Phosphorothioate-Conjugated Peptides for Intracellular Delivery

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Solution Overview

Problem

Targeting intracellular molecules for therapeutic purposes is challenging due to the need for biostable compositions that can penetrate the cell membrane and maintain stability in a physiological environment, which existing technologies have not effectively addressed.

Innovation Solution

Development of nucleic acid-peptide conjugates, specifically non-cell penetrating peptides conjugated with phosphorothioate nucleic acids at their C-terminus, which enhance intracellular delivery and biostability, allowing for effective targeting of intracellular molecules involved in disease pathology.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If non-cell penetrating peptides are used to target intracellular molecules, then specificity to intracellular targets is improved, but cellular penetration ability deteriorates

Engineering Contradiction:
Improvespecificity to intracellular targetsVSAvoidcellular penetration ability
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent merges a non-cell penetrating peptide (providing target specificity) with a phosphorothioate nucleic acid (providing cellular penetration capability) to create a conjugate that exhibits both high specificity for intracellular targets and efficient cellular delivery. The peptide and nucleic acid are covalently linked through a chemical connector, allowing the conjugate to function as an integrated therapeutic agent that overcomes the limitation of individual components.

Inventive Principle:
Principle #5Merging (Combining)

2Ease of operation

If peptides are designed to penetrate cell membranes, then cellular delivery is improved, but biostability in physiological environment deteriorates

Engineering Contradiction:
Improvecellular deliveryVSAvoidbiostability in physiological environment
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent creates a composite conjugate consisting of a peptide component, a phosphorothioate nucleic acid component, and a chemical connector. The phosphorothioate backbone provides enhanced biostability by resisting nucleases and proteases in physiological environments, while the peptide component maintains target binding specificity. This composite structure resolves the contradiction between cellular delivery and biostability.

Inventive Principle:
Principle #40Composite materials

3Productivity

If cell penetrating peptides are used, then intracellular delivery efficiency is improved, but loss of therapeutic agent through rapid clearance deteriorates

Engineering Contradiction:
Improveintracellular delivery efficiencyVSAvoidloss of therapeutic agent through rapid clearance
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The phosphorothioate nucleic acid acts as an intermediary carrier that facilitates intracellular delivery of the therapeutic peptide while protecting it from rapid clearance. The nucleic acid component enables cellular uptake through endocytosis or other nucleic acid delivery pathways, and its stable phosphorothioate backbone protects the conjugate from degradation by cellular enzymes, thereby reducing loss of the therapeutic agent.

Inventive Principle:
Principle #24Intermediary (Mediator)

Data Source

PatentEP3651807B1Phosphorothioate-conjugated peptides and methods of using the same
Publication Date: 2023.11.01 CITY OF HOPE
  • EP3651807B1 patent drawingFigure 1
  • EP3651807B1 patent drawingFigure 2
  • EP3651807B1 patent drawingFigure 3A

AI summary

Provided herein are, inter alia, nucleic acid-peptide conjugates including a non-cell penetrating protein attached at its C-terminus to a phosphorothioate nucleic acid. Attachment of the phosphorothioate nucleic acid to the non-cell penetrating protein conveys stability to and allows for efficient intracellular delivery of the non-cell penetrating peptide. The nucleic acid-peptide conjugates provided herein including embodiments thereof are useful, inter alia, for the treatment of cancer, inflammatory disease, pain, and viral infection.