Synthetic Access to Benzimidacarbocyanine Dyes to Tailor Their Aggregation Properties

Roth, Sophia M.; Press, David J.; Heyne, Belinda; Sutherland, Todd C.

doi:10.1021/acs.joc.1c00385

Cited by 6 publications

(4 citation statements)

References 48 publications

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“…Intermolecular dipole–dipole interaction is a main factor promoting the formation of cyanin dye J-aggregates . Halogen atoms bound to carbon have strong electron affinity and can induce molecular polarization, thus facilitating intermolecular dipole–dipole interaction. , The electron affinity of Cl is higher than that of F, so compared to SCY-4, SCY-5 has a stronger tendency to form J-aggregates . The main mechanism of K + induced SCY-5 aggregation is that K + replaces triethylamine cations and permeates into the interior of the aggregates, effectively weakening the electrostatic repulsion between cyanine dyes .…”

Section: Resultsmentioning

confidence: 99%

A Cyanine Dye for Highly Specific Recognition of Parallel G-Quadruplex Topology and Its Application in Clinical RNA Detection for Cancer Diagnosis

Sun,

Yang

et al. 2024

J. Am. Chem. Soc.

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G-quadruplex (G4), an unconventional nucleic acid structure, shows polymorphism in its topological morphology. The parallel G4 topology is the most prevalent form in organisms and plays a regulatory role in many biological processes. Designing fluorescent probes with high specificity for parallel G4s is important but challenging. Herein, a supramolecular assembly of the anionic cyanine dye SCY-5 is reported, which selectively identifies parallel G4 topology. SCY-5 can clearly distinguish parallel G4s from other G4s and non-G4s, even including hybrid-type G4s with parallel characteristics. The high specificity mechanism of SCY-5 involves a delicate balance between electrostatic repulsion and π−π interaction between SCY-5 and G4s. Using SCY-5, cellular RNA extracted from peripheral venous blood was quantitatively detected, and a remarkable increase in RNA G4 content in cancer patients compared to healthy volunteers was confirmed for the first time. This study provides new insights for designing specific probes for parallel G4 topology and opens a new path for clinical cancer diagnosis using RNA G4 as a biomarker.

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Section: Resultsmentioning

confidence: 99%

A Cyanine Dye for Highly Specific Recognition of Parallel G-Quadruplex Topology and Its Application in Clinical RNA Detection for Cancer Diagnosis

Sun,

Yang

et al. 2024

J. Am. Chem. Soc.

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“…14,[24][25][26][27][28][29][30][31] Recent work used synthetic modifications on the C8S3 monomer to affect aggregation properties; larger halogen substitutions have been shown to increase the tube diameter, while placement of the halogen atoms was found to be critical in achieving H-vs. J-aggregation. 32,33 We expand on this body of work by synthesizing elongated C8S3 dyes with redshifted absorption and emission.…”

Section: Introductionmentioning

confidence: 99%

Exploring the design of superradiant J-aggregates from amphiphilic monomer units

et al. 2023

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“…14,[23][24][25][26][27][28][29][30] Recent work used synthetic modifications on the C8S3 monomer to affect aggregation properties; larger halogen substitutions have been shown to increase the tube diameter, while placement of the halogen atoms was found to be critical in achieving H-vs. Jaggregation. 31,32 We expand on this body of work by synthesizing elongated C8S3 dyes with redshifted absorption and emission.…”

Section: Introductionmentioning

confidence: 99%

Exploring the Design of Superradiant J-Aggregates from Amphiphilic Monomer Units

Bailey

Deshmukh

Atallah

et al. 2022

Preprint

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Excitonic chromophore aggregates have wide-ranging applicability in fields such as imaging and energy harvesting, however their rational design requires adapting principles of self-assembly to the requirements of excited state coupling. Using the well-studied amphiphilic cyanine dye C8S3 as a template—known to assemble into tubular excitonic aggregates—we synthesize several redshifted variants and study their self-assembly and photophysics. The new pentamethine dyes retain their tubular self-assembly and demonstrate nearly identical bathochromic shifts and lineshapes well into near-infrared wavelengths. However, detailed photophysical analysis finds that the new aggregates show a significant decline in superradiance. Additionally, cryo-TEM reveals that these aggregates readily form short bundles of nanotubes that have nearly half the radii of their trimethine comparators. We employ computational screening to gain intuition on how the structural components of these new aggregates affect their excitonic states, finding that the narrower tubes are able to assemble into a larger number of arrangements, resulting in more disordered aggregates (i.e. less superradiant) with highly similar degrees of redshift.

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Synthetic Access to Benzimidacarbocyanine Dyes to Tailor Their Aggregation Properties

Cited by 6 publications

References 48 publications

A Cyanine Dye for Highly Specific Recognition of Parallel G-Quadruplex Topology and Its Application in Clinical RNA Detection for Cancer Diagnosis

A Cyanine Dye for Highly Specific Recognition of Parallel G-Quadruplex Topology and Its Application in Clinical RNA Detection for Cancer Diagnosis

Exploring the design of superradiant J-aggregates from amphiphilic monomer units

Exploring the Design of Superradiant J-Aggregates from Amphiphilic Monomer Units

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