Synthesis and Anti‐proliferative Activity of <i>N</i>,<i>N′</i>‐bis‐substituted 1,2,4‐Triazolium Salts against Breast Cancer and Prostate Cancer Cell Lines

Lin, Zi Jie; Bies, Jared; Johnson, Shanina Sanders; Gorden, John D.; Strickland, Jacqueline F.; Frazier, Monica; Meyers, Jonathan M.; Shelton, Kerri L.

doi:10.1002/jhet.3428

Cited by 10 publications

(5 citation statements)

References 13 publications

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“…Attaching different substituents at different sites can affect the bioactivities and selectivity of the triazolium salt compounds. For instance, the N , N ′‐bis‐substituted 1,2,4‐triazolium salt 30 bearing naphthalene methyl substituents at the N1‐ and N4‐position showed the best anticancer activity against breast cancer cells [34] . Besides, 1,2,4‐triazolium compound 33 containing a 4‐phenylbutan‐2‐one group at N3‐ position exhibited excellent selectivity with SI approach 1430, which was higher than the SI of other compounds [6] …”

Section: Structure‐activity Relationship Of 124‐triazolium Saltsmentioning

confidence: 96%

“…Of all the structural factors in triazolium compounds, the electronic properties of the triazolium cations may have the greatest influence on the bioactivities of the compounds. The introduction of triazolium cations can greatly enhance the antibacterial, [29,30,32] antifungal, [18,27] anticancer, [5,20,34] and antiplasmodium [6] activities of the bioactive compounds. The triazolium cation group with localized positive charge can easily interact with anionic components such as glucans, mannans, proteins, and the lipids on the microbial cell wall to form electrostatic interactions to exhibit antimicrobial activities.…”

Section: Effects Of the Triazolium Electronic Properties On Bioactivi...mentioning

confidence: 99%

“…A series of N,N'-bis-substituted 1,2,4-triazolium salts with functional groups at the N1-and N4-position were synthesized by Shelton et al [34] in 2019. The inhibitory effect of the triazolium salt 30 showed an IC 50 value of 15.79 μM against breast cancer cells, which was stronger than that of the control drug Tamoxifen (IC 50 = 22.5 μM).…”

Section: Anticancer Activities Of Mono-124-triazolium Saltsmentioning

confidence: 99%

“…A series of N,N′ ‐bis‐substituted 1,2,4‐triazolium salts with functional groups at the N1‐ and N4‐position were synthesized by Shelton et al [34] . in 2019.…”

Section: Bioactivities Of Mono‐124‐triazolium Saltsmentioning

confidence: 99%

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Bioactivities of Triazolium‐Based N‐Heterocyclic Carbene Salts

Song

Zou

Jin

et al. 2023

Chemistry A European J

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1,2,4-Triazolium salts are precursors of N-heterocyclic carbenes (NHCs), which have been extensively used as effective catalysts and ligands for both asymmetric and nonenantioselective reactions. Nevertheless, they are also a kind of quaternary ammonium compounds (QACs) that possess amphipathic properties. The unique chemical and physical properties of 1,2,4-triazolium salts have received significant attention from scientists focusing on the development of novel bioactive molecules as pesticides and medicines. It is timely and meaningful to summarize the bioactivities of 1,2,4triazolium salt derivatives against various bacteria, fungi, cancer cells, and other pathogens in the past 30 years. Meanwhile, the structure-activity relationship (SAR) of 1,2,4triazolium salts was also summarized. Finally, our perspective on the future development and applications of triazolium salts as agrichemicals or human drugs is presented.

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Section: Structure‐activity Relationship Of 124‐triazolium Saltsmentioning

confidence: 96%

Section: Effects Of the Triazolium Electronic Properties On Bioactivi...mentioning

confidence: 99%

Section: Anticancer Activities Of Mono-124-triazolium Saltsmentioning

confidence: 99%

“…A series of N,N′ ‐bis‐substituted 1,2,4‐triazolium salts with functional groups at the N1‐ and N4‐position were synthesized by Shelton et al [34] . in 2019.…”

Section: Bioactivities Of Mono‐124‐triazolium Saltsmentioning

confidence: 99%

See 2 more Smart Citations

Bioactivities of Triazolium‐Based N‐Heterocyclic Carbene Salts

Song

Zou

Jin

et al. 2023

Chemistry A European J

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“…The AAT Bioquest IC 50 calculator (ATT Bioquest, Inc., Sunnyvale, CA, USA) was used to compute IC 50 values [43].…”

