Ferrocene-appended anthraquinone and coumarin as redox-active cytotoxins

Houshmand, Aryan; Heroux, Devon; Liu, Dennis Y.; Zhou, Wen; Linington, Roger G.; Bally, Marcel B.; Warren, Jeffrey J.; Walsby, Charles J.

doi:10.1039/d2dt01251k

Cited by 8 publications

(5 citation statements)

References 79 publications

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“…Using a sol- We also made coumarin containing triazoles 4-ferrocene-((1H-1,2,3-triazol-1-yl)methyl)-7-hydroxy-2H-chromen-2-one (Triazole 6) and a mixture of (3R,4S,5R)-3,4,5,6-tetrahydroxy-2-(4-(((2-oxo-2H-chromen-4-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)hexanal with 4-((1-((4R,5S, 6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-chromen-2-one (Triazole 7) by CuAAC reaction with Complex 1 immobilized on Tentagel resin as catalyst. New triazole derivatives such as Triazole 6 and Triazole 7 formed by combining coumarin with ferrocene or D-deoxy glucose, show potential for anion labeling [25], may have anticancer [26,27] and antimicrobial [28] properties and can be used for glycolysis inhibition [29] and imaging in cancer cells [30]. The yield of Triazole 6 (Supplementary Materials Figures S-17 and S-18) was 43% after 24 h in a D 2 O/ t BuOH/ACN (33.33:33.33:33.33) solvent mixture (condition 6H).…”

Section: Efficiency Of Cuaac Reactions With Complex 1 Catalyst Immobi...mentioning

confidence: 99%

Development of Novel Immobilized Copper–Ligand Complex for Click Chemistry of Biomolecules

Kandler,

Benaragama,

Bera

et al. 2024

Molecules

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Copper-catalyzed azide–alkyne cycloaddition click (CuAAC) reaction is widely used to synthesize drug candidates and other biomolecule classes. Homogeneous catalysts, which consist of copper coordinated to a ligand framework, have been optimized for high yield and specificity of the CuAAC reaction, but CuAAC reaction with these catalysts requires the addition of a reducing agent and basic conditions, which can complicate some of the desired syntheses. Additionally, removing copper from the synthesized CuAAC-containing biomolecule is necessary for biological applications but inconvenient and requires additional purification steps. We describe here the design and synthesis of a PNN-type pincer ligand complex with copper (I) that stabilizes the copper (I) and, therefore, can act as a CuAAC catalyst without a reducing agent and base under physiologically relevant conditions. This complex was immobilized on two types of resin, and one of the immobilized catalyst forms worked well under aqueous physiological conditions. Minimal copper leaching was observed from the immobilized catalyst, which allowed its use in multiple reaction cycles without the addition of any reducing agent or base and without recharging with copper ion. The mechanism of the catalytic cycle was rationalized by density functional theory (DFT). This catalyst’s utility was demonstrated by synthesizing coumarin derivatives of small molecules such as ferrocene and sugar.

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Section: Efficiency Of Cuaac Reactions With Complex 1 Catalyst Immobi...mentioning

confidence: 99%

Development of Novel Immobilized Copper–Ligand Complex for Click Chemistry of Biomolecules

Kandler,

Benaragama,

Bera

et al. 2024

Molecules

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“…[76] The anthraquinone derivatives inhibit a variety of enzymes and intercalates with the DNA. [77] C. J. Walsby and co-workers have reported [78] on the synthesis of ferrocenyl coumarin and anthraquinone triazoles, presence of CuI, DBU or TMEDA in DMF/toluene mixture (Scheme 30).…”

Section: Ferrocenyl Coumarin Triazolesmentioning

confidence: 99%

“…Ferrocenylthiohydantoin triazoles [71] Ferrocenylcoumarin and anthraquinone triazoles [78] 2 A549 and SKOV3 cancer cell lines SKOV3: IC 50 = 11.39 μM 4.8 Ferrocenyl-erlotinib triazoles [81] Ferrocenyl-benzene sulphonamide triazoles [85,86] 12 CA inhibition CA II inhibition (K is = 3.2 nm) 4.10…”

Section: 2mentioning

confidence: 99%

“…C. J. Walsby and co‐workers have reported [78] on the synthesis of ferrocenyl coumarin and anthraquinone triazoles, 402 and 404 , respectively; by the copper catalyzed 1,3‐dipolar cycloaddition reaction of O ‐alkylated coumarin 401 and anthraquinone 403 with (1‐azidoethyl) ferrocene 395 in presence of CuI, DBU or TMEDA in DMF/toluene mixture (Scheme 30).…”

