N., and Bakry, N. M. (2006)

<04 Article Title>. JOURNAL OF ECONOMIC ENTOMOLOGY; 89 <25 Page(s)>.

Chemical of Concern: FVL; Habitat: <40 Habitat Code>; Effect Codes: <08 Effects Code>.

MICHEL, F. C. JR, REDDY CA, and FORNEY LJ (1997). Fate of carbon-14 diazinon during the composting of yard trimmings. JOURNAL OF ENVIRONMENTAL QUALITY; 26 200-205.
Chem Codes: Chemical of Concern: DZ Rejection Code: FATE.

BIOSIS COPYRIGHT: BIOL ABS. The fate of lawn care pesticides during the composting of yard trimmings is largely unknown. In this study we investigated the fate of diazinon (O,O-diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl)phosphorothioate), the most widely used lawn care pesticide, during the composting of a mixture of leaves and grass (2:1 w/w). The yard trimmings were amended with (DELTAA-2-14C) labeled diazinon (10 mg kg-1 wet wt.) and composted in a laboratory scale compost system for 54 d. During composting, 48% of the initial total organic matter (OM) was lost as CO2, the pH increased from 6.2 to 8.2, the oxygen uptake rate declined from 3.5 to 0.09 (mg O2 g OM-1 h-1), the humification index dropped from 1.0 to 0.37, and 11% of the 14C-diazinon was mineralized to 14CO2. Initially most of the added 14C-diazinon was ether extractable (83%) but < 1% was ether extractable after composting. A water extract of the finished compost contained 36% of the added 14C. Thin layer chromatography and m Biochemistry/ Air Pollution/ Soil Pollutants/ Water Pollution/ Herbicides/ Pest Control/ Pesticides

Mikulski, C. M., Pytlewski, L. L., and Karayannis, N. M. (1975). Metal dialkoxythiophosphates. Journal of Inorganic and Nuclear Chemistry 37: 2411-2416.
Chem Codes: Chemical of Concern: DZ Rejection Code: METHODS.

Reactions of triethyl or tri-n-butyl thiophosphates with Fe(II), VO2+, M(III)(M = Ti, V, Cr, Fe) or M(IV)(M=Th, U) chlorides at elevated temperatures lead to the formation of dialkoxythiophosphato metal complexes. These compounds were characterized by means of spectral and magnetic studies. The evidence favors polynuclear structures, involving in most cases exclusively bridging, bidentate -S-P(OR)2-O- ligands. The new complexes are of the following types (DETP and DBTP are, respectively, the diethoxy- and di-n-butoxy-thiophosphato ligands): Pentacoordinated: VOL2(L=DETP, DBTP): Fe(DBTP)2; Fe(DETP)2(OH2)2; the latter complex involves both bridging, bidentate, and monodentate, O-bonded, DETP ligands. Hexacoordinated: ML3(M=Ti, V, Cr, Fe; L=DETP, DBTP). Octacoordinated: ML4(M=Th, U; L=DETP, DBTP). Approximate Dq value calculations suggest that the (RO)2POS- ligands are stronger than their (RO)2POO- or (RO)2PSS- analogs.

Mikulski, Chester M., Moore, Terrance, Smith, Yale, and Karayannis, Nicholas M. (1986). Addition and reaction products of triethyl thiophosphate and metal perchlorates at just over ambient and elevated temperatures. Inorganica Chimica Acta 115: 179-186.
Chem Codes: Chemical of Concern: DZ Rejection Code: METHODS.

