Substituted carboranes and polyhedral hydroborate salts as anti-neoplastics

Anticancer Research

Volumn 18, Issue 4 A, 1998, Pages 2617-2622

  Hall, Iris H ^a   Elkins, Amy ^a   Powell, Walda J ^b   Karthikeyan, S ^b   Sood, Anup ^b   Spielvogel, Bernard F ^b  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b Boron Biologicals Inc   (United States)

Author keywords

Anti leukemic; Cytotoxicity; Purine inhibitor; Substituted carboranes

Indexed keywords

AMINO O CARBORANE HYDROCHLORIDE; ANTINEOPLASTIC AGENT; BORIC ACID; CARBORANE DERIVATIVE; DEOXYRIBONUCLEOTIDE; DIETHYL N (3 (1,2 DICARBADOCECABORANYL)PROPYL)PHOSPHORAMIDATE; DIETHYL N METHYL N (O CARBORANYLMETHYL)PHOSPHORAMIDATE; DIHYDROFOLATE REDUCTASE; DNA; INOSINATE DEHYDROGENASE; N ACETYL N METHYL AMINOMETHYL O CARBORANE; N ACETYL N METHYLPROPARGYLAMINE; N METHYLAMINOMETHYL O CARBORANE; PROTEIN KINASE; PURINE; TRANSFERASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER INHIBITION; COLON ADENOCARCINOMA; CONTROLLED STUDY; DNA SYNTHESIS INHIBITION; ENZYME INHIBITION; GLIOMA; HUMAN; HUMAN CELL; LEUKEMIA; LUNG CARCINOMA; MOUSE; NONHUMAN; PRIORITY JOURNAL; PURINE SYNTHESIS; UTERUS CANCER;

ADENOCARCINOMA; ANIMALS; ANTINEOPLASTIC AGENTS; BORON COMPOUNDS; CARCINOMA, EHRLICH TUMOR; CELL SURVIVAL; DRUG DESIGN; GLIOMA; HELA CELLS; HUMANS; KB CELLS; LEUKEMIA; LEUKEMIA L1210; LEUKEMIA, T-CELL; LUNG NEOPLASMS; MICE; MICE, INBRED STRAINS; MOLECULAR STRUCTURE; OSTEOSARCOMA; TUMOR CELLS, CULTURED;

