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PubMed2006

Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH=CH2: Catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions.

The chloro and azido complexes trans-[PdCl(4-C5NF4)(PiPr3)2] (3) and trans-[Pd(N3)(4-C5NF4)(PiPr3)2] (4) can be prepared by reaction of [PdF(4-C5NF4)(PiPr3)2] (2) with Et3SiCl or MeSiN3, respectively. In contrast, reactions of 2 with Ph3SiH or Me2FSiSiFMe2 give the products of reductive elimination 2,3,5,6-tetrafluoropyridine (5) or 4-(fluorodimethylsilyl)tetrafluoropyridine (6) as well as [Pd(PiPr3)2] (1). In a catalytic experiment, pentafluoropyridine can be converted with Ph3SiH into 5 in 62% yield, when 10% of 2 is employed as catalyst. Treatment of trans-[PdF(4-C5NF4)(PiPr3)2] (2) with Bu3SnCH=CH2 in THF at 50 degrees C results in the formation of [Pd(PiPr3)2] (1) and 4-vinyltetrafluoropyridine (7). Complex 2 is also active as a catalyst towards a Stille cross-coupling reaction of pentafluoropyridine with Bu3SnCH=CH2 to give 4-vinyltetrafluoropyridine (7) with a TON of 6. The molecular structure of the complex 3 has been determined by X-ray crystallography.

Carbon↗
PubMedDate not supplied

Permeation of substituted silanes and siloxanes through selected gloves and protective clothing.

Testing of the permeation resistance of eight glove and suit barriers against commercially available substituted silanes and siloxanes was performed using the ASTM F739-96 standard test method. In addition to barrier performance to the pure organosilanes, the permeation rates of the hydrolysis product (usually ethanol or methanol) were investigated. The silanes and siloxanes used as the challenge agents were N-2-(aminoethyl)-3-aminopropyltrimethoxysilane; 3-aminopropyltriethoxysilane; 3-chloropropyltrimethoxysilane; ethyltriacetoxysilane; 3-glycidoxypropyltrimethoxysilane; 1,1,1,3,3,3-hexamethyldisilazane; hexamethyldisiloxane; 3-methacryloxypropyltrimethoxysilane; methyltriacetoxysilane (50%)/ethyltriacetoxysilane (50%); methyltrimethoxysilane; methyltris(methylethylketoxime)silane; phenyltrimethoxysilane; polydimethyl siloxanes (PS 340); octamethylcyclotetrasiloxane (D4); tetraethoxysilane; tetramethoxysilane; 1,1,3,3-tetramethyl disiloxane; triethoxysilane; trimethoxysilane; vinyltrimethoxysilane; and vinyltris(methylethylketoxime)silane. Protective gloves tested were nitrile rubber, neoprene rubber, butyl rubber, 4H laminate, and polyvinyl chloride. Garments tested included Tyvek/Saranex 23P, CPF 2, and Responder, all made by Kappler Safety Group. In all cases the protective suit materials lasted 8 hours or more. The only glove that lasted 8 hours against all chemicals was the 4H laminate. The polyvinyl chloride glove lasted 10 min to 8 hours or more depending on the chemical. The nitrile, neoprene, and butyl rubber gloves lasted from 53 min to 8 hours or more depending on the chemical. The alcohol permeation was similar to the organosilicon compounds. The suit materials and the butyl glove all lasted more than 8 hours for both methanol and ethanol.

Ethanol↗
PubMedDate not supplied

Silperisone: a centrally acting muscle relaxant.

Silperisone is a tolperisone like organosilicon compound with centrally acting muscle relaxant properties. Studies in mice showed that silperisone may have less propensity to cause CNS depressant or motor side effects than tolperisone or other antispastic drugs. In cats and rats, silperisone was an effective suppressant of monosynaptic and polysynaptic spinal reflexes and decerebrate rigidity. Its suppressant effect on the spinal reflexes was also demonstrated in the isolated hemisected rat spinal cord in vitro. The in vivo potency and efficacy of silperisone by i.v administration were similar to those of tolperisone and eperisone. However, in cats by intraduodenal administration and in mice by oral administration its duration of action was much longer and its functional bioavailability much higher than of the other two drugs. With regard to its profile of actions silperisone was similar to tolperisone with minor differences. The most striking difference was in pontine facilitation and bulbar inhibition of the patellar reflex. Tolperisone depressed both, whereas silperisone inhibited only the former. The mechanism underlying the spinal reflex depressant effects of silperisone involves the blockade of voltage gated neuronal sodium and calcium channels leading to a decreased release of excitatory transmitter and reduced neuronal excitability. In addition, silperisone has potassium channel blocking effect, which is stronger than that of tolperisone. Silperisone is absorbed rapidly and is extensively metabolized in rats. However, its metabolism in dogs and particularly in humans is much less extensive. The elimination half-life of silperisone in humans is 12 to 16 h, so that it can be administered once or twice daily. Phase I clinical studies with silperisone at doses up to 150 mg/day failed to detect any adverse effects at plasma concentrations considered to be effective in the preclinical tests. These findings suggested that silperisone might be a useful antispastic drug. However, findings in chronic animal toxicity studies led to the discontinuation of silperisone's development.

