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Journal articles on the topic 'Organotin compounds'

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Published: 4 June 2021

Last updated: 18 May 2024

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1

White, Jane S., John M. Tobin, and Joseph J. Cooney. "Organotin compounds and their interactions with microoganisms." Canadian Journal of Microbiology 45, no. 7 (August 1, 1999): 541–54. http://dx.doi.org/10.1139/w99-048.

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Organotin compounds are ubiquitous in the environment. The general order of toxicity to microorganisms increases with the number and chain length of organic groups bonded to the tin atom. Tetraorganotins and inorganic tin have little toxicity. Because of their lipophilicity, organotins are regarded as membrane active. There is evidence that the site of action of organotins may be both at the cytoplasmic membrane and intracellular level. Consequently, it is not known whether cell surface adsorption or accumulation within the cell, or both is a prerequisite for toxicity. Biosorption studies on a fungus, cyanobacteria, and microalgae indicates that cell surface binding alone occurred in these organisms, while studies on the effects of TBT (tributyltin) on certain microbial enzymes indicated that in some bacteria TBT can interact with cytosolic enzymes. Microorganism-organotin interactions are influenced by environmental conditions. In aquatic systems, both pH and salinity can determine organotin speciation and therefore reactivity. These environmental factors may also alter selectivity for resistant microorganisms in polluted systems. Tin-resistant microorganisms have been identified, and resistance can be either plasmid or chromosomally mediated. In one TBT-resistant organism, an Altermonas sp., an efflux system was suggested as the resistance mechanism. Biotransformation of organotin compounds by debutylation or methylation has been observed. These reactions may influence the toxicity, mobility, and environmental fate of organotin compounds.Key words: inorganic tin, organotins, microorganisms, organotin resistance, biosorption, biotransformation.

2

Podestá, J. C., A. B. Chopa, A. D. Ayala, and L. C. Koll. "Organotin compounds." Journal of Organometallic Chemistry 333, no. 1 (October 1987): 25–36. http://dx.doi.org/10.1016/s0022-328x(00)99028-4.

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3

Ayala, A. D., N. Giagante, J. C. Podestá, and W. P. Neumann. "Organotin compounds." Journal of Organometallic Chemistry 340, no. 3 (February 1988): 317–29. http://dx.doi.org/10.1016/0022-328x(88)80025-1.

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4

Podestá, Julio C., Alicia D. Ayala, Alicia B. Chopa, and Nelda N. Giagante. "Organotin compounds." Journal of Organometallic Chemistry 364, no. 1-2 (March 1989): 39–55. http://dx.doi.org/10.1016/0022-328x(89)85329-x.

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5

Martin, F., FM Corrigan, Ofx Donard, J. Kelly, Jao Besson, and DF Horrobin. "Organotin compounds in trimethyltin-treated rats and in human brain in Alzheimer's Disease." Human & Experimental Toxicology 16, no. 9 (September 1997): 512–15. http://dx.doi.org/10.1177/096032719701600906.

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As blood tin concentrations are elevated in Alzheimer's disease and as some low molecular weight organotin compounds are neurotoxic, we have attempted to detect organotins in brain in Alzheimer's Disease. First we measured the concentration of trimethyltin (TMT) in the brains of rats which had been exposed to memory- impairing concentrations of TMT and, as the method of linking hydride generation, cryogenic trapping, gas chromatographic separation and atomic absorption spec trophotometric detection permitted the measurements of organotin compounds when the total tin was greater than 0.2 nanograms, we applied these techniques to human brain tissue, some of which showed neuropathological evidence of Alzheimer's Disease. No low molecular weight organotin compounds were detected in the human brain tissue, but it is possible that tin may be complexed with large organic molecules, the hydrides of which would not be volatile, but which could be identified by liquid chromatography.

6

Terraza, V. Fabricio, Darío C. Gerbino, and Julio C. Podestá. "Stereoselective Hydrostannation of Diacrylate and Dimethacrylate Esters of Galactaric Acid Derivatives: Cyclohydrostannation vs. Diaddition." Proceedings 9, no. 1 (November 14, 2018): 55. http://dx.doi.org/10.3390/ecsoc-22-05688.

