Cyanine dye mediated mitochondrial targeting enhances the anti-cancer activity of small-molecule cargoes

Nödling, Alexander R.; Mills, Emily M.; Li, Xuefei; Cardella, Davide; Sayers, Edward J.; Wu, Shih‐Hsiung; Jones, Arwyn Tomos; Luk, Louis Y. P.; Tsai, Yu‐Hsuan

doi:10.1039/c9cc07931a

Cited by 49 publications

(42 citation statements)

References 40 publications

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“…15 These two indocyanine dyes have also been found useful in targeting mitochondria in cancer cells and delivering cargoes to them. 16 EvaGreen, also shown in Fig. 2, displays enhanced and redshied uorescence when bound in the DNA minor groove and is an effective reagent for detection of autoimmune antibodies in qPCR methods.…”

Section: Cyanine Dyesmentioning

confidence: 97%

Unspecified verticality of Franck–Condon transitions, absorption and emission spectra of cyanine dyes, and a classically inspired approximation

Alia

Flack

2020

RSC Adv.

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Section: Cyanine Dyesmentioning

confidence: 97%

Unspecified verticality of Franck–Condon transitions, absorption and emission spectra of cyanine dyes, and a classically inspired approximation

Alia

Flack

2020

RSC Adv.

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“…For this reason, major interest has been directed toward study of cationic compounds as well as positively charged vesicles as chemotherapeutic agents. Several publications from the literature document that these type of compounds are attracted to, and accumulate more selectively, in this organelle of cancer cells, resulting in disruption of ATP synthesis and subsequent induction of cell death [16,17,22,89,108,109].…”

Section: Gumbos and Nanogumbos As Chemotherapeutic Agentsmentioning

confidence: 99%

“…With increasing global commercialization of state-of-the-art optoelectronic displays, the demand for higher performance and flexible materials has also increased [108][109][110][111]. In general, these devices are comprised of emissive layers between electrodes along with several other electronically active layers.…”

Section: Optoelectronic Developmentsmentioning

confidence: 99%

“…In general, these devices are comprised of emissive layers between electrodes along with several other electronically active layers. Organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs) have been the central target for a multitude of research groups, from organic emissive layer development to full device performance [108][109][110][111][112]. Counterion strategies using cations and anions within active layers for enhancement on optoelectronic device fabrication to effects on emission and device function will be discussed in the following sections.…”

Section: Optoelectronic Developmentsmentioning

confidence: 99%

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Group of Uniform Materials Based on Organic Salts (GUMBOS): A Review of Their Solid State Properties and Applications

Pérez¹,

Ayala²,

Warner³

2021

Ionic Liquids - Thermophysical Properties and Applications

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Ionic liquids (ILs) are defined as organic salts with melting points below 100 °C. Such ionic compounds are typically formed using bulky cations and/or bulky anions in order to produce liquids or lower melting solids. ILs have been widely explored in several research areas including catalysis, remediation, solvents, separations, and many others. The utility of such compounds has also been recently broadened to include solid phase ionic materials. Thus, researchers have pushed the boundaries of ILs chemistry toward the solid state and have hypothesized that valuable properties of ILs can be preserved and fine-tuned to achieve comparable properties in the solid state. In addition, as with ILs, tunability of these solid-phase materials can be achieved through simple counterion metathesis reactions. These solid-state forms of ILs have been designated as a group of uniform materials based on organic salts (GUMBOS). In contrast to ILs, these materials have an expanded melting point range of 25 to 250 °C. In this chapter, we focus on recent developments and studies from the literature that provide for fine tuning and enhancing properties through transformation and recycling of diverse ionic compounds such as dyes, antibiotics, and others into solid state ionic materials of greater utility.

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“…Also, the use of cyanine dyes as vectors for delivering drugs to mitochondria of cancer cells by conjugating the drugs to the dyes can increase cytotoxicity against cancer cells. [ 21 ] This study aimed to synthesize and characterize new carbocyanine dyes, as well as screen their anticancer activity against two different cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel cyanine dyes as antitumor agents

Fadda

Tawfik

Abdel‐Motaal

et al. 2020

Archiv der Pharmazie

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In this study, some novel cyanine dyes, 1, 3, and 5−15, were synthesized by a one‐pot step reaction of pyridinium salts 2 and/or 4 with benzenaminium salt 1. N‐{[1‐Chloro‐3,4‐dihydronaphthalen‐2‐yl)methylene]benzenaminium} chloride 1 was obtained by the reaction of α‐tetralone with Vilsmeier−Haack reagent, followed by a mixture of an equimolar ratio of anilin/ethanol (1:1). All new cyanine dyes were evaluated in vitro for their anticancer activity against two cell lines, that is, HepG2 (human hepatocellular liver carcinoma) and MCF‐7 (breast cancer). The obtained results were compared with human lung fibroblasts (WI‐38) and Vero cells (derived from the kidney of an African green monkey) as normal cells. In particular, some of these compounds, 6, 9, 13, and 14, were found to be the most potent derivatives against all the cancer cell lines, without effect on the normal cells. According to the structure–activity relationship, compound 13 (IC50 = 8.8 µg/ml) exhibited a higher activity against HepG2 cells, as it contains the azo group and two phenyl rings and due to the presence of the π‐conjugated system attached to the two pyridine rings. Compound 6 (IC50 = 8 µg/ml) exhibited a higher activity against MCF‐7 cells, as it contains two chlorine atoms and the π‐conjugated system of the pyridine rings.

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Cyanine dye mediated mitochondrial targeting enhances the anti-cancer activity of small-molecule cargoes

Abstract: Conjugation of small molecules to a simple cyanine dye can lead to organelle-specific delivery.

Cited by 49 publications

References 40 publications

Unspecified verticality of Franck–Condon transitions, absorption and emission spectra of cyanine dyes, and a classically inspired approximation

Unspecified verticality of Franck–Condon transitions, absorption and emission spectra of cyanine dyes, and a classically inspired approximation

Group of Uniform Materials Based on Organic Salts (GUMBOS): A Review of Their Solid State Properties and Applications

Synthesis of novel cyanine dyes as antitumor agents

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