Tandem mass spectrometry characterization of a conjugate between oleuropein and hydrated <i>cis</i>‐diammineplatinum(II)

Ventura, Giovanni; Abbattista, Ramona; Calvano, Cosima Damiana; Ceglie, Cristina De; Losito, Ilario; Palmisano, Francesco; Cataldi, Tommaso R. I.

doi:10.1002/rcm.8394

Cited by 5 publications

(5 citation statements)

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“…This complex binds to DNA purine base forming adduct which inhibits transcription and finally kills the cancerous cell. This study shows that Ole or HTyr and hydrated CP form conjugate in water solution, what could be of interest when considering the mechanisms by which they might contribute to reducing CP-induced toxicity (116).…”

Section: Olive Oil Polyphenols Combined With Anticancer Drugsmentioning

confidence: 78%

“…CP increased 8-OHdG, malondialdehyde (MDA) and total oxidative stress (TOS) and also caused severe tissue damages, while Ole (200 mg kg -1 ) decreased these parameters and improved tissue damages. In addition, the interaction between Ole and HTyr with hydrated CP was investigated by the use of reverse-phase liquid chromatography coupled to electrospray ionization and mass spectrometry (RPLC-ESI-MS) and by MS/MS measurements (116). Hydrated CP is the active form of CP, with labile chloride ligands in CP complex exchanged by water.…”

Section: Olive Oil Polyphenols Combined With Anticancer Drugsmentioning

confidence: 99%

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Anticancer effects of olive oil polyphenols and their combinations with anticancer drugs

et al. 2019

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Cancer presents one of the leading causes of death in the world. Current treatment includes the administration of one or more anticancer drugs, commonly known as chemotherapy. The biggest issue concerning the chemotherapeutics is their toxicity on normal cells and persisting side effects. One approach to the issue is chemoprevention and the other one is the discovery of more effective drugs or drug combinations, including combinations with polyphenols. Olive oil polyphenols (OOPs), especially hydroxytyrosol (HTyr), tyrosol (Tyr) and their derivatives oleuropein (Ole), oleacein and oleocanthal (Oc) express anticancer activity on different cancer models. Recent studies report that phenolic extract of virgin olive oil may be more effective than the individual phenolic compounds. Also, there is a growing body of evidence about the combined treatment of OOPs with various anticancer drugs, such as cisplatin, tamoxifen, doxorubicin and others. These novel approaches may present an advanced strategy in the prevention and treatment of cancer.

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Section: Olive Oil Polyphenols Combined With Anticancer Drugsmentioning

confidence: 78%

Section: Olive Oil Polyphenols Combined With Anticancer Drugsmentioning

confidence: 99%

Anticancer effects of olive oil polyphenols and their combinations with anticancer drugs

et al. 2019

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“…Hypocholesterolemic [118] and hypoglycemic [119] activities, together with the lipid metabolism enhancement effect, potentially useful to alleviate obesity [120], have been also attested in the literature. The role of oleuropein as a mitigating agent for kidney injury induced by the well-known anti-tumoral drug cisplatin, through conjugate generation, has been explored by LC-ESI-MS/MS [121].…”

Section: Olive Leavesmentioning

confidence: 99%

Bioactive Compounds in Waste By-Products from Olive Oil Production: Applications and Structural Characterization by Mass Spectrometry Techniques

