O-nitro compounds for selective tumor cell killing via radical generation

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing therapies for treating or preventing abnormal cell proliferation, such as cancer, face challenges in selectively targeting abnormal cells without forming toxic byproducts and achieving sufficient radical density under dose-limiting toxicity, particularly in hypoxic tumor environments.

Innovation Solution

Pharmaceutical compositions of O-nitro compounds that are intracellularly activated by reducing environments within tumor cells or externally activated by irradiation, leading to the formation of free radicals that inhibit cell replication and kill cancer cells without generating toxic byproducts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing radiosensitizers (thiols, nitroimidazoles, metal texaphyrin compounds) are used to target abnormal cell proliferation, then radiation sensitivity is improved, but toxic byproducts are formed which limits usefulness in cancer therapy

Engineering Contradiction:
Improveradiation sensitivityVSAvoidtoxic byproducts
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent converts the potentially harmful nitro group into a beneficial therapeutic element. The O-nitro compound, when activated by radiation or reduction, generates free radicals that selectively kill tumor cells. The nitro group itself is not toxic but becomes an active site for radical formation, transforming a potentially harmful chemical group into a beneficial therapeutic mechanism that eliminates cancer cells without forming toxic byproducts.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The patent modifies the chemical structure by placing the nitro group at the ortho position (O-nitro) rather than using conventional radiosensitizers. This structural parameter change creates a compound that maintains radiation sensitivity while avoiding toxic byproduct formation. The specific chemical structure (O-nitro compound with formula I) enables selective activation in tumor cells through intracellular reduction or radiation, generating cytotoxic free radicals only where needed.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If bioreductive compounds are used to selectively activate in reducing environment, then selectivity for tumor cells is improved, but sufficient radical density is not achieved under dose limiting toxicity

Engineering Contradiction:
Improveselectivity for tumor cellsVSAvoidradical density
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent merges two activation mechanisms into a single compound system: bioreductive activation (via intracellular reduction in hypoxic tumor environments) and radiation activation. The O-nitro compound can be activated either by the reducing environment of tumor cells or by external radiation, and both pathways lead to free radical formation. This merging of activation modes ensures sufficient radical density is achieved while maintaining selectivity for tumor cells, as both activation pathways are preferentially available in the tumor microenvironment.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent changes the redox potential parameter of the compound to enable selective activation in the reducing environment of tumor cells. The O-nitro compound is designed with appropriate redox properties that allow it to be reduced intracellularly in hypoxic tumors, generating free radicals. This parameter optimization ensures that sufficient radical density is achieved at therapeutically relevant doses without causing excessive toxicity to normal tissues.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If conventional therapies are used to treat abnormal cell proliferation, then treatment efficacy is achieved, but selective distinction between normal and abnormal cell proliferation is not achieved

Engineering Contradiction:
Improvetreatment efficacyVSAvoidselectivity between normal and abnormal cells
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent applies local quality by creating a compound that is selectively activated in the specific microenvironment of tumor cells. The O-nitro compound utilizes the hypoxic (low oxygen tension) conditions found in tumor tissues to trigger intracellular reduction and free radical formation. Normal tissues with adequate oxygenation do not activate the compound, thereby achieving local differentiation between tumor and normal cells. This enables treatment efficacy to be achieved selectively in the tumor microenvironment while sparing normal tissues.

Inventive Principle:
Principle #3Local quality

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 O-nitro compounds effectively treat or prevent abnormal cell proliferation by enhancing the efficacy of radiation therapy and reducing systemic toxicity, demonstrating synergistic or additive effects when combined with conventional treatments like cis-platin and radiation.

Implementation Method 1

compounds with low redox potentials (i.e., bioreductive compounds) may be selectively activated in the reducing environment of tumor cells without external activation

Methodology Applied
Scientific EffectReduction: Reduction

Implementation Method 2

the patient is irradiated to activate the O-nitro compound

Methodology Applied
Scientific EffectPhotodissociation: Photodissociation

Implementation Method 3

leading to the formation of free radicals that inhibit cell replication and kill cancer cells

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP2433495B1O-nitro compounds, pharmaceutical compositions thereof and uses thereof
Publication Date: 2016.10.05 ORBITAL ATK INC
  • EP2433495B1 patent drawingFigure 1
  • EP2433495B1 patent drawingFigure 2
  • EP2433495B1 patent drawingFigure 3

AI summary

The present invention provides O-nitro compound, pharmaceutical compositions of O-nitro compounds and methods of using O-nitro compounds and/or pharmaceutical compositions thereof to treat or prevent diseases or disorders characterized by abnormal cell proliferation, such as cancer, inflammation, cardiovascular disease and autoimmune disease.