The interaction of the anti-cancer drug cisplatin with phospholipids is specific for negatively charged phospholipids and takes place at low chloride ion concentration

Speelmans, Gea; Sips, Wendy; Grisel, R.J.H.; Staffhorst, Rutger W.H.M.; Fichtinger-Schepman, Anne Marie J.; Reedijk, Jan; Kruijff, Ben de

doi:10.1016/0005-2736(96)00080-6

Cited by 65 publications

(58 citation statements)

References 22 publications

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“…It has been reported that when cisplatin [(NH3)2PtC12]+0 is dissolved in aqueous solvents, the C1 ions are replaced by water molecules, resulting in positively-charged species, which are able to interact with hydroxyapatite: the monohydrated-monochloro derivative [(NH3),PtCl(H20)]+' and the dehydrated species [ ( N H I )~P~( H~O ) , ] +~ [26,29,33,35]. These hydrated species may also lose a proton to form the corresponding conjugate-bases.…”

Section: Discussionmentioning

confidence: 99%

Hydroxyapatite crystals as a local delivery system for cisplatin: adsorption and release of cisplatin in vitro

Barroug

Glimcher

2002

Journal Orthopaedic Research

146

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This study describes the characteristics of the in vitro binding and release of the anti-tumor drug cisplatin by slurries of synthetic hydroxyapatite crystals carried out in aqueous media. The adsorption of cisplatin by slurries of hydroxyapatite and its release were found to depend significantly on the ionic composition of the aqueous media used. At a constant p H of 7.4, significantly more cisplatin is adsorbed by the hydroxyapatite crystals in the slurry from a chloride-free phosphate buffered solution or a Tris buffered solution than from a buffered phosphate solution containing chloride ions. The amount of hydroxyapatite-bound cisplatin desorbed into solution was also progressively increased as a function of the increasing concentration of chloride in the equilibrating solution. Very little hydroxyapatite-bound cisplatin was released from the crystals in either a Tris or phosphate buffer. These results suggest that it is the hydrated derivatives of cisplatin which are involved in the adsorption of cisplatin by hydroxyapatite crystals. The adsorption data can be expressed as a Freundlich isotherm from which the association constant can be calculated. The rate of release of cisplatin bound to crystals of hydroxyapatite is relatively slow even at the maximum concentration of chloride ions in the phosphate buffer. Approximately 33% of the total cisplatin bound to the crystals of hydroxyapatite was released after 4.35 days. An additional l5'% of the remaining cisplatin bound to the hydroxyapatite cyrstals was released after an additional equilibration with fresh buffer for two weeks (58% of the total cisplatin originally bound). These findings suggest that cisplatin bound to slurries of hydroxyapatite crystals may be useful in the local treatment of malignant tumors.

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Section: Discussionmentioning

confidence: 99%

Hydroxyapatite crystals as a local delivery system for cisplatin: adsorption and release of cisplatin in vitro

Barroug

Glimcher

2002

Journal Orthopaedic Research

146

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“…4 Meanwhile, much information has been gathered on the interactions between transition metal ions and lipids bilayers. 5 Earlier work of Reedijk et al investigated the role of metal-lipid interactions in cis-platin chemotherapy, 6,7 whereas Constable, 8 Hunter 9,10 and Lehn 11 showed how coordination of transition metal ions to membrane-embedded ligands could induce vesicle aggregation and fusion. It was for example highlighted that when ligands are embedded in the two dimensions of a lipid bilayer their coordination chemistry might be different compared to bulk solution.…”

Section: Introductionmentioning

confidence: 99%

Zinc coordination to the bapbpy ligand in homogeneous solutions and at liposomes: zinc detection via fluorescence enhancement

et al. 2013

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In this work, the complexation of the bapbpy ligand to zinc dichloride is described (bapbpy = 6,6'-bis(2-aminopyridyl)-2,2'-bipyridine). The water-soluble, colorless complex [Zn(bapbpy)Cl]Cl·2H 2 O (compound 2·H 2 O) was synthesized; its X-ray crystal structure shows a mononuclear, pentacoordinated geometry with one chloride ligand in apical position. Upon excitation of its lowest-energy absorption band

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“…The aquated platinum species binds preferentially to the highly nucleophilic N-7 positions of guanine and adenine (5). Apart from DNA and RNA, cisplatin also interacts with intracellular proteins and polypeptides (6) and with negatively charged phospholipids in intact human erythrocytes and tumor cells (7)(8)(9). Despite the obvious interactions of cisplatin with membrane components, few studies have been done on entry of cisplatin into target cells and its facilitated transport (10,11).…”

Section: Introductionmentioning

confidence: 99%

Endocytic Recycling Compartments Altered in Cisplatin-Resistant Cancer Cells

et al. 2006

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The clinical utility of cisplatin to treat human malignancies is often limited by the development of drug resistance. We have previously shown that cisplatin-resistant human KB adenocarcinoma cells that are cross-resistant to methotrexate and heavy metals have altered endocytic recycling. In this work, we tracked lipids in the endocytic recycling compartment (ERC) and found that the distribution of the ERC is altered in KB-CP.5 cells compared with parental KB-3-1 cells. A tightly clustered ERC is located near the nucleus in parental KB-3-1 cells but it appears loosely arranged and widely dispersed throughout the cytoplasm in KB-CP.5 cells. The altered distribution of the ERC in KB-CP.5 cells is related to the amount and distribution of stable detyrosinated microtubules (Glu-A-tubulin), as previously shown in Chinese hamster ovary B104-5 cells that carry a temperature-sensitive Glu-A-tubulin allele. In addition, B104-5 cells with a dispersed ERC under nonpermissive conditions were more resistant to cisplatin compared with B104-5 cells with a clustered ERC under permissive conditions. We conclude that resistance to cisplatin might be due, in part, to reduced uptake of cisplatin resulting from an endocytic defect reflecting defective formation of the ERC, possibly related to a shift in the relative amounts and distributions of stable microtubules.

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The interaction of the anti-cancer drug cisplatin with phospholipids is specific for negatively charged phospholipids and takes place at low chloride ion concentration

Cited by 65 publications

References 22 publications

Hydroxyapatite crystals as a local delivery system for cisplatin: adsorption and release of cisplatin in vitro

Hydroxyapatite crystals as a local delivery system for cisplatin: adsorption and release of cisplatin in vitro

Zinc coordination to the bapbpy ligand in homogeneous solutions and at liposomes: zinc detection via fluorescence enhancement

Endocytic Recycling Compartments Altered in Cisplatin-Resistant Cancer Cells

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