Synthesis and antifungal activity of a novel series of alkyldimethylamine cyanoboranes and their derivatives

Journal of Medicinal Chemistry

Volumn 49, Issue 16, 2006, Pages 4879-4885

  Takrouri, Khuloud ^a   Oren, Gal ^b   Polacheck, Itzhack ^b   Sionov, Edward ^b   Shalom, Eli ^a   Katzhendler, Jehoshua ^a   Srebnik, Morris ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b HADASSAH HEBREW UNIVERSITY MEDICAL CENTER   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AMINE; AMPHOTERICIN B DEOXYCHOLATE; ANTIFUNGAL AGENT; BORANE DERIVATIVE; CARBON; DIMETHYLAMINE CYANOBORANE DERIVATIVE; DIMETHYLUNDECYLAMINE CYANOBORANE; DIMETHYLUNDECYLAMINE DIBROMOCYANOBORANE; FLUCONAZOLE; NITROGEN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIBIOTIC RESISTANCE; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS; CANDIDA ALBICANS; CANDIDA GLABRATA; CANDIDA KRUSEI; CONTROLLED STUDY; COVALENT BOND; CULTURE MEDIUM; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS CULTURE; MALE; MAXIMUM TOLERATED DOSE; MINIMUM INHIBITORY CONCENTRATION; MOUSE STRAIN; NONHUMAN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TOXICITY TESTING;

ANIMALS; ANTIFUNGAL AGENTS; BORANES; DRUG RESISTANCE, FUNGAL; FLUCONAZOLE; HUMANS; MALE; MICE; MICE, INBRED ICR; MICROBIAL SENSITIVITY TESTS; NITRILES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33746913105     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060476e     Document Type: Article

References (47)