Animals↗
PubMed1993

Apoptosis during photodynamic therapy-induced ablation of RIF-1 tumors in C3H mice: electron microscopic, histopathologic and biochemical evidence.

Very little is known about the applicability of the metabolic and biochemical events observed in cell culture systems to in vivo tumor shrinkage following photodynamic therapy (PDT). The purpose of this study was to assess whether PDT induces apoptosis during tumor ablation in vivo. We treated radiation-induced fibrosarcoma (RIF-1) tumors grown in C3H/HeN mice with PDT employing three photosensitizers, Photofrin-II, chloroaluminum phthalocyanine tetrasulfonate, or Pc IV (a promising phthalocyanine developed in this laboratory). Each photosensitizer was injected intraperitoneally and 24 h later the tumors were irradiated with an appropriate wavelength of red light using an argon-pumped dye laser. During the course of tumor shrinkage, the tumors were removed at 1, 2, 4 and 10 h post-PDT for DNA fragmentation, histopathologic, and electron microscopic studies. Markers of apoptosis, viz. the ladder of nucleosome-size DNA fragments, increased apoptotic bodies, and condensation of chromatin material around the periphery of the nucleus, were evident in tumor tissue even 1 h post-PDT; the extent of these changes increased during the later stages of tumor ablation. No changes were observed in tumors given photosensitizer alone or irradiation alone. Our data suggest that the damage produced by in vivo PDT may activate endonucleolysis and chromatin condensation, and that apoptosis is an early event in tumor shrinkage following PDT.

Animals↗
PubMed1997

Primary targets for photoinactivation of vesicular stomatitis virus by AIPcS4 or Pc4 and red light.

Phthalocyanines are useful sensitizers for the photodynamic sterilization of red blood cell concentrates. The mechanism of photoinactivation of lipid-enveloped viruses is not completely understood. Vesicular stomatitis virus (VSV) was used as a model virus to study the primary targets of photoinactivation by aluminum phthalocyanine tetrasulfonate (AIPcS4) or silicon phthalocyanine HOSiPcOSi(CH3)2(CH2)3N(CH3)2 (Pc4) and red light. Inactivation conditions for VSV in buffer were determined using an end point dilution assay, and viral RNA synthesis in host cells was measured to determine the loss of infectivity in a direct way. The very rapid decrease in the viral RNA synthesis after photodynamic treatment was correlated with respect to different potential primary targets that are involved in different steps of the viral replication cycle. Damage to the viral proteins, induced by treatment with AIPcS4 or Pc4 and analyzed by gel electrophoresis, could not account for the observed loss of infectivity. Binding of VSV to host cells was only slightly impaired after photodynamic treatment with both sensitizers and could therefore not be responsible for the rapid decrease in viral RNA synthesis in cells. A very strong inhibition of viral RNA polymerase activity after treatment with AIPcS4 and red light was detectable using an in vitro assay. This decrease correlated well with the loss of infectivity, indicating that either the RNA or the viral RNA polymerase is the primary target for photoinactivation of VSV with AIPcS4. Treatment with Pc4 did not cause inhibition of viral RNA polymerase activity to an extent that could account for the observed very rapid loss of infectivity. It was therefore concluded that neither the viral proteins nor the binding to the host cells nor the RNA or RNA polymerase are the primary targets for photoinactivation of VSV by Pc4.

Animals↗
PubMed1997

Silicon-related syndrome in dialysis patients.

Two dialysis patients with markedly elevated plasma silicon (Si) levels (3,849 and 2,350 micrograms/l, respectively) and a presumed Si-related syndrome are described in this report. One patient presented with transient hypercalcemia in the face of low PTH, vitamin D and plasma A1 levels. Both patients had painful, nodular skin eruptions and aberrant hair growth, characterized as perforating folliculitis on skin biopsy, compatible with known effects of organosilicon compounds in man and animals. Plasma Si was found to be moderately elevated in 30 dialysis patients studied at random (710 +/- 53 micrograms/l, dialysis, vs. 152 +/- 9 micrograms/l, normal control), but there was no significant difference between the arterial values before and after dialysis, implying that the source of Si was ingested foods and fluids rather than dialysate. In these patients, plasma Si was weakly correlated with serum calcium as well as with serum calcium corrected for serum albumen, indicating that Si, like aluminum, may affect calcium metabolism.

Adult↗
PubMed1993

Photodynamic therapy of human squamous cell carcinoma in vitro and in xenografts in nude mice.

