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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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DNA-Intercalative Platinum Anticancer Complexes Photoactivated by Visible Light.

Huayun Shi1, Jana Kasparkova2, Clément Soulié3

  • 1Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 28, 2021
PubMed
Summary

Photoactivatable platinum(IV) complexes conjugated with naphthalimide derivatives show potent cancer cell killing with visible light. These novel agents combat drug resistance with low side effects and enhanced DNA crosslinking capabilities.

Keywords:
DFT calculationsDNA intercalationanticancer activityinterstrand crosslinkingphotoactive platinum complexes

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Area of Science:

  • Inorganic Chemistry
  • Medicinal Chemistry
  • Cancer Therapy

Background:

  • Photoactivatable agents offer targeted cancer therapy with reduced side effects.
  • 1,8-Naphthalimides function as light-harvesting groups, fluorescent probes, and DNA intercalators.
  • Platinum(IV) complexes are explored for their therapeutic potential in cancer treatment.

Purpose of the Study:

  • To synthesize and characterize novel photoactivatable platinum(IV) complexes conjugated with naphthalimide derivatives.
  • To evaluate the photo-cytotoxicity and cellular accumulation of these complexes in various cancer cell lines.
  • To investigate the mechanism of action, including DNA interaction and photo-induced crosslinking.

Main Methods:

  • Conjugation of N-(carboxymethyl)-1,8-naphthalimide (gly-R-Nap) with R substituents to photoactive diazido Pt(IV) complexes.
  • Synthesis of t,t,t-[Pt(py)2(N3)2(OH)(gly-R-Nap)], R=H (1), 3-NO2 (2), or 4-NMe2 (3).
  • Assessment of photo-oxidation, cellular uptake, dark and photo-cytotoxicity using A2780, A549, and PC3 cancer cell lines under visible light irradiation.

Main Results:

  • Complexes 1-3 demonstrated enhanced photo-oxidation, cellular accumulation, and significant photo-cytotoxicity against ovarian, lung, and prostate cancer cells.
  • Low dark cytotoxicity was observed, indicating high selectivity for light-activated therapy.
  • Complexes 1 and 2 showed pre-intercalation into DNA, leading to enhanced photo-induced DNA crosslinking.
  • Complex 3 exhibited red-shifted absorption at 450 nm, enabling photoactivation and photo-cytotoxicity with green light.

Conclusions:

  • The synthesized platinum(IV)-naphthalimide conjugates are effective photoactivatable anticancer agents.
  • These compounds exhibit promising efficacy against a range of cancer types with visible light activation.
  • The ability to combat drug resistance and target cancer cells selectively positions these agents for future therapeutic development.