On the hydrolytic stability of unsymmetric platinum(<scp>iv</scp>) anticancer prodrugs containing axial halogens

Xu, Zoufeng; Tang, Wai Kit; Zhou, Qiyuan; Chen, Shu; Siu, Chi‐Kit; Zhu, Guangyu

doi:10.1039/d1qi00208b

Cited by 15 publications

(15 citation statements)

References 52 publications

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“…The selectivity of those compounds relies on the more inert structure, which is activated via reduction in the tumor. While conceptually promising, the physiopathology and the metabolic heterogeneity of cancer, [240][241][242] together with the diversity in the nature and behavior of prodrugs 116,243,244 has resulted in diverse unpredictable outcomes. Even for prodrugs which show high stability and inertness in in vitro studies, the safety improvement with respect to the corresponding Pt(II) active drug has not been enough for approval, such as satraplatin in combination with prednisolone for the treatment of metastatic hormone-refractory prostate cancer.…”

Section: Drawbacks Of Metallodrugs In Clinical Translationmentioning

confidence: 99%

Metallodrugs in cancer nanomedicine

et al. 2022

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Section: Drawbacks Of Metallodrugs In Clinical Translationmentioning

confidence: 99%

Metallodrugs in cancer nanomedicine

et al. 2022

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“…The same trend occurred when fluorine is replaced with chlorine and later bromine; they have peaks at 579.5031 and 1549.4873 ppm, respectively. This proves that the NMR peaks generated by the members of the halogen family in ascorbic acid have a close linear relationship with their electronegativity Table gives the precise individual positions of the halogen members in terms of ppm.…”

Section: Resultsmentioning

confidence: 56%

“…This proves that the NMR peaks generated by the members of the halogen family in ascorbic acid have a close linear relationship with their electronegativity. 38 Table 3 gives the precise individual positions of the halogen members in terms of ppm.…”

Section: Resultsmentioning

confidence: 99%

Halogen Doping to Control the Band Gap of Ascorbic Acid: A Theoretical Study

et al. 2022

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Ascorbic acid is an important antioxidant agent that acts as an electron donor and is involved in many physiological processes. Structural modification in ascorbic acid is a subject of extensive biochemical research due to its involvement in a variety of relevant phenomena including electron transport, complex redox reactions, neurochemical reactions, enzymatic reactions, and chemotherapeutic potential. In this work, the structure of ascorbic acid is modified via doping with the first three members of the halogen group to investigate the changes in the electronic structure and spectroscopic parameters using first-principles methods. To obtain the lowest-energy structures, different basis sets in density functional theory (DFT) and Hartree−Fock approaches were employed in the geometry optimization process. The potential energy maps of the structures were computed to study the molecular orientations and their optical and electrical properties. The spectroscopic properties were computed via UV−vis and nuclear magnetic resonance (NMR) spectroscopies to study the effects of doping into the compound. To obtain further insights into the chemical structure, the Fourier transform infrared (FT-IR) spectra of the materials were theoretically investigated. It was found that the band gap is sensitive to doping as we moved from fluorine to chlorine and then to bromine.

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“…In the axial positions, the choice of different ligands brings versatile functions and significantly changes solubility, targeting ability, and pharmacological properties of Pt(IV) prodrugs. This makes the axial modification an excellent strategy, deserving further explorations ( Xu et al, 2021a ). Although the nature of the ligands and the length of the linker between ligands and Pt center in the axial positions remarkably affect the properties of Pt(IV) prodrugs, no apparent regularity has been found.…”

Section: Remarks and Prospectsmentioning

confidence: 99%

Ligand Evolution in the Photoactivatable Platinum(IV) Anticancer Prodrugs

et al. 2022

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Photoactivatable Pt(IV) anticancer prodrugs with the structure of [PtIV(N1)(N2)(L1)(L2)(A1)(A2)], where N1 and N2 are non-leaving nitrogen donor ligands, L1 and L2 are leaving ligands, and A1 and A2 are axial ligands, have attracted increasing attention due to their promising photo-cytotoxicity even to cisplatin-resistant cancer cells. These photochemotherapeutic prodrugs have high dark-stability under physiological conditions, while they can be activated by visible light restrained at the disease areas, as a consequence showing higher spatial and temporal controllability and much more safety than conventional chemotherapy. The coordinated ligands to the Pt center have been proved to be pivotal in determining the function and activity of the photoactivatable Pt(IV) prodrugs. In this review, we will focus on the development of the coordinated ligands in such Pt(IV) prodrugs and discuss the effects of diverse ligands on their photochemistry and photoactivity as well as the future evolution directions of the ligands. We hope this review can help to facilitate the design and development of novel photoactivatable Pt(IV) anticancer prodrugs.

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On the hydrolytic stability of unsymmetric platinum(iv) anticancer prodrugs containing axial halogens

Abstract: The longstanding notion that Pt(IV) complexes are inert under physiological conditions where there are limited reducing agents is facing a great challenge. Herein, we systematically investigated the hydrolytic stability of...

Cited by 15 publications

References 52 publications

Metallodrugs in cancer nanomedicine

Metallodrugs in cancer nanomedicine

Halogen Doping to Control the Band Gap of Ascorbic Acid: A Theoretical Study

Ligand Evolution in the Photoactivatable Platinum(IV) Anticancer Prodrugs

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