EID: 0031840690     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Davis MA, Soloway AHi Carboranes III. Boron containing acridines. J Med Chem 10: 730-732, 1967.
2. Larsson BS, Larsson B, Roberto A: Boron neutron capture therapy for malignant melanoma: a experimental approach. Pigment Cell Res 2: 356-360, 1989.
3. Barth RF, Soloway AH, Alam F, Clendenon NR, Blue TE, Mafune N, Goodman JH, Gordon W, Bapat B, Adams DM, Staubus AE, Moescherger MJ, Gahbauer R, Yates AJ, Boesel CP, Mengers TF, Curran JF, Wang CK, Makrogliou GE, Tzeng J-J, Fairchild RG: Preclinical studies on neutron capture therapy. Basic Life Sci 50: 95-105, 1989.
4. Sweet F: Boron estrogens: synthesis, biochemical and biological testing of estrone and estradiol-17ß 3-carboranylmethyl ethers. Steroids 37: 223-238, 1981.
5. Wellmann F, Abrahan R, Muller R, Gabel D: Synthesis and biological behavior of a boronated analogue of the antiestrogen U-23,469 M. Z. Naturforsch. 46c: 252-256, 1991.
6. 3 Leukemic Cells Anticancer Res 17: 151-156, 1997.
7. Wiesboeck, RA and Hawthorne MF: Dicarbaundecaborane (13) and derivatives, J Am Chem Soc 86: 1642-1643, 1964.
8. - amino derivatives, Collect Czech Chem Commun 49: 1559-1562, 1984.
9. Heying TI, Ager JW, Jr, Clark SL, Alexander RP, Papetti S, Reid JA, Trotz SI: A new series of organoboranes. III. Some reactions of 1,2-dicarbaclovododecaborane (12) and its derivatives, Inorg Chem 2: 1097-1105, 1963.
10. Boone JL: Isolation of the hexahydroclovohexaborate (2-) anion, B6H62-, J Am Chem Soc 86: 5036-5036, 1964.
11. 2, Inorg Chem 3: 444-451, 1964.
12. Miller HC and Muetterties EL: Chapter 2 Boron compounds, Inorg Chem 10: 81-91, 1967.
13. Miller HC, Miller NE and Muetterties EL: Synthesis of polyhedral boranes, J Am Chem Soc 85: 3885-3886, 1963.
14. Hawthorne MF and Pilling RL: Bis(triethylammonium)decahydrodecarborate(2-1), Inorg. Synth. 9: 16-19, 1967.
15. Wilson JG, Anisuzzaman AKM, Alam F and Soloway AH: Development of carborane synthons: Synthesis and chemistry of (aminoalkyl)carboranes, Inorg Chem 31: 1955-1958, 1992.
16. Sood CK, Sood A, Spielvogel BF, Yousef JA, Bumham B, Hall IH:Synthesis and antineoplastic activity of some cyano-, carboxy-, carbo-methoxy-, and carbamyl-borane adducts of heterocyclic amines. J Phamm Sci 80: 1133-1140, 1991.
17. Geran RJ, Greenburg NH, MacDonald MM, Schumacher AM, Abbott BJ: Protocols for screening chemical agents and natural products against animal tumors and other biological systems. Cancer Chemo Rep 9-11, 1972.
18. Leibovitz AL, Stinson JC, McComb WB III, McCoy CE, Mazur KC, Mabry ND: Classification of human colorectal adenocarcinoma cell lines. Cancer Res 36: 4562-4569, 1976.
19. Liao LL, Kupchan SM, Horwitz SB: Mode of action of the antitumor compound bruceatin, an inhibitor of protein synthesis. Mol Pharmacol 12: 167-176, 1976.
20. 1210 cells. J Biol Chem 256: 1695-1704, 1981.
21. Christopherson RI, Yu ML, Jones ME: An overall radioassay for the first three reactions of de novo pyrimidine synthesis. Anal Biochem 11: 240-249, 1981.
22. Eichler DC, Fisher PA, Kom D: Effect of calcium on the recovery distribution of DNA polymerase from cultured human cells. J Biol Chem 252: 4011-4014, 1977.
23. Mamaril FP, Dobrjasky A, Green: A rapid method for isolated of nuclei of Ehrlich ascites tumor cells. Cancer Res 30: 352-356, 1970.
24. 1210 cells. Cancer Res 34: 3341-3346, 1974.
25. Anderson KM, Mendelson IS, Guzik G: Solubilized DNA-dependent nuclear RNA polymerases from the mammary glands of late-pregnant rats. Biochem Biophys Acta 383: 56-66, 1975.
26. Hall IH, Carlson GL, Abernathy GS, Piantadosi C: Cycloalkanones IV. Antifertility agents. J Med Chem 17: 1253-1257, 1974.
27. Moore EC, Hurlbert RB: Regulation of mammalian deoxyribonucletide biosynthesis by nucleotide or activators and inhibitors. J Biol Chem 241: 4802-4809, 1966.
28. Maley F, Ochoa S. Enzymatic phosphorylation of deoxycytidylic acid. J Biol Chem 1958; 233, 1538.
29. Kalman SM, Duffield PH, Brzozwki TJ: Purification and properties of a bacterial carbamyl phosphate synthetase. J Biol Chem 241: 1871-1877, 1966.
30. Archibald RM: Determination of citrulline and allontoin and demonstration of citrulline in blood plasma. J Biol Chem 156: 121-142, 1944.
31. Koritz SB, Gohen PP: Colorimetic determination of carbamyl amino acid and related compounds. J Biol Chem 209: 145-150, 1954.
32. Kampf A, Barfknecht RL, Schaffer PJ, Osaki S, Mertes MP: Synthetic inhibitors of Escherichia coli calf thymus and Ehrlich ascites tumor thymidylate synthetase. J Med Chem 19: 903-908, 1976.
33. Ho YK, Hakala T, Zakrzewski SF. 5-(1-Adamantyl) pyrimidines as inhibitors of folate metabolism. Cancer Res 32: 1023-1028, 1971.
34. Becker JH, Lohr GW: Inosine-5'-phosphate dehydrogenase activity in normal and leukemic blood cells. Klin Wochenschr 57: 1109-1115, 1979.
35. Lowry OH, Rosebrough J, Farr AL, Randall RJ: Protein measurement with folin phenol reagent. J Biol Chem 193: 265-275, 1951.
36. Bagnara AS, Finch LR: Quantitative extraction and estimation of intracellular nucleotide-triphosphate in Escherichia coli. Anal Biochem 45: 24-34, 1971.
37. Hunting D, Henderson JF: Determination of deoxyribonucleoside triphosphates using DNA polymerase: a critical evaluation. Can J Biochem 59: 723-727, 1982.
38. Suzuki H, Nishimura T, Muto SK Tanaka N: Mechanism of action of macromomycin: DNA strand scission, inhibition of DNA synthesis mitosis. J Antibacteriol 32: 875-883, 1978.
39. Pera JF Sr, Rawlings CJ, Shackleton J, Roberts JJ: Quantitative aspects of the formation and loss of DNA. Biochem Biophy Acta 655: 152-166, 1981.
40. Woynarowski JW, Beerman TA, Konopa J: Introduction of deoxyribonucleic acid damage in HeLa S3 cells by cytotoxic and antitumor sesquiterpine lactones. Biochem Pharmacol 30: 3005-3007, 1981.
41. Zhao Y, Hall IH, Oswald CB, Yokoi T, Lee KH: Anti-malarial agents III. Mechanism of action of artesunate against Plasmodium berghi infection. Chem Phar Bull 35: 2052-2061, 1987.