Synthesis of Platinum Complexes from Sugar Derivatives

Almeida, Mauro Vieira de; César, Eloi Teixeira; Fontes, Ana Paula Soares; Felício, Emanoel de Castro Antunes

doi:10.1080/07328300008544081

Cited by 10 publications

(8 citation statements)

References 4 publications

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“…d ‐Galactose derivatives were prepared using a method previously described (10). d‐ galactose was first converted into 6‐deoxy‐6‐iodo‐1,2:3,4‐di‐ O ‐isopropylidene‐α‐ d‐ galactopyranose 7 according to the literature procedure (11–13) and then treated with five different amino alcohols in ethanol under reflux (Scheme 2). Purification of the crude products was carried out by column chromatography (hexane:ethyl acetate) resulting in the isolation of amino alcohols 8a–e at 40–80% yields.…”

Section: Resultsmentioning

confidence: 99%

“…Optical rotations were measured with a Perkin-Elmer 341 polarimeter (Perkin Elmer, Waltham, MA, USA), using a sodium lamp at 20°C. 1 H and 13 C NMR spectra were recorded on Bruker Advance DRX300 spectrometer (Bruker Corporation, Billerica, MA, USA). Thin-layer chromatography (TLC) was performed on glass plates and silica gel sheets (Silica Gel F254; Merck, Whitehouse Station, NJ, USA), visualized with iodine vapor, and ⁄ or revealed with ethanolic H 2 SO 4 solution.…”

Section: General Methodsmentioning

confidence: 99%

“…All the compounds were purified by column chromatography. The structure was assigned by Infrared, 1 H NMR, 13 C NMR, and COSY experiments.…”

Section: Preparation Of Amino Alcohols Condensed With Carbohydratesmentioning

confidence: 99%

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Preparation of Amino Alcohols Condensed with Carbohydrates: Evaluation of Cytotoxicity and Inhibitory Effect on NO Production

et al. 2010

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This work reports the preparation of several amino alcohols condensed with D-arabinose, D-glucose, and D-galactose derivatives. These compounds were evaluated in vitro for their cytotoxicity and ability to decrease nitric oxide production in J774A.1 cells. Arabinofuranoside derivatives 5a, 5b and 5c showed a significant inhibition of nitric oxide production (>80% at 5 lg ⁄ mL), while the galactopyranoside derivative 8d showed a notable nitric oxide inhibitory activity (126% at 0.5 lg ⁄ mL).

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Section: Resultsmentioning

confidence: 99%

Section: General Methodsmentioning

confidence: 99%

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Preparation of Amino Alcohols Condensed with Carbohydrates: Evaluation of Cytotoxicity and Inhibitory Effect on NO Production

et al. 2010

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“…Linkage through an ethylenediamine was also carried out with D-galactose and D-ribose, but the activity of the complexes was not investigated. 96 …”

Section: Platinum(ii) Compounds With a Mechanism Of Action Similarmentioning

confidence: 99%

The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs

2016

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The platinum drugs, cisplatin, carboplatin, and oxaliplatin, prevail in the treatment of cancer,, but new platinum agents have been very slow to enter the clinic. Recently, however, there has been a surge of activity, based on a great deal of mechanistic information, aimed at developing non-classical platinum complexes that operate via mechanisms of action distinct from those of the approved drugs. The use of nanodelivery devices has also grown and many different strategies have been explored to incorporate platinum warheads into nanomedicine constructs. In this review, we discuss these efforts to create the next generation of platinum anticancer drugs. The introduction provides the reader with a brief overview of the use, development, and mechanism of action of the approved platinum drugs to provide the context in which more recent research has flourished. We then describe approaches that explore non-classical platinum(II) complexes with trans geometry and with a monofunctional coordination mode, polynuclear platinum(II) compounds, platinum(IV) prodrugs, dual-treat agents, and photoactivatable platinum(IV) complexes. Nanodelivery particles designed to deliver platinum(IV) complexes will also be discussed, including carbon nanotubes, carbon nanoparticles, gold nanoparticles, quantum dots, upconversion nanoparticles, and polymeric micelles. Additional nanoformulations including supramolecular self-assembled structures, proteins, peptides, metal-organic frameworks, and coordination polymers will then be described. Finally, the significant clinical progress made by nanoparticle formulations of platinum(II) agents will be reviewed. We anticipate that such a synthesis of disparate research efforts will not only help to generate new drug development ideas and strategies, but also reflect our optimism that the next generation of platinum cancer drugs is about to arrive.

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“…However, the water-soluble platinum complexes archived by means of amine ligands instead of ammonia are most intriguing because the carrier ligands provide broad spectrum of antitumor activity [30]. For instance, water-soluble platinum(II) complexes of diamine chelating ligands bearing amino-acid type substituents [31], the carbohydrate-metal complexes, have been proved a potential effective method [32–36]. But the synthesis of this complex is extremely laborious, which also lacks clinical data.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Interaction with Biomolecules of Platinum(II) Complexes with Shikimic Acid-Based Ligands

Peng

Chen

et al. 2013

Bioinorganic Chemistry and Applications

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Starting from the active ingredient shikimic acid (SA) of traditional Chinese medicine and NH2(CH2)nOH, (n = 2–6), we have synthesized a series of new water-soluble Pt(II) complexes PtLa–eCl2, where La–e are chelating diamine ligands with carbon chain covalently attached to SA (La–e = SA-NH(CH2)nNHCH2CH2NH2; La, n = 2; Lb, n = 3; Lc, n = 4; Ld, n = 5; Le, n = 6). The results of the elemental analysis, LC-MS, capillary electrophoresis, and 1H, 13C NMR indicated that there was only one product (isomer) formed under the present experimental conditions, in which the coordinate mode of PtLa–eCl2 was two-amine bidentate. Their in vitro cytotoxic activities were evaluated by MTT method, where these compounds only exhibited low cytotoxicity towards BEL7404, which should correlate their low lipophilicity. The interactions of the five Pt(II) complexes with DNA were investigated by agarose gel electrophoresis, which suggests that the Pt(II) complexes could induce DNA alteration. We also studied the interactions of the Pt(II) complexes with 5′-GMP with ESI-MS and 1H NMR and found that PtLbCl2, PtLcCl2, and PtLdCl2 could react with 5′-GMP to form mono-GMP and bis-GMP adducts. Furthermore, the cell-cycle analysis revealed that PtLbCl2, PtLcCl2 cause cell G2-phase arrest after incubation for 72 h. Overall, these water-soluble Pt(II) complexes interact with DNA mainly through covalent binding, which blocks the DNA synthesis and replication and thus induces cytotoxicity that weakens as the length of carbon chain increases.

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Synthesis of Platinum Complexes from Sugar Derivatives

Abstract: Six new platinum(II) complexes containing a diamino sugar, analogs of cisplatin and carboplatin, have been prepared and characterized. The new ligands were obtained by reaction of D-galactose and D-ribose derivatives with ethylenediamine.

Cited by 10 publications

References 4 publications

Preparation of Amino Alcohols Condensed with Carbohydrates: Evaluation of Cytotoxicity and Inhibitory Effect on NO Production

Preparation of Amino Alcohols Condensed with Carbohydrates: Evaluation of Cytotoxicity and Inhibitory Effect on NO Production

The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs

Synthesis, Characterization, and Interaction with Biomolecules of Platinum(II) Complexes with Shikimic Acid-Based Ligands

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