Photoactive Small Molecule Analogs for Deep Tissue Imaging

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Solution Overview

Problem

Conventional methods for targeting and delivering diagnostic or therapeutic agents to specific sites in the body, such as tumors, face challenges due to the unfavorable diffusion of high molecular weight bioconjugates and fluorescence quenching issues with small molecule drugs, especially when substituting large functional units like dyes or photosensitizers into small molecule drugs.

Innovation Solution

The development of integrated photoactive analogs of non-photoactive bioactive molecules by replacing non-photoactive functional groups with photoactive moieties of similar size and molecular topology, allowing for both diagnostic and therapeutic applications while minimizing tissue damage and enhancing penetration depth.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If large functional units such as dyes or photosensitizers are substituted into small molecule drugs, then photoactive capabilities are improved, but molecular topology and binding affinity are compromised

Engineering Contradiction:

Improvephotoactive capabilitiesVSAvoidmolecular topology

Core Design Contradiction:

Use of energy by moving objectVSManufacturing precision

Solution Approach 1:

The patent changes the molecular parameters by replacing aromatic rings with photoactive moieties of similar size, maintaining molecular topology while introducing photoactive capabilities. This parameter substitution allows the small molecule to retain its binding affinity to biological targets while gaining optical properties for imaging and therapy.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention introduces photoactive moieties at specific locations within the small molecule structure where they can perform optical functions without disrupting the overall molecular topology. The local substitution of aromatic rings with photoactive groups allows targeted introduction of optical properties while preserving the global structural features necessary for biological activity.

Inventive Principle:

Principle #3Local quality

2Reliability

If high molecular weight bioconjugates are used for targeting, then diagnostic and therapeutic functions are improved, but diffusion to tumor cells is unfavorable

Engineering Contradiction:

Improvediagnostic and therapeutic functionsVSAvoiddiffusion to tumor cells

Core Design Contradiction:

ReliabilityVSSpeed

Solution Approach 1:

The patent extracts the photoactive and targeting functions from large bioconjugate structures and incorporates them directly into small molecule drugs. This extraction eliminates the need for large molecular weight carriers while retaining the essential functions of targeting and imaging/therapy, thereby improving diffusion characteristics.

Inventive Principle:

Principle #2Taking out (Extraction)

Solution Approach 2:

The invention merges the photoactive moiety, targeting functionality, and drug activity into a single integrated small molecule structure. This consolidation of multiple functions into one small molecule eliminates the need for separate bioconjugate components, improving diffusion while maintaining all necessary therapeutic and diagnostic capabilities.

Inventive Principle:

Principle #5Merging (Combining)

3Speed

If small molecule drugs are used, then diffusion to tumor cells is improved, but fluorescence quenching occurs

Engineering Contradiction:

Improvediffusion to tumor cellsVSAvoidfluorescence signal

Core Design Contradiction:

SpeedVSReliability

Solution Approach 1:

The patent changes the chemical parameters of the small molecule by incorporating photoactive moieties with specific optical properties that resist aggregation-induced quenching. These modified small molecules maintain fast diffusion characteristics while exhibiting stable fluorescence signals suitable for optical imaging.

Inventive Principle:

Principle #35Parameter changes

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

These integrated photoactive analogs enable effective diagnostic imaging and therapeutic treatments with reduced tissue damage, as they absorb, excite, and emit light in the near-infrared or visible spectrum, allowing for deeper tissue penetration and targeted photofragmentation of diseased tissues.

Implementation Method 1

these integrated photoactive small molecules absorb, excite and emit light in the near-infrared or visible spectrum of 350 nm or greater

Methodology Applied

Scientific EffectLight absorption and emission: Absorption (EM radiation)

Implementation Method 2

irradiating the patient with a wavelength of light that causes photofragmentation of the molecule

Methodology Applied

Scientific EffectPhotofragmentation: Photodissociation

Data Source

PatentUS8313729B2Integrated photoactive small molecules and uses thereof

Publication Date: 2012.11.20 MEDIBEACON INC

AI summary

This invention is directed to the general method of transforming non-photoactive bioactive small molecule compounds of known structure and function into photoactive analogs of the small molecules which exhibit both photoactivity and the original biological targeting activity. The general method for the design of the photoactive analogs of the small molecules includes: (a) selecting a desired bioactive molecule; (b) identifying the region of the molecule that contains an aromatic or a heteroaromatic motif; and (c) either replacing said motif with a photoactive functional group of similar size, or modifying said motif to make it photoactive. Other aspects include photoactive analog compounds and photodiagnostic and phototherapeutic uses thereof.