Triethyl thiophosphate (tetp) invariably forms adducts with various metal perchlorates (M=Mg2+, Al3+, Cr3+, Mn2+, Fe2+, Fe3+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+) at 35-40[deg]C in ethanol-triethyl orthoformate (teof). Only certain of these adducts, which involve S-bonded tetp in the thione form for soft or borderline metal ions and O-bonded tetp in the thiol tautomeric form for hard metal ions, could be isolated in solid form, owing to their tendency to decompose yielding diethylthiophosphato (detp) metal complexes and ethyl perchlorate, at temperatures ranging between ambient and 80-90[deg]C, depending on the metal ion. Several well-defined detp and detpperchlorato metal complexes were obtained by heating solutions of mixtures of tetp and metal perchlorates in ethanol-teof at 80-90[deg]C, and characterized. In most cases, linear polymeric or dimeric complexes involving double or triple bridges of O,S-bonded bidentate detp between adjacent metal ions were isolated. However, in a number of occasions, heavily hydrated monomeric species, containing terminal S-bonded detp were obtained.

Miles, J. R. W. (1976). Insecticide residues on stream sediments in Ontario, Canada. Pestic. Monit. J. Vol. 10, no. 3, pp. 87-91. 1976.
Chem Codes: Chemical of Concern: DZ Rejection Code: FATE.

Descriptors: Insecticides

Descriptors: Sediment pollution
Descriptors: Sediment analysis
Descriptors: DDT
Descriptors: Water analysis
Descriptors: Canada, Ontario
Abstract: Insecticide residues on suspended and bottom sediments of streams of Ontario, Canada, have been studied in a tobacco-growing and a vegetable muck area. The proportion of TDE to DDT was<1 in water and>1 in bottom sediments. The ratio of TDE to DDT in bottom material increased linearly from the contamination point at stream source to the mouth of Big Creek in Norfolk County, Ontario. Bed load samples contained 3 to 6 times greater concns of insecticides than bottom material. Adsorption of insecticides on suspended sediment decreased in order DDT>TDE>dieldrin>diazinon, which is consistent with the water solubility of these compounds.
Records keyed from 1977 ASFA printed journals.
Language: English
English
Publication Type: Journal Article
Environmental Regime: Freshwater
Classification: Q5 01505 Prevention and control
Subfile: ASFA 3: Aquatic Pollution & Environmental Quality

Milhaud, J., Ponsinet, V., Takashi, M., and Michels, B. (2002). Interactions of the drug amphotericin B with phospholipid membranes containing or not ergosterol: new insight into the role of ergosterol. Biochimica et Biophysica Acta (BBA) - Biomembranes 1558: 95-108.

Chem Codes: Chemical of Concern: DZ Rejection Code: METHODS.

Amphotericin B (AmB) is an amphipathic polyene antibiotic which permeabilizes ergosterol-containing membranes, supposedly by formation of pores. In water, AmB forms chiral aggregates, modelled as stacks of planar dimers in which the joined polyene chains in each dimer turn round, from one dimer to the following in these stacks, by forming a helical array. Studies of the binding of AmB with -dipalmitoylphosphatidylcholine (-DPPC) and -dilauroylphosphatidylcholine (-DLPC) bilayers disclose the main following results. (1) An inversion of the helicity of the -DPPC-bound AmB aggregates, when the -DPPC bilayers are in the gel phase, is inferred from the evolution of the circular dichroism spectra of AmB+-DPPC mixtures. (2) An AmB-induced gel-to-subgel transformation of -DPPC bilayers, in the previous mixtures, is revealed by a differential scanning calorimetry study. (3) The role played by ergosterol in the location of phospholipid-bound AmB aggregates with respect to a phospholipid bilayer is directly demonstrated from atomic force microscopy observations of mica-supported AmB+-DLPC mixtures, in the presence or absence of ergosterol. While in the absence of ergosterol AmB aggregates remained at the surface of the bilayer, in the presence of ergosterol they appeared embedded within this bilayer and became hollow-centered. As such an embedding in the hydrophobic core of a bilayer requires a rearrangement of the aggregates with respect to their architecture in water, this rearrangement is held responsible for the hollowing of aggregates. The hollow-centered sublayer-embedded AmB aggregates are thought to be the precursors of the formation of AmB pores. Helical amphotericin B aggregate/ Amphotericin B pore/ Ergosterol-containing bilayer/ Chirality/ Differential scanning calorimetry/ Atomic force microscopy

Miller, B. E., Forcum, D. L., Weeks, K. W., Wheeler, J. R., and Rail, C. D. (1970). An Evaluation of Insecticides for Flea Control on Wild Mammals. J.Med.Entomol. 7: 697-702.

