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  • 1
    Electronic Resource
    Electronic Resource
    Cyanoborane chemistry. I. Preparation of a novel series of macrocyclic cyanoboranes (1972)
    s.l. : American Chemical Society
    Journal of the American Chemical Society 94 (1972), S. 8597-8598 
    Details
    ISSN: 1520-5126
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/ja00779a061
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  • 2
    Electronic Resource
    Electronic Resource
    Correlations between carbon-13 and boron-11 chemical shifts. III. Pairwise interaction parameters (1971)
    s.l. : American Chemical Society
    Journal of the American Chemical Society 93 (1971), S. 4418-4426 
    Details
    ISSN: 1520-5126
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/ja00747a014
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  • 3
    Electronic Resource
    Electronic Resource
    Correlations between carbon-13 and boron-11 chemical shifts. II. Chemical shift parameters for amine boranes and related compounds (1968)
    s.l. : American Chemical Society
    Inorganic chemistry 7 (1968), S. 2156-2157 
    Details
    ISSN: 1520-510X
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/ic50068a041
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  • 4
    Electronic Resource
    Electronic Resource
    The effects of boron containing peptides on L1210 lymphoid leukemia metabolism (1993)
    Springer
    Amino acids 4 (1993), S. 287-302 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Antineoplastic agents ; Boron peptide methyl esters ; Cytotoxicity ; L1210 leukemia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The purpose of this study was to establish the efficacy and mode of action of peptide boron derivatives as antineoplastic agents and to evaluate their safety in vivo. Boron-containing phenylalanine and tyrosine methyl esters were found to be potent cytotoxic agents in a number of murine and human cancer cell lines. DNA, RNA and protein syntheses were inhibited by selected agents, e.g. [(trimethylamine boryl)carbonyl]-phenylalanine-acetyl ester (9) andN-acetyl-p-boron-phenyl-alanyl-phenlalanine-methyl ester (10), in L1210 lymphoid leukemia cells. IMP dehydrogenase, OMP decarboxylase, m-RNA, t-RNA, r-RNA polymerase and ribonucleoside reductase activities were inhibited. d(CTP) levels were reduced. DNA strand scission occurred after 24 hr incubation. Acute toxicity studies in mice demonstrated that the key derivative was safe at therapeutic levels with no effects on histology of major organs, hematopoietic parameters and clinical values.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00805829
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  • 5
    Electronic Resource
    Electronic Resource
    Cytotoxicity of boron containing dipeptide analogs (1995)
    Springer
    Amino acids 8 (1995), S. 323-335 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Boron ; Dipeptides ; Antineoplastic agents ; Cytotoxicity ; L 1210 leukemia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary This work is an extension of our previous work (Hall et al., 1993) on the synthesis and cytotoxic activity of boronated peptides. The aim of this work was to carry out structural modifications of the amine terminal in compounds1 and2, to increase water solubility, and its effect on the cytotoxicity to tumor cell lines. Surprisingly, only compounds4,7 and8 were more water soluble than the parent compounds. With the exception of compound4, the new derivatives were generally less effective than the parent compounds (1 and2). There was no apparent correlation between structure and activity. Cytotoxic effect was more pronounced in single cell suspended cells. The growth of solid tumor cell lines was not significantly reduced. The most active derivative, (methanamine)dihydro[[[1-(phenylmethyl)-2-methylamino-2-oxoethyl]amino]carboxy]boron (4), inhibited DNA, RNA, and protein synthesis in Tmolt3 cells. Enzymatic activities, e.g., DNA polymeraseα, m-RNA polymerase, PRPP amidotransferase, carbamyl phosphate synthetase, TMP-kinase, TDP-kinase, dihydrofolate reductase, and ribonucleoside reductase were reduced after 60 min incubation with4. d(TTP) and d(CTP) pool levels were also reduced by 60 min incubation with4.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00806550
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  • 6
    Electronic Resource
    Electronic Resource
    The anti-neoplastic activity of ethylamine-carboxyborane and triphenylphosphine-carboxyborane in L-1210 lymphoid leukemia cells (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 6 (1992), S. 229-239 
    Details
    ISSN: 0268-2605
