<scp>L</scp>-Methionine increases the rate of reaction of 5′-guanosine monophosphate with the anticancer drug cisplatin: mixed-ligand adducts and reversible methionine binding

Barnham, Kevin J.; Djuran, Miloš I.; Murdoch, Piedad del Socorro; Ranford, John D.; Sadler, Peter J.

doi:10.1039/dt9950003721

Cited by 82 publications

(61 citation statements)

References 14 publications

(2 reference statements)

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“…However, from the differences in sequence-dependent binding rates of the hydrolysis products of cisplatin to double-stranded oligonucleotides, it has been concluded that the diaqua and/or the aqua/ hydroxo complex resulting from hydrolysis of both chloro ligands rather than the chloro/ aqua complex seems to be the major species interacting with DNA in vivo (Kozelka et al 1999;Legendre et al 2000). Entirely different, hydrolysis-independent routes to DNA adduct formation involving intermediates with reversibly bound thioether ligands have been proposed based on the observation that methionine (Barnham et al 1995b) and other thioether ligands (van Boom et al 1999) bound monodentally to the platinum centre may be exchanged for GMP (for a review see Reedijk 1999). However, the following recent findings argue against the assumption that such pathways of DNA platination contribute significantly to the tumour-inhibiting activity of cisplatin: thioether-containing intermediates bind to oligonucleotides with rather slow kinetics , while replacement of thioether ligands by thiol-containing ligands in the presence of the latter proceeds much faster and results in species which appear unlikely to serve as intermediates due to their high stability .…”

Section: The First Generation -Cisplatinmentioning

confidence: 97%

Tumour-inhibiting platinum complexes—state of the art and future perspectives

Jakupec

Galanski

Keppler

2003

Reviews of Physiology, Biochemistry and Pharmacology

381

349

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Thirty years after the onset of the first clinical studies with cisplatin, the development of antineoplastic platinum drugs continues to be a productive field of research. This article reviews the current preclinical and clinical status, including a discussion of the molecular basis for the activity of the parent drug cisplatin and platinum drugs of the second and third generation, in particular their interaction with DNA. Further emphasis is laid on the development of third generation platinum drugs with activity in cisplatin-resistant tumours, particularly on chelates containing 1,2-diaminocyclohexane (DACH) and on the promising and more recently evolving field of non-classic ( trans- and multinuclear) platinum complexes. The development of oral platinum drugs and drug targeting strategies using liposomes, polymers or low-molecular-weight carriers in order to improve the therapeutic index of platinum chemotherapy are also covered.

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Section: The First Generation -Cisplatinmentioning

confidence: 97%

Tumour-inhibiting platinum complexes—state of the art and future perspectives

Jakupec

Galanski

Keppler

2003

Reviews of Physiology, Biochemistry and Pharmacology

381

349

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“…However, these bridged complexes are unlikely to be reactive towards DNA bases, although the ammine complexes can slowly release ammonia. [29,30] Reactions carried out with [PtCl(dien)]Cl and methionine (Met) or methylated glutathione (GSMe) [26,27] and 5Ј GMP have indicated that the platinumϪsulfur adducts [Pt(dien)(Met-S)] 2ϩ and [Pt(dien)-(GSMe-S)] 2ϩ are formed initially with subsequent intermolecular displacement of the thioether in the PtϪS adducts by 5Ј GMP-N7. Interestingly, this displacement of guanine-N7 has been observed only with thioether adducts and not for reactions with thiolate complexes.…”

Section: Introductionmentioning

confidence: 99%

Novel Adducts of the Anticancer Drug Oxaliplatin with Glutathione and Redox Reactions with Glutathione Disulfide

et al. 2003

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Reactions of [Pt(rac‐1,2‐DACH)Cl2], [Pt(1R,2R‐DACH)Cl2] and the anticancer drug oxaliplatin with the tripeptide glutathione and glutathione disulfide have been studied by HPLC, ESI‐MS and NMR methods. The same two major products are formed in each reaction: a thiolate‐bridged dimer and a novel thiolate‐bridged dinuclear macrochelate containing a nine‐membered chelate ring. Redox reactions of PtII anticancer drugs with biological disulfides are of potential importance to their mechanism of action. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…92, 93 In contrast to the reversibility of thioether binding, glutathione is not readily displaced from Pt(II) by nucleotides. MT is another target with a high affinity for Pt(II); it has the ability to react directly with cisplatin without preliminary hydrolysis to the aqueous species.…”

Section: -88mentioning

confidence: 99%

Metal‐Based Drugs

Shaw

2005

Encyclopedia of Inorganic Chemistry

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Metallopharmaceuticals have a long history in the development of chemotherapy. The more recent success of cisplatin and six related Pt‐based antitumor drugs, and longer histories of chrysotherapy (gold treatments) for arthritis, bismuth antiulcer agents, and silver‐, antimony‐ and arsenic‐based antimicrobial agents demonstrate that the periodic table represents a potential wealth of medicinal agents to be explored and developed in the future. This article reviews the use of twelve elements (Ag, As, Au, Bi, Ga, Li, Pt, Ru, Sb, Sn, Ti, V) for a wide variety of diseases and disorders. The current state of research on particular applications varies widely – from promising treatments that have not yet reached the clinic to those that are well established empirically despite uncertain mechanisms of action. The array of antitumor agents licensed or in clinical trials includes compounds of As, Ga, Ru, and Ti, in addition to platinum. There are also exciting efforts to apply known treatments or biological properties to new diseases by taking advantage of extensive databases, for example, developing antitumor agents from organotin complexes that have long been used as fungicides and antifouling agents, and antimicrobial agents from gold complexes. The ability to modulate the properties of metal complexes by choice of the oxidation state (Au I vs Au III ; Pt II vs Pt IV ; V III , V IV & V V , etc.) and design of the medical carrier ligands (e.g. 1,2‐diaminocyclohexane vs two ammine ligands for Pt antitumor agents) allows targeting of particular tissues or cells and balancing of lipophilicity, solubility, and reactivity to balance therapeutic activity against toxicity. Many, if not most, metallopharmaceuticals are prodrugs that undergo redox changes and/or ligand exchange reactions in vivo to generate the active species. Hence, research on metallodrug metabolism and pharmacology is as important as the initial medicinal screening of the agents.

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L-Methionine increases the rate of reaction of 5′-guanosine monophosphate with the anticancer drug cisplatin: mixed-ligand adducts and reversible methionine binding

Cited by 82 publications

References 14 publications

Tumour-inhibiting platinum complexes—state of the art and future perspectives

Tumour-inhibiting platinum complexes—state of the art and future perspectives

Novel Adducts of the Anticancer Drug Oxaliplatin with Glutathione and Redox Reactions with Glutathione Disulfide

Metal‐Based Drugs

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