EcoReference No.: 69363

Chemical of Concern: DZ,CBL,CPY,MLN; Habitat: T; Effect Codes: POP; Rejection Code: OK TARGET(DZ),OK(ALL CHEMS).

Miller, C. W., Zuckerman, B. M., and Charig, A. J. (1966). Water Translocation of Diazinon-C14 and Parathion-S35 Off a Model Cranberry Bog and Subsequent Occurrence in Fish and Mussels. Trans.Am.Fish.Soc. 95: 345-349.

EcoReference No.: 2095

Chemical of Concern: DZ,PRN; Habitat: A; Effect Codes: ACC,MOR; Rejection Code: NO CONTROL(ALL CHEMS).

Mineau, P., Collins, B. T., and Baril, A. (1996). On the Use of Scaling Factors to Improve Interspecies Extrapolation of Acute Toxicity in Birds. Regul.Toxicol.Pharmacol. 24: 24-29.

Chem Codes: Chemical of Concern: STCH,4AP,STAR,DLD,MOM,ADC,CBF,MCB,PIM,PPX,CPY,CMPH,DEM,DZ,DCTP,FNT,MVP,PRN,PPHD,PPX,TMP,TCF,BDF Rejection Code: MODELING.

MINELLI EV, ANGIONI, A., CABRAS, P., GARAU VL, MELIS, M., PIRISI FM, CABITZA, F., and CUBEDDU, M. (1996). Persistence of some pesticides in peach fruit. ITALIAN JOURNAL OF FOOD SCIENCE; 8 : 57-62.

Chem Codes: Chemical of Concern: DMT Rejection Code: NO TOX DATA.

BIOSIS COPYRIGHT: BIOL ABS. The persistence of five pesticides (acephate, azinphos methyl, carbendazim, diazinon and dimethoate) in peach fruit was studied in real operating conditions. Pesticides showed different degradation rates. Diazinon was degraded with a half-life (t1/2) of 5.2 days, acephate, azinphos methyl and dimethoate with t1/2 of ca 12 days and carbendazim with t1/2 of 15.5 days. After the pre-harvest interval (PHI) all pesticide residues were within the limits established by Italian law. Legislation/ Organization and Administration/ Biology/ Biochemistry/ Food Technology/ Fruit/ Nuts/ Vegetables/ Food Analysis/ Food Technology/ Food Additives/Poisoning/ Food Additives/Toxicity/ Food Contamination/ Food Poisoning/ Food Preservatives/Poisoning/ Food Preservatives/Toxicity/ Climate/ Fruit/ Nuts/ Herbicides/ Pest Control/ Pesticides/ Plants, Medicinal

MINELLI EV, ANGIONI, A., CABRAS, P., GARAU VL, MELIS, M., PIRISI FM, CABITZA, F., and CUBEDDU, M. (1996). Persistence of some pesticides in peach fruit. ITALIAN JOURNAL OF FOOD SCIENCE; 8 57-62.
Chem Codes: Chemical of Concern: DZ Rejection Code: FATE.

BIOSIS COPYRIGHT: BIOL ABS. The persistence of five pesticides (acephate, azinphos methyl, carbendazim, diazinon and dimethoate) in peach fruit was studied in real operating conditions. Pesticides showed different degradation rates. Diazinon was degraded with a half-life (t1/2) of 5.2 days, acephate, azinphos methyl and dimethoate with t1/2 of ca 12 days and carbendazim with t1/2 of 15.5 days. After the pre-harvest interval (PHI) all pesticide residues were within the limits established by Italian law. Legislation/ Organization and Administration/ Biology/ Biochemistry/ Food Technology/ Fruit/ Nuts/ Vegetables/ Food Analysis/ Food Technology/ Food Additives/Poisoning/ Food Additives/Toxicity/ Food Contamination/ Food Poisoning/ Food Preservatives/Poisoning/ Food Preservatives/Toxicity/ Climate/ Fruit/ Nuts/ Herbicides/ Pest Control/ Pesticides/ Plants, Medicinal