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This paper reports a study on the free radical hydrostannation of ((4S,4′R,5R,5′S)-2,2,2′,2′-tetramethyl-[4,4′-bi(1,3-dioxolane)]-5,5′-diyl)bis(diphenyl methylene) diacrylate (1) and dimethacrylate (2) with triorganotin hydrides, R3SnH (R = Me, n-Bu, Ph). Preliminary investigations show that these reactions could lead to mixtures of products of cyclohydrostannation and/or mono- or diaddition according to the organotin hydrides employed and the reaction conditions used. The addition of Me3SnH to 1 afforded a mixture of three organotin compounds from which the pure new 13-membered macrodiolide 3 (48%) was obtained. The other two organotins could not be separated. The addition of n-Bu3SnH to diester 1 led to a mixture of two organotins, the one in major proportion (91%) being the product of diaddition 7. The minor product 6a (9%) could not be isolated pure. The hydrostannation of 1 with Ph3SnH led to one organotin: The product of diaddition 8. The hydrostannation of the dimethacrylate 2 with the organotin hydrides R3SnH (R = Me, n-Bu, Ph) under the same reaction conditions, led in the three cases to mixtures containing mainly diaddition products, and no cyclization products were detected. Some physical characteristics of the new compounds including selected values of 1H, 13C, and 119Sn NMRs are included.

7

Cheng, Shuming, and Jing Yang. "A Theoretical Study of Organotin Binding in Aromatase." International Journal of Molecular Sciences 24, no. 10 (May 18, 2023): 8954. http://dx.doi.org/10.3390/ijms24108954.

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The widely used organotin compounds are notorious for their acute toxicity. Experiments revealed that organotin might cause reproductive toxicity by reversibly inhibiting animal aromatase functioning. However, the inhibition mechanism is obscure, especially at the molecular level. Compared to experimental methods, theoretical approaches via computational simulations can help to gain a microscopic view of the mechanism. Here, in an initial attempt to uncover the mechanism, we combined molecular docking and classical molecular dynamics to investigate the binding between organotins and aromatase. The energetics analysis indicated that the van der Waals interaction is the primary driving force of binding the organic tail of organotin and the aromatase center. The hydrogen bond linkage trajectory analysis revealed that water plays a significant role in linking the ligand–water–protein triangle network. As an initial step in studying the mechanism of organotin inhibiting aromatase, this work provides an in-depth understanding of the binding mechanism of organotin. Further, our study will help to develop effective and environmentally friendly methods to treat animals that have already been contaminated by organotin, as well as sustainable solutions for organotin degradation.

8

Fent, Karl. "Ecotoxicology of Organotin Compounds." Critical Reviews in Toxicology 26, no. 1 (January 1996): 3–117. http://dx.doi.org/10.3109/10408449609089891.

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9

Fait, Antonella, Adalberto Ferioli, and Franco Barbieri. "Chapter 11 Organotin compounds." Toxicology 91, no. 1 (June 1994): 77–82. http://dx.doi.org/10.1016/0300-483x(94)90244-5.

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10

Appel, Klaus E. "Organotin Compounds: Toxicokinetic Aspects." Drug Metabolism Reviews 36, no. 3-4 (January 2004): 763–86. http://dx.doi.org/10.1081/dmr-200033490.

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11

Brown, Paul, Mary F. Mahon, and Kieran C. Molloy. "Sterically hindered organotin compounds." Journal of Organometallic Chemistry 435, no. 3 (September 1992): 265–73. http://dx.doi.org/10.1016/0022-328x(92)83397-z.

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12

Dodokhova, Margarita A., Andrei V. Safronenko, Inga M. Kotieva, Margarita S. Alkhuseyn-Kulyaginova, Dmitry B. Shpakovsky, and Elena R. Milaeva. "Impact of organotin compounds on the growth of epidermoid Lewis carcinoma." Research Results in Pharmacology 7, no. 4 (December 20, 2021): 81–88. http://dx.doi.org/10.3897/rrpharmacology.7.71455.

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Introduction: Search for new compounds with a broad antitumor and antimetastatic potency due to multiple targeting remains important in medicinal chemistry, pharmacology and oncology. We report the efficacy of hybrid organotin agents bis-(3,5-di-tert-butyl-4-hydroxyphenylthiolate) dimethyltin (Ме3) and (3,5-di-tert-butyl-4-hydroxyphenylthiolate) triphenyltin (Ме5). Materials and methods: The compounds were administered to mice bearing the spontaneously metastatic epidermoid Lewis lung carcinoma (LLC). The efficacy of the treatment was evaluated by mean life span, percentage of tumor growth inhibition, number of lung metastases, frequency of metastasis, tumor weight 21 days after tumor cell inoculation, and a degree of lung damage according to the method of D. Tarin and J.E. Price. Results and discussion: For new organotin compounds containing an antioxidant protective fragment of 2,6-di-tert-butylphenol, moderate antitumor and pronounced antimetastatic effects were revealed in the Lewis model of epidermoid lung carcinoma; more active for Me5. Some features of the development of the process of metastasis were recorded with the introduction of various doses of hybrid organotin compounds. Conclusion: Substances Ме3 and Ме5 possess specific activity on the model under investigation, which allows one to suggest these organotins as promising series of antitumor and antimetastatic agents with multiple targeting mode of action.

