The assessment of physicochemical properties of Cisplatin complexes with purines and vitamins B group

Szefler, Beata; Czeleń, Przemysław; Kruszewski, Stefan; Siomek-Górecka, Agnieszka; Krawczyk, Przemysław

doi:10.1016/j.jmgm.2022.108144

Cited by 5 publications

(8 citation statements)

References 63 publications

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“…Thiamine (vitamin B1) has the second addition center for interaction such as the nitrogen atom N 1 . The affinities of all vitamins to cis-platinum were analyzed for the first time [ 49 , 50 , 51 , 52 ]. The estimated values of Gibbs free energy (ΔG r ) of reaction for mono- and diaqua platinum complexes of the studied vitamins were compared with the results for guanine in this review ( Figure 7 , Figure 8 , Figure 9 and Figure 10 , Table 1 , Table 2 , Table 3 and Table 4 ).…”

Section: Resultsmentioning

confidence: 99%

“…Cisplatin and oxaliplatin have a similar mechanism of action where for the activation of the relatively inert platinum (II) complexes, the hydrolysis of non-active drugs to diaqua complexes via the monoaqua form is necessary [ 47 , 48 , 49 , 50 , 51 , 52 ] ( Figure 2 , Figure 3 and Figure 4 ).…”

Section: Introductionmentioning

confidence: 99%

“…During the study, the reactivity of hydrolysis products such as monoaqua and diaqua derivatives of three platinum (II)-based drugs, cisplatin, carboplatin and oxaliplatin, was analyzed [ 47 , 48 , 49 , 50 , 51 , 52 ]. Such products as [(cis~[Pt(NH 3 ) 2 Cl(H 2 O)] + ) and (cis~[Pt(NH 3 ) 2 (H 2 O) 2 ] 2+ )] in the case of cisplatin, [Pt(H 2 O)ClDACH] + and [Pt(H 2 O) 2 DACH] 2+ in the case of oxaliplatin and Pt(NH 3 ) 2 H 2 O(OH) + plus Pt(NH 3 ) 2 (OH) 2 in the case of carboplatin can interact not only with nucleobases ( Figure 3 and Figure 4 ), which is the basis of their therapeutic action, but also with all compounds which have aromatic rings in their structures with lone-pair orbitals analogous to N 7 in purine ( Figure 5 and Figure 6 ).…”

Section: Introductionmentioning

confidence: 99%

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Will the Interactions of Some Platinum (II)-Based Drugs with B-Vitamins Reduce Their Therapeutic Effect in Cancer Patients? Comparison of Chemotherapeutic Agents such as Cisplatin, Carboplatin and Oxaliplatin—A Review

Szefler

Czeleń

2023

IJMS

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Pt (II) derivatives show anti-cancer activity by interacting with nucleobases of DNA, thus causing some spontaneous and non-spontaneous reactions. As a result, mono- and diaqua products are formed which further undergo complexation with guanine or adenine. Consequently, many processes are triggered, which lead to the death of the cancer cell. The theoretical and experimental studies confirm that such types of interactions can also occur with other chemical compounds. The vitamins from B group have a similar structure to the nucleobases of DNA and have aromatic rings with single-pair orbitals. Theoretical and experimental studies were performed to describe the interactions of B vitamins with Pt (II) derivatives such as cisplatin, oxaliplatin and carboplatin. The obtained results were compared with the values for guanine. Two levels of simulations were implemented at the theoretical level, namely, B3LYP/6-31G(d,p) with LANL2DZ bases set for platinum atoms and MN15/def2-TZVP. The polarizable continuum model (IEF–PCM preparation) and water as a solvent were used. UV-Vis spectroscopy was used to describe the drug–nucleobase and drug–B vitamin interactions. Values of the free energy (ΔGr) show spontaneous reactions with mono- and diaqua derivatives of cisplatin and oxaliplatin; however, interactions with diaqua derivatives are more preferable. The strength of these interactions was also compared. Carboplatin products have the weakest interaction with the studied structures. The presence of non-covalent interactions was demonstrated in the tested complexes. A good agreement between theory and experiment was also demonstrated.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Will the Interactions of Some Platinum (II)-Based Drugs with B-Vitamins Reduce Their Therapeutic Effect in Cancer Patients? Comparison of Chemotherapeutic Agents such as Cisplatin, Carboplatin and Oxaliplatin—A Review

Szefler

Czeleń

2023

IJMS

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“…Since a few recent reviews dealing with cisplatin [111] and other platinum complexes [112] bearing nucleic acid derivatives have been published, we have focused our attention on other metal centres. The main contributions in this research area involve the use of ruthenium complexes.…”

