Peptide-Phospholipid Conjugates for KDR Targeting

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Solution Overview

Problem

Current methods for diagnosing and treating angiogenesis, particularly in tumors, lack effective targeting mechanisms for VEGF and KDR, limiting the precision of imaging and therapeutic interventions.

Innovation Solution

Development of highly pure dimeric peptide-phospholipid conjugates with high binding affinity to KDR, which can be incorporated into gas-filled ultrasound contrast agents for targeted imaging and therapy, enabling precise localization at KDR-bearing tissues.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If conventional imaging and therapeutic agents are used, then general coverage of tissue is achieved, but precision and specificity for KDR-bearing tissues is insufficient

Engineering Contradiction:
Improveimaging precisionVSAvoidtargeting capability
Core Design Contradiction:
Measurement precisionVSAdaptability or versatility

Solution Approach 1:

The invention segments the therapeutic and diagnostic approach by creating distinct conjugate structures with specific peptide sequences (e.g., RGD motifs) that selectively bind to KDR receptors. This segmentation allows precise targeting of angiogenic vessels while leaving other tissues unaffected, resolving the contradiction between general coverage and specific precision.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The peptide-phospholipid conjugates serve as intermediary molecules that bridge the gap between conventional imaging agents and KDR-bearing tissues. These conjugates contain both the imaging/therapeutic payload and the targeting peptide, acting as mediators that enable precise localization without requiring direct modification of existing agents.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of manufacture

If non-specific agents are used for therapy, then broad tissue coverage is achieved, but delivery precision to target site is limited

Engineering Contradiction:
Improveproduction simplicityVSAvoidconjugate purity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The invention employs parameter changes in the form of specific peptide sequences and phospholipid compositions that can be systematically varied to optimize both manufacturing and targeting performance. The standardized conjugate structures with defined molecular weights and peptide sequences enable reproducible manufacturing while maintaining high purity through controlled synthesis parameters.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If high purity conjugates are produced, then therapeutic efficacy is improved, but production complexity increases

Engineering Contradiction:
Improvetherapeutic reliabilityVSAvoidproduction process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention applies preliminary action by incorporating purification steps and quality control measures early in the production process. The conjugates are designed with features that facilitate easy purification (such as specific phospholipid head groups and peptide sequences), allowing high purity to be achieved through streamlined processes rather than complex multi-step procedures.

Inventive Principle:
Principle #10Preliminary action

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 peptide-phospholipid conjugates effectively target KDR-bearing tissues, enhancing imaging capabilities and allowing for precise delivery of therapeutic agents, thereby improving diagnostic and therapeutic outcomes for angiogenic processes.

Implementation Method 1

high binding affinity for a desired target (such as, for example, KDR or the VEGF/KDR complex)

Methodology Applied
Scientific EffectReceptor binding:

Implementation Method 2

gas filled ultrasound contrast agents are exceptionally efficient ultrasound reflectors for echography

Methodology Applied
Scientific EffectUltrasound reflection: Reflection

Data Source

PatentEP2359864B1Targeting Vector-Phospholipid Conjugates
Publication Date: 2019.04.17 BRACCO SUISSE SA
  • EP2359864B1 patent drawingFigure 1
  • EP2359864B1 patent drawingFigure 2
  • EP2359864B1 patent drawingFigure 3

AI summary

Peptide vectors having high KDR binding affinity and processes for making such vectors are provided. The peptide vectors may be conjugated to phospholipids and included in ultrasound contrast agent compositions. Such ultrasound contrast agents are particularly useful in therapeutic and diagnostic methods, such as in imaging KDR-containing tissue and in the evaluation and treatment of angiogenic processes associated with neoplastic conditions. The present invention also provides processes for the large scale production of highly pure dimeric and monomeric peptide phospholipid conjugates as well as precursor materials used to form the conjugates. The present invention further provides processes for the large scale production of highly pure peptide phospholipid conjugates which contain very low levels of TFA.