Mass Spectroscopy of the Antileukemic Drug MGBG and Related Bis(Amidinohydrazones) [‘Bis(Guanylhydrazones)’]

References

• Bis(amidinohydrazones) are commonly called ‘bis(guanylhydrazones)’ Therefore, their established abbreviations contain the letters GBG, preceded by an indication of the substituents (e.g., DE for diethyl or EM for ethyl methyl). The term ‘bis(amidinohydrazone)’ is, however, more appropriate. The Chemical Abstracts' systematic name of methylglyoxal bis(amidinohydrazone) is 2,2′-(1-methyl-1,2-ethanediylidene)bis(hydrazinecarboximidamide), and other congeners are named analogously
   Google Scholar
• Thiele , J. and Dralle , E. 1989 . Zur Kenntniss des Amidoguanidins. I. Condensationsproducte des Amidoguanidins mit Aldehyden und Ketonen der Fettreihe . Liebig's Ann. Chem. , 302 : 275
   Google Scholar
• Freedlander , BL. and French , FA. 1958 . Carcinostatic Action of Polycarbonyl Compounds and Their Derivatives . Cancer Res. , 18 : 360
   PubMedGoogle Scholar
• Freireich , EJ. , Frei , E. and Karon , M. 1962 . Methylglyoxal Bis(guanylhydrazone): A New Agent Active Against Acute Myelocytic Leukemia . Cancer Chemother. Rep. , 16 : 183
   PubMedGoogle Scholar
• Mihich , E. 1975 . “ Bis-Guanylhydrazones ” . In Handbook of Experimental Pharmacology , Edited by: Sartorelli , AC. and Johns , DG. Vol. 38/2 , 766 – 788 . Berlin, New York : Springer Verlag .
   Google Scholar
• Seppänen , P. , Fagerström , R. , Alhonen-Hongisto , L. , Elo , H. , Lumme , P. and Jänne , J. 1984 . Glyoxal Bis(guanylhydrazone) as an Inhibitor of Polyamine Biosynthesis in Tumour Cells . Biochem. J. , 221 : 483
   PubMed Web of Science ®Google Scholar
• Williams-Ashman , HG. and Schenone , A. 1972 . Methyl Glyoxal Bis(guanylhydrazone) as a Potent Inhibitor of Mammalian and Yeast S-Adenosylmethionine Decarboxylases . Biochem. Biophys. Res. Commun. , 46 : 288
   PubMed Web of Science ®Google Scholar
• Alhonen-Hongisto , L. , Seppänen , P. , Nikula , P. , Elo , H. and Jänne , J. 1985 . Structure-Activity Relationship of Bis(guanylhydrazones) . Recent Progr. Polyamine Res. , : 261
   Google Scholar
• Jänne , J. , Alhonen-Hongisto , L. , Nikula , P. and Elo , H. 1986 . S-Adenosylmethionine Decarboxylase as Target of Chemotherapy . Adv. Enz. Regul. , 24 : 125
   Google Scholar
• Podrebarac , EG. , Nyberg , WH. , French , FA. and Cheng , CC. 1963 . Studies on Methylglyoxal Bis(guanylhydrazone) Analogs. I. Homologs of Methylglyoxal Bis(guanylhydrazone) . J. Med. Chem. , 6 : 283
   PubMedGoogle Scholar
• Baiocchi , F. , Cheng , CC. , Haggerty , WJ. , Lewis , LR. , Liao , TK. , Nyberg , WH. , O'Brien , DE. and Podrebarac , EG. 1963 . Studies on Methylglyoxal Bis(guanylhydrazone) Analogs. II. Structural Variations on Methylglyoxal Bis(guanylhydrazone) . J. Med. Chem. , 6 : 431
   PubMedGoogle Scholar
• Elo , H. , Laine , R. , Alhonen-Hongisto , L. , Jänne , J. , Mutikainen , I. and Lumme , P. 1985 . Biochemical Characterization of Propylglyoxal Bis(guanylhydrazone). Facile Synthesis of Monoalkylglyoxal Bis(guanylhydrazones) . Z. Naturforsch. , 40c : 839
   Google Scholar
• Elo , H. , Mutikainen , I. , Alhonen-Hongisto , L. , Laine , R. , Jänne , J. and Lumme , P. 1986 . Biochemical Properties and Crystal Structure of Ethylmethylglyoxal Bis(guanylhydrazone) Sulfate an Extremely Powerful Novel Inhibitor of Adenosylmethionine Decarboxylase . Z. Naturforsch , 41c : 851
   Google Scholar
• Kourou-Daley , S. , Peace , JN. and Nielsen , CJ. 1981 . A Gas Chromatographic and Mass Spectral Apporach to the Analysis of the Anticancer Drug Methyl-G as the Trimethylsilyl Derivative . Biomed. Mass. Spectrom. , 8 : 219
   Google Scholar
• Elo , H. , Mutikainen , I. , Alhonen-Hongisto , L. , Laine , R. and Jänne , J. 1988 . Diethylglyoxal Bis(guanylhydrazone): a Novel Highly Potent Inhibitor of S-Adenosylmethionine Decarboxylase with Promising Properties for Potential Chemotherapeutic use . Cancer Lett. , 41 : 21
   PubMed Web of Science ®Google Scholar
• Elo , H. Unpublished results
   Google Scholar
• Elo , H. 1989 . Bis(amidinohydrazones) [‘Bis(guanylhydrazones)’] as Antineoplastic Agents. Chemical and Biochemical Studies , Ph.D. Thesis Helsinki, , Finland : Department of Biochemistry, University of Helsinki .
   Google Scholar
• Elo , H. 1989 . Proton Nuclear Magnetic Resonance Spectroscopy of Bis(aminohydrazones) (Bis(guanylhydrazones)), and its Use for Studies on the Isomerism and Tautomerism of the Compounds . Spectroscopy Lett. , 22 : 123
   Web of Science ®Google Scholar
• Elo , H. 1989 . Carbon-13 NMR Spectroscopy of the Antileukemic Drug MGBG and Related Bis(amidinohydrazones) [‘Bis(guanylhydrazones)’] . Spectroscopy Lett. , 22 : 161
   Web of Science ®Google Scholar
• Elo , H. and Soljamo , K. 1989 . Unambiguous Assignment of the 13C NMR Resonances of the Side-Chain Carbon Atoms of Dipropylglyoxal Bis(amidinohydrazone) by DEPT and Selective Heteronuclear Proton Decoupling Techniques . Spectroscpy Lett. , 22 : 1141
   Web of Science ®Google Scholar
• Lumme , P. , Mutikainen , I. and Elo , H. 1986 . Structure of Propylglyoxal Bis(amidinohydrazone) Sulfate Dihydrate . Acta Cryst. , C42 : 1209
   Google Scholar
• Mutikainen , I. , Elo , H. and Tilus , P. Manuscript in preparation
   Google Scholar