Carotenoid Derivative Side Chain Design for Water Solubility

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Solution Overview

Problem

Astaxanthin derivatives have unsatisfactory water solubility and oral absorbability, limiting their administration forms and effectiveness as therapeutic agents.

Innovation Solution

Development of carotenoid derivatives with novel side chain structures that enhance water solubility and oral absorbability, allowing for broader administration methods including oral, injectable, and topical forms.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If astaxanthin derivatives are used as therapeutic agents, then anti-oxidation activity is improved, but water solubility and oral absorbability deteriorate

Engineering Contradiction:

Improveanti-oxidation activityVSAvoidwater solubility and oral absorbability

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the chemical structure of astaxanthin derivatives by changing physical and chemical parameters - specifically introducing hydrophilic side chains with carboxyl, hydroxyl, or amino groups at defined positions (R1 and R2) on the carotenoid molecule. This structural parameter change transforms the molecule from highly hydrophobic to amphiphilic, improving water solubility while preserving the core conjugated structure responsible for anti-oxidation activity.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining the hydrophobic carotenoid core with hydrophilic side chains. This composite approach allows the molecule to interact with both lipid and aqueous environments, enhancing oral absorbability and enabling various administration forms (oral, injectable, topical) while maintaining the therapeutic anti-oxidation properties.

Inventive Principle:

Principle #40Composite materials

2Reliability

If astaxanthin derivatives are administered to improve therapeutic efficacy, then anti-oxidation activity is enhanced, but administration form flexibility deteriorates

Engineering Contradiction:

Improvetherapeutic efficacyVSAvoidadministration form flexibility

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent achieves multi-functionality by designing astaxanthin derivatives with amphiphilic characteristics that allow them to be effectively administered through multiple routes - oral ingestion, intravenous injection, ocular administration, and topical application. The modified molecular structure serves multiple purposes: maintaining anti-oxidation activity while enabling compatibility with different administration systems, thereby expanding therapeutic applicability.

Inventive Principle:

Principle #6Universality (Multi-functionality)

Data Source

PatentUS10125104B2Carotenoid derivative, pharmaceutically acceptable salt thereof, or pharmaceutically acceptable ester or amide thereof

Publication Date: 2018.11.13 FUJI CHEM IND CO LTD

AI summary

The object of the present invention is to find a carotenoid compound that is excellent in water solubility.A carotenoid derivative having a formula (I):whereinX represents a carbonyl group or a methylene group, one of R1 and R2 represents (a) or (b) and the other represents (a), (b), (c) or a hydrogen atom:(a): —CO-A-B-D wherein A represents an alkylene group an alkenylene group, etc., B represents a formula of —S(O)n— or a formula of —NR4CONR5— and D represents a hydrogen atom, a carboxy group, etc.,(b): —CO-E-F wherein E represents an alkylene group or a formula of —NR3— wherein R3 represents (a1) a hydrogen atom, (b1) an alkyl group etc., and F represents a sulfo group and(c): —CO-G wherein G represents a hydrogen atom, an alkyl group, etc.,a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable ester or amide thereof.