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(12) United States Patent (10) Patent No.: US 8,519,146 B2 Youngs Et Al

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(12) United States Patent (10) Patent No.: US 8,519,146 B2 Youngs Et Al USOO8519146B2 (12) United States Patent (10) Patent No.: US 8,519,146 B2 Youngs et al. (45) Date of Patent: Aug. 27, 2013 (54) METAL COMPLEXES OF N-HETEROCYCLIC Kascatan-Nebioglu et al., Synthesis and structural characterization of CARBENES AS ANTIBOTCS N-heterocyclic carbene complexes of silver (I) and rhodium(I) from caffeine. Organomet. 23, 1928-1931 (published online Mar. 19. (75) Inventors: Wiley J. Youngs, Akron, OH (US); 2004).* Ramnial et al. A Monomeric Imidazol-2-ylidene Silver(I) Chloride Claire A. Tessier, Akron, OH (US); Complex: Synthesis, Structure, and Solid State 109Ag and 13C Jered Garrison, Columbia, MO (US); CP/MASNMR Characterization. Inorg. Chem.42, 1391-93 (2003).* Carol Quezada, Canal Fulton, OH (US); Richard S. Simons et al.: “Formation of N-Heterocyclic Complexes Abdulkareem Melaiye, Akron, OH of Rhodium and Palladium from a Pincer Silver(I) Carbene Com (US); Matthew Panzner, Akron, OH plex:” Organometallics; vol. 22, No. 9; 2003; pp. 1979 to 1982. (US): Semih Durmus, Akron, OH (US) Jered Garrison et al., “Synthesis and structural characterization of a silver complex of a mixed-donor N-heterocyclic carbene linked (73) Assignee: The University of Akron, Akron, OH cyclophane;” Chemical Communications, No. 18; Sep. 21, 2001; pp. (US) 1780 to 1781. Andreas A. Danopoulos et al., “Chelating and pincer dicarbene (*) Notice: Subject to any disclaimer, the term of this complexes of palladium; synthesis and structural studies,” Journal of patent is extended or adjusted under 35 the Chemical Society, Dalton Transactions; 2003; pp. 1009 to 1015. U.S.C. 154(b) by 1160 days. Ermitas Alcalde et al.; “Open-Chain Dications and Betaines with Imidazolium Molecular Motifs: Synthesis and Structural Aspects;” European Journal of Organic Chemistry; vol. 2002; Issue 7: pp. 1221 (21) Appl. No.: 11/482.410 to 1231. David J. Nielsen et al.; "A pyridine bridged dicarbene ligand and its (22) Filed: Jul. 7, 2006 silver(I) and palladium(II) complexes; synthesis, structures, and cata lytic applications;” Inorganica Chimica Acta 327; 2007: pp. 116 to (65) Prior Publication Data 125. US 2007/OO214O1 A1 Jan. 25, 2007 European Search Report for European Patent Application No. 04788633, dated Nov. 6, 2007. Simons, Richard S., et al., “Formation of N-Heterocyclic Complexes of Rhodium and Palladium from a Pincer Silver (1) Carbene Com Related U.S. Application Data plex”. Organometallics, ACS, Washington, DC, vol. 22, No. 22. (63) Continuation-in-part of application No. 10/569,563, (2003). filed as application No. PCT/US2004/029285 on Sep. (Continued) 7, 2004, now abandoned. Primary Examiner — Barbara P Badio (51) Int. Cl. Assistant Examiner — Sara E Townsley C07F 15/00 (2006.01) (74) Attorney, Agent, or Firm — REnner Kenner Greive C07F I/00 (2006.01) Bobak Taylor Weber (52) U.S. Cl. USPC ........................................... 548/103; 544/225 (57) ABSTRACT (58) Field of Classification Search A method for inhibiting microbial growth comprises admin USPC .......................................... 544/225; 548/103 istering an effective amount of a silver complex of a N-het See application file for complete search history. erocyclic amine. A method for treating cancer cells or a method for imaging one or more tissues of a patient includes (56) References Cited administering an effective amount of a complex of a N-het U.S. PATENT DOCUMENTS erocyclic amine and a radioactive metal. A method for treat ing urinary tract infections utilizing silver complexes of 4,677,143 A * 6/1987 Laurin et al. .................. 424,618 5,262.532 A 11/1993 Tweedle et al. N-heterocyclic carbenes. N-heterocyclic carbenes of the 5,405,957 A 4/1995 Tang et al. present invention may be represented by the formula 5,703,269 A 12/1997 Herrmann et al. 5,728,839 A 3, 1998 Herrmann et al. 5,994,365 A 11/1999 Zaworotko et al. Z 6,025,496 A 2, 2000 Herrmann et al. 6,288,197 B1 9/2001 Youngs et al. 6,316,380 B1 1 1/2001 Nolan et al. 6,492.525 B1 12/2002 Bertrand et al. R5 O Kl R2 6,794,327 B2 9/2004 Youngs et al. 6,919,448 B2 7/2005 Youngs et al. R R 2003/O190370 A1* 10, 2003 Kim et al. ..................... 424,618 FOREIGN PATENT DOCUMENTS wherein Z is a heterocyclic group, and R and R2 are, inde WO WOO2O85385 * 10/2002 pendently or in combination, hydrogen or a C-C organic WO WO2005/023760 * 3/2005 group selected from the group consisting of alkyl, cycloalkyl, OTHER PUBLICATIONS alkenyl, cycloalkenyl, alkynyl, aryl, arylalkyl, alkylaryl, het erocyclic, and alkoxy groups and Substituted derivatives Melaiye et al., Formation of water-soluble pincer silver(I)-carbene thereof. complexes: a novel antimicrobial agent. J. Med. Chem. 47,973-77 (published online Jan. 14, 2004).