MINIST AGRIC FISH FOOD HEALTH SAF EXECUTIVE UK (1990). REPORT OF THE WORKING PARTY ON PESTICIDE RESIDUES 1988-89. MINISTRY OF AGRICULTURE FISHERIES AND FOOD HEALTH AND SAFETY EXECUTIVE. REPORT OF THE WORKING PARTY ON PESTICIDE RESIDUES: 1988-89. V+86P. HER MAJESTY'S STATIONERY OFFICE: LONDON, ENGLAND, UK. PAPER. ISBN 0-11-242902-5.; 0 V+86P.
Chem Codes: Chemical of Concern: DZ Rejection Code: SURVEY.

BIOSIS COPYRIGHT: BIOL ABS. RRM BOOK BREAD MILK FRUITS VEGETABLES CEREALS MEAT FISH EGGS Biochemistry/ Food Technology/ Fruit/ Nuts/ Vegetables/ Cookery/ Food Technology/ Food Technology/ Meat/ Meat Products/ Dairy Products/ Food Technology/ Eggs/ Food Technology/ Poultry/ Fish Products/ Fishes/ Food Technology/ Food Analysis/ Food Technology/ Food Additives/Poisoning/ Food Additives/Toxicity/ Food Contamination/ Food Poisoning/ Food Preservatives/Poisoning/ Food Preservatives/Toxicity/ Herbicides/ Pest Control/ Pesticides

Misra, Debjani, Bhuyan, Sasmita, Adhya, T. K., and Sethunathan, N. (1992). Accelerated degradation of methyl parathion, parathion and fenitrothion by suspensions from methyl parathion-and p-nitrophenol-treated soils. Soil Biology and Biochemistry 24: 1035-1042.
Chem Codes: Chemical of Concern: DZ Rejection Code: FATE.

Soils (an alluvial and a laterite) contained in pots were treated with methyl parathion, fenitrothion or p-nitrophenol at 15 day intervals under flooded or non-flooded (60% WHC) conditions. Suspensions (non-sterile and sterile) of these treated and untreated soils were tested for their ability to degrade methyl parathion, parathion, fenitrothion and diazinon in a mineral salts medium. Only non-sterile suspensions of methyl parathion- and p-nitrophenol-enriched soils (flooded or non-flooded) distinctly effected accelerated hydrolysis of methyl parathion, parathion and fenitrothion; in contrast, diazinon was not hydrolysed by the suspension of methyl parathion-enriched soils. p-Nitrophenol, formed from methyl parathion or parathion, was eventually metabolized to nitrite by the enrichment cultures while 3-methyl-4-nitrophenol, formed from fenitrothion, resisted further degradation. As in soil enrichment cultures, two bacterial isolates, one each from methyl parathion-enriched alluvial and laterite soils (flooded), effected rapid hydrolysis of methyl parathion, parathion and fenitrothion and then metabolized p-nitrophenol and not 3-methyl-4-nitrophenol, to nitrite. Fenitrothion-retreated soils (flooded or non-flooded) were not conditioned for accelerated hydrolysis of fenitrothion and related phosphorothioate insecticides.

Mitchell, D. (1985). Bioassay Testing of Herbicide H2 and Insecticidal Soap/Diazinon with Rainbow Trout and Daphnia. U.S.EPA-OPP Registration Standard.

EcoReference No.: 13004

Chemical of Concern: DZ; Habitat: A; Effect Codes: MOR; Rejection Code: NO CONTROL(DZ).

Mitsue Yasoshima and Yasusuke Masuda (1986). Effect of carbon disulfide on the anticholinesterase action of several organophosphorus insecticides in mice. Toxicology Letters 32: 179-184.

Chem Codes: Chemical of Concern: DZ Rejection Code: MIXTURE.