13

Abd Aziz, Nurul Amalina, Normah Awang, Kok Meng Chan, Nurul Farahana Kamaludin, and Nur Najmi Mohamad Anuar. "Organotin (IV) Dithiocarbamate Compounds as Anticancer Agents: A Review of Syntheses and Cytotoxicity Studies." Molecules 28, no. 15 (August 3, 2023): 5841. http://dx.doi.org/10.3390/molecules28155841.

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Organotin (IV) dithiocarbamate has recently received attention as a therapeutic agent among organotin (IV) compounds. The individual properties of the organotin (IV) and dithiocarbamate moieties in the hybrid complex form a synergy of action that stimulates increased biological activity. Organotin (IV) components have been shown to play a crucial role in cytotoxicity. The biological effects of organotin compounds are believed to be influenced by the number of Sn-C bonds and the number and nature of alkyl or aryl substituents within the organotin structure. Ligands target and react with molecules while preventing unwanted changes in the biomolecules. Organotin (IV) dithiocarbamate compounds have also been shown to have a broad range of cellular, biochemical, and molecular effects, with their toxicity largely determined by their structure. Continuing the investigation of the cytotoxicity of organotin (IV) dithiocarbamates, this mini-review delves into the appropriate method for synthesis and discusses the elemental and spectroscopic analyses and potential cytotoxic effects of these compounds from articles published since 2010.

14

Rabiee, Navid, Moein Safarkhani, and Mostafa M. Amini. "Investigating the structural chemistry of organotin(IV) compounds: recent advances." Reviews in Inorganic Chemistry 39, no. 1 (March 26, 2019): 13–45. http://dx.doi.org/10.1515/revic-2018-0014.

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AbstractOrganotin(IV) compounds have been considered for their outstanding industrial, medical and specific applications in the synthesis of various types of chemical compounds. In this review, we have focused on the structural chemistry of organotin(IV) compounds, including coordination chemistry, the effect of structure on reactions, bond formations from the perspective of structure and investigation of the structure of organotin(IV) compounds in different phases. The structural chemistry of organotin(IV) compounds is subject to interest due to their major impact on predicting the properties and drumming up support for pushing back the frontiers of synthesis of organotin(IV) compounds with advanced properties.

15

Allef, Petra, and Horst Kunz. "Stereoselective Synthesis of α-Arylalkylamines by Glycosylation-induced Asymmetric Addition of Organometallic Compounds to Imines." Zeitschrift für Naturforschung B 64, no. 6 (June 1, 2009): 646–52. http://dx.doi.org/10.1515/znb-2009-0609.

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Activation of imines of aromatic aldehydes by N-glycosylation with O-pivaloyl-galactopyranosyl bromide (pivalobromogalactose) and subsequent addition of organotin, organolithium, Grignard, or organozinc reagents afforded α-arylalkylamines with moderate to high diastereoselectivity.

16

Plasseraud, Laurent. "Organotin(IV) Complexes Containing Sn–O–Se Moieties: A Structural Inventory." Synthesis 50, no. 18 (June 14, 2018): 3653–61. http://dx.doi.org/10.1055/s-0037-1610164.

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This review focuses on organotin compounds exhibiting Sn–O–Se moieties, the molecular structures of which have been previously resolved by single-crystal X-ray diffraction analysis. Three distinct classes of compounds have been identified. Thus, the various modes of coordination of selenite, selenate and organoseleninate anions with tin atoms of organotin(IV) fragments are illustrated and detailed.1 Introduction2 Organotin(IV) Selenite Complexes3 Organotin(IV) Selenate Complexes4 Organotin(IV) Organoseleninate Complexes5 Summary

17

Ghani, Hassan, and Emad Yousif. "Chemistry of Some Organotin Compounds." Al-Nahrain Journal of Science 24, no. 3 (September 1, 2021): 9–15. http://dx.doi.org/10.22401/anjs.24.3.02.