1. Hall, I. H.; Starnes, C. O.; Mcphail, A. T.; Wisian-Neilson, P.; Das, M. K.; Harchelroad, F., Jr.; Spielvogel, B. F. Anti-inflammatory activity of amine cyanoboranes, amine carboxyboranes, and related compounds. J. Pharm. Sci. 1980, 69, 1025-1029.
2. Kemp, B.; Kalbag, S.; Geanangel, R. A. Synthesis and characterization of the cyano- and carboxyborane adducts of quinuclidine. Inorg. Chem. 1984, 23, 3063-3065.
3. Hall, I. H.; Hall, E. S.; Chi, L. K.; Shaw, B. R.; Sood, A.; Spielvogel, B. F. Antineoplastic activity of boron-containing thymidine nucleosides in Tmolt3 leukemic cells. Anticancer Res. 1992, 12, 1091-1097.
4. Miller M. C., III; A. Sood; Spielvogel, B. F.; Hall, I. H. The synthesis and antitumor activity of metal complexes of amine-carboxyborane adducts. Appl. Organomet. Chem. 1998, 12, 87-97.
5. Hall, I. H.; Starnes, C. O.; Spielvogel, B. F.; Wisian-Neilson, P.; Das, M. K.; Wojnowich, L. Boron betaine analogs: antitumor activity and effects on Ehrlich ascites tumor cell metabolism. J. Pharm. Sci. 1979, 68, 685-688.
6. Spielvogel, B. F.; Wojnowich, L.; Das, M. K.; McPhail, A. T.; Hargrave, K. D. Boron analogues of amino acids. Synthesis and biological activity of boron analogues of betaine. J. Am. Chem. Soc. 1976, 98, 5702-5703.
7. Miller, M. C., III; Sood, A., Spielvogel, B. F.; Hall, I. H. Effects of alkylamine carboxyboranes on L1210 DNA fragmentation and nucleic acid metabolism. Arch. Pharm. Med. Chem. 1998, 331, 153-162.
8. Miller, M. C., III; Woods, C. M.; Murphy, M. E.; Elkins, A.; Spielvogel, B. F.; Hall, I. H. Relationship between amine-carboxyboranes and TNFα for the regulation of cell growth in different tumor cell lines. Biomed. Pharmacother. 1998, 52, 169-179.
9. Hall, I. H.; Chen, S. Y.; Rajendran, K. G.; Sood, A.; Spielvogel, B. F.; Shih, J. Hypolipidemic, anti-obesity, anti-inflammatory, antiosteoporotic, and anti-neoplastic properties of amine carboxyboranes. Environ. Health Perspect. 1994, 102, 21-30.
10. Hall, I. H.; Das, M. K.; Harchelroad, F., Jr.; Wisian-Neilson, P.; McPhail, A. T.; Spielvogel, B. F. Antihyperlipidemic activity of amine cyanoboranes, amine carboxyboranes, and related compounds. J. Pharm. Sci. 1981, 70, 339-341.
11. Murphy, M. E.; Elkins, A. L.; Shrewsbury, R. P.; Sood, A.; Speilvogel, B. F.; Hall, I. H. The effects of amine-carboxyborane related derivatives on umr-106 bone metabolism. Met.-Based Drugs 1996, 3, 31-56.
12. Hall, I. H.; Starnes, C. O.; Mcphail, A. T.; Wisian-Neilson, P.; Das, M. K. Harchelroad, F., Jr.; Spielvogel, B. F. Anti-inflammatory activity of amine cyanoboranes, amine carboxyboranes, and related compounds. J. Pharm. Sci. 1980, 69, 1025-1029.
13. Hall, I. H.; Burnham, B. S.; Chen, S. Y.; Sood, A.; Spielvogel, B. F., Morse, K. W. The anti-inflammatory activity of boron derivatives in rodents. Met.-Based Drugs 1995, 2, 1-12.
14. Hall, I. H.; Williams, W. L., Jr.; Gilbert, C. J.; McPhail, A. T.; Spielvogel, B. F. Hypolipidemic activity of tetrakis-μ-(trimethylamine- boranecarboxylato)-bis(trimethylamine- carboxyborane)-di-copper(II) in rodents and its effect on lipid metabolism. J. Pharm. Sci. 1984, 73, 973-977.
15. Hall, I. H.; Gilbert, C. J.; McPhail, A. T.; Morse, K. W.; Hassett, K.; Speilvogel, B. F. Antineoplastic activity of a series of boron analogues of α-amino acids. J. Pharm. Sci. 1985, 74, 755-758.
16. Sood, C. K.; Sood, A.; Speilvogel, B. F.; Yousef, J. A.; Burnham, B.; Hall, I. H. Synthesis and antineoplastic activity of some cyano-, carboxy-, carbomethoxy-, and carbamoylborane adducts of heterocyclic amines. J. Pharm. Sci. 1991, 80, 1133-1140.
17. Dembitsky, V. M.; Srebnik, M. Synthesis and biological activity of α-aminoboronic acids, amine-carboxyboranes and their derivatives. Tetrahedron 2003, 59, 579-593.
18. Fauci, A. S.; Touchette, N. A.; Folkers, G. K. Emerging infectious diseases: a 10-year perspective from the National Institute of Allergy and Infectious Diseases. Emerging Infect. Dis. 2005, II, 519-525.
19. Steinbach, W. J.; Perfect, J. R. Newer antifungal therapy for emerging fungal pathogens. Int. J. Infect. Dis. 2003, 7, 5-20.
20. Hazen, K. C. New and emerging yeast pathogens. Clin. Microbiol. Rev. 1995, 8, 462-478.
21. Barraja, P.; Diana, P.; Lauria, A.; Passannanti, A.; Almerico, A. M.; Minnei, C.; et al. Indolo[3,2-c]cinnolines with antiproliferative, antifungal, and antibacterial activity. Bioorg. Med. Chem. 1999, 7, 1591-1596.
