Synthesis, structural investigations on organotin(IV) chlorin-e6 complexes, their effect on sea urchin embryonic development and induced apoptosis

Pellerito, Claudia; D'Agati, Paolo; Fiore, Tiziana; Mansueto, C.; Mansueto, Valentina; Stocco, G. C.; Nagy, László; Pellerito, Lorenzo

doi:10.1016/j.jinorgbio.2005.03.002

Cited by 70 publications

(35 citation statements)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Organotin(IV) compounds are a widely studied class of metal-based antitumour drugs and their intensive investigation has led to the discovery of compounds with excellent in vitro antitumour activity, but, in many cases, disappointingly low in vivo potency or high in vivo toxicity [3][4][5]. It is well established that organotin(IV) compounds are very important in cancer chemotherapy because of their apoptotic inducing character [6,7]. The design of improved organotin(IV) antitumour agents occupies a significant place in cancer chemotherapy, as revealed from their remarkable therapeutic potential reflected in recent research reports [8][9][10][11][12][13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies

Baul

Basu

Vos³

et al. 2008

Invest New Drugs

View full text Add to dashboard Cite

Potassium 2-{[(2Z)-(3-hydroxy-1-methyl 2-butenylidene)]amino}-4-methyl-pentanoate (L1HK) and potassium 2-{[(E)-1-(2-hydroxyphenyl)alkylidene]amino}-4-methyl-pentanoates (L2HK-L3HK) underwent reactions with PhnSnCl4-n (n = 2 and 3) to give the amino acetate functionalized Schiff base organotin(IV) complexes [Ph3SnLH]n (1-3) and [Ph2SnL] (4), respectively. These complexes have been characterized by 1H, 13C, 119Sn NMR, IR spectroscopic techniques in combination with elemental analyses. The crystal structures of 1 and 3 were determined. The crystal structures reveal that the complexes exist as polymeric chains in which the L-bridged Sn-atoms adopt a trans-R3SnO2 trigonal bipyramidal configuration with the Ph groups in the equatorial positions and the axial locations occupied by a carboxylate oxygen atom from one carboxylate ligand and the alcoholic or phenolic oxygen atom of the next carboxylate ligand in the chain. The carboxylate ligands coordinate in the zwitterionic form with the alcoholic/phenolic proton moved to the nearby nitrogen atom. The solution structures were predicted by 119Sn NMR spectroscopy. When these organotin(IV) complexes were tested against A498, EVSA-T, H226, IGROV, M19 MEL, MCF7 and WIDR human tumor cell lines, the average ID50 values obtained were 55, 80 and 35 ng/ml for triphenyltin(IV) compounds 1-3, respectively. The most cytotoxic triphenyltin(IV) compound in the present report (3) with an average ID50 value of around 35 ng/ml is found to be morer cytotoxic for all the cell lines studied than doxorubicin, cisplatin, 5-fluorouracil and etoposide. (3) with an average ID 50 value of around 35 ng/ml is found to be morer cytotoxic for all the cell lines studied than doxorubicin, cisplatin, 5-fluorouracil and etoposide.

show abstract

Section: Introductionmentioning

confidence: 99%

Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies

Baul

Basu

Vos³

et al. 2008

Invest New Drugs

View full text Add to dashboard Cite

show abstract

“…60 The cell chromatin of some of the Liza organs appeared fragmentated: many xenobiotics, such as organotins, induce this process which could be the first step in apoptosis in different species. 60 -63 Recently, Pellerito et al 64 demonstrated a programmed cell death in Paracentrotus lividus 2-cell embryos treated with several organotin(IV)chlorine 6 derivatives. It is probable that the phenomenon could also occur in some L. saliens cells.…”

Section: Discussionmentioning

confidence: 99%

Effects of sublethal levels of tributyltin chloride on a new toxicity test organism, Liza saliens (osteichthyes, mugilidae): a histological study