Photodynamic therapy (PDT) of cancer is an experimental tumor therapy which is based on the combined use of a systematically administered photosensitizer to a tumor-bearing host and local illumination of the lesion by a high-intensity visible light source, typically a tunable argon dye laser. Human squamous cell carcinoma (HSCC) is the most frequently encountered malignancy of the head and neck. In this study, responses of HSCC cells to PDT were examined in in vitro and in vivo systems. In in vitro studies, the HSCC cells showed a positive photodynamic response with Photofrin-II (Pf-II), chloroaluminum phthalocyanine tetrasulfonate (AlPcTS), and a newly synthesized silicon phthalocyanine (SiPc IV). Single cell suspension of HSCC injected subcutaneously on the back of athymic nude mice resulted in a well-circumscribed tumor mass. The animals required a low tumor dose for the successful establishment of a tumor. The tumor was minimally immunogenic and showed neither macroscopic signs of early metastasis to lung, kidney, liver, or spleen nor evidence of surrounding erythema, fluctuation, or tenderness until the late stages of necrosis. Intraperitoneal administration of AlPcTS or SiPc IV to tumor-bearing mice resulted in rapid uptake of the photosensitizers in liver, skin, and tumor tissue. Twenty-four hours following the intraperitoneal administration of AlPcTS or SiPc IV to tumor-bearing animals, the tumor to normal skin ratio of the photosensitizer was 1.6 or 1.5, respectively. Administration of Pf-II (5 mg/kg) to tumor-bearing animals followed 24 hours later by irradiation of the tumor (135 J/cm2, 630 nm light from an argon pumped-dye laser) resulted in greater than 80% ablation in tumor volume 24 hours post-PDT. These characteristics make this tumor model system suitable for PDT studies of human tumor cells in vitro as well as in vivo.

Aluminum↗
PubMed1999

Inhibition of various steps in the replication cycle of vesicular stomatitis virus contributes to its photoinactivation by AlPcS4 or Pc4 and red light.

Vesicular stomatitis virus (VSV) was used as a model virus to study the processes involved in photoinactivation by aluminum phthalocyanine tetrasulfonate (AlPcS4) or silicon phthalocyanine HOSiPcOSi(CH3)2(CH2)3N(CH3)2 (Pc4) and red light. Previously a very rapid decrease in the intracellular viral RNA synthesis after photodynamic treatment was observed. This decrease was correlated to different steps in the replication cycle. Binding of VSV to host cells and internalization were only slightly impaired and could be visualized by electron microscopy. The capability of the virus to fuse with membranes in an acidic endosomal environment was studied using both pyrene-labeled liposomes and a hemolysis assay as a model. These tests indicate a rapid decrease of fusion capacity after AlPcS4 treatment, which correlated with the decrease in RNA synthesis. For Pc4 treatment no such correlation was found. The fusion process is the first step in the replication cycle, affected by AlPcS4 treatment, but also in vitro RNA polymerase activity was previously shown to be inhibited. Inactivation of VSV by Pc4 treatment is apparently caused by damage to a variety of viral components. Photodynamic treatment of virus suspensions with both sensitizers causes formation of 8-oxo-7,8-dihydroguanosine in viral RNA as measured by HPLC with electrochemical detection. This damage might be partly responsible for inhibition of the in vitro viral RNA polymerase activity by photodynamic treatment.

Animals↗
PubMed1983

Cisobitan in treatment of prostatic cancer. A prospective controlled multicentre study.

Cisobitan, an organosilicon compound with estrogenic and antigonadotropic properties has been evaluated clinically in comparison with an estrogen preparation. In a multicenter study a total of 140 patients with well and moderately well differentiated prostatic cancer were randomly allocated to treatment with Cisobitan or Estradurin/Etivex, 70 to each group. Of 34 patients with poorly differentiated prostatic cancer 18 were given Cisobitan--and 16 were given Estracyt-treatment. Among the patients with well and moderately well differentiated prostatic cancer there were, disregarding mortality, no major differences in subjective, objective or laboratory response to the two kinds of treatment. The pattern of side effects was similar, but oedema requiring diuretics occurred more often in the estrogen treated group. There was a significant difference in mortality at 12 months between the groups, two in the Cisobitan group and ten in the estrogen treated group. Cancer was the cause of death in two patients in the estrogen treated group. All other patients succumbed in cardiovascular diseases. At 24 months the difference in mortality rate was less pronounced: Another ten patients had died in the Cisobitan treated group and seven among the estrogen treated patients. Cancer was responsible for the deaths in seven of the Cisobitan patients compared to four of the estrogen treated patients. Within three years one more patient in both groups had died. Of the 34 patients with poorly differentiated cancer, twelve were alive at the 24 months' follow up, six in the Cisobitan group and six in the Estracyt group.

