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Flavin-Conjugated Pt(IV) Anticancer Agents.

Juan Sánchez-Camacho1, Sonia Infante-Tadeo2, Ana C Carrasco1

  • 1Donostia International Physics Center, Paseo Manuel de Lardizabal 4, Donostia 20018, Spain.

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|March 29, 2023
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Summary
This summary is machine-generated.

New platinum(IV) complexes with a tetraacetylriboflavin moiety show targeted activation to platinum(II) anticancer drugs. Covalent bonding enhances selective toxicity in breast cancer cells via redox activation.

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Area of Science:

  • Medicinal Chemistry
  • Inorganic Chemistry
  • Cancer Therapeutics

Background:

  • Platinum(IV) complexes offer a strategy to improve anticancer drug efficacy and reduce toxicity.
  • In situ activation of Pt(IV) to Pt(II) species allows for controlled drug release.
  • Classic platinum agents face challenges with off-target toxicity.

Purpose of the Study:

  • To design and synthesize novel asymmetric Pt(IV) derivatives of cisplatin and oxaliplatin.
  • To investigate the in situ activation of these Pt(IV) complexes.
  • To evaluate the selective anticancer activity of the novel compounds.

Main Methods:

  • Synthesis of Pt(IV) complexes 1·TARF and 2·TARF with a tetraacetylriboflavin (TARF) moiety.
  • Characterization using 1H and 195Pt NMR spectroscopy.
  • In vitro studies on MDA-MB-231 breast cancer cells with varying redox conditions.
  • Density functional theory (DFT) for mechanistic insights.

Main Results:

  • Pt(IV) complexes 1·TARF and 2·TARF were successfully synthesized and activated to Pt(II) species.
  • Activation was confirmed using various reducing agents and conditions (dark/light).
  • Complex 2·TARF showed enhanced toxicity (1-2 orders of magnitude) in breast cancer cells via redox activation, dependent on covalent TARF binding.

Conclusions:

  • Covalently linked tetraacetylriboflavin moieties enable targeted in situ activation of Pt(IV) anticancer agents.
  • Redox-triggered activation of 2·TARF leads to selective enhancement of cytotoxicity in cancer cells.
  • The covalent linkage is crucial for achieving targeted drug activation and improved therapeutic effect.