D'Agati

Mansueto

et al. 2006

Applied Organom Chemis

View full text Add to dashboard Cite

The histopathological effects of 10 −7 and 10 −9 M tributyltin(IV)chloride,TBTCl, solutions on different Liza saliens organs have been studied by light microscope. The fish were sacrificed after 3-4 h incubation in 10 −7 M TBTCl solution or after 15 days incubation in 10 −9 M solution. The observed histopathological changes were dose-and time-dependent. The 10 −7 M TBTCl concentration resulted in major damage to the gill epithelium, indicating that TBTCl primarily interfered with the respiration, osmoregulation, acid balance and nitrogenous waste excretion processes. After incubation in 10 −9 M TBTCl solution the fish lived 20 or more days, but many of the organs were altered. Thymus atrophy, reduced spleen and altered head kidney were observed. These histological results indicated that TBTCl interfered with organ immunodefense and altered main metabolic pathways in Liza saliens. The presence of melano-macrophage centers, only in TBT-treated liver and spleen, can be considered a tool to facilitate, with other biomarkers, the detection of alterations by toxicants. Regarding the pancreas activity in 10 −7 M solutions, it has been noted that, in the exocrine cells, very few zymogen granules were still present and the Langerhans islets were more altered. In 10 −9 M solution the exocrine pancreatic cells had no granules and the islet cells presented degenerative alterations. In addition, TBTCl, which altered the pancreas and gonad morphology, could again be considered an endocrine disrupter even if biochemical data are still necessary. Finally, the Liza saliens juveniles could be considered an interesting biological model for experiments with contaminants, due to their ease of adaptation to experimental conditions and food chain position.

show abstract

“…TBT treatment also alters the expression of AChE activity, which is considered to be a sensitive biomarker for environmental contamination (Mansueto et al 2012). Cytotoxic and genotoxic effects of TBT, including the induction of stress response proteins and DNA damage, have also been observed in sea urchins (Pellerito et al 2005), bivalve molluscs (Clayton et al 2000;Mičić et al 2001Mičić et al , 2002, and polychaetes (Hagger et al 2002). In salmon, TBT exposure causes both the elevation and inhibition of P450aromA, P450aromB, and aromatase activity, in addition to elevating and inhibiting Erα and plasma Vtg while antagonizing the EE2-induced expression of those enzymes.…”

Section: Lethal Toxicitymentioning

confidence: 99%

Mini-review: Molecular mechanisms of antifouling compounds

2013

View full text Add to dashboard Cite

Various antifouling (AF) coatings have been developed to protect submerged surfaces by deterring the settlement of the colonizing stages of fouling organisms. A review of the literature shows that effective AF compounds with specific targets are ones often considered non-toxic. Such compounds act variously on ion channels, quorum sensing systems, neurotransmitters, production/release of adhesive, and specific enzymes that regulate energy production or primary metabolism. In contrast, AF compounds with general targets may or may not act through toxic mechanisms. These compounds affect a variety of biological activities including algal photosynthesis, energy production, stress responses, genotoxic damage, immunosuppressed protein expression, oxidation, neurotransmission, surface chemistry, the formation of biofilms, and adhesive production/release. Among all the targets, adhesive production/release is the most common, possibly due to a more extensive research effort in this area. Overall, the specific molecular targets and the molecular mechanisms of most AF compounds have not been identified. Thus, the information available is insufficient to draw firm conclusions about the types of molecular targets to be used as sensitive biomarkers for future design and screening of compounds with AF potential. In this review, the relevant advantages and disadvantages of the molecular tools available for studying the molecular targets of AF compounds are highlighted briefly and the molecular mechanisms of the AF compounds, which are largely a source of speculation in the literature, are discussed.

show abstract

Synthesis, structural investigations on organotin(IV) chlorin-e6 complexes, their effect on sea urchin embryonic development and induced apoptosis

Cited by 70 publications

References 63 publications

Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies

Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies

Effects of sublethal levels of tributyltin chloride on a new toxicity test organism, Liza saliens (osteichthyes, mugilidae): a histological study

Mini-review: Molecular mechanisms of antifouling compounds

Contact Info

Product

Resources

About