Clinical Trials as Topic↗
PubMedDate not supplied

[Atranes: their ulcerostatic effect and its possible mechanisms].

The ulcerostatic activity of methylethyl (sylathrane-1-ilmethyl) sulfoiodide, 1-(chlormethyl) sylatrane, and 1-(isopropoxy)hermatrane has been revealed at experimental acetate ulcer in rats. The effect of atranes was equal to that of oxyferriscorbone and exceeded that of methyluracil. All the compounds studied inhibited peroxide oxidation of lipids in blood and stomach tissues from ulcer and in model experiments in egg yolk liposomes. The processes of ulcer development and photodynamic effects of lipid peroxidation in biological objects have been summarized. The data obtained allow to conclude that the ulcerostatic mechanism of action effect of atranes and the comparable drugs is based on their antioxidative effect.

Acetates↗
PubMed1978

Prostatic carcinoma treated with 2,6-cis-diphenylhexamethylcyclotetrasiloxane (Cisobitan).

Thirteen patients with stage III or IV carcinoma of the prostate were treated with 2,6-cis-Diphenylhexamethylcyclotetrasiloxane (Cisobitan, a new organosilicon compound. The drug proved to be a strong antiandrogen and exerted all the known effects of estrogens, including feminization and cardiovascular complications. It is therefore doubtful whether Cisobitan will be a reasonable alternative to estrogens in the treatment of patients with advanced prostatic cancer.

Aged↗
PubMedDate not supplied

[Dopaminergic component in the mechanism of action of gamma-aminobutyric acid derivatives and structural analogs].

In experiments on rats and male mice the GABA derivatives fenibut, fepiron and the organosilicon compound N-methyl (3-trimethylsilil)pyrrolidone (IA) antagonized apomorphine sterotypy and aggressiveness. Fenibut and IA potentiated haloperidol catalepsy. Fenibut, fepiron, sodium hydroxybutyrate and IA also antagonized the effects of phenamine. The biochemical investigations have shown that fenibut and IA produce acceleration of the intraneuronal synthesis and catabolism of DA. It is suggested that the behavioral effects of the GABA derivatives are partly relative to inhibition of the dopamin--ergic system.

Amphetamine↗
PubMed1998

Variation in photodynamic efficacy during the cellular uptake of two phthalocyanine photosensitizers.

A decrease in the efficacy of photodynamic therapy (PDT) with phthalocyanine photosensitizers was observed for lymphoblastic murine and human cell lines as the time between the addition of the photosensitizer, aluminum phthalocyanine (AIPc), to the culture medium and exposure to light was increased from 4 h to 18 h. The total intracellular concentration of photosensitizer did not decrease significantly during this 18 h interval. For the murine cell lines, the maximum cytotoxic and mutagenic effects were observed when the time between addition of the photosensitizer and irradiation was between 1 and 4 h. The time course of the variations in efficacy did not vary greatly from one murine cell line to another, even though the cell lines differ markedly in the extent of their cytotoxic and mutagenic response. The time course of the variation was similar for cytotoxicity and mutagenicity, as well as for the induction of DNA fragmentation. The human lymphoblastic cell line, WTK1, showed less variation in survival and mutability with time than did the murine cell lines. With Pc 4 (HOSiPcOSi[CH3]2[CH2]3N[CH3]2) as the photosensitizer, the photocytotoxicity for murine L5178Y (LY)-S1 cells did not change significantly as the time between addition of Pc 4 and irradiation was increased from 2 to 18 h. However, the mutagenicity decreased by a factor of three during this interval. The mutagenicity of PDT with Pc 4 was much less in LY-S1 cells than that with AlPc. The results suggest that the variation in the efficacy observed for AlPc-induced photocytotoxicity is caused by changes in the intracellular distribution and/or the aggregation of the photosensitizer with time after its addition.

Aluminum↗
PubMed2003

Allylation reactions of carbonyl compounds using an organosilicon reagent in aqueous media.

Allylation reactions of carbonyl compounds such as aldehydes and reactive ketones using allyltrimethoxysilane in aqueous media proceeded smoothly in the presence of 5 mol% of a CdF2-terpyridine complex; the presence of the ligand plays an important role for the catalytic activity; the catalyst was easily recovered and reused without loss of activity.

Journal Article↗
PubMed2001

A Disilane Containing Two Heptacoordinate Silicon Atoms and Dithiocarboxylate Ligands This work was partially supported by a Grant-in-Aid for Scientific Research on Priority Area "Creation of Delocalized Electronic Systems" from the Ministry of Education, Science, Sports and Culture, Japan (No. 12020215). We also thank Shin-etsu Chemical Co., Ltd. and Tosoh Finechem Corporation for gifts of organosilicon and alkyllithium compounds, respectively.

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Journal Article↗