Organometallic compounds in oncology: implications of novel organotins as antitumor agents

Alama, Angela; Tasso, Bruno; Novelli, Federica; Sparatore, Fabio

doi:10.1016/j.drudis.2009.02.002

Cited by 230 publications

(149 citation statements)

References 56 publications

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“…In fact, only the butyl-MnTPPS derivatives induce the apoptosis showing to be still effective at the lower concentrations at which they affect the growth of A375 cells. Moreover, among the butyltin complexes, a stronger and interesting effect of tributyltin (MnTPPS4) is evident compared with dibutyltin (MnTPPS2), in agreement with what previously reported by us (18,19) and others (31).…”

Section: Discussionsupporting

confidence: 81%

“…Organometallic compounds have been gaining growing importance in oncology, especially tin-derivatives that, together with gold-, are enjoying an increasing interest and appear very promising as potential drugs (31). Those investigated by us in early (18,19) and in the present studies have the peculiarity to contain the organometallic moieties bonded to the oxygen atoms of the side chain sulfonatophenyl groups of a porphyrin ring.…”

Section: Discussionmentioning

confidence: 90%

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Apoptosis and cell growth arrest in A375 human melanoma cells by diorganotin(IV) and triorganotin(IV) complexes of [meso-Tetra(4-sulfonatophenyl)porphine] manganese(III)chloride

Costa

Zito

Emma³

et al. 2011

Int J Oncol

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Abstract.In previous studies we have demonstrated that two derivatives of meso-Tetra(4-sulfonatophenyl)porphine (TPPS), (Bu 2 Sn) 2 TPPS and (Bu 3 Sn) 4 TPPS, cause apoptotic death of A375 melanoma cells and, at lower concentrations, arrest of cell proliferation. In the present study, we examined if the manganese metal inside the porphyrin cavity could improve the efficacy of this class of compounds. Thus, [mesoTetra(4-sulfonatophenyl)porphine]Mn(III)Cl (=MnTPPS) derivatives, namely (Me 2 Sn) 2 MnTPPS, (Bu 2 Sn) 2 MnTPPS, (Me 3 Sn) 4 MnTPPS and (Bu 3 Sn) 4 MnTPPS, were tested on the A375 human melanoma cell line. A cytotoxicity assay showed that (Bu 2 Sn) 2 MnTPPS and (Bu 3 Sn) 4 MnTPPS were highly cytotoxic by inducing apoptosis in melanoma cells, as shown by DNA fragmentation analysis and by apoptotic nuclei fluorescence, and when used at lower concentrations, they affected only cellular proliferation. An arrest of cell proliferation was also observed with (Me 3 Sn) 4 MnTPPS, but at the highest concentrations used. Moreover, the lower concentration of (Bu 3 Sn) 4 MnTPPS induced a change in cell morphology, from a polygonal to an elongated and spindleshaped phenotype, likewise to its cognate (Bu 3 Sn) 4 TPPS, previously tested. Western blotting analysis showed indeed that both tributyltin compounds, i.e. (Bu 3 Sn) 4 MnTPPS and (Bu 3 Sn) 4 TPPS, lowered levels of the major proteins involved in tumorigenesis: ß-catenin, c-myc and snail. We also demonstrated that all compounds entered the cells and localized in the nuclei. In conclusion, our results show that, in spite of the Mn(III) metal introduction, the butyl derivatives always have a higher efficacy than methyl derivatives, and the tributyltin compounds in particular have an interesting effect in vitro on A375 cell proliferation.

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Section: Discussionsupporting

confidence: 81%

Section: Discussionmentioning

confidence: 90%

Apoptosis and cell growth arrest in A375 human melanoma cells by diorganotin(IV) and triorganotin(IV) complexes of [meso-Tetra(4-sulfonatophenyl)porphine] manganese(III)chloride

Costa

Zito

Emma³

et al. 2011

Int J Oncol

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“…In an organotin compound, the organotin moiety exerts the cytotoxicity [20]. It is the nature and the number of alkyl groups bonded to the tin atom that give organotin compounds varying degrees of toxicity [1,21].…”

Section: Synthesis and Characterization Of Novel Diorganotin(iv) Compmentioning

confidence: 99%

“…Meanwhile, the ligand plays an important role in transporting the molecules to the target while preventing premature interactions with biomolecules. For this purpose, sulfur-containing ligands are particularly suitable to carry out the task [20].…”

Section: Synthesis and Characterization Of Novel Diorganotin(iv) Compmentioning

confidence: 99%

Synthesis and Characterization of Novel Diorganotin(IV) Complexes Derived from N-Methyl-phenethyl Dithiocarbamate and Bis(2-ethoxyethyl) Dithiocarbamate

Pim

Awang²,

Mohamad

et al. 2018

Asian J. Chem.

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“…The organotin (IV) compounds possess significant biological activities Wu et al 2009;Alama et al 2009;Affan et al 2009). These compounds have been found as antitumor (Mohan et al, 1988;Ruan et al, 2011), antibacterial (Maiti et al, 1988;Gleeson et al 2008), antifungal (Manav et al, 2000;Singh and Kaushik, 2008) and antiviral (Singh et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Activities of Organotin (IV) Methylcyclohexyldithiocarbamate Compounds

Awang¹,

Baba

Yamin³

et al. 2011

American Journal of Applied Sciences

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Problem statement:The growing interest in the chemistry of sulphur donor ligands are due to their encouraging anticancer, antibacterial and antifungal activities as well as their widespread industrial application. Dithiocarbamates belong to this class and much attention has been paid to them. Approach: Novel organotin compounds with the molecular formula R m Sn[S 2 CN(CH 3 )(C 6 H 11 )] 4-m (where m = 2, R = CH 3 , C 2 H 5; m = 3, R = C 6 H 5 ) have been synthesized using in situ method. These compounds were characterized by elemental analysis, IR, 1 H and 13 C NMR spectroscopy. Results: Elemental analysis revealed that all compounds were of good purity. Infrared spectra of the compounds showed that the thioureide ν(C-N) band was in the region 1450-1500 cm . Conclusion:The studied compounds were found to have the potential in biological activity especially in cytotoxicity where this possibly can be used for clinical trials after further research.

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Organometallic compounds in oncology: implications of novel organotins as antitumor agents

Cited by 230 publications

References 56 publications

Apoptosis and cell growth arrest in A375 human melanoma cells by diorganotin(IV) and triorganotin(IV) complexes of [meso-Tetra(4-sulfonatophenyl)porphine] manganese(III)chloride

Apoptosis and cell growth arrest in A375 human melanoma cells by diorganotin(IV) and triorganotin(IV) complexes of [meso-Tetra(4-sulfonatophenyl)porphine] manganese(III)chloride

Synthesis and Characterization of Novel Diorganotin(IV) Complexes Derived from N-Methyl-phenethyl Dithiocarbamate and Bis(2-ethoxyethyl) Dithiocarbamate

Synthesis, Characterization and Biological Activities of Organotin (IV) Methylcyclohexyldithiocarbamate Compounds

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