide chelator. This segmentation allows each module to be optimized and synthesized separately, then assembled through well-defined coupling reactions, reducing overall chemical complexity while maintaining high binding affinity through the multivalent architecture

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The dendron scaffold is designed with universal coupling sites that can accommodate different PSMA-targeting ligands and radionuclide chelators. This multi-functionality allows the same core structure to be used for creating various multivalent conjugates with different therapeutic or diagnostic payloads, simplifying the chemical synthesis pathway across different applications

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Adaptability or versatility

If a bifunctional chelator is attached to a separately multimerized construct, then radionuclide incorporation is enabled, but the chemistry becomes even more complicated

Engineering Contradiction:
Improveradionuclide incorporationVSAvoidchemistry complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The bifunctional chelator is merged into the dendron scaffold structure itself during the multimerization process, rather than being attached as a separate post-processing step. This integration means the chelator is positioned optimally within the multivalent construct and reduces the number of separate chemical operations required, simplifying the overall synthesis while maintaining radionuclide incorporation capability

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The chelator functionality is built into the dendron structure in advance during scaffold construction, before the final conjugation with PSMA-targeting ligands. This preliminary action ensures the chelator is already in place and properly oriented when the multivalent construct is completed, eliminating the need for separate chelator attachment steps and reducing chemical complexity

Inventive Principle:
Principle #10Preliminary action

3Device complexity

If monovalent forms are used, then the structure is simpler, but binding affinity and in vivo retention are reduced

Engineering Contradiction:
Improvestructure simplicityVSAvoidbinding affinity
Core Design Contradiction:
Device complexityVSReliability

Solution Approach 1:

The multivalent scaffold employs a nested dendron architecture where multiple PSMA-targeting ligand arms are arranged in a hierarchical structure around a central core. This nested arrangement maximizes the local concentration of binding sites, enhancing binding affinity through avidity effects while maintaining a compact overall structure that is more manageable than fully extended multivalent configurations

Inventive Principle:
Principle #7Nested doll (Nesting)

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 multivalent scaffold allows for enhanced PSMA targeting with increased binding affinity and retention in vivo, enabling effective imaging and potential therapeutic applications by facilitating prolonged tumor retention and reduced non-target tissue clearance.

Implementation Method 1

utilizing a DOTA chelating agent for radiometal incorporation

Methodology Applied
Scientific EffectChelation:

Data Source

PatentEP3524277B1PSMA-targeting compound and uses thereof
Publication Date: 2023.03.08 JOHNS HOPKINS UNIVERSITY
  • EP3524277B1 patent drawingFigure 1
  • EP3524277B1 patent drawingFigure 2
  • EP3524277B1 patent drawingFigure 3

AI summary

The present invention provides a compound contains a PSMA binding Lys-Glu urea moiety linked to DOTA in complex with 111In3+ and its use in imaging PSMA cells.