Effect of carbon disulfide (CS2) on toxic action of 11 organophosphorus (OP) insecticides were examined by determining the plasma cholinesterase activity in mice. CS2 pretreatment potentiated the anticholinesterase action of parathion and EPN, but suppressed that of dimethoate and diazinon. CS2 had no significant effect or a slightly suppressive effect on the other compounds. Some of these effects were contrasted with the reported alteration of the toxicity following phenobarbital pretreatment. CS2 administration suppressed both detoxification and activation of parathion and EPN by liver microsomes in vitro, as measured by p-nitrophenol production and cholinesterase inhibition, respectively. Causal relationship between the in vitro and in vivo observations, however, remains to be clarified.

Mitsuhashi, J., Grace, T. D. C., and Waterhouse, D. F. (1970). Effects of Insecticides on Cultures of Insect Cells. Entomol.Exp.Appl. 13: 327-341.

EcoReference No.: 2797

Chemical of Concern: CBL,DZ,HCCH,MLN,PPB,PYN,RTN,ATN,As; Habitat: A; Effect Codes: MOR; Rejection Code: NO CONTROL(ALL CHEMS).

Mitsuru Uchiyama, Takemi Yoshida, Keiko Homma, and Tsutomu Hongo (1975 ). Inhibition of hepatic drug-metabolizing enzymes by thiophosphate insecticides and its drug toxicological implications. Biochemical Pharmacology 24: 1221-1225.

Chem Codes: Chemical of Concern: DZ Rejection Code: IN VITRO.

Thiophosphate insecticides--fenitrothion, diazinon and methylparathion--inhibit hepatic drug-metabolizing enzyme activity, which was assayed using aminopyrine and aniline as substrates. About 50 per cent inhibition was noted 4 hr after the injection of 25 mg/kg of fenitrothion into mice. The addition of thiophosphates to a microsomal drug-metabolizing enzyme system in vitro also produced an effective inhibition: 50 was ca 10-5 M for fenitrothion. DDVP and an oxygenated metabolite of fenitrothion did not show any inhibiting effect either in vitro or in vivo. The inhibition in vitro was competitive, while the kinetics of inhibition in vivo appeared to be noncompetitive. Drug metabolism by a rat liver preparation was also inhibited by thiophosphate in vitro, but treatment of male rats in vivo resulted in little inhibition. The responses of female rats were similar to those of mice. The administration of fenitrothion to mice prolonged the hexobarbital sleeping time and suppressed the oxidative metabolism of parathion in liver preparations.

Miyagi, I., Toma, T., ZAYASU, N., and TAKASHITA, Y. (1994). Insecticide Susceptibility of Culex quinquefasciatus Larvae (Diptera: Culicidae) in Okinawa Prefecture, Japan in 1989. Jpn.J.Sanit.Zool. 45: 7-11.
Chem Codes: Chemical of Concern: DZ Rejection Code: NO DURATION.

MIYAJIMA, A., SUNOUCHI, M., GUO X-B, OHNO, Y., and TAKANAKA, A. (1993). EFFECT OF ORGANOPHOSPHORUS COMPOUNDS AND THEIR METABOLITES ON RAT FRESHLY ISOLATED HEPATOCYTES. 20TH ANNUAL MEETING OF THE JAPANESE SOCIETY OF TOXICOLOGICAL SCIENCES, CHIBA, JAPAN, JULY 29-30, 1993. JOURNAL OF TOXICOLOGICAL SCIENCES; 18 417.

Chem Codes: Chemical of Concern: DZ Rejection Code: ABSTRACT.