* 2 Claims, 16 Drawing Sheets US 8,519,146 B2 Page 2 (56) References Cited Aldalde E., et al., “Open-Chain Dications and Betaines with OTHER PUBLICATIONS Imidazolium Molecular Motifs: Synthesis and Structural Aspects', Chemistry—A European Journal, VCH Publishers, US, 2002, pp. Garrison, J.C., et al., “Synthesis and Structural Characterization of a 1221-1231. Silver Complex of a Mixed-Donor N-Heterocyclic Carbene Linked Nielsen, et al., “A Pyridine Bridged Dicarbene Ligand and its Cyclophane'. Chemical Communications 21, Sep. 2001, United Kingdom No. 18. Silver(a) and Palladium(II) Complexes: Synthesis, Structures, and Danopoulos, A.A., et al: “Chelating and Pincer: Dicarbene Com Catalytic Applications'. Inorganica Chimica ACTA, X, XX. vol.327. plexes of Palladium; Synthesis and Structural Studies”,Journal of the 2002 pp. 116-125. Chemical Society, Dalton Transactions, Chemical Society, Letchworth, GB Jan. 30, 2003. * cited by examiner U.S. Patent Aug. 27, 2013 Sheet 1 of 16 US 8,519,146 B2 U.S. Patent Aug. 27, 2013 Sheet 2 of 16 US 8,519,146 B2 FG 2 FG3 U.S. Patent Aug. 27, 2013 Sheet 3 of 16 US 8,519,146 B2 FIG. 4 U.S. Patent Aug. 27, 2013 Sheet 4 of 16 US 8,519,146 B2 F.G. 7 U.S. Patent Aug. 27, 2013 Sheet 5 of 16 US 8,519,146 B2 U.S. Patent Aug. 27, 2013 Sheet 6 of 16 US 8,519,146 B2 FIG. 11 FIG. 12 U.S. Patent Aug. 27, 2013 Sheet 7 of 16 US 8,519,146 B2 U.S. Patent Aug. 27, 2013 Sheet 8 of 16 US 8,519,146 B2 FIG. 17 F.G. 18 U.S. Patent Aug. 27, 2013 Sheet 9 of 16 US 8,519,146 B2 FG, 21 U.S. Patent Aug. 27, 2013 Sheet 10 of 16 US 8,519,146 B2 FG. 23 U.S. Patent Aug. 27, 2013 Sheet 11 of 16 US 8,519,146 B2 FG. 24 U.S. Patent Aug. 27, 2013 Sheet 12 of 16 US 8,519,146 B2 FG. 25 U.S. Patent Aug. 27, 2013 Sheet 13 of 16 US 8,519,146 B2 FIG. 26a FIG. 26b U.S. Patent Aug. 27, 2013 Sheet 14 of 16 US 8,519,146 B2 FIG. 27a FG.27b. FG, 28a. FG. 28b. FG, 28c U.S. Patent Aug. 27, 2013 Sheet 15 of 16 US 8,519,146 B2 OO 5OO -- Time (hr)ws CFU for SSD g -- Time(hr) vs CFU for 0.25% AgNO, s 4O -A- Time(hr) vs CFU for 25% (3/tecophilic) -- Time(hr) vs CFU for 75% (3/tecophilic) 5 300 O - - S 200 D L () 1OO U.S. Patent Aug. 27, 2013 Sheet 16 of 16 US 8,519,146 B2 US 8,519,146 B2 1. 2 METAL COMPLEXES OF N-HETEROCYCLC also demonstrated the ease of removal of the dressing in CARBENES AS ANTIBOTCS contrast to conventional wound dressings treated with silver nitrate. Acticoat has shown an increase in antibacterial func This is a continuation-in-part of International Application tion over both silver nitrate and silver sulfadiazine. Acticoat is PCT/US2004/029285, with an international filing date of 5 made up of nanocrystalline silver particles. Antibiotic-resis Sep. 7, 2004. The application entered the national stage in the tant strains have developed rarely to both silver nitrate and United States on Feb. 27, 2006 as application Ser. No. 10/569, silver sulfadiazine but not to nanocrystalline silver. The 563. broader range of activity of nanocrystalline silver is appar ently due to the release of both silver cations and uncharged STATEMENT REGARDING FEDERALLY 10 silver species. Due to the continuing emergence of antibiotic SPONSORED RESEARCH ORDEVELOPMENT resistant strains of infectious agents, a need exists for novel This invention was made with government Support under antibiotics. grants, Award Number NIH R15 CA 96739-01; and Award Metal compounds have also played a significant role in Number NSF CHE-01 16041. The government may have cer 15 other therapeutic applications. One example of the usefulness tain rights to the invention. of the metals can be seen in the field of radiopharmaceuticals. The use of radiation therapy to destroy tumor cells is well BACKGROUND OF THE INVENTION known, but tumors can reappear after therapy. Hypoxic cells within the tumor are 2.5 to 3 times more resistant to X-ray This invention relates to metal-containing, therapeutic, radiation than other tumor cells. For this reason, these cells antimicrobial, and antifungal compounds. More particularly, are more likely to Survive radiation therapy or chemotherapy this invention relates to metal complexes of N-heterocyclic and lead to the reappearance of the tumor. Targeting of radio carbenes and their use as antimicrobial agents, antifungal nuclides to hypoxic cells will serve as a method to visualize agents and radiopharmaceutical compositions. them. Silver has long been used for its antimicrobial properties.
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