Dimeric Peptide Inhibitors for PSD-95 Affinity and BBB Permeability

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Solution Overview

Problem

Current PSD-95 inhibitors, such as the Tat-NR2B9c peptide, have low affinity and selectivity for PDZ1-2 domains, limiting their therapeutic effectiveness in treating ischemic stroke, traumatic brain injury, and chronic pain conditions, and are associated with side effects due to non-specific NMDA receptor antagonism.

Innovation Solution

Development of dimeric peptide analogues linked by a PEG linker, with specific sequences and a Cell Penetrating Peptide (CPP) attached, that target PDZ1 and PDZ2 domains of PSD-95, enhancing affinity and stability, and allowing for improved blood-brain barrier permeability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If monomeric peptide inhibitors (e.g., Tat-NR2B9c) are used to target PSD-95, then they can penetrate the blood-brain barrier, but they exhibit low affinity and selectivity for PDZ1-2 domains

Engineering Contradiction:
Improveaffinity and selectivity for PDZ1-2 domainsVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The inhibitor is divided into distinct functional segments: a dimeric peptide core containing two PDZ-binding motifs (each recognizing PDZ1 or PDZ2 domains) and a separate CPP moiety (e.g., Tat peptide) responsible for blood-brain barrier penetration. This segmentation allows optimization of affinity through the dimeric core while maintaining permeability through the attached CPP

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention merges two previously separate functions into a single hybrid molecule: the high-affinity dimeric peptide inhibitor (providing specific binding to PDZ1-2) and the cell-penetrating peptide (providing blood-brain barrier permeability). The CPP is covalently attached to the dimeric peptide via a linker, creating a unified therapeutic agent that achieves both high affinity and brain penetration

Inventive Principle:
Principle #5Merging (Combining)

2Reliability

If dimeric peptide analogues are developed to increase affinity for PDZ1-2 domains, then binding strength improves, but molecular size and complexity increase

Engineering Contradiction:
Improvebinding affinity to PDZ1-2VSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The dimeric structure is constructed by joining two identical or similar peptide motifs (e.g., two copies of the NR2B9c sequence) through a flexible linker. Each motif independently binds to a PDZ domain, and the modular design allows systematic optimization of affinity while maintaining a relatively simple overall structure that can be synthesized using standard peptide chemistry techniques

Inventive Principle:
Principle #1Segmentation

3Reliability

If NMDA receptor antagonists are used to reduce excitotoxicity, then neuroprotection is achieved, but physiological important processes are prevented and side effects occur

Engineering Contradiction:
Improveneuroprotection efficacyVSAvoidside effects from non-specific NMDA receptor antagonism
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention extracts and targets only the specific pathological interaction between PSD-95 and NMDA receptors that mediates excitotoxicity. By designing inhibitors that bind specifically to the PDZ domains of PSD-95 (particularly PDZ1 and PDZ2), the therapy disrupts the harmful nNOS/PSD-95/NMDA receptor complex formation without blocking the broader NMDA receptor functions that are physiologically important, thereby achieving neuroprotection with reduced side effects

Inventive Principle:
Principle #2Taking out (Extraction)

Data Source

PatentEP2707014B1High-affinity, dimeric inhibitors of PSD-95 and their use for treating ischemic brain damage and pain
Publication Date: 2015.06.17 KBENHAVNS UNIV UNIV OF COPENHAGEN
  • EP2707014B1 patent drawingFigure 1
  • EP2707014B1 patent drawingFigure 2
  • EP2707014B1 patent drawingFigure 3

AI summary

The invention provides novel potent inhibitors of the ternary protein complex of nNOS, PSD-95, and the NMDA receptor and pharmaceutical compositions comprising the inhibitors for prophylaxis and/or treatment of excitotoxic-related disease and chronic pain conditions in a subject. The inhibitors are dimeric PSD-95 inhibitors comprising a first peptide or peptide analogue linked to a second peptide or peptide analogue by a linker, wherein the first and the second peptide or peptide analogue comprise at least four amide-bonded residues having a sequence YTXV or YSXV, wherein a. Y is selected from among E, Q, and A, or an analogue thereof, and b. X is selected from among A, Q, D, N, N-Me-A, N-Me-Q, N-Me-D, and N-Me-N or an analogue thereof, and wherein a Cell Penetrating Peptide (CPP) is linked to the linker or to an amino acid side chain of the first and second peptide or peptide analogue. The linker can be a PEG or NPEG linker.