BIOSIS COPYRIGHT: BIOL ABS. RRM MEETING PAPER ETHYL P-NITROPHENYL PHENYLPHOSPHONATE O O-BIS1-METHYLETHYL-S-PHENYLMETHYLPHOSPHOROTHIOATE DIFENPHOS ERUSAN DIAZINON FENTHION TRICHLOROFON DISULFOTON METHYL ACID PHOSPHATE ETHYL ACID PHOSPHATE ISOPROPYL ACID PHOSPHATE BENZYLMERCAPTAN Congresses/ Biology/ Animals/ Cytology/ Histocytochemistry/ Biochemistry/ Digestive System Diseases/Pathology/ Digestive System/Pathology/ Poisoning/ Animals, Laboratory/ Herbicides/ Pest Control/ Pesticides/ Muridae

MIYAMOTO, T. and YAMAMOTO, I. (1995). Inhibition of housefly glutathione S-transferase by chalcone and comparison of its isozymes with rat. JOURNAL OF PESTICIDE SCIENCE; 20 75-82.
Chem Codes: Chemical of Concern: DZ Rejection Code: IN VITRO.

BIOSIS COPYRIGHT: BIOL ABS. 2-, 3- and 4-Chloro-4'-phenylchalcones were weakly inhibitory against glutathione S-transferases (GST) from resistant (R) and susceptible (S) housefly abdomens. However, each of glutathione (GSH) conjugates of the above chalcones inhibited strongly both GSTs in an incompetitive fashion with respect to CDNB or DCNB. The inhibitory activity was in the order of 2-, 4- and 3-chloro-compounds which was similar to the case of mouse liver GST. These facts indicated that the rate of GSH conjugation was slow in vitro insect system. On the other hand, the above chalcones increased the insecticidal activity of diazinon to R-fly in the order of 2-, 4- and 3-chloro-compounds. Diazinon is known to be more detoxified in R-fly than in S-fly by GST. Therefore, it is conceivable that such synergism is due to the conversion of the chalcones to the GSH conjugates by GST and the inhibition of GST by the conjugates, which decrease the detoxication of diazinon. There were differences between Biochemistry/ Enzymes/Physiology/ Herbicides/ Pest Control/ Pesticides/ Animals/ Arachnida/ Entomology/Economics/ Pest Control/ Arachnida/ Entomology/Economics/ Insecticides/ Pest Control/ Pesticides/ Animal/ Insects/Physiology/ Physiology, Comparative/ Pathology/ Diptera/ Muridae

MMOCHI AJ and MBEREK RS (1998). Trends in the types, amounts, and toxicity of pesticides used in Tanzania: Efforts to control pesticide pollution in Zanzibar, Tanzania. AMBIO; 27 669-676.
Chem Codes: Chemical of Concern: DZ Rejection Code: NO TOX DATA.

BIOSIS COPYRIGHT: BIOL ABS. The amount of pesticides used in Tanzania increased from 330 g capita-1 in 1977 to 500 g capita-1 in 1988. With population growth at 2.7%, this implies a significant increase (140%) in pesticide use. The control of importation, formulation, and use of pesticides is inefficient. Imported amounts can exceed the authorized amounts, because of donations and the specific projects that import pesticides without official authority from the licensing agent (Tropical Pesticides Research Institute). The types of pesticides used in Zanzibar have changed significantly over the last 10 years. The more toxic pesticides have been phased out and replaced by less toxic ones. The pesticides used decreased from 13 tons in 1990 to about 2 tons in 1995. Among the reasons for the decreases are the efforts by the Plant Protection Department and the Ministry of Agriculture to support a more organic form of agriculture, and the removal of government subsidies on agrochemicals. The pesticides di Conservation of Natural Resources/ Ecology/ Air Pollution/ Soil Pollutants/ Water Pollution/ Plants/Growth & Development/ Soil/ Herbicides/ Pest Control/ Pesticides

Mohamed, A. K. A., Pratt, J. P., and Nelson, F. R. S. (1987). Compatibility of Metarhizium anisopliae var. anisopliae with Chemical Pesticides. Mycopathologia 99: 99-105.

EcoReference No.: 70030

Chemical of Concern: MTPN,CPY,Zineb,Maneb,BMY,CHD,TXP,MOM,CBF,CBL,DZ,TMP,FNTH,RSM; Habitat: T; Effect Codes: POP,REP; Rejection Code: NO ENDPOINT(ALL CHEMS).

