Spiro-Ring Si Rhodamine Dye for Single-Molecule Detection

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing fluorescent dyes with Si rhodamine backbones have a high duty cycle, making it difficult to detect single-molecule luminescence effectively for super-resolution microscopy.

Innovation Solution

A novel fluorescent dye is developed by incorporating a spiro-ring structure with an Si atom as the spiro atom into the Si rhodamine backbone, reducing the duty cycle and enhancing sporadic light emission.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a fluorescent dye with Si rhodamine backbone is used, then the dye maintains structural stability and fluorescence properties, but the duty cycle is high making single-molecule luminescence detection difficult

Engineering Contradiction:
Improvefluorescence stabilityVSAvoidsingle-molecule luminescence detection
Core Design Contradiction:
ReliabilityVSDifficulty of detecting and measuring

Solution Approach 1:

The patent introduces a spiro-ring structure that can dynamically open and close, transitioning the fluorescent dye between fluorescent and non-fluorescent states. This dynamic structural change reduces the duty cycle by controlling the time the dye spends in the fluorescent state, thereby improving detectability of single-molecule luminescence while maintaining overall fluorescence stability when open.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent modifies the molecular structure by incorporating a spiro-ring with specific substituents (R1-R11) that can change the photophysical parameters of the dye. The spiro-ring opening/closing action changes the conjugation and electron distribution, thereby altering the duty cycle parameter to optimize both stability and detectability.

Inventive Principle:
Principle #35Parameter changes

2Difficulty of detecting and measuring

If the duty cycle is reduced to improve single-molecule detection, then detectability improves, but the duration of fluorescent emission is shortened

Engineering Contradiction:
Improvesingle-molecule luminescence detectionVSAvoidfluorescent emission duration
Core Design Contradiction:
Difficulty of detecting and measuringVSDuration of action of moving object

Solution Approach 1:

The spiro-ring structure provides periodic opening and closing cycles, creating intermittent fluorescent emission. This periodic action allows the dye to spend more time in the non-fluorescent closed state (reducing duty cycle) while still providing sufficient fluorescent bursts for detection when open, effectively decoupling detection efficiency from continuous emission duration.

Inventive Principle:
Principle #19Periodic action

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 novel fluorescent dye exhibits a decreased duty cycle, facilitating easier detection of single-molecule luminescence and improving the suitability for super-resolution microscopy.

Implementation Method 1

a state where an intramolecular spiro ring in which the spiro atom is a carbon atom located at position-9 in a xanthene ring moiety is formed (i.e., a ring-closed form) and a state where the spiro ring is cleaved (i.e., a ring-opened form) are in equilibrium with each other

Methodology Applied
Scientific EffectSpiro ring formation and cleavage:

Implementation Method 2

A rhodamine compound in the ring-opened form exerts absorption and fluorescence, while a rhodamine compound in the ring-closed form is colorless and non-fluorescent

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentUS12253526B2Fluorescent dye and use thereof
Publication Date: 2025.03.18 EISAI R&D MANAGEMENT CO LTD
  • US12253526B2 patent drawing
  • US12253526B2 patent drawing
  • US12253526B2 patent drawing

AI summary

Disclosed is: a fluorescent dye comprising a compound, a tautomer of the compound, or a salt of the compound or the tautomer; a labeled composite substance comprising the fluorescent dye and a composite substance which are bonded to each other; a composition containing the fluorescent dye or the labeled composite substance; and a method for acquiring information about a substance of interest by a super-resolution microscopy.