Optimized Heptamethine Cyanines for Photodynamic Therapy

Usama, Syed Muhammad; Thavornpradit, Sopida; Burgess, Kevin

doi:10.1021/acsabm.8b00414

Cited by 62 publications

(61 citation statements)

References 52 publications

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“…Unsymmetrical Cy7 dyes are important because they allow differential functionalization of two different side-chains, or subtle modulation of physiochemical properties. Previously, we have made unsymmetrical cyanine dyes via a stepwise condensation sequence 25. The SI illustrates (Scheme S2) synthesis of one unsymmetrical QuatCy derivative 4 indicating that a series of other dyes of this kind could be prepared.…”

Section: Resultsmentioning

confidence: 99%

QuatCy: A Heptamethine Cyanine Modification With Improved Characteristics

et al. 2019

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A major restriction on optical imaging techniques is the range of available fluorophores that are compatible with aqueous media without aggregation, absorb light above 750 nm with high extinction coefficients, fluoresce with relatively high quantum yields, and resist photodecomposition. Indocyanine green (ICG or A in this paper) is an important example of a fluorophore that fits this description. Other dyes that are becoming increasingly prevalent are select heptamethine cyanine dyes (Cy7) which feature a cyclohexyl framework to rigidify the conjugated alkenes, and meso -chlorine substitution; MHI-148 ( B ) is one example. Methods : Research described here was initiated to uncover the consequences of a simple isoelectronic substitution to MHI-148 that replaces a cyclohexyl methylene with a dialkyl ammonium fragment. Solubility experiments were carried out in aqueous and cell culture media, photophysical properties including fluorescence quantum yields, brightness and stability were measured. Moreover, in vivo pharmacokinetics, distribution and tumor seeking properties were also explored. Results : Modification to incorporate dialkyl ammonium fragment leads to a brighter, more photostable fluorophore, with a decreased tendency to aggregation, complementary solubility characteristics, and a lower cytotoxicity. Conclusion : All the above-mentioned parameters are favorable for many anticipated applications of the new dye we now call quaternary cyanine-7 or QuatCy .

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Section: Resultsmentioning

confidence: 99%

QuatCy: A Heptamethine Cyanine Modification With Improved Characteristics

et al. 2019

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“…The use of compounds already established for NIR‐I imaging could significantly ease the establishment of imaging in the NIR‐II window [63–64] . Likewise, further development of cyanine dyes for applications such as PDT is of great interest, due to the penetration depth of light in the NIR window and their high molar absorptivity [3b, 41, 43, 65] …”

Section: Discussionmentioning

confidence: 99%

Explorations into the Effect of meso‐Substituents in Tricarbocyanine Dyes: A Path to Diverse Biomolecular Probes and Materials

2020

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Polymethine cyanine dyes have been widely recognized as promising chemical tools for a range of life science and biomedical applications, such as fluorescent staining of DNA and proteins in gel electrophoresis, fluorescence guided surgery, or as ratiometric probes for probing biochemical pathways. The photophysical properties of such dyes can be tuned through the synthetic modification of the conjugated backbone, for example, by altering aromatic cores or by varying the length of the conjugated polymethine chain. Alternative routes to shaping the absorption, emission, and photostability of dyes of this family are centered around the chemical modifications on the polymethine chain. This Minireview aims to discuss strategies for the introduction of substituents in the meso‐position, their effect on the photophysical properties of these dyes and some structure–activity correlations which could help overcome common limitations in the state of the art in the synthesis.

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“…Glassware was dried in an oven at 140 °C for a minimum of 6 h prior to use for all reactions. IR-783 and IR-780 were purchased from Sigma Aldrich (Atlanta, GA, USA) and abcr GmBH (Karlsruhe, Germany), respectively, and DZ-1 and MHI-148 were synthesized according to literature protocol [ 7 , 12 , 14 , 34 ]. All other reagents were purchased at a high commercial quality (typically 97% or higher) and used without further purification, unless otherwise stated.…”

Section: Methodsmentioning

confidence: 99%

Site-Specific Labeling of Proteins with Near-IR Heptamethine Cyanine Dyes

2018

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Convenient labeling of proteins is important for observing its function under physiological conditions. In tissues particularly, heptamethine cyanine dyes (Cy-7) are valuable because they absorb in the near-infrared (NIR) region (750–900 nm) where light penetration is maximal. In this work, we found Cy-7 dyes with a meso-Cl functionality covalently binding to proteins with free Cys residues under physiological conditions (aqueous environments, at near neutral pH, and 37 °C). It transpired that the meso-Cl of the dye was displaced by free thiols in protein, while nucleophilic side-chains from amino acids like Tyr, Lys, and Ser did not react. This finding shows a new possibility for convenient and selective labeling of proteins with NIR fluorescent probes.

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Optimized Heptamethine Cyanines for Photodynamic Therapy

Cited by 62 publications

References 52 publications

QuatCy: A Heptamethine Cyanine Modification With Improved Characteristics

QuatCy: A Heptamethine Cyanine Modification With Improved Characteristics

Explorations into the Effect of meso‐Substituents in Tricarbocyanine Dyes: A Path to Diverse Biomolecular Probes and Materials

Site-Specific Labeling of Proteins with Near-IR Heptamethine Cyanine Dyes

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