Stepwise assembly of platinum–folic acid conjugates

Gabano, Elisabetta; Ravera, Mauro; Cassino, Claudio; Bonetti, Samuele; Palmisano, Giovanni; Osella, Domenico

doi:10.1016/j.ica.2007.09.020

Cited by 22 publications

(19 citation statements)

References 37 publications

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“…Therefore, [PtCl 2 (en)] (en: ethylenediamine) was treated with AgNO 3 to form the respective diaqua complex [Pt(OH 2 ) 2 (en)](NO 3 ) 2 , which was then further reacted with the sodium salt of ibuprofen. [18a, c, 19] The reaction, however, led to a mixture of the desired product 2 and side products, which probably resulted from salt formation between the starting materials. Therefore, conjugate 2 was instead prepared by reaction of ibuprofen with a platinum(II) carbonato complex [Pt(CO 3 )(en)], which was formed by reacting [PtCl 2 (en)] with Ag 2 CO 3 .…”

Section: Resultsmentioning

confidence: 99%

Conjugation of Cisplatin Analogues and Cyclooxygenase Inhibitors to Overcome Cisplatin Resistance

et al. 2014

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Cyclooxygenase (COX) is an enzyme involved in tumorigenesis and is associated with tumor cell resistance against platinum-based antitumor drugs. Cisplatin analogues were conjugated with COX inhibitors (indomethacin, ibuprofen) to study the synergistic effects that were previously observed in combination treatments. The conjugates ensure concerted transport of both drugs into cells, and subsequent intracellular cleavage enables a dual-action mode. Whereas the platinum(II) complexes showed cytotoxicities similar to those of cisplatin, the platinum(IV) conjugates revealed highly increased cytotoxic activities and were able to completely overcome cisplatin-related resistance. Although some of the complexes are potent COX inhibitors, the conjugates appear to execute their cytotoxic action via COX-independent mechanisms. Instead, the increased lipophilicity and kinetic inertness of the conjugates seem to facilitate cellular accumulation of the platinum drugs and thus improve the efficacy of the antitumor agents. These conjugates are important tools for the elucidation of the direct influence of COX inhibitors on platinum-based anticancer drugs in tumor cells.

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Section: Resultsmentioning

confidence: 99%

Conjugation of Cisplatin Analogues and Cyclooxygenase Inhibitors to Overcome Cisplatin Resistance

et al. 2014

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“…Therefore, we followed the method developed by Kamiń ski (see Supporting Information), which proved to be successful in the synthesis of peptide bonds. [21][22][23] We carried out the coupling at the NH 2 group of commercially available diethyl 2-aminomalonate hydrochloride or ditert-butyl-2-(3-aminopropyl)malonate [24] to the benzoic acid derivatives (Scheme 1). According to the conditions for the coupling developed by Kamiń ski, subjection of diethyl 2-aminomalonate hydrochloride to 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmorpholine (NMM) (0 8C!room temperature, 20 h) in the presence of the above-mentioned benzoic acid derivatives in DMF, led to diethyl esters L4-L6, with yields ranging from satisfactory to excellent.…”

Section: Synthesis Of the Ligands Derived From Malonatementioning

confidence: 99%

The Relevance of Polar Surface Area (PSA) in Rationalizing Biological Properties of Severalcis‐Diamminemalonatoplatinum(II) Derivatives

et al. 2009

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A panel of six cis-diamminemalonatoplatinum(II) derivatives were designed and synthesized, and their physicochemical properties and in vitro biological activity were experimentally evaluated and studied in silico. All the complexes showed higher IC(50) values (> or =20 microM) than those observed for cisplatin and its malonato analogue on three different human tumor cell lines, namely A2780 ovarian carcinoma, A549 lung carcinoma, and MCF-7 breast carcinoma. In silico studies revealed that polar surface area (PSA) is the best descriptor to explain the poor biological activity observed for this series of new compounds, which in turn is likely due to poor cellular uptake. This finding is in line with general rules that assign a major role to PSA in characterizing the transport properties of drugs, in the actual case of antiproliferative metallopharmaceuticals.

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“…For instance, transferrin has been exploited for the delivery of CDDP into proliferating malignant cells that over-express transferrin receptors [14]. On the same score, biomolecules such as folic acid [15,16], estrogen [17], herceptin [18], and galactose residues [19,20] have also been incorporated into hybrid complexes to enhance the targeting property of the drugs towards tumor tissues with respective receptors. In our recent work, the demineralized ferritin, i.e.…”

Section: Introductionmentioning

confidence: 99%

Characterization and cellular uptake of platinum anticancer drugs encapsulated in apoferritin

Xing

Wang

Zhang

et al. 2009

Journal of Inorganic Biochemistry

115

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Stepwise assembly of platinum–folic acid conjugates

Cited by 22 publications

References 37 publications

Conjugation of Cisplatin Analogues and Cyclooxygenase Inhibitors to Overcome Cisplatin Resistance

Conjugation of Cisplatin Analogues and Cyclooxygenase Inhibitors to Overcome Cisplatin Resistance

The Relevance of Polar Surface Area (PSA) in Rationalizing Biological Properties of Severalcis‐Diamminemalonatoplatinum(II) Derivatives

Characterization and cellular uptake of platinum anticancer drugs encapsulated in apoferritin

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