Ferrocene-based modulators of cancer-associated tumor pyruvate kinase M2

Jadhav, Jyotika; Das, Rudradip; Kamble, Sayali; Chowdhury, Moumita Ghosh; Kapoor, Saumya; Gupta, Astha; Vyas, Het; Shard, Amit

doi:10.1016/j.jorganchem.2022.122338

Cited by 14 publications

(26 citation statements)

References 43 publications

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“…Melting points were determined on a Buchi M-560 capillary melting points apparatus in an open glass capillary and are reported without any standard deviation. 39 General Procedure for the Synthesis of 7-Ferrocenyl-Substituted Pyrazolopyrimidines. The synthesis was carried out in a single step via the classical multicomponent reaction (Scheme 1a).…”

Section: ■ Concluding Remarksmentioning

confidence: 99%

“…All the products were fully characterized by their 1 H and 13 C NMR spectra and HRMS values. 39 General Procedure for the Synthesis of 5-Ferrocenyl-Substituted Pyrazolopyrimidines. The reaction proceeded in two steps in one pot (Scheme 1b).…”

Section: ■ Concluding Remarksmentioning

confidence: 99%

“…Consequently, EDS analysis was also performed. 39 X-ray Crystallography. The data were collected from a single crystal at 297 K on a Bruker APEX-II CCD diffractometer equipped with a PHOTON II detector using graphite monochromated Mo Kα radiation (λ = 0.7107 Å).…”

Section: -Cyclopropyl-7-ferrocenyl-5-(2′-hydroxy)phenylpyrazolo[15a]p...mentioning

confidence: 99%

“…The ORTEP diagram of the compound was generated using ORTEP-3, and packing diagrams were generated using Mercury CSD 2020.3.0. 39 The crystal and refinement data for the compound are shown in Table S1. Full details are reported in the Supporting Information.…”

Section: -Cyclopropyl-7-ferrocenyl-5-(2′-hydroxy)phenylpyrazolo[15a]p...mentioning

confidence: 99%

“…38 Recently, our group has reported a set of ferrocene-based triazolopyrimidines that were potent against oral cancer. 39 We hereby report the syntheses and characterization of a series of FPPs and their biological activities. In all the modifications, the ferrocene ring was maintained around the heterocyclic pyrazolopyrimidine core.…”

Section: ■ Introductionmentioning

confidence: 99%

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A Series of Ferrocene-Containing Pyrazolo[1,5-a]pyrimidines Induce a Strong Antiproliferative Effect against Oral Cancer Cells

et al. 2022

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Bio-organometallic agents confer superior physicochemical profiles inaccessible to purely organic molecules. As current chemotherapeutic regimes are maligned by the toxicity and chemoresistance of cisplatin and carboplatin, the development of an arsenal of metallodrugs becomes indispensable. Metallocenes such as ferrociphenols, JAHA, and ferrocene-labeled estradiol exhibit potent anticancer profiles. Oral squamous cell carcinomas are shown to be an excellent model to assess the impact of ferrocene-based pyrazolopyrimidines (FPPs) as chemotherapeutic agents. We show here synthesis and preliminary mechanistic investigations of FPPs in the CAL 27 cell line. The results established that some of the FPPs like 4u display strong antiproliferative behavior selectively against cisplatin-resistant oral cancer cells with an IC 50 value of 7.49 μM. It was also found to activate tumor pyruvate kinase M2 (PKM2), a critical metabolic conduit in cancer. Furthermore, 4u induced apoptosis in cells and arrested cell growth in the S-phase of the cell cycle. In silico studies established that the molecule binds at the DASA-58 binding site of PKM2.

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Section: ■ Concluding Remarksmentioning

confidence: 99%

Section: ■ Concluding Remarksmentioning

confidence: 99%

Section: -Cyclopropyl-7-ferrocenyl-5-(2′-hydroxy)phenylpyrazolo[15a]p...mentioning

confidence: 99%

Section: -Cyclopropyl-7-ferrocenyl-5-(2′-hydroxy)phenylpyrazolo[15a]p...mentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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A Series of Ferrocene-Containing Pyrazolo[1,5-a]pyrimidines Induce a Strong Antiproliferative Effect against Oral Cancer Cells

et al. 2022

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Recent Progress on the Synthesis, Biological Activity of Fused Pyrimidines from Azole Amines

Zhuang,

Wang,

Liu

et al. 2024

Eur J Org Chem

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Fused pyrimidines are a class of heterocyclic compounds that have gained considerable interest due to their extensive biological activities and potential applications in drug development. This review article aims to provide a comprehensive overview of the latest synthetic approaches to fused pyrimidines, including Michael reactions, multicomponent reactions, metal‐catalyzed reactions, photocatalytic reactions, peroxide‐mediated reactions, and inverse electron demand Diels–Alder reactions. Furthermore, the biological activities of these compounds, such as their ability to combat cancer and microbial infections, are also discussed. This review article summarizes the existing literature on the synthesis and biological activity of fused pyrimidines from 2020 to 2023. We hope this review article will inspire the development of more effective and less toxic fused pyrimidine drugs with well‐designed structures.

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Self‐Amplifying Iridium(III) Photosensitizer for Ferroptosis‐Mediated Immunotherapy Against Transferrin Receptor‐Overexpressing Cancer

Ling

Wang

Liu

et al. 2022

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Photoimmunotherapy is attractive for cancer treatment due to its spatial controllability and sustained responses. This work presents a ferrocene‐containing Ir(III) photosensitizer (IrFc1) that can bind with transferrin and be transported into triple‐negative breast cancer (TNBC) cells via a transferrin receptor‐mediated pathway. When the ferrocene in IrFc1 is oxidized by reactive oxygen species, its capability to photosensitize both type I (electron transfer) and type II (energy transfer) pathways is activated through a self‐amplifying process. Upon irradiation, IrFc1 induces the generation of lipid oxidation to cause ferroptosis in TNBC cells, which promotes immunogenic cell death (ICD) under both normoxia and hypoxia. In vivo, IrFc1 treatment elicits a CD8+ T‐cell response, which activates ICD in TNBC resulting in enhanced anticancer immunity. In summary, this work reports a small molecule‐based photosensitizer with enhanced cancer immunotherapeutic properties by eliciting ferroptosis through a self‐amplifying process.

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Ferrocene-based modulators of cancer-associated tumor pyruvate kinase M2

Cited by 14 publications

References 43 publications

A Series of Ferrocene-Containing Pyrazolo[1,5-a]pyrimidines Induce a Strong Antiproliferative Effect against Oral Cancer Cells

A Series of Ferrocene-Containing Pyrazolo[1,5-a]pyrimidines Induce a Strong Antiproliferative Effect against Oral Cancer Cells

Recent Progress on the Synthesis, Biological Activity of Fused Pyrimidines from Azole Amines

Self‐Amplifying Iridium(III) Photosensitizer for Ferroptosis‐Mediated Immunotherapy Against Transferrin Receptor‐Overexpressing Cancer

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