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Organotin compounds (OTCs) are characterized as having at minimum one covalent bond between carbon and tin atoms, and are usually denoted by the formula RnSnX4-n (n =1-3, R =aryl or alkyl, X =halogen ion or a carboxylate, etc.). There are several methods to synthesis organotin compounds, they are Grignard and Kocheshkov reactions, Wurtz reaction and alkylation method. The tin has two stable state,(II) and (IV). Sn(II) forms pyramidal sp3complexes as well as trigonal bipyramidal sp3d complexes, whereas Sn(IV) forms trigonal bipyramidal sp3d complexes or octahedral sp3d2complexes.

18

Saito, Haruko. "Health effects of organotin compounds." Japan journal of water pollution research 10, no. 12 (1987): 719–25. http://dx.doi.org/10.2965/jswe1978.10.719.

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19

Pichler, Johann, Philipp Müller, Ana Torvisco, and Frank Uhlig. "Novel diaminopropyl substituted organotin compounds." Canadian Journal of Chemistry 96, no. 4 (April 2018): 411–18. http://dx.doi.org/10.1139/cjc-2017-0713.

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A novel synthetic pathway involving the desilylation of a tin trimethylsilyl species (Ph2Sn(SiMe3)2) towards nonprotected di(3-aminopropyl)tin dichloride ((H2N(CH2)3)2SnCl2) is described. Di(3-aminopropyl)tin dichloride is then converted to the respective dicarboxylates species (H2N(CH2)3)2Sn(OCOR)2 containing carboxylic acids of different lengths (R = –CH3, –(CH2)10CH3). Depending on the nature of R, discrete packing effects are observed in the solid state of di(3-aminopropyl)tin dicarboxylate derivatives. All the synthesized substances were characterized by 1H, 13C, and 119Sn nuclear magnetic resonance data and also single crystal X-ray analysis. These compounds are a promising class of substances for biological, pharmaceutical, and technical applications.

20

Ross, Alexander. "INDUSTRIAL APPLICATIONS OF ORGANOTIN COMPOUNDS." Annals of the New York Academy of Sciences 125, no. 1 (December 16, 2006): 107–23. http://dx.doi.org/10.1111/j.1749-6632.1965.tb45382.x.

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21

Ritter, Kurt. "Claisen rearrangement of organotin compounds." Tetrahedron Letters 31, no. 6 (January 1990): 869–72. http://dx.doi.org/10.1016/s0040-4039(00)94650-1.

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22

Davies, Alwyn G. "Organotin Compounds in Modern Technology." Journal of Organometallic Chemistry 293, no. 1 (September 1985): C22. http://dx.doi.org/10.1016/0022-328x(85)80262-x.

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23

Lin, Ja-Liang, and Swei Hsueh. "Acute Nephropathy of Organotin Compounds." American Journal of Nephrology 13, no. 2 (1993): 124–28. http://dx.doi.org/10.1159/000168601.

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24

MIMURA, HARUO. "Biological toxicity of organotin compounds." Kagaku To Seibutsu 32, no. 6 (1994): 405–8. http://dx.doi.org/10.1271/kagakutoseibutsu1962.32.405.

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25

Barbieri, Renato, Arturo Silvestri, Anna M. Giuliani, Vincenzo Piro, Francesco Di Simone, and Grazia Madonia. "Organotin compounds and deoxyribonucleic acid." Journal of the Chemical Society, Dalton Transactions, no. 4 (1992): 585. http://dx.doi.org/10.1039/dt9920000585.

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26

Meinema, Harry. "Organotin Compounds in Modern Technology." Organometallics 4, no. 9 (September 1, 1985): 1696. http://dx.doi.org/10.1021/om00128a602.

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27

Saxena, A. K., and F. Huber. "Organotin compounds and cancer chemotherapy." Coordination Chemistry Reviews 95, no. 1 (June 1989): 109–23. http://dx.doi.org/10.1016/0010-8545(89)80003-7.

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28

Ibadi, Falih, Emad Yousif, Mohammed Al-Mashhadani, Nany Hairunisa, and Muna Bufaroosh. "Recent Studies on Cancer Cell's Inhibition by Organotin (IV) Materials: An Overview." Al-Nahrain Journal of Science 26, no. 2 (June 1, 2023): 23–29. http://dx.doi.org/10.22401/anjs.26.2.04.