    Keywords: Boron ; anti-neoplastic ; leukemia ; topoisomerase II ; RNA polymerase ; DNA polymerases ; acute toxicity ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Studies on the mode of action of two boroncontaining anti-neoplastic agents, ethylamine-carboxyborane and triphenylphosphine-carboxyborane, are reported. The major site of inhibition was in the pyrimidine de nove synthetic pathway at orotidine monophosphate decarboxylase activity. Additional sites which may facilitate the inhibition of cell growth were IMP dehydrogenase, thymidine kinase, TMP kinase and TDP kinase, m-RNA, r-RNA and t-RNA polymerase activities as well as topoisomerase II activity. The reduction in enzyme activities led to sufficient reduction of d(NTP) levels to suppress DNA synthesis and cell growth. DNA strand scission was evident in the presence of drug. Multiple modes of action are common with amine-carboxyboranes. Acute toxicity studies in mice showed that both agents were safe in their therapeutic range based on organ weights, histological tissue sections, clinical chemistry values and hematopoietic parameters.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590060218
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  • 7
    Electronic Resource
    Electronic Resource
    The anti-inflammatory activity of metal complexes and salts of amine carboxyboranes (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 8 (1994), S. 473-480 
    Details
    ISSN: 0268-2605
    Keywords: Inflammation ; amine carboxyboranes ; metal complexes ; HCT-8 toxicity ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The metal complexes and salts of amine carboxyboranes were shown to be potent anti-inflammatory agents in rodents at 8 mg kg-1. They were effective in blocking induced edema, pleurisy and endotoxic shock while blocking both local and central pain processes. The ability of the agents to function as anti-inflammatory agents is multi-fold. First, lysosomal enzymes of specific cells, e.g. macrophages, were inhibited with IC50 values in the range of 10-6 M. Collagenase I and II activities were inhibited with IC50 values approximately equal to 10-4 M. The anti-inflammatory activity of these agents at the molecular levels appears to be due to inhibition of the release of TNFα and Il-1 from macrophages which indirectly control chemotaxic migration of white blood cells as indicated by the suppression of PMN and macrophage invasion into sponges implanted subcutaneously (SC) in mice. Furthermore, in these invading cells, the agents' blockage of TNFα and Il-1 or Il-2 release down-regulates prostaglandin and leukotriene enzymatic synthetic rates and, consequently, their release, resulting in a reduction of the inflammation process.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590080507
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  • 8
    Electronic Resource
    Electronic Resource
    Anti-Osteoporotic activity of metal complexes of amine carboxyboranes (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 9 (1995), S. 111-119 
    Details
    ISSN: 0268-2605
    Keywords: osteoporosis ; metal complexes ; boron ; bone ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Metal complexes of trimethylamine carboxyborane successfully suppressed calcium flux from both paired pup calvaria bones and rat UMR-106 osteosarcoma cultured cells over a 48 h period. These agents increased uptake of calcium into the cell cultures and accelerated [3H]proline incorporation into collagen. Copper and iron complexes of the trimethylamine carboxyborane were more potent compared with the cobalt and chromium complexes. The agents effectively reduced Iysosomal enzyme activity and also proteolytic enzyme activities of macrophages. Since macrophages invade the bone surface and assist in the demineralization and digestion of collagen, those agents may be potentially useful to retard diseases involving bone reconstruction. Influx of white blood cells and macrophages to sites of degradation most probably would be inhibited by the agents, based on sponge test observations in mice. Osteoporosis induced by ovariectomy was minimized by injections of tetrakis[u-(trimethylamine-boranecarboxylato)-bis(trimethylamine-carboxyborane)dicopper(II)] into rats at 3.5 mg kg-1 day-1 for 14 days. Bone volume, density, weight and calcium content returned to normal baseline control values. In addition, the copper complex returned serum calcium, serum parathyroid hormone (PTH) and vitamin D3 values to normal levels. One possible mode of action of these derivatives is the regulation of the production and release of chemical mediators initiating bone loss, e.g. tumor necrosis factor, TNF α and interleukins 11 or 11-2.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590090204
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