Section: Metal-based Lipid and Nucleic Acid Drug Conjugatesmentioning

confidence: 99%

“…The last topic presented in this review concerns vitamin metal complexes. Vitamins are essential organic molecules with a specific role in several phases of cell Since a few recent reviews dealing with cisplatin [111] and other platinum complexes [112] bearing nucleic acid derivatives have been published, we have focused our attention on other metal centres. The main contributions in this research area involve the use of ruthenium complexes.…”

Section: Metal-based Vitamin Drug Conjugatesmentioning

confidence: 99%

Recent Advances in Bioconjugated Transition Metal Complexes for Cancer Therapy

2023

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The introduction of biologically relevant organic moieties in the coordination sphere of transition metal complexes has recently become a well-established strategy to increase the selectivity and biocompatibility of metallodrugs. In this review, the major advances achieved in this area of research in the last three years are described in detail. Particular attention is given to the metal complexes bearing the main biomolecules of life: carbohydrates, lipids, nucleotides, proteins and vitamins. Each paragraph summarizes the synthetic strategy employed to obtain the complexes of interest as well as the most interesting biological results obtained with these potential metallodrugs. Moreover, the structure–activity relationships observed by the different research groups are described and discussed, with the goal of suggesting to the reader the ligand/metal centre combinations that provide the most promising results in the fight against cancer. Some of the compounds examined in this review as well as other bioconjugated metal complexes published in recent decades exhibit interesting selectivity towards cancer cells over normal ones and a specific mode of action. These latter aspects are the basis of what is commonly known as anticancer target therapy.

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Capsaicin reverses cisplatin resistance in tongue squamous cell carcinoma by inhibiting the Warburg effect and facilitating mitochondrial‐dependent apoptosis via the AMPK/AKT/mTOR axis

Liu,

Li,

Zhao

et al. 2024

Cell Biology International

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Cisplatin is commonly used for the chemotherapy of tongue squamous cell carcinoma (TSCC); however, adverse side effects and drug resistance impact its therapeutic efficacy. Capsaicin is an active ingredient in chili peppers that exerts antitumor effects, whether it exerts antitumor effects on cisplatin‐resistant cells remains unknown. Therefore, in this study, we investigated the effect of capsaicin on cisplatin resistance in TSCC cells and explored the underlying mechanisms. A cisplatin‐resistant TSCC cell line was established by treated with increasing cisplatin concentrations. Combined treatment with cisplatin and capsaicin decreased the glucose consumption and lactate dehydrogenase activity and increased the adenosine triphosphate production both in vitro and in vivo, suggesting the inhibition of the Warburg effect. Moreover, this combined treatment induced cell apoptosis and significantly upregulated the levels of proapoptotic proteins, such as Bax, cleaved caspase‐3, ‐7, and ‐9, and apoptosis‐inducing factor. In contrast, levels of the antiapoptotic protein, Bcl‐2, were downregulated. Additionally, LKB1 and AMPK activities were stimulated, whereas those of AKT and mTOR were suppressed. Notably, AMPK knockdown abolished the inhibitory effects of capsaicin and cisplatin on the AKT/mTOR signaling pathway and Warburg effect. Overall, combined treatment with capsaicin and cisplatin reversed cisplatin resistance by inhibiting the Warburg effect and facilitating mitochondrial‐dependent apoptosis via the AMPK/AKT/mTOR axis. Our findings suggest combination therapy with capsaicin and cisplatin as a potentially novel strategy and highlight capsaicin as a promising adjuvant drug for TSCC treatment.

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The assessment of physicochemical properties of Cisplatin complexes with purines and vitamins B group

Cited by 5 publications

References 63 publications

Will the Interactions of Some Platinum (II)-Based Drugs with B-Vitamins Reduce Their Therapeutic Effect in Cancer Patients? Comparison of Chemotherapeutic Agents such as Cisplatin, Carboplatin and Oxaliplatin—A Review

Will the Interactions of Some Platinum (II)-Based Drugs with B-Vitamins Reduce Their Therapeutic Effect in Cancer Patients? Comparison of Chemotherapeutic Agents such as Cisplatin, Carboplatin and Oxaliplatin—A Review

Recent Advances in Bioconjugated Transition Metal Complexes for Cancer Therapy

Capsaicin reverses cisplatin resistance in tongue squamous cell carcinoma by inhibiting the Warburg effect and facilitating mitochondrial‐dependent apoptosis via the AMPK/AKT/mTOR axis

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