Skip to main content

Diazo and Diazonium DNA Cleavage Agents: Studies on Model Systems and Natural Product Mechanisms of Action

  • Chapter
  • First Online:
Heterocyclic Antitumor Antibiotics

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 2))

Abstract

Diazonium salts have been previously used to cleave DNA via generation of carbon centered radicals and cations. Efforts have been made in the past decade or so to develop diazo compounds and α-diazoketones for physiologically relevant DNA cleavage. These efforts, coupled with their relevance to the mechanism of action of kinamycin and lomaiviticin antibiotics and other naturally occurring diazo compounds, will be discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Griess P (1858) Liebigs Ann Chem 106:123

    Google Scholar 

  2. Griess P (1859) Liebigs Ann Chem 109:295

    Google Scholar 

  3. Griess P (1860) Liebigs Ann Chem 113:205

    Google Scholar 

  4. Wulfman DS (1978) The chemistry of diazonium and diazo groups. Wiley, New York

    Google Scholar 

  5. Zollinger H (1991) Color chemistry. Synthesis, properties and applications of organic dyes and pigments. Wiley, Weinheim

    Google Scholar 

  6. Regitz M (1978) The chemistry of diazonium and diazo groups. Wiley, New York

    Google Scholar 

  7. Galli C (1988) Chem Rev 88:765

    Article  CAS  Google Scholar 

  8. Farnsworth DW, Wink DA, Roscher NM, Michedja CJ, Smith RHJ (1994) J Org Chem 59:5942

    Article  CAS  Google Scholar 

  9. White EH, Scherre H (1961) Tetrahedron Lett 2:758

    Article  Google Scholar 

  10. Issacs NS, Rannala E (1974) J Chem Soc Perkin Trans 2:899

    Google Scholar 

  11. Jones CC, Kelly MA, Sinnott ML, Smith PJ, Tzotzos GT (1982) J Chem Soc Perkin Trans 2:1655

    Google Scholar 

  12. Jones CC, Kelly MA, Sinnott ML, Smith PJ (1980) J Chem Soc Chem Commun, p 322

    Google Scholar 

  13. Yongfeng WS, Stevens MFG, Thomson W (1994) J Chem Soc Chem Commun 14:1687

    Google Scholar 

  14. Lowe PR, Sansom CE, Scwalbe CH, Stevens MFG, Clark AS (1992) J Med Chem 35:3377

    Article  PubMed  CAS  Google Scholar 

  15. Wheelhouse RTS, Stevens MFG (1993) J Chem Soc Chem Commun 15:1177

    Article  Google Scholar 

  16. Ljinsky W (1992) Chemistry and biology of N-nitroso compouds. Cambridge University Press, Cambridge, UK

    Google Scholar 

  17. Finneman JI, Fishbein JC (1995) J Am Chem Soc 117:4228

    Article  CAS  Google Scholar 

  18. Ho J, Fishbein JCH (1994) J Am Chem Soc 116:6611

    Article  CAS  Google Scholar 

  19. Finneman JI, Hovinen J, Ho J, Fishbein JC (1992) J Am Chem Soc 114:10321

    Article  Google Scholar 

  20. Finneman JI, Ho J, Fishbein JC (1993) J Am Chem Soc 115:3016

    Article  CAS  Google Scholar 

  21. Moss RA (1974) Acc Chem Res 7:421

    Article  CAS  Google Scholar 

  22. Wheeler GP (1978) ACS Symposium Series 30. American Chemical Society, Washington, DC

    Google Scholar 

  23. Naghipur A, Ikonomou MG, Kebarle P, Lown WJ (1990) J Am Chem Soc 112:31783187

    Article  Google Scholar 

  24. Augusto O, Cavalier EL, Rogan EG, Ramakrishna NVS, Kolar C (1990) J Biol Chem 265:22093

    PubMed  CAS  Google Scholar 

  25. Leite LCC, Augusto O (1989) Arch Biochem Biophys 270:560

    Article  PubMed  CAS  Google Scholar 

  26. Bregant TM, Groppe J, Little DR (1994) J Am Chem Soc 116:3635

    Article  CAS  Google Scholar 

  27. Nicolaou KC, Zuccarello G, Reimer C, Estevez VA, Dai WM (1992) J Am Chem Soc 114:7360

    Article  CAS  Google Scholar 

  28. Nicolaou KC, Skokotas G, Maligres P, Zuccarello G, Scweiger EJ, Toshima K, Wendeborn S (1989) Angew Chem Int Ed Eng 28