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organotin (IV) compounds have been the focus of recent studies for their potential use in the treatment of cancer. This review provides an overview of recent studies on the inhibition of cancer cells by organotin (IV) materials. The literature suggests that organotin (IV) compounds can selectively target cancer cells and induce apoptosis, making them promising candidates for anticancer drugs. The review covers various types of organotin (IV) compounds, including those containing alkyl, aryl, and amino groups, and their mechanisms of action against cancer cells. Additionally, the study explores the potential toxicity and biocompatibility of these compounds and their derivatives, as well as their potential use in combination therapy. Overall, the results of recent studies suggest that organotin (IV) compounds show great potential for the treatment of cancer. However, more research is needed to fully understand their mechanism of action and potential side effects. The review highlights the need for continued investigation of these compounds and their derivatives to develop effective and safe anticancer therapies

29

Rasli, Nur Rasyiqin, Asmah Hamid, Normah Awang, and Nurul Farahana Kamaludin. "Series of Organotin(IV) Compounds with Different Dithiocarbamate Ligands Induced Cytotoxicity, Apoptosis and Cell Cycle Arrest on Jurkat E6.1, T Acute Lymphoblastic Leukemia Cells." Molecules 28, no. 8 (April 11, 2023): 3376. http://dx.doi.org/10.3390/molecules28083376.

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The discovery of cisplatin has influenced scientists to study the anticancer properties of other metal complexes. Organotin(IV) dithiocarbamate compounds are gaining attention as anticancer agents due to their potent cytotoxic properties on cancer cells. In this study, a series of organotin compounds were assessed for their toxic effects on the Jurkat E6.1 cell line. WST-1 assay was used to determine the cytotoxic effect of the compounds and showed that six out of seven organotin(IV) dithiocarbamate compounds exhibited potent cytotoxic effects toward T-lymphoblastic leukemia cells, Jurkat E6.1 with the concentration of IC50 ranging from 0.67–0.94 µM. The apoptosis assay by Annexin V-FITC/PI staining showed that all tested compounds induced cell death mainly via apoptosis. Cell cycle analysis assessed using RNase/PI staining showed that organotin(IV) dithiocarbamate compounds induced cell cycle arrest at different phases. In conclusion, the tested organotin(IV) dithiocarbamate compounds demonstrated potent cytotoxicity against Jurkat E6.1 cells via apoptosis and cell cycle arrest at low IC50 value. However, further studies on the mechanisms of action are required to probe the possible potential of these compounds on leukemia cells before they can be developed into anti-leukemic agents.

30

Eaborn, Colin. "Gmelin handbook of inorganic and organometallic chemistry. 8th Ed. Sn. organotin compounds. Part 19. Organotin-nitrogen compounds (concluded), Organotin-Phosphorus, -Arsenic, -Antimony, -Bismuth Compounds." Journal of Organometallic Chemistry 436, no. 2 (September 1992): C22. http://dx.doi.org/10.1016/0022-328x(92)85056-3.

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31

Zhou, Qun-fang, Gui-bin Jiang, and Ji-yan Liu. "Organotin Pollution in China." Scientific World JOURNAL 2 (2002): 655–59. http://dx.doi.org/10.1100/tsw.2002.136.

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A preliminary investigation of the occurrence of butyltin compounds was made in various environmental samples including water, sediment, sea products, and other commodities from China. Detection was carried out by the method of hydrogenation coupled with SPME or Grignard derivatization, followed by GC-FPD analysis. The results showed the universal existence of butyltin compounds in a wide range of tested samples, which was a potential danger for human health. Urgent control or management of organotin compounds is necessary to prevent the underlying hazard caused by this kind of pollutant.

32

Paredes-Cervantes, Vladimir, Jane Castillo-Vera, Federico Gomez-Reynoso, Francisco Diaz-Cedillo, and Miguel Aguilar-Santelises. "Wastewater from Mexico City contains organotin compounds and organotin-resistant bacteria." Cogent Environmental Science 3, no. 1 (January 1, 2017): 1347996. http://dx.doi.org/10.1080/23311843.2017.1347996.

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33

Lima, Aline Fernandes Alves de, Ítalo Braga de Castro, and Cristina de Almeida Rocha-Barreira. "Imposex induction in Stramonita haemastoma floridana (Conrad, 1837) (Mollusca: Gastropoda: Muricidae) submitted to an organotin-contaminated diet." Brazilian Journal of Oceanography 54, no. 1 (March 2006): 85–90. http://dx.doi.org/10.1590/s1679-87592006000100008.

