Synthesis and anticancer activity of lipophilic platinum(II) complexes of 3,5-diisopropylsalicylate

Yu, Yanyan; Lou, Liguang; Liu, Weiping; Zhu, Hua‐Jie; Ye, Qingsong; Chen, Xi-Zhu; Gao, Wengui; Hou, Shuhua

doi:10.1016/j.ejmech.2007.09.006

Cited by 30 publications

(10 citation statements)

References 20 publications

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“…One of the earliest leads in the development of Pt complexes with activity in resistant tumor cells was a series of complexes with 1,2-diaminocyclohexane (DACH) carrier ligand (Burchenal et al 1978;Burchenal et al 1979). Consequently many substituted DACH complexes have been evaluated (Chaney 1995;Kidani 1991;Hoeschele et al 1994) for their cytotoxicity and some of them have entered into preclinical and clinical trials (Yu et al 2006;Liu et al 2007;Rothenburger et al 2006;Yu et al 2008). Thus, it can be deduced that 1R,2R-DACH is an effective carrier group in designing DACH-type platinum derivatives.…”

Section: Introductionmentioning

confidence: 97%

Synthesis, characterization and theoretical calculations of (1,2-diaminocyclohexane)(1,3-diaminopropane)gold(III) chloride complexes: in vitro cytotoxic evaluations against human cancer cell lines

et al. 2015

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The gold(III) complexes of the type (1,2-diaminocyclohexane)(1,3-diaminopropane)gold(III) chloride, [(DACH)Au(pn)]Cl3, [where DACH = cis-, trans-1,2- and S,S-1,2-diaminocyclohexane and pn = 1,3-diaminopropane] have been synthesized and characterized using various spectroscopic and analytical techniques including elemental analysis, UV-Vis and FTIR spectroscopy; solution as well as solid-state NMR measurements. The solid-state (13)C NMR shows that 1,2-diaminocyclohexane (1,2-DACH) and 1,3-diaminopropane (pn) are strongly bound to the gold(III) center via N donor atoms. The stability of the mixed diamine ligand gold(III) was checked by UV-Vis spectroscopy and NMR measurements. The molecular structure of compound 1 (containing cis-1,2-DACH) was determined by X-ray diffraction analysis. The structure of 1 consists of [(cis-DACH)Au(pn)](3+) complex ion and chloride counter ions. Each gold atom in the complex ion adopts a distorted square-planar geometry. The structural details and relative stabilities of the four possible isomers of the complexes were also estimated at the B3LYP/LANL2DZ level of theoretical calculations. The computational study demonstrates that trans- conformations are slightly more stable than the cis- conformations. The antiproliferative effects and cytotoxic properties of the mixed ligand gold(III) complexes were evaluated in vitro on human gastric SGC7901 and prostate PC3 cancer cells using MTT assay. The antiproliferative study of the gold(III) complexes on PC3 and SGC7901 cells indicate that complex 3 (containing 1S,2S-(+)-1,2-(DACH)) is the most effective antiproliferative agent. The IC50 data reveal that the in vitro cytotoxicity of complex 3 against SGC7901 cancer cells manifested similar and very pronounced cytotoxic effects with respect to cisplatin. Moreover, the electrochemical behavior, and the interaction of complex 3 with two well-known model proteins, namely, hen egg white lysozyme and bovine serum albumin is also reported.

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Section: Introductionmentioning

confidence: 97%

Synthesis, characterization and theoretical calculations of (1,2-diaminocyclohexane)(1,3-diaminopropane)gold(III) chloride complexes: in vitro cytotoxic evaluations against human cancer cell lines

et al. 2015

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“…Basically, the platinum(II) oxaliplatin derivatives can be divided into two groups. The first one involves dachbased platinum(II) complexes containing various isomers and derivatives of 1,2-diaminocyclohexane (dach) as N-donor carrier ligands, while a leaving group differs from the oxalate dianion [5][6][7]. The second one comprises the platinum(II) oxalato complexes with bidentate oxalate dianion as a leaving group, and on the other hand, the carrier N-donor ligand differs from dach [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Platinum(II) oxalato complexes with adenine-based carrier ligands showing significant in vitro antitumor activity

Štarha¹,

Trávníček²,

Popa³

2010

Journal of Inorganic Biochemistry

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“…The test compound, dissolved in cell culture medium, was added in final concentrations ranging from 0 to 100 lM. After 72 h, the cellular survival was evaluated by using sulforhodamine B (SRB) assay [14]. The optical density was read at 490 nm.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and anticancer activity of a new water-soluble derivative of heptaplatin, cis-{Pt(II)[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane](3-acetoxyl-cyclobutane-1,1-dicarboxylato)}

et al. 2014

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A new water-soluble derivative of heptaplatin, cis-{Pt(II)[(4R,5R)-4,5bis(aminomethyl)-2-isopropyl-1,3-dioxolane](3-acetoxyl-cyclobutane-1,1-dicarboxylato)} has been synthesized, characterized by elemental analysis, MS, IR, and 1 H, 13 C NMR, and evaluated for in vitro anticancer activity in four human cancer cell lines. The stability of the derivative in water was also investigated by monitoring the changes of 1 H NMR in D 2 O. The results reveal that the new derivative has good solubility and stability in water and also shows high anticancer activity against gastric cancer cells, ovarian cancer cells, and colon cancer cells. Therefore, it is worthy of further evaluation for in vivo antitumor activity and toxicity.

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Synthesis and anticancer activity of lipophilic platinum(II) complexes of 3,5-diisopropylsalicylate

Cited by 30 publications

References 20 publications

Synthesis, characterization and theoretical calculations of (1,2-diaminocyclohexane)(1,3-diaminopropane)gold(III) chloride complexes: in vitro cytotoxic evaluations against human cancer cell lines

Synthesis, characterization and theoretical calculations of (1,2-diaminocyclohexane)(1,3-diaminopropane)gold(III) chloride complexes: in vitro cytotoxic evaluations against human cancer cell lines

Platinum(II) oxalato complexes with adenine-based carrier ligands showing significant in vitro antitumor activity

Synthesis and anticancer activity of a new water-soluble derivative of heptaplatin, cis-{Pt(II)[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane](3-acetoxyl-cyclobutane-1,1-dicarboxylato)}

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