    Google Scholar 

  29. Nicolaou KC, Maligres P, Shin J, Leon ED, Rideout D (1990) J Am Chem Soc 12:7825

    Article  Google Scholar 

  30. Jones GB, Fouad FS (2002) Curr Pharm Des 8:2415

    Article  PubMed  CAS  Google Scholar 

  31. Sullivan RWC, Coghlan VM, Munk SA, Reed MW, Moore HW (1994) J Org Chem 59:2276

    Article  CAS  Google Scholar 

  32. Burckhardt GZ, Zimmer CH, Baguley B (1987) J Biomolec Str Dyn 4:813

    CAS  Google Scholar 

  33. Arya DP, Warner PM, Jebaratnam DJ (1993) Tetrahedron Letters 34:7823

    Article  CAS  Google Scholar 

  34. Luck G, Reinert KE, Baguley B, Zimmer CH (1987) J Biomolec Str Dyn 4:1079

    CAS  Google Scholar 

  35. Arya DP, Devlin TA, Jebaratnam D, Warner P (1998) US patent no 5770736 (Northeastern University, USA) p 20

    Google Scholar 

  36. Arya DP, Jebaratnam DJ (1995) Tetrahedron Letters 36:4369

    Article  CAS  Google Scholar 

  37. Jebaratnam DJ, Arya DP, Chen H, Kugabalasooriar CS, Vo D (1995) Bioorg Med Chem Lett 5:1191

    Article  CAS  Google Scholar 

  38. Jebaratnam DJ, Kugabalasooriar S, Chen H, Arya DP (1995) Tetrahedron Letters 36:3123

    Article  CAS  Google Scholar 

  39. Behr JP (1989) J Chem Soc Chem Commun, p 101

    Google Scholar 

  40. Hata T, Omura S, Iwai Y, Nakagawa A, Otani M (1971) J Antibiot 24:353

    PubMed  CAS  Google Scholar 

  41. Gould SJT, Nuria, Melville CR, Chris R, Cone MC, Martha C (1994) J Am Chem Soc 116:2207

    Article  CAS  Google Scholar 

  42. Mithani S, Weeratunga G, Taylor NJ, Dmitrienko GI (1994) J Am Chem Soc 116:2209

    Article  CAS  Google Scholar 

  43. Hauser FM, Zhou MJ (1996) J Org Chem 61:5722

    Article  CAS  Google Scholar 

  44. Seaton PJ, Gould SJ (1989) J Antibiot (Tokyo) 42:189

    CAS  Google Scholar 

  45. Gould SJ, Chen J, Cone MC, Gore MP, Melville CR, Tamayo N (1996) J Org Chem 61:5720

    Article  CAS  Google Scholar 

  46. Isshiki K, Sawa T, Naganawa H, Matsuda N, Hattori S, Hamada M, Takeuchi T, Oosono M, Ishizuka M, Yang ZZ et al. (1989) J Antibiot (Tokyo) 42:467

    CAS  Google Scholar 

  47. Gore MP, Gould SJ, Weller DD (1992) J Org Chem 57:2774

    Article  CAS  Google Scholar 

  48. Cone MC, Hassan AM, Gore MP, Gould SJ, Borders DB, Alluri MR (1994) J Org Chem 59:1923

    Article  CAS  Google Scholar 

  49. Cone MCM, Melville CR, Gore MP, Gould SJ (1993) J Org Chem 58:1058

    Article  CAS  Google Scholar 

  50. Fusari SA, Frohardt RP, Ryder A, Haskell TH, Johannessen DW, Elder CC, Bartz QR (1954) J Am Chem Soc 76:2878

    Article  CAS  Google Scholar 

  51. Nihei Y, Hasegawa M, Suzuki K, Yamamoto S, Hanada MF, Furumai T, Fukagawa Y, Oki T (1993) J Antibiot (Tokyo) 46(6):900

    CAS  Google Scholar 

  52. He H, Ding WD, Bernan VS, Richardson AD, Ireland CM, Greenstein M, Ellestad GA, Carter GT (2001) J Am Chem Soc 123:5362