Mohn, Georges (1973). 5-Methyltryptophan resistance mutations in Escherichia coli K-12 mutagenic activity of monofunctional alkylating agents including organophosphorus insecticides. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis 20: 7-15.

Chem Codes: Chemical of Concern: DZ Rejection Code: BACTERIA.

The induction of 5-methyltryptophan (5-MT) resistance mutations was assayed as a test system for mutagenic chemicals in Escherichia coli. It is assumed that different premutational alterations in several genes of the Escherichia coli chromosome will lead to 5-MT-resistant mutants. The chemicals used were three monofunctional alkylating agents as reference compounds, namely [beta]-propiolactone ([beta]-PL), N-methyl-N′-nitro-N-nitrosoguanidine (MNNG), and methyl methanesulfonate (MMS), which are all mutagenic in the 5-MT system; of the eight organophosphorus insecticides tested, four have definite mutagenic activity (Dichlorvos, Oxydemetonmethyl, Dimethoate, and Bidrin), one is probably mutagenic (Methylparathion) and the remaining three (Parathion, Malathion and Diazinon) do not induce 5-MT resistance mutations in the conditions used here ( MMS > Dichlorvos > Oxydemetonmethyl, Dimethoate and Bidrin. The concentration-dependent mutagenic activity of all mutagenic compounds is nearly linear when plotted on a log-log scale (with slopes varying from 1.0 to 1.5) and could be taken as an indication that one premutational reaction will be sufficient for the induction of one 5-MT-resistant mutant.

Molina, Pedro, Arques, Antonio, and Alias, Asuncion (1991). Preparation of fused [1,3,5] benzotriazepines by a tandem aza wittig/carbodiimide-mediated annelation reaction. Tetrahedron Letters 32: 2979-2982.
Chem Codes: Chemical of Concern: DZ Rejection Code: METHODS.

AzaWittig type reaction of bis(iminophosphorane) 2, available from the diazide 1 and triphenylphosphine, with one mole of isothiocyanate leads to the iminophosphoranes 3 derived from the [1,2 ,4 ]triazolo[2,3-b] indazole ring, which by treatment with a second mol of isothiocyanate afforded pentacyclic [1,3,5]benzotriazepines 4. Direct conversion of 2 to 4 was achieved using two moles of isothiocyanate.

Molotkovsky, Julian G., Manevich, Yefim M., Babak, Vyacheslav I., and Bergelson, Lev D. (1984). Perylenoyl- and anthrylvinyl-labeled lipids as membrane probes. Biochimica et Biophysica Acta (BBA) - Biomembranes 778: 281-288.
Chem Codes: Chemical of Concern: DZ Rejection Code: METHODS.

The properties of a new family of lipid-specific fluorescent probes, a fatty acid, a phosphatidylcholine and a sphingomyelin, bearing a 3-perylenoyl-labeled hydrophobic chain, are described. Perylenoyl-labeled lipids readily enter the lipid bilayer, the fluorophore being localized in the apolar region of the membrane. The perylenoyl fluorophore is characterized by a high quantum yield, its fluorescence parameters ([lambda]ex 446 nm, [lambda]em 479-545 nm) permit to apply it as an acceptor of excitation energy from the 9-anthrylvinyl fluorophore used earlier for phospholipid labeling (Molotkovsky, Jul. G.; Manevich, Y.M., Gerasimova, E.N., Molotkovskaya, I.M., Polessky, V.A. and Bergelson, L.D. (1982) Eur. J. Biochem. 122, 573-579). The anthrylvinyl-labeled lipids were shown to be capable to report phase segregation between the corresponding prototype lipids in model systems. The combined use of anthrylvinyl- and perylenoyl-labeled lipids opens additional possibilities for investigation of lipid-lipid and lipid-protein interactions in artificial and biological membranes. Perylenoyl-labeled lipids appeared also to be useful as fluorescent dyes in cytological studies. Perylenoyl-labeled lipid/ Anthrylvinyl-labeled lipid/ Fluorescent lipid/ Model membrane/ Fluorescence/ NMR