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. 1980 Mar 1;185(3):659–666. doi: 10.1042/bj1850659

Alkylation by 1,2:5,6-dianhydrogalactitol of deoxyribonucleic acid and guanosine.

E Institóris, J Tamás
PMCID: PMC1161443  PMID: 7387628

Abstract

DNA was alkylated in neutral solution at 37 degrees C with 1,2:5,6-dianhydrogalactitol and hydrolysed to yield two principal products, identified as 7-galactitylguanine and 1,6-dideoxy-1,6-di(guanin-7-yl)galactitol. The reaction products were separated by chromatography on Sephadex G-10 and Dowex 50 (H+ form). The two compounds were also obtained by reaction between dianhydrogalactitol and guanosine in acetic acid. The products were characterized from their u.v.-spectral data by comparison with those of the 7-alkylguanines and were also identified by mass spectrometry.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Ahmann D. L., O'Connell M. J., Bisel H. F., Edmonson J. H., Hahn R. G., Frytak S. Phase II study of dianhydrogalactitol and ICRF-159 in patients with advanced breast cancer previously exposed to cytotoxic chemotherapy. Cancer Treat Rep. 1977 Jan-Feb;61(1):81–82. [PubMed] [Google Scholar]
  2. Brookes P., Lawley P. D. The reaction of mono- and di-functional alkylating agents with nucleic acids. Biochem J. 1961 Sep;80(3):496–503. doi: 10.1042/bj0800496. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Eagan R. T., Ingle J. N., Frytak S., Rubin J., Kvols L. K., Carr D. T., Coles D. T., O'Fallon J. R. Platinum-based polychemotherapy versus dianhydrogalactitol in advanced non-small cell lung cancer. Cancer Treat Rep. 1977 Oct;61(7):1339–1345. [PubMed] [Google Scholar]
  4. Espana P., Wiernik P. H., Walker M. D. Phase II study of dianhydrogalactitol in malignant glioma. Cancer Treat Rep. 1978 Aug;62(8):1199–1200. [PubMed] [Google Scholar]
  5. Hoogstraten B., O'Bryan R., Jones S. 1,2:5,6-Dianhydrogalactitol in advanced breast cancer. Cancer Treat Rep. 1978 May;62(5):841–842. [PubMed] [Google Scholar]
  6. Institoris E., Fox B. W. The interaction of dianhydrogalactitol with DNA in cultured Yoshida sarcoma cells. Chem Biol Interact. 1978 Jul;22(1):99–107. doi: 10.1016/0009-2797(78)90153-9. [DOI] [PubMed] [Google Scholar]
  7. LAWLEY P. D., BROOKES P. FURTHER STUDIES ON THE ALKYLATION OF NUCLEIC ACIDS AND THEIR CONSTITUENT NUCLEOTIDES. Biochem J. 1963 Oct;89:127–138. doi: 10.1042/bj0890127. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Lawley P. D., Jarman M. Alkylation by propylene oxide of deoxyribonucleic acid, adenine, guanosine and deoxyguanylic acid. Biochem J. 1972 Feb;126(4):893–900. doi: 10.1042/bj1260893. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Lawley P. D., Orr D. J., Jarman M. Isolation and identification of products from alkylation of nucleic acids: ethyl- and isopropyl-purines. Biochem J. 1975 Jan;145(1):73–84. doi: 10.1042/bj1450073. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Lawley P. D., Thatcher C. J. Methylation of deoxyribonucleic acid in cultured mammalian cells by N-methyl-N'-nitro-N-nitrosoguanidine. The influence of cellular thiol concentrations on the extent of methylation and the 6-oxygen atom of guanine as a site of methylation. Biochem J. 1970 Feb;116(4):693–707. doi: 10.1042/bj1160693. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Miller V., Pacáková V., Smolková E. Gas-liquid chromatographic analysis of trimethylsilyl derivatives of pyrimidine and purine bases and nucleosides. J Chromatogr. 1976 Apr 28;119:355–367. doi: 10.1016/s0021-9673(00)86799-0. [DOI] [PubMed] [Google Scholar]
  12. Németh L., Institóris L., Somfai S., Gál F., Pályi I., Sugár J., Csuka O., Szentirmay Z., Kellner B. Pharmacologic and antitumor effects of 1,2:5,6-dianhydrogalactitol (NSC-132313). Cancer Chemother Rep. 1972 Oct;56(5):593–602. [PubMed] [Google Scholar]
  13. Pályi I. Survival and phase sensitivity of HeLa cells treated with dianhydrogalactitol (NSC-132313). Cancer Chemother Rep. 1975 May-Jun;59(3):493–499. [PubMed] [Google Scholar]

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