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Marine organisms are affected by organotin compounds due to the cumulative, deleterious effects of these latter. The most evident and well known consequence of organotin contamination is imposex, a hormonal disruption that causes a superimposition of sexual male features in females of prosobranchia neogastropod molluscs such as Stramonita haemastoma floridana. Molluscs accumulate organotins mainly because of their poor ability to eliminate TBT and DBT from their tissues. The aim of this study was to analyze organotin uptake by ingestion experimentally, using uncontaminated subjects (S. haemastoma floridana) fed with organotin-contaminated oysters (Crassostrea rhizophorae). A total of 248 gastropods, distributed in 7 tanks with uncontaminated water and contaminated food, were used in this study, a control group being fed uncontaminated oysters. Every 15 days, the individuals of one of the tanks were examined for the presence of imposex. Development of imposex was measured using the VDSI, RPSI and RPLI indexes. The animals had already developed imposex within the first 15 days, all the indexes measured (RPLI, RPSI and VDSI) having increased significantly with duration of exposure, indicating that the animals were probablycontaminated by the food and had accumulated the pollutant. New paths of imposex development were also observed.

34

Storozhenko, P. A., K. D. Magdeev, A. A. Grachev, N. I. Kirilina, and V. I. Shiryaev. "Organotin Compounds in Industrial Catalysis. II. Polyurethanes Formation Processes." Kataliz v promyshlennosti 20, no. 3 (May 28, 2020): 203–15. http://dx.doi.org/10.18412/1816-0387-2020-3-203-215.

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This is the second part of a series of reviews on the application of organotin compounds as the catalysts for some important industrial processes. This review considers the application of organotin compounds in the processes of polyurethanes formation.

35

Beg, Mohd A., Md A. Beg, Ummer R. Zargar, Ishfaq A. Sheikh, Osama S. Bajouh, Adel M. Abuzenadah, and Mohd Rehan. "Organotin Antifouling Compounds and Sex-Steroid Nuclear Receptor Perturbation: Some Structural Insights." Toxics 11, no. 1 (December 27, 2022): 25. http://dx.doi.org/10.3390/toxics11010025.

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Organotin compounds (OTCs) are a commercially important group of organometallic compounds of tin used globally as polyvinyl chloride stabilizers and marine antifouling biocides. Worldwide use of OTCs has resulted in their ubiquitous presence in ecosystems across all the continents. OTCs have metabolic and endocrine disrupting effects in marine and terrestrial organisms. Thus, harmful OTCs (tributyltin) have been banned by the International Convention on the Control of Harmful Antifouling Systems since 2008. However, continued manufacturing by non-member countries poses a substantial risk for animal and human health. In this study, structural binding of common commercial OTCs, tributyltin (TBT), dibutyltin (DBT), monobutyltin (MBT), triphenyltin (TPT), diphenyltin (DPT), monophenyltin (MPT), and azocyclotin (ACT) against sex-steroid nuclear receptors, androgen receptor (AR), and estrogen receptors (ERα, ERβ) was performed using molecular docking and MD simulation. TBT, DBT, DPT, and MPT bound deep within the binding sites of AR, ERα, and Erβ, showing good dock score, binding energy and dissociation constants that were comparable to bound native ligands, testosterone and estradiol. The stability of docking complex was shown by MD simulation of organotin/receptor complex with RMSD, RMSF, Rg, and SASA plots showing stable interaction, low deviation, and compactness of the complex. A high commonality (50–100%) of interacting residues of ERα and ERβ for the docked ligands and bound native ligand (estradiol) indicated that the organotin compounds bound in the same binding site of the receptor as the native ligand. The results suggested that organotins may interfere with the natural steroid/receptor binding and perturb steroid signaling.

36

Yusof, Enis Nadia Md, Muhammad A. M. Latif, Mohamed I. M. Tahir, Jennette A. Sakoff, Michela I. Simone, Alister J. Page, Abhi Veerakumarasivam, Edward R. T. Tiekink, and Thahira B. S. A. Ravoof. "o-Vanillin Derived Schiff Bases and Their Organotin(IV) Compounds: Synthesis, Structural Characterisation, In-Silico Studies and Cytotoxicity." International Journal of Molecular Sciences 20, no. 4 (February 15, 2019): 854. http://dx.doi.org/10.3390/ijms20040854.

