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In vitro and in vivo (32)P-postlabeling analysis of 4-vinyl-1-cyclohexene (butadiene dimer) diepoxide-DNA adducts.

4-Vinyl-1-cyclohexene diepoxide (VCD), and industrial chemical, and its parent compound, 4-vinyl-1-cyclohexene (VCH), are potential health hazards, a they destroy oocytes in follicles in rodents. VCD is also a skin carcinogen at the site of application in both female and male mice and rats and after gavage, induces ovarian tumors in mice and forestomach tumors in rats. A (32)P-postlabeling assay was developed for the detection and measurement of VCD-DNA adducts. VCD, a direct-acting carcinogen, was reacted with DNA in vitro, as well as through mouse skin painting for 3 days with different doses of VCD. (32)P-Labeled adducts were separated by polyethyleneimine (PEI)-cellulose TLC and detected by screen-enhanced autoradiography. Comparable adduct profiles were obtained in vitro and in vivo. At higher doses (36-225 micro mol/mouse), adduct levels in vivo showed a linear dose response, while there was no difference between 14 and 36 micro mol/mouse. The limit of detection was estimated to be 1-3 adducts in 10(8) DNA nucleotides. The results show that VCD exposure gives rise to (presumably pre-mutagenic) DNA adducts in vivo and that (32)P-postlabeling can be applied to biomonitoring of VCD exposure.

Animals↗

Hydroboration of unsaturated phosphonic esters: synthesis of boronophosphonates and trisubstituted vinylphosphonates.

[figure: see text] Hydroboration of vinyl phosphonates with pinacolborane (PBH) proceeds to give phosphonoboronates, 2. Surprisingly, such compounds have not been reported before. The reaction works well with terminal alkenylphosphonates. Internal alkenylphosphonates give complex mixtures. Hydroboration/Suzuki coupling of alkynylphosphonates, with PBH, in a one-pot procedure gives trisubstituted vinylphosphonates in good overall yields and provides a new synthesis of these compounds.

Boron Compounds↗