Section: Ferrocenyl‐123‐triazolesmentioning

confidence: 99%

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Ferrocenyl Azoles: Versatile N‐Containing Heterocycles and their Anticancer Activities

Sadanala,

Trivedi

2024

The Chemical Record

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The medicinal chemistry of ferrocene has gained its momentum after the discovery of biological activities of ferrocifen and ferroquine. These ferrocenyl drugs have been designed by replacing the aromatic moiety of the organic drugs, tamoxifen and chloroquine respectively, with a ferrocenyl unit. The promising biological activities of these ferrocenyl drugs have paved a path to explore the medicinal applications of several ferrocenyl conjugates. In these conjugates, the ferrocenyl moiety has played a vital role in enhancing or imparting the anticancer activity to the molecule. The ferrocenyl conjugates induce the cytotoxicity by generating reactive oxygen species and thereby damaging the DNA. In medicinal chemistry, the five membered nitrogen heterocycles (azoles) play a significant role due to their rigid ring structure and hydrogen bonding ability with the biomolecules. Several potent drug candidates with azole groups have been in use as chemotherapeutics. Considering the importance of ferrocenyl moiety and azole groups, several ferrocenyl azole conjugates have been synthesized and screened for their biological activities. Hence, in the view of a wide scope in the development of potent drugs based on ferrocenyl azole conjugates, herein we present the details of synthesis and the anticancer activities of ferrocenyl compounds bearing azole groups such as imidazole, triazoles, thiazole and isoxazoles.

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“…Up to now, the CuAAC reaction has been extensively applied in various scientific fields, including materials, − medicine, − biology, , and catalysis . One prominent application is utilizing 1,2,3-triazole as a linker group to connect two functional segments.…”

Section: Introductionmentioning

confidence: 99%

Triphenylene Discotic Pd(II) Metallomesogens Based on Triazole Ligands Derived from the Click Reaction

Bai,

Lan,

et al. 2024

Crystal Growth & Design

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Two palladium complexes (Pd[DiTP-triazole] 2 Cl 2 and Pd[TrTP-triazole] 2 Cl 2 ) bearing a 1,2,3-triazole segment as ligands were synthesized. The 1,2,3-triazole moiety in Pd[DiTP-triazole] 2 Cl 2 was synthesized by the Cu(I)-catalyzed azide−alkyne cycloaddition reaction. Meanwhile, the 1,2,3-triazole in Pd[TrTP-triazole] 2 Cl 2 were synthesized through the Click reaction involving an internal alkyne and an organic azide. These two complexes feature soft spacers of comparable length between the triphenylene cores and the 1,2,3-triazole units, which are designed to enhance the molecular symmetry and improve the liquid crystalline properties. The structures of both complexes were fully characterized, with a specific focus on their confirmation through single-crystal X-ray diffraction (XRD) analysis of two model molecules, Pd[DiB-triazole] 2 Cl 2 and Pd[TrB-triazole] 2 Cl 2 . Additional techniques, such as differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and powder XRD, were used to confirm the room temperature discotic liquid crystal (DLC) properties of all palladium complexes. It was found that both complexes Pd[DiTP-triazole] 2 Cl 2 and Pd[TrTP-triazole] 2 Cl 2 exhibit hexagonal columnar mesophases at room temperature. Significantly, the temperature ranges of these mesophases were substantially extended, showing increases of 70 and 56 °C, respectively, compared to their ligands. Additionally, upon excitation at 279 nm, all the ligands and complexes emit ultraviolet to visible blue light as for the critical role of the triphenylene cores.

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Ferrocene-appended anthraquinone and coumarin as redox-active cytotoxins

Abstract: Appending ferrocene to coumarin and anthraquinone promotes generation of hydroxyl radicals and modulates anticancer activity.

Cited by 8 publications

References 79 publications

Development of Novel Immobilized Copper–Ligand Complex for Click Chemistry of Biomolecules

Development of Novel Immobilized Copper–Ligand Complex for Click Chemistry of Biomolecules

Ferrocenyl Azoles: Versatile N‐Containing Heterocycles and their Anticancer Activities

Triphenylene Discotic Pd(II) Metallomesogens Based on Triazole Ligands Derived from the Click Reaction

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