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Abstract:

Six new organotin(IV) compounds of Schiff bases derived from S-R-dithiocarbazate [R = benzyl (B), 2- or 4-methylbenzyl (2M and 4M, respectively)] condensed with 2-hydroxy-3-methoxybenzaldehyde (oVa) were synthesised and characterised by elemental analysis, various spectroscopic techniques including infrared, UV-vis, multinuclear (1H, 13C, 119Sn) NMR and mass spectrometry, and single crystal X-ray diffraction. The organotin(IV) compounds were synthesised from the reaction of Ph2SnCl2 or Me2SnCl2 with the Schiff bases (S2MoVaH/S4MoVaH/SBoVaH) to form a total of six new organotin(IV) compounds that had a general formula of [R2Sn(L)] (where L = Schiff base; R = Ph or Me). The molecular geometries of Me2Sn(S2MoVa), Me2Sn(S4MoVa) and Me2Sn(SBoVa) were established by X-ray crystallography and verified using density functional theory calculations. Interestingly, each experimental structure contained two independent but chemically similar molecules in the crystallographic asymmetric unit. The coordination geometry for each molecule was defined by thiolate-sulphur, phenoxide-oxygen and imine-nitrogen atoms derived from a dinegative, tridentate dithiocarbazate ligand with the remaining positions occupied by the methyl-carbon atoms of the organo groups. In each case, the resulting five-coordinate C2NOS geometry was almost exactly intermediate between ideal trigonal-bipyramidal and square-pyramidal geometries. The cytotoxic activities of the Schiff bases and organotin(IV) compounds were investigated against EJ-28 and RT-112 (bladder), HT29 (colon), U87 and SJ-G2 (glioblastoma), MCF-7 (breast) A2780 (ovarian), H460 (lung), A431 (skin), DU145 (prostate), BE2-C (neuroblastoma) and MIA (pancreatic) cancer cell lines and one normal breast cell line (MCF-10A). Diphenyltin(IV) compounds exhibited greater potency than either the Schiff bases or the respective dimethyltin(IV) compounds. Mechanistic studies on the action of these compounds against bladder cancer cells revealed that they induced the production of reactive oxygen species (ROS). The bladder cancer cells were apoptotic after 24 h post-treatment with the diphenyltin(IV) compounds. The interactions of the organotin(IV) compounds with calf thymus DNA (CT-DNA) were experimentally explored using UV-vis absorption spectroscopy. This study revealed that the organotin(IV) compounds have strong DNA binding affinity, verified via molecular docking simulations, which suggests that these organotin(IV) compounds interact with DNA via groove-binding interactions.

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Davies, Alwyn G. "Organotin compounds in technology and industry." Journal of Chemical Research 2010, no. 4 (April 1, 2010): 181–90. http://dx.doi.org/10.3184/030823410x12698696585509.

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Herber, Rolfe H., and Israel Nowik. "Metal Atom Dynamics of Organotin Compounds." Phosphorus, Sulfur, and Silicon and the Related Elements 186, no. 6 (June 1, 2011): 1336–40. http://dx.doi.org/10.1080/10426507.2010.543103.

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Baba, Ibrahim, Amirah Faizah Abdul Muthalib, Yang Farina Abdul Aziz, and Ng Seik Weng. "New Dithiocarbamate Compounds from Organotin(IV)." Phosphorus, Sulfur, and Silicon and the Related Elements 186, no. 6 (June 1, 2011): 1326–29. http://dx.doi.org/10.1080/10426507.2010.548841.

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Joshi, Ravi R., and Sudhir K. Gupta. "Ecotoxicity studies of some organotin compounds." Toxicological & Environmental Chemistry 34, no. 2-4 (March 1992): 133–38. http://dx.doi.org/10.1080/02772249209357786.

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Mitchell, Terence N. "Palladium-Catalysed Reactions of Organotin Compounds." Synthesis 1992, no. 09 (1992): 803–15. http://dx.doi.org/10.1055/s-1992-26230.

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Dubalska, Kinga, Małgorzata Rutkowska, Gabriela Bajger-Nowak, Piotr Konieczka, and Jacek Namieśnik. "Organotin Compounds: Environmental Fate and Analytics." Critical Reviews in Analytical Chemistry 43, no. 1 (January 15, 2013): 35–54. http://dx.doi.org/10.1080/10408347.2012.743846.

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Sakai, Fumihiko, Hideaki Fujiwara, and Yoshio Sasaki. "The solution chemistry of organotin compounds." Journal of Organometallic Chemistry 310, no. 3 (August 1986): 293–301. http://dx.doi.org/10.1016/0022-328x(86)80193-0.

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Watta, Baerbel, Wilhelm P. Neumann, and Josef Sauer. "Organotin compounds. 31. Dodecamethylcyclohexastannane and dodecaperdeuteriomethylcyclohexastannane." Organometallics 4, no. 11 (November 1985): 1954–57. http://dx.doi.org/10.1021/om00130a006.

