Biological activity of organotin compounds—An overview

Snoeij, N.J.; Penninks, André; Seinen, Willem

doi:10.1016/s0013-9351(87)80242-6

Cited by 345 publications

(136 citation statements)

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“…In the case of the Stille reaction, an additional disadvantage is the very high toxicity of organotin compounds. [ 67 ] For these reasons, chemists seek alternative methods of biaryl bond synthesis that are free of the above-mentioned drawbacks. Such methods may include direct arylation via the C-H bond activation [ 66a ] and oxidative coupling of aromatic compounds through C-H/C-H activation.…”

Section: Reviewmentioning

confidence: 99%

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Grzybowski

Gryko

2015

Advanced Optical Materials

326

293

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First reported by Farnum as much as 40 years ago, diketopyrrolopyrroles (2,5‐dihydropyrrolo[4,3‐c]pyrrolo‐1,4‐diones) are currently one of the most widely used dyes, with applications that span high‐quality pigments, field‐effect transistors, bulk‐heterojunction solar cells, dye‐sensitized solar cells, and fluorescence imaging. Due to the breadth of their utility, there have been several focused reviews on this topic since 1988. Considering the growing importance of these dyes, this review describes the overall progress made in four decades in both synthesis and the elucidation of their reactivity, and offers a critical comparison of various methods reported in the literature. The relationship between their structure and optical properties is also reviewed in detail. The extension of diketopyrrolopyrroles' chromophore leads to a significant change in both linear and nonlinear optical properties. A very strong bathochromic shift in the absorption and an increase in the two‐photon absorption cross‐section are typical for these analogues. Straightforward synthesis combined with good stability and a near‐unity fluorescence quantum yield ensures that diketopyrrolopyrroles will continue to attract attention for years to come. The goal of this review is to systematize knowledge on these dyes, enabling their use in more real‐world applications.

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Section: Reviewmentioning

confidence: 99%

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Grzybowski

Gryko

2015

Advanced Optical Materials

326

293

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“…Organotins, one of possible environmental hazards, exert specific toxic actions on respec tive target organs and organ systems such as the central nervous system and the immune system (1). Among the organotin toxicities, immunotoxicity has been histologically stud ied.…”

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confidence: 99%

“…Immune function studies with rats fed tributyltin or triphenyltin compounds revealed that the thymus-dependent immune responses were suppressed (5,6). In contrast with our know ledge concerning the immunotoxicity of orga notins in experimental animals fed these com pounds, there is little information on the cellu lar mechanism for their immunotoxicity (1,7). In this study, therefore, we have examined the effect of triphenyltin on mouse thymocytes us ing a flow-cytometer with fluorescent dyes for membrane potential and intracellular Ca 2+ ([Ca 2+]i).…”

mentioning

confidence: 99%

“…Mitochon dria have a tremendous ability to buffer against changes in [Ca 2+1i primarily when there is a high [Ca 2+]i loading (14). Triorga notins at concentrations higher than 1 X 10-7 M are suggested to inhibit ATP formation by binding to the ATP synthase complex in the mitochondria of rat thymocytes (1,7). If so, it would increase the mismatch between the abnormally-increased [Ca2+Ji and the cellular ability to buffer against changes in [Ca 2+]i in organotin-exposed thymocytes.…”

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Cytotoxic Action of Triphenyltin on Mouse Thymocytes: A Flow-Cytometric Study Using Fluorescent Dyes for Membrane Potential and Intracellular Ca2+.

et al. 1991

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“…Fig. 2(a) (d) oral LD 50 value for trimethyltin acetate in the rat is 9 µg/g [9] . The acute oral LD 50 values for many other organotin compounds in the rat are also at µg/g level.…”

Section: Gc-ms Analysismentioning

confidence: 92%

Speciation analysis of organotin compounds in lard poisoning accident in Jiangxi Province, China

Jiang

Zhou

et al. 2000

Sc. China Ser. B-Chem.

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Samples including organotin contaminated lard, urine, blood, and main organs of the poisoned bodies were collected in the incident which took place in Longnan and Dingnan counties, Jiangxi Province, China around the new year' s day of 1999. The organotin compounds in these samples were identified and determined by gas chromatography-flame photometric detector (GC-FPD), gas chromatography-mass spectroscopy (GC-MS) and inductively coupled plasma-mass spectroscopy (ICP-MS). Experiments confirmed that tri-and dimethyltin are the main components that caused the poisoning accident. Monomethyltin, dioctyltin and inorganic tin were also found in several samples. Keywords: organotin, pentylation, GC-FPD, GC-MS, ICP-MS.The extensive use of butyltin compounds as antifouling paint has seriously polluted the harbor and estuary water, which has caused much attention in the world. But the environmental contamination resulting from industrial and agricultural usage of organotins has not been taken into serious account yet. Around the new year' s day of 1999, in Longnan and Dingnan counties, Jiangxi Province, more than 1 000 people were seriously poisoned by the industrial lard contaminated with organotin. Over 100 people were hospitalized and three of them died. In this paper, gas chromatography coupled with flame photometric detector using quartz surface-induced luminescence (GC-FPD), gas chromatography-mass spectroscopy (GC-MS) and inductively coupled plasma-mass spectroscopy (ICP-MS) were used for analyzing the samples collected from Longnan and Dingnan counties. These samples included the contaminated lard, the urine and blood of the patients and the organs of the dead bodies. Experiments confirmed that di-and trimethyltin are the main components causing this accident. Monomethyltin, dioctyltin, inorganic tin and several trace metal elements were also detected in some samples as well. To our knowledge, this is the first case of organotin compounds especially methyltin species found in human organs. Experimental ReagentsTrimethyltin chloride (TMT, 98%), dimethyltin chloride (DMT, 97%) and monomethyltin (MMT, 97%) were obtained from Aldrich Chem. Co. (USA). Suitable amount of the compound 532 SCIENCE IN CHINA (Series B) Vol. 43 was directly weighed and dissolved in methanol to form a concentration of 1 mg/mL (as Sn), which was used as the stock solution and stored in refrigerator maintained at 4 . Working standard solution (10 g/mL) was prepared by diluting the stock solution with cyclohexane.The Sn (IV) stock solution was obtained by dissolving metal Sn in 6 mol/L HCl solution, and then diluting to 4 mg (Sn)/mL with methanol. Working solution (5 g/mL) was obtained by diluting the stock solution with cyclohexane-acetone (1 1).Dioctyltin oxide (DOT, pure) was bought from M&T Chemical Inc. (USA). Because DOT is difficult to dissolve in common organic solvents, the oxide was weighed and dissolved in 12 mol/L HCl in a 40 water bath. When the white solid completely dissolved, the solution was diluted with methanol to...

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Biological activity of organotin compounds—An overview

Cited by 345 publications

References 100 publications

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties

Cytotoxic Action of Triphenyltin on Mouse Thymocytes: A Flow-Cytometric Study Using Fluorescent Dyes for Membrane Potential and Intracellular Ca2+.

Speciation analysis of organotin compounds in lard poisoning accident in Jiangxi Province, China

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