Antiproliferative and anti-tumor activity of organotin compounds

Hadjikakou, Sotiris K.; Hadjiliadis, Nick

doi:10.1016/j.ccr.2007.12.026

Cited by 398 publications

(270 citation statements)

References 63 publications

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“…Many of them exhibited interesting activity against specific cancer cell lines, and moreover, many of them turned out to be more effective than traditional heavy-metal anticancer drugs [1][2][3][4][5][6][7][8][9][10][11][12]. Therefore, investigation of new compounds with potential antitumor activity and side effects as low as possible has attracted considerable attention.…”

Section: Introductionmentioning

confidence: 99%

Lipid and DNA interaction with the triorganotin dimethylaminophenylazobenzoates studied by DSC and spectroscopy methods

Pruchnik

Kral

Hof

2018

J Therm Anal Calorim

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The aim of the study was to investigate and compare the interaction of tributyltin (TBTA) and triphenyltin (TPhTA) 2-[4 (dimethylamino)phenylazo]benzoates complexes with the lipid membrane and plasmid DNA. Both TBTA and TPhTA belong to the group of promising anticancer agents. Differential scanning calorimetry method was employed to examine the heat signal associated with phase transitions of liposomes formed from dipalmitoylphosphatidylcholine (DPPC) or DPPC/cholesterol and modified with TBTA and TPhTA. The investigated compounds influence the thermotropic parameters of the DPPC and DPPC/cholesterol lipid bilayer in a slightly different way: Although the temperature of the main phase transition of the DPPC remains almost unaffected, the addition of TPhTA can abolish sub-and pre-transition when added in sufficiently high concentrations. At the same time, the addition of the TBTA practically does not change the sub-transition and only slightly influences the pre-transition. The effect of organotin compounds on plasmid DNA was investigated using single-molecule florescence technique and time-correlated single-photon counting fluorescence correlation spectroscopy. Influence of TBTA and TPhTA on DNA resulted only in fractional conformation change which did not lead to the tightly packed conformation however, analysis of the diffusion times indicates that TPhTA interacts with DNA in a different mode than TBTA.

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Section: Introductionmentioning

confidence: 99%

Lipid and DNA interaction with the triorganotin dimethylaminophenylazobenzoates studied by DSC and spectroscopy methods

Pruchnik

Kral

Hof

2018

J Therm Anal Calorim

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“…The compounds show a wide variety of biological activity: bactericidal, fungicidal, caricidal, and pesticidal [1][2][3][4][5][6]. In recent years, many triorgano-and diorganotin compounds have been synthesized and tested for their antitumor activity in vitro against a large variety of tumor lines.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, many triorgano-and diorganotin compounds have been synthesized and tested for their antitumor activity in vitro against a large variety of tumor lines. Many of them are more effective than traditional heavy metal anticancer drugs [3,6]. A series of triorgano-and diorganotin carboxylates, aminocarboxylates, oxamates etc., display interesting antitumor activity.…”

Section: Introductionmentioning

confidence: 99%

“…The most active antitumor agents are diorganotin and triorganotin compounds [1][2][3][4][5][6][7][8][9]. Antitumor activity depends on the properties of group coordinated to tin atom and most frequently diminishes in the order: [2][3][4][5][6][7][8][10][11][12]. The mechanism of biological action of organotin derivatives is still not clear but due to their lipophilicity organotins are membrane-active-for example, disruption of membrane integrity may occur because of organotin binding or insertion into the membrane.…”

Section: Introductionmentioning

confidence: 99%

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Interaction of new butyltin citrate complex with lipid model membrane and DNA

Pruchnik

Kral

Hof

2014

J Therm Anal Calorim

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Organotin(IV) complexes show a wide variety of biological activity: bactericidal, fungicidal, caricidal, and pesticidal. Many of them are more effective than traditional heavy metal anticancer drugs. The aim of the present study was to investigate the interaction of a new dibutyltin complex with citric acid (DBTC) with lipid membrane and plasmid DNA. The effect of this compound on the multilamellar liposomes formed with dipalmitoylphosphatidylcholine, dimyristoylphosphatidylcholine, and dimyristoylphosphatidylethanolamine was studied mainly by the means of differential scanning calorimetry and additionally by the steady-state fluorimetry. Calorimetrical results together with fluorescence spectroscopy suggest that investigated complex interacts with lipids and probably locates itself in the hydrophilic part of the membrane. The effect of DBCT on plasmid DNA was investigated using single-molecule florescence technique and time-correlated single photon counting fluorescence correlation spectroscopy. We could conclude then that DBTC-DNA interaction occurs due to the interaction with the DNA phosphate group and charge neutralization which then leads to DNA compaction.