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Saxena, Anil K. "Organotin compounds: Toxicology and biomedicinal applications." Applied Organometallic Chemistry 1, no. 1 (1987): 39–56. http://dx.doi.org/10.1002/aoc.590010107.

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Laughlin, Roy B., W. French, H. Guard, R. B. Johannesen, and F. E. Brinckman. "Structure-activity relationships for organotin compounds." Environmental Toxicology and Chemistry 4, no. 3 (June 1985): 343–51. http://dx.doi.org/10.1002/etc.5620040309.

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47

Harino, Hiroya, Minoru Fukushima, Yuko Kurokawa, and Shin’ichiro Kawai. "Susceptibility of bacterial populations to organotin compounds and microbial degradation of organotin compounds in environmental water." Environmental Pollution 98, no. 2 (November 1997): 157–62. http://dx.doi.org/10.1016/s0269-7491(97)00133-4.

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Milaeva, E. R., M. A. Dodokhova, D. B. Shpakovsky, T. A. Antonenko, A. V. Safronenko, I. M. Kotieva, E. F. Komarova, E. V. Gantsgorn, and M. S. Alkhuseyn-Kulyaginova. "Mechanisms of the Cytotoxic Action of Organotin Compounds." Journal Biomed 17, no. 2 (June 26, 2021): 88–99. http://dx.doi.org/10.33647/2074-5982-17-2-88-99.

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Abstract:

This review analyzed the literature data on the in vitro preclinical study of the cytotoxic properties of organotin compounds, as well as the main mechanisms of their action. The latter consist in interacting with SH groups of proteins, initiating oxidative stress, binding to DNA, interacting with receptors, as well as activate apoptosis by increasing the expression of caspases, proapoptotic proteins, and decreasing antiapoptotic proteins. Organotin compounds, depending on the donor ligand, exhibit specifi c cytotoxicity towards certain tumor cell lines. The high cytotoxic potential indicates the possibility of further development in vivo and research of organotin compounds as candidates for the creation of drugs for anticancer and antimetastatic therapy.

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Wezel, Annemarie P. "Chemical and biological aspects of ecotoxicological risk assessment of ionizable and neutral organic compounds in fresh and marine waters: a review." Environmental Reviews 6, no. 2 (June 1, 1998): 123–37. http://dx.doi.org/10.1139/a98-007.

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The effects of salinity and pH on the partitioning behaviour and toxicity of ionizable and neutral organics and organotin compounds in aquatic ecosystems are reviewed. The pH and pKa are of importance for the distribution over n-octanol and water (Dow) of ionizable compounds. Dow increases with salinity for ionized organics up to 3 times and for organotins up to 1000 times. Neutral acids partition more strongly to the phospholipids than their ions; however, differences are smaller than for Dow. For dissociated phenols, the distribution over the membrane and water (Dmw) depends on counterion concentration. For pentachlorophenol (PCP) and organotins, the uptake rate constant (k1) for the neutral form is up to a factor 10 higher than for the ion. The formation of ion_counterion pairs at higher salinity does not contribute to a higher uptake rate. The adaptation to salinity does not result in different bioconcentration kinetics. There is no general intrinsic susceptibility difference between salt water and freshwater organisms. For ionized organic acids, an increase in toxicity up to 4 times with decreasing salinity is reported frequently. Differences in pH are important for toxicity for compounds with a pKa between 6 and 9. For organophosphates a toxicity increase up to 2.5-fold with salinity was found. Bioconcentration and toxicity of ionizable organics aren't influenced by salinity in the way that Dow is influenced. Quantitative structure activity relationships developed for neutral compounds cannot be used to estimate the bioconcentration or toxicity of partly ionized organics. The deviating partitioning behaviour over water and octanol is no reason to set separate quality criteria for ionizable compounds for marine water and freshwater. However, their toxicity can differ as a result of pH differences. Toxicity data for fresh and marine organisms should always be compared, because unexpected differences in sensitivity can be detected in this way.Key words: salinity, sensitivity, acids, bases, organotin compounds.

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Melník, Milan, Ján Garaj, Aladär Valent, and Mária Kohútová. "Isomers of Organotin Compounds II. Di - to Polymeric Compounds." Main Group Metal Chemistry 32, no. 1 (January 2009): 1–36. http://dx.doi.org/10.1515/mgmc.2009.32.1.1.

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