Synthesis of Pt(II) complexes of the type [Pt(1,10-phenanthroline)(SArFn)2] (SArFn = SC6H3-3,4-F2; SC6F4-4-H; SC6F5). Preliminary evaluation of their in vitro anticancer activity

Backman-Blanco, Geraldine; Valdés, Hugo; Ramírez‐Apán, María Teresa; Cano‐Sánchez, Patricia; Hernández‐Ortega, Simón; Orjuela, Adrián L.; Alí‐Torres, Jorge; Flores‐Gaspar, Areli; Reyes-Martínez, Reyna; Morales‐Morales, David

doi:10.1016/j.jinorgbio.2020.111206

Cited by 19 publications

(4 citation statements)

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“…The mechanism of action of most optimized platinum drugs still relies primarily on interaction with DNA, resulting in unselective activity and toxicity. , Therefore, the search for new lead structures to design complexes with more tumor selectivity or with an alternative mode of action is ongoing. , …”

Section: Introductionmentioning

confidence: 99%

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Development of Cytotoxic GW7604-Zeise’s Salt Conjugates as Multitarget Compounds with Selectivity for Estrogen Receptor- Positive Tumor Cells

Grabher,

Kapitza,

Hörmann

et al. 2024

J. Med. Chem.

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but-1-enyl)phenyl)acrylic acid (GW7604) as a carrier was esterified with alkenols of various lengths and coordinated through the ethylene moiety to PtCl 3 , similar to Zeise's salt (K-[PtCl 3 (C 2 H 4 )]). The resulting GW7604-Alk-PtCl 3 complexes (Alk = Prop, But, Pent, Hex) degraded in aqueous solution only by exchange of the chlorido ligands. For example, GW7604-Pent-PtCl 3 coordinated the amino acid alanine in the cell culture medium, bound the isolated nucleotide 5′-GMP, and interacted with the DNA (empty plasmid pSport1). It accumulated in estrogen receptor (ER)-positive MCF-7 cells primarily via cytosolic vesicles, while it was only marginally taken up in ER-negative SKBr3 cells. Accordingly, GW7604-Pent-PtCl 3 and related complexes were inactive in SKBr3 cells. GW7604-Pent-PtCl 3 showed high affinity to ERα and ERβ without mediating agonistic or ER downregulating properties. GW7604-Alk ligands also increased the cyclooxygenase (COX)-2 inhibitory potency of the complexes. In contrast to Zeise's salt, the GW7604-Alk-PtCl 3 complexes inhibited COX-1 and COX-2 to the same extent.

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Section: Introductionmentioning

confidence: 99%

“… 21 , 22 Therefore, the search for new lead structures to design complexes with more tumor selectivity or with an alternative mode of action is ongoing. 23 , 24 …”

Section: Introductionmentioning

confidence: 99%

Development of Cytotoxic GW7604-Zeise’s Salt Conjugates as Multitarget Compounds with Selectivity for Estrogen Receptor- Positive Tumor Cells

Grabher,

Kapitza,

Hörmann

et al. 2024

J. Med. Chem.

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“…Consequently, further platinum complexes have been developed with distinctly different mechanisms of action as a way to address the limitations of clinically used platinum(II) drugs. This includes platinum(II) complexes that incorporate a broader range of ligands such as heteroaromatic, iminoether, or asymmetric aliphatic amine ligands that allow them to form monofunctional adducts or bind noncovalently to biological target(s). , Complexes that incorporate non-labile ligands are unlikely to form covalent bonds with macrobiomolecules. A prominent example of this is a class of complexes in the [Pt(P L )(A L )] 2+ type framework, where P L is a polyaromatic ligand and A L is a chiral ancillary ligand.…”

Section: Introductionmentioning

confidence: 99%

Novel Platinum(II) and Platinum(IV) Antitumor Agents that Exhibit Potent Cytotoxicity and Selectivity

et al. 2022

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A novel platinum(II) complex 47OMESS(II) and its platinum(IV) derivative 47OMESS(IV) were synthesized and characterized. Cytotoxicity studies against mesenchymal cells (MCs) and lung (A549), breast (MDA-MB-231), and melanoma (A375) cancer cells demonstrated 7−20-fold superior activity for both complexes relative to cisplatin. Remarkably, 47OMESS(IV) demonstrated 17−22-fold greater selectivity toward the cancerous cells compared to the non-cancerous MCs. Western blot analysis on A549 cells showed the involvement of the intrinsic apoptotic pathway. Cellular fractionation and uptake experiments in A549 cells using ICPmass spectrometry (MS) indicated that 47OMESS(II) and 47OMESS(IV) cross the cellular membrane predominantly via active transport mechanisms. The significant improvement in selectivity that is exhibited by 47OMESS(IV) is reported for the first time for this class of complexes.

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“…In this way, we have recently published the supramolecular analysis of complexes [Pt(1,10-phen)(SR F ) 2 ] (SR F = SC 6 H 3 F 2 -3,4-F, SC 6 F 4 -4-H, and SC 6 F 5 ) (REF CODE: LUQMIW, LUQMOC and LUQMUI). 26 Supramolecular analysis revealed that in the complex containing the difluorinated thiolate, crystal stabilization was carried out mainly by phen⋯phen (π-π intermolecular interaction) and C-F⋯H interactions. In the case of the other two complexes, the supramolecular organization in both the interaction phen⋯phen was observed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a series of Pd(ii) complexes of the type [Pd(1,10-phen)(SR_F)₂]: an interesting case of solvatomorphism

et al. 2022

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Synthesis of Pt(II) complexes of the type [Pt(1,10-phenanthroline)(SArFn)2] (SArFn = SC6H3-3,4-F2; SC6F4-4-H; SC6F5). Preliminary evaluation of their in vitro anticancer activity

Cited by 19 publications

References 56 publications

Development of Cytotoxic GW7604-Zeise’s Salt Conjugates as Multitarget Compounds with Selectivity for Estrogen Receptor- Positive Tumor Cells

Development of Cytotoxic GW7604-Zeise’s Salt Conjugates as Multitarget Compounds with Selectivity for Estrogen Receptor- Positive Tumor Cells

Novel Platinum(II) and Platinum(IV) Antitumor Agents that Exhibit Potent Cytotoxicity and Selectivity

Synthesis of a series of Pd(ii) complexes of the type [Pd(1,10-phen)(SR_F)₂]: an interesting case of solvatomorphism

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Synthesis of Pt(II) complexes of the type [Pt(1,10-phenanthroline)(SArFn)2] (SArFn = SC6H3-3,4-F2; SC6F4-4-H; SC6F5). Preliminary evaluation of their in vitro anticancer activity

Cited by 19 publications

References 56 publications

Development of Cytotoxic GW7604-Zeise’s Salt Conjugates as Multitarget Compounds with Selectivity for Estrogen Receptor- Positive Tumor Cells

Development of Cytotoxic GW7604-Zeise’s Salt Conjugates as Multitarget Compounds with Selectivity for Estrogen Receptor- Positive Tumor Cells

Novel Platinum(II) and Platinum(IV) Antitumor Agents that Exhibit Potent Cytotoxicity and Selectivity

Synthesis of a series of Pd(ii) complexes of the type [Pd(1,10-phen)(SRF)2]: an interesting case of solvatomorphism

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Product

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Synthesis of a series of Pd(ii) complexes of the type [Pd(1,10-phen)(SR_F)₂]: an interesting case of solvatomorphism