    Article  PubMed  CAS  Google Scholar 

  53. Dion HW, Fusari SA, Jakubowski ZL, Zora JG, Bartz QR (1956) J Am Chem Soc 78:3075

    Article  CAS  Google Scholar 

  54. Moore JAD, Dice JR, Nicolaides ED, Westland RD, Wittle EL (1954) J Am Chem Soc 76:2884

    Article  CAS  Google Scholar 

  55. Nakatani K, Maekawa S, Tanabe K, Saito I (1995) J Am Chem Soc 117:10635

    Article  CAS  Google Scholar 

  56. Myers AG, Kuo EY, Finney NS (1989) J Am Chem Soc 111:8057

    Article  CAS  Google Scholar 

  57. Myers AG, Dragovich PS (1989) J Am Chem Soc 111:9130

    Article  CAS  Google Scholar 

  58. Arya DP, Jebaratnam DJ (1995) J Org Chem 60:3268

    Article  CAS  Google Scholar 

  59. Cone MC, Seaton PJ, Halley KA, Gould SJ (1989) J Antibiot (Tokyo) 42:179

    CAS  Google Scholar 

  60. Jebaratnam DJ, Kugabalasooriar S, Chen H, Arya DP (1995) Tetrahedron Lett 36:3123

    Article  CAS  Google Scholar 

  61. Jebaratnam DJ, Arya DP, Chen H, Kugabalasooriar S, Vo D (1995) Bio Med Chem Lett 5:1191

    Article  CAS  Google Scholar 

  62. Arya DP, Jebaratnam DJ (1995) Tetrahedron Lett 36:4369

    Article  CAS  Google Scholar 

  63. Patai S (1978) The chemistry of diazonium and diazo groups, Part 2. Wiley, New York

    Book  Google Scholar 

  64. Patai S (1978) The chemistry of diazonium and diazo groups, Part 1. Wiley, New York

    Google Scholar 

  65. Laufer RS, Dmitrienko GI (2002) J Am Chem Soc 124:1854

    Article  PubMed  CAS  Google Scholar 

  66. Roberts JD, Watanabe W (1950) J Am Chem Soc 72:4869

    Article  CAS  Google Scholar 

  67. Moore HW (1977) Science 197:527

    Article  PubMed  ADS  CAS  Google Scholar 

  68. Bartlett PD, Traylor TG (1962) J Am Chem Soc 84:3407

    Article  Google Scholar 

  69. Hamilton GA, Giacin JR (1966) J Am Chem Soc 88:1584

    Article  CAS  Google Scholar 

  70. Christner DF, Frank BL, Kozarich JW, Stubbe J, Golik J, Doyle TW, Rosenberg IE, Krishnan B (1992) J Am Chem Soc 114:8763

    Article  CAS  Google Scholar 

  71. Rabow LE, Stubbe J, Kozarich JW (1990) J Am Chem Soc 112:3196

    Article  CAS  Google Scholar 

  72. Schönberg A, Awad WI, Latif N, Mustafa A, Goodman I, McIlroy RJ, Badcock WE, Pausacker KH, Ross IG, Hall DM, Mitchell RK, Albert A, Baker W, Coates GE, Glockling F, Atkinson RO, Poppelsdorf F (1951) J Chem Soc Chem Commun, p 1368

    Google Scholar 

  73. Dave V, Warnhoff EW (1970) Org Reactions 18:217

    CAS  Google Scholar 

  74. Marchand AP, Brockway NM (1974) Chem Rev 74:431

    Article  CAS  Google Scholar 

  75. Jones MJ, Hochman RN, Walton JD (1970) Tetrahedron Lett 11(30):2617

    Article  Google Scholar 

  76. Jones MJR, Rettig KR (1965) J Am Chem Soc 87:4013

    Article  CAS  Google Scholar 

  77. Kirmse W, Arnold H (1968) Angew Chem Int Ed Eng 7:539

    Article  CAS  Google Scholar 

  78. Shirafuji T, Yamamoto Y, Nozaki H (1971) Tetrahedron 27(22):5353

    Article  CAS  Google Scholar 

  79. Moser WR (1969) J Am Chem Soc 91:1135

    Article  CAS  Google Scholar 

  80. Eppley HJ, Sato SM, Ellington AD, Zaleski JM (1999) J Chem Soc Chem Commun, p 2405

    Google Scholar 

  81. Murray RW, Trozzolo AM (1961) J Org Chem 26:3109

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The author is grateful for financial support from NSF-CAREER (CHE/MCB-0134972).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dev P. Arya .

Editor information

Moses Lee

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Arya, D.P. Diazo and Diazonium DNA Cleavage Agents: Studies on Model Systems and Natural Product Mechanisms of Action. In: Lee, M. (eds) Heterocyclic Antitumor Antibiotics. Topics in Heterocyclic Chemistry, vol 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_018

Download citation

Publish with us

Policies and ethics