Abbattista

Ventura

Calvano

et al. 2021

Foods

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In recent years, a remarkable increase in olive oil consumption has occurred worldwide, favoured by its organoleptic properties and the growing awareness of its health benefits. Currently, olive oil production represents an important economic income for Mediterranean countries, where roughly 98% of the world production is located. Both the cultivation of olive trees and the production of industrial and table olive oil generate huge amounts of solid wastes and dark liquid effluents, including olive leaves and pomace and olive oil mill wastewaters. Besides representing an economic problem for producers, these by-products also pose serious environmental concerns, thus their partial reuse, like that of all agronomical production residues, represents a goal to pursue. This aspect is particularly important since the cited by-products are rich in bioactive compounds, which, once extracted, may represent ingredients with remarkable added value for food, cosmetic and nutraceutical industries. Indeed, they contain considerable amounts of valuable organic acids, carbohydrates, proteins, fibers, and above all, phenolic compounds, that are variably distributed among the different wastes, depending on the employed production process of olive oils and table olives and agronomical practices. Yet, extraction and recovery of bioactive components from selected by-products constitute a critical issue for their rational valorization and detailed identification and quantification are mandatory. The most used analytical methods adopted to identify and quantify bioactive compounds in olive oil by-products are based on the coupling between gas- (GC) or liquid chromatography (LC) and mass spectrometry (MS), with MS being the most useful and successful detection tool for providing structural information. Without derivatization, LC-MS with electrospray (ESI) or atmospheric pressure chemical (APCI) ionization sources has become one of the most relevant and versatile instrumental platforms for identifying phenolic bioactive compounds. In this review, the major LC-MS accomplishments reported in the literature over the last two decades to investigate olive oil processing by-products, specifically olive leaves and pomace and olive oil mill wastewaters, are described, focusing on phenolics and related compounds.

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“…[CblCo III —C≡N—Pt II (NH 3 ) 2 Cl] + , where CblCo III —C≡N represents the CNCbl molecule ( 1 ). The purified reaction mixture solution of unreacted CNCbl and CNCbl‐mCP was injected into the RPLC/ESI‐MS system and the separation was carried out using a RP column packed with an amide‐embedded C18 stationary phase bonded to superficially porous type‐B silica microparticles (2.6 μm) 26 . The gradient elution program and mobile phase composition have been discussed elsewhere 27 .…”

Section: Resultsmentioning

confidence: 99%

In vitro reactions of a cyanocobalamin–cisplatin conjugate with nucleoside monophosphates

Ventura

Calvano

Losito

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Cisplatin (CP) is a widely used anticancer drug characterized by toxic side effects that could be alleviated using novel delivery systems including CP prodrugs. The in vitro incubation of a putative prodrug, obtained from cyanocobalamin (CNCbl) and cis‐diamminemonochloroplatinum(II) (mCP), with nucleoside monophosphates (NMPs) was investigated. Methods The in vitro reactions between the putative prodrug CNCbl‐mCP and the NMPs of adenosine (AMP), guanosine (GMP), cytidine (CMP) and uridine (UMP) were carried out in slightly acidic water–methanol solutions at 37°C for 24 h. Each sample was examined using reversed‐phase liquid chromatography coupled with electrospray ionization in positive ion mode and tandem mass spectrometry (RPLC/ESI‐MS/MS) by collision‐induced dissociation in a linear ion‐trap mass spectrometer. Results Seven adducts were recognized as formed by substitution reactions of the chloride ligand in planar CP. Comparison between observed and theoretical isotopic patterns together with MS/MS fragmentation pathways revealed the presence of single or multiple binding sites depending on the NMP involved. The CNCbl‐mCP conjugate was found to interact with N7 or O4 atoms of GMP and UMP, respectively, generating single adducts, while two isomeric adducts were observed for CMP. Finally, AMP gave rise to three isomeric adducts. Conclusions In agreement with literature data relevant to the interaction between CP and NMPs, the most reactive nucleotides were AMP and GMP. The present RPLC/ESI‐MS/MS approach is very promising for investigation of the reactions of CP conjugates with ribonucleotides not only in vitro but also in vivo.

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Tandem mass spectrometry characterization of a conjugate between oleuropein and hydrated cis‐diammineplatinum(II)

Cited by 5 publications

References 50 publications

Anticancer effects of olive oil polyphenols and their combinations with anticancer drugs

Anticancer effects of olive oil polyphenols and their combinations with anticancer drugs

Bioactive Compounds in Waste By-Products from Olive Oil Production: Applications and Structural Characterization by Mass Spectrometry Techniques

In vitro reactions of a cyanocobalamin–cisplatin conjugate with nucleoside monophosphates

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