Section: In Vitro Evaluation Of the Anti-proliferative Activity Of Th...mentioning

confidence: 99%

Synthesis of Novel Conjugated Linoleic Acid (CLA)-Coated Superparamagnetic Iron Oxide Nanoparticles (SPIONs) for the Delivery of Paclitaxel with Enhanced In Vitro Anti-Proliferative Activity on A549 Lung Cancer Cells

et al. 2022

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The application of Superparamagnetic Iron Oxide Nanoparticles (SPIONs) as a nanomedicine for Non-Small Cell Lung Carcinoma (NSCLC) can provide effective delivery of anticancer drugs with minimal side-effects. SPIONs have the flexibility to be modified to achieve enhanced oading of hydrophobic anticancer drugs such as paclitaxel (PTX). The purpose of this study was to synthesize novel trans-10, cis-12 conjugated linoleic acid (CLA)-coated SPIONs loaded with PTX to enhance the anti-proliferative activity of PTX. CLA-coated PTX-SPIONs with a particle size and zeta potential of 96.5 ± 0.6 nm and −27.3 ± 1.9 mV, respectively, were synthesized. The superparamagnetism of the CLA-coated PTX-SPIONs was confirmed, with saturation magnetization of 60 emu/g and 29 Oe coercivity. CLA-coated PTX-SPIONs had a drug loading efficiency of 98.5% and demonstrated sustained site-specific in vitro release of PTX over 24 h (i.e., 94% at pH 6.8 mimicking the tumor microenvironment). Enhanced anti-proliferative activity was also observed with the CLA-coated PTX-SPIONs against a lung adenocarcinoma (A549) cell line after 72 h, with a recorded cell viability of 17.1%. The CLA-coated PTX-SPIONs demonstrated enhanced suppression of A549 cell proliferation compared to pristine PTX, thus suggesting potential application of the nanomedicine as an effective site-specific delivery system for enhanced therapeutic activity in NSCLC therapy.

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S‐Aryl Substitution Enhances Acidity of the 1,2,4‐Triazolium Scaffold

Smith,

Blundell,

Hickson

et al. 2024

Eur J Org Chem

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The 1,2,4‐triazolium scaffold in asymmetric organocatalysis results in remarkable rate accelerations, with reactions typically occurring via N‐heterocyclic carbene (NHC) intermediates. Although the most acidic NHC pre‐catalyst class, there remains scope for further increases in acidity particularly for aqueous organocatalysis applications. The acidity‐enhancing effects of thio‐substituents on carbon acidity are well‐documented but not explored in the 1,2,4‐triazolium scaffold. Herein, we report the synthesis of a large series of N, N‐dialkyl‐C(3)‐S‐aryltriazolium ions and quantitative kinetic evaluation of C(5)‐H acidity. The direct attachment of S‐aryl substituents to the triazolium heterocycle results in substantial increases in protofugalities (kinetic acidities) with second order rate constants (kDO) for C(5)‐H deprotonation by DO− base that are 2.9‐60.3 fold higher than for reference 1,4‐dimethyl‐1,2,4‐triazolium iodide in D2O solution. Protofugalities for the N, N‐dialkyl‐C(3)‐S‐aryltriazolium series are similar to commonly used bicyclic N‐aryl‐1,2,4‐triazolium organocatalysts despite having two electron donating N‐alkyl substituents. This highlights the future potential of this NHC design which could enable the introduction of two chiral alkyl substituents close to the C(5) carbenic position with pre‐catalyst acidity controlled by distal C(3)‐S‐aryl substitution. Detailed X‐ray structural data‐protofugality correlations enabled evaluation of the S‐aryl substituent effect origins. C(5)‐H pKa values (16.9‐18.6) were calculated by utilisation of experimental protofugalities.

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Synthesis and Anti‐proliferative Activity of N,N′‐bis‐substituted 1,2,4‐Triazolium Salts against Breast Cancer and Prostate Cancer Cell Lines

Cited by 10 publications

References 13 publications

Bioactivities of Triazolium‐Based N‐Heterocyclic Carbene Salts

Bioactivities of Triazolium‐Based N‐Heterocyclic Carbene Salts

Synthesis of Novel Conjugated Linoleic Acid (CLA)-Coated Superparamagnetic Iron Oxide Nanoparticles (SPIONs) for the Delivery of Paclitaxel with Enhanced In Vitro Anti-Proliferative Activity on A549 Lung Cancer Cells

S‐Aryl Substitution Enhances Acidity of the 1,2,4‐Triazolium Scaffold

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