22. Cardenas, M. E.; Cruz, M. C.; Del Poeta, M.; Chung, N.; Perfect, J. R.; Heitman, J. Antifungal activities of antineoplastic agents: Saccharomyces cerevisiae as a model system to study drug action. Clin. Microbiol. Rev. 1999, 12, 583-611.
23. Brown, J. M. Fungal infections in bone marrow transplant patients. Curr. Opin. Infect. Dis. 2004, 17, 347-352.
24. Garber, G. An overview of fungal infections. Drugs 2001, 61, 1-12.
25. Walsh, T. J.; Groll, A. H. Emerging fungal pathogens: evolving challenges to immunocompromised patients for the twenty-first century. Transpl. Infect. Dis. 1999, 1, 247-261.
26. Anaissie, E. Opportunistic mycoses in the immunocompromised host: experience at a cancer center and review. Clin. Infect. Dis. 1992, 14, S43-53.
27. Eggimann, P.; Garbino, J.; Pittet, D. Epidemiology of Candida species infections in critically ill non-immunosuppressed patients. Lancet Infect. Dis. 2003, 3, 685-702.
28. Ampel, N. M. Emerging disease issues and fungal pathogens associated with HIV infection. Emerging Infect. Dis. 1996, 2, 109-116.
29. Fanos, V.; Cataldi, L. Amphotericin B-induced nephrotoxicity: a review. J. Chemother. 2000, 12, 463-470.
30. Sheehan, D. J.; Hitchcock, C. A.; Sibley, C. M. Current and emerging azole antifungal agents. Clin. Microbiol. Rev. 1999, 12, 40-79.
31. Deray, G. Amphotericin B nephrotoxicity. J. Antimicrob. Chemother. 2002, 49, 37-41.
32. Dupont, B. Overview of the lipid formulations of amphotericin B. J. Antimicrob. Chemother. 2002, 49, 31-36.
33. Baddley, J. W.; Moser, S. A. Emerging fungal resistance. Clin. Lab. Med. 2004, 24, 721-735.
34. Ghannoum, M. A.; Rice, L. B. Antifungal agents: mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance. Clin. Microbiol. Rev. 1999, 12, 501-517.
35. Perfect, J. R. Antifungal resistance: the clinical front. Oncology (Williston Park) 2004, 18, 15-22.
36. Krcmery, V. C., Jr. Antifungal chemotherapeutics. Med. Princ. Pract. 2005, 14, 125-135.
37. Takrouri, K.; Katzhendler, J.; Srebnik, M. C-Lithiation/alkylation of trimethylamine cyanoborane. Organometallics 2004, 23, 2817-2820.
38. Takrouri, K.; Shalom, E.; Goldberg, I.; Katzhendler, J.; Srebnik, M. Diborane (4) derivatives via coupling of amine monobromocyanoboranes: Study of the bromination of amine cyanoborane and molecular structures of the amine dibromocyanoboranes. J. Organomet. Chem. 2005, 690, 4150-4158.
39. Shalom, E.; Takrouri, K.; Goldberg, I.; Katzhendler, J.; Srebnik, M. Preparation and structure determination of trimethylamine dibromo carboxyborane esters. Organometallics 2004, 23, 4396-4399.
40. Shalom, E.; Takrouri, K.; Goldberg, I.; Katzhendler, J.; Srebnik, M. Preparation and Structure Determination of Novel Fluoro Derivatives of Amine cyanoboranes and amine carboxyborane esters. Organometallics 2005, 24, 5776-5779.
41. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved Standard; 2nd ed.; M27-A2; NCCLS: Wayne, PA, 1997.
42. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of filamentous fungi. Approved Standard; 2nd ed.; M38-A; NCCLS: Wayne, PA, 2002.
43. Espinel-Ingroff, A.; Fothergill, A.; Ghannoum, M.; Manavathu, E.; Ostrosky-Zeichner, L.; Pfaller, M.; et al. Quality control and reference guidelines for CLSI broth microdilution susceptibility method (M 38-A document) for amphotericin B, itraconazole, posaconazole, and voriconazole. J. Clin. Microbiol. 2005, 43, 5243-5246.
44. Gomez-Lopez, A.; Garcia-Effron, G.; Mellado, E.; Monzon, A.; Rodriguez-Tudela, J. L.; Cuenca-Estrella, M. In vitro activities of three licensed antifungal agents against Spanish clinical isolates of Aspergillus spp. Antimicrob. Agents Chemother. 2003, 47, 3085-3088.
45. Falk, R.; Domb, A. J.; Polacheck, I. A novel injectable water-soluble amphotericin B-arabinogalactan conjugate. Antimicrob. Agents Chemother. 1999, 43, 1975-1981.
46. Wisian-Neilson, P.; Das, M. K.; Spielvogel, B. F. A general synthesis of amine-cyanoboranes. Inorg. Chem. 1978, 17, 2327-2329.
47. Pfaller, M. A.; Messer, S. A.; Hollis, R. J.; Jones, R. N.; Doern, G. V.; Brandt, M. E.; Hajjeh, R. A. Trends in species distribution and susceptibility to fluconazole among blood stream isolates of Candida species in the United States. Diagn. Microbiol. Infect. Dis. 1999, 33, 217-222.