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“…Recently, interests in organotin(IV) carboxylates are increasing due to their possible medical uses as antitumor agents [12]. Novel organotin(IV) complexes of L-Arginine (HArg), N a -t-Boc-Arginine (Boc-Arg-OH) along with complexes with the dipeptide, L-Alanyl-L-Arginine (H 2 Ala-Arg) were synthesized.…”

Section: Introductionmentioning

confidence: 99%

New organotin(IV) complexes with l-Arginine, Nα-t-Boc-l-Arginine and l-Alanyl-l-Arginine: Synthesis, structural investigations and cytotoxic activity

Girasolo

Rubino

Portanova

et al. 2010

Journal of Organometallic Chemistry

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Organotin(IV) NMR Cytotoxic activity a b s t r a c tNovel diorganotin(IV) derivatives of L-Arginine (HArg), N a -(tert-Butoxycarbonyl)-L-Arginine (Boc-Arg-OH) and L-Ala-L-Arg (H 2 Ala-Arg), H 2 NC(@NH)NH(CH 2 ) 3 CH(NHR 0 )CO 2 H, where H COSY NMR spectroscopy, in solution. The spectroscopic characterization leading to the proposed molecular structures was accomplished on the basis of these experiments. L-Arginine appears to behave as a chelating ligand through carboxylate and -NH 2 groups in Me 2 Sn(Arg) 2 , while in N a -t-Boc-L-Arginine complex, the N a -protected amino group being exempted from coordination, only the carboxylate groups are effectors of bonding to the organometallic moieties. FT-IR spectra give a clear indication that guanidino groups in all the complexes are not involved in coordination, since m(C@N-H) frequency of the terminal guanidino group is fairly constant and unshifted relative to the free ligand. The biological activity of organotin(IV)-complexes was also investigated by use of human HT29 colorectal carcinoma cells. The cytotoxic activity of the compounds was determined by the MTT quantitative colorimetric assay, capable of detecting viable cells in comparison with that exerted by cisplatin. A marked cytotoxic activity for nearly all complexes, is evident being higher than that exerted by cisplatin, while no significant improvement of activity was observed for Me 2 Sn(Arg) 2 and Me 2 Sn(Ala-Arg), which was confirmed by IC 50 values. Then, we assessed whether the cytotoxicity induced by organotin(IV) complexes was associated with the induction of apoptosis. Light microscopy analysis, performed to study the morphological changes induced in HT29 cells, confirmed the results obtained with MTT test. No significant morphological alterations were observed in HT29 cells after treatment with Me 2 Sn(Ala-Arg) and Me 2 Sn(L-Arg) 2 . Cells treated with n Bu 2 Sn(Boc-Arg) 2 , n Bu 2 Sn(Ala-Arg), n Bu 3 Sn(Boc-Arg) and Me 3 Sn(Boc-Arg), appeared rounded, isolated and detached from culture substrate, indicating the commitment to apoptotic cell death.

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Antiproliferative and anti-tumor activity of organotin compounds

Cited by 398 publications

References 63 publications

Lipid and DNA interaction with the triorganotin dimethylaminophenylazobenzoates studied by DSC and spectroscopy methods

Lipid and DNA interaction with the triorganotin dimethylaminophenylazobenzoates studied by DSC and spectroscopy methods

Interaction of new butyltin citrate complex with lipid model membrane and DNA

New organotin(IV) complexes with l-Arginine, Nα-t-Boc-l-Arginine and l-Alanyl-l-Arginine: Synthesis, structural investigations and cytotoxic activity

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