Cyclodextrins improve the antimicrobial activity of the chloride salt of Ruthenium(II) chloro-phenanthroline-trithiacyclononane

BioMetals

Volumn 22, Issue 3, 2009, Pages 541-556

  Marques, Joana ^a   Braga, Teresa M ^b   Almeida Paz, Filipe A ^a   Santos, Teresa M ^a   De Fátima Silva Lopes, Maria ^b   Braga, Susana S ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

Author keywords

CD; Antimicrobial activity; Phenanthroline; Ruthenium(II) complexes; TRIMEB

Indexed keywords

BETA CYCLODEXTRIN; PHENANTHROLINE DERIVATIVE; RUTHENIUM CHLOROPHENANTHROLINE TRITHIACYCLONONANE; RUTHENIUM COMPLEX; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS; BACTERIAL GROWTH; COMPARATIVE STUDY; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENTEROCOCCUS; ESCHERICHIA; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; INFRARED SPECTROSCOPY; LISTERIA; LOW TEMPERATURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SALMONELLA; STOICHIOMETRY; SYNCHROTRON RADIATION; THERMOGRAVIMETRY; X RAY DIFFRACTION; X RAY POWDER DIFFRACTION;

ANTI-INFECTIVE AGENTS; BACILLUS; CYCLODEXTRINS; ENTEROCOCCUS; ESCHERICHIA; LISTERIA; MAGNETIC RESONANCE SPECTROSCOPY; PHENANTHROLINES; RUTHENIUM COMPOUNDS; SALMONELLA; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STAPHYLOCOCCUS; X-RAY DIFFRACTION;

BACILLUS (BACTERIUM); BACTERIA (MICROORGANISMS); ENTEROCOCCUS; ESCHERICHIA; LISTERIA; NEGIBACTERIA; POSIBACTERIA; SALMONELLA;

EID: 67349156637     PISSN: 09660844     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10534-009-9211-x     Document Type: Article

References (48)

1. APEX2 (2006) Data collection software version 2.1-RC13. Bruker AXS, Delft
2. SS Balula AC Coelho SS Braga A Hazell AA Valente M Pillinger JD Seixas CC Romão IS Gonçalves 2007 Influence of cyclodextrins on catalytic olefin epoxidation with metal-carbonyl compounds. Crystal structure of the TRIMEB complex with CpFe(CO)(2)Cl Organometallics 26 6857 6863
3. 2) with beta-cyclodextrin J Organomet Chem 632 11 16 (Pubitemid 33618282)
4. 2) in 2-hydroxypropyl- and trimethyl-beta- cyclodextrin: structural and biological properties J Organomet Chem 690 2905 2912
5. Braga SS, Paz FAA, Pillinger M, Seixas JD, Romão CC, Gonçalves IS (2006a) Structural studies of beta-cyclodextrin and permethylated beta-cyclodextrin inclusion compounds of cyclopentadienyl metal carbonyl complexes. Eur J Inorg Chem 1662-1669
6. SS Braga S Gago JD Seixas AA Valente M Pillinger TM Santos IS Gonçalves CC Romão 2006 beta-Cyclodextrin and permethylated beta-cyclodextrin inclusion compounds of a cyclopentadienyl molybdenum tricarbonyl complex and their use as cyclooctene epoxidation catalyst precursors Inorg Chim Acta 359 4757 4764
7. MR Caira 2001 On the isostructurality of cyclodextrin inclusion complexes and its practical utility Rev Roum Chim 46 371 386 (Pubitemid 33631749)
8. Caira MR, Bourne SA, Mhlongo WT, Dean PM (2004) New crystalline forms of permethylated beta-cyclodextrin. Chem Commun 2216-2217 (Pubitemid 39472546)
9. Cryopad (2006) Remote monitoring and control, version 1.451. Oxford Cryosystems, Oxford
10. Favre-Nicolin V, Cerny R (2000) FOX-a program for ab initio structure solution from powder diffraction data, program developed for the Swiss National Science Foundation. University of Geneva, Switzerland
11. V Favre-Nicolin R Cerny 2002 FOX, 'free objects for crystallography': a modular approach to ab initio structure determination from powder diffraction J Appl Crystallogr 35 734 743 (Pubitemid 35423539)
12. Fit2D (1987-2005) version 12.077. Andy Hammersley, ESRF
13. Fitch AN (1996) European powder diffraction: Epdic Iv, Pts 1 and 2-materials science forum. Transtec Publications Ltd, Zurich-Uetikon, pp 219-221
14. AN Fitch 2004 The high resolution powder diffraction beam line at ESRF J Res Natl Inst Stand Technol 109 133 142
15. MJ Gidley SM Bociek 1988 C-13 CP-MAS NMR studies of amylose inclusion complexes, cyclodextrins, and the amorphous phase of starch granules- relationships between glycosidic linkage conformation and solid-state C-13 chemical-shifts J Am Chem Soc 110 3820 3829 (Pubitemid 18148855)
16. BJ Goodfellow V Felix SMD Pacheco JP de Jesus MGB Drew 1997 Structural characterisation of Ru-II [9]aneS(3) polypyridyl complexes by NMR spectroscopy and single crystal X-ray diffraction Polyhedron 16 393 401 10.1016/0277-5387(96) 00310-5 (Pubitemid 127348461)
17. A Habtemariam M Melchart R Fernandez S Parsons IDH Oswald A Parkin FPA Fabbiani JE Davidson A Dawson RE Aird DI Jodrell PJ Sadler 2006 Structure-activity relationships for cytotoxic Ruthenium(II) arene complexes containing N, N-, N, O-, and O, O-chelating ligands J Med Chem 49 6858 6868 10.1021/jm060596m
18. A Harada K Saeki S Takahashi 1989 Preparation and properties of inclusion-compounds of (eta-6-arene)tricarbonylchromium(0) complexes with cyclodextrins Organometallics 8 730 733
19. 5]. J Chem Soc Dalton Trans 2429-2932
20. SJ Heyes NJ Clayden CM Dobson 1992 C-13 CP-MAS NMR studies of the cyclomalto-oligosaccharide (cyclodextrin) hydrates Carbohydr Res 233 1 14 (Pubitemid 23580013)
21. G Horvath T Premkumar A Boztas E Lee S Jon KE Geckler 2008 Supramolecular nanoencapsulation as a tool: solubilization of the anticancer drug trans-dichloro(dypyridine)platinum (II) by complexation with beta-cyclodextrin Mol Pharm 5 358 363
22. Jakupec MA, Galanski M, Arion VB, Hartinger CG, Keppler BK (2008) Antitumour metal compounds: more than theme and variations. Dalton Trans 183-194. doi: 10.1039/b712656p (Pubitemid 350278321)
23. T Kottke D Stalke 1993 Crystal handling at low-temperatures J App Cryst 26 615 619
24. 3=1,4,7-trithiacyclononane). J Chem Soc Dalton Trans 1885-1893
25. Madureira J (2005) Ruthenium complexes with polithioether and/or polypyridil ligands: syntesis, structural characterization and DNA interactions. Dissertation, University of Aveiro
26. Madureira J, Santos TM, Goodfellow BJ, Lucena M, de Jesus JLP, Santana-Marques MG, Drew MGB, Félix V (2000) Structural characterisation of new Ru-II[9]aneS(3) polypyridylic complexes. Dalton Trans 4422-4431
27. 3)(bpy)Cl]Cl J Organomet Chem 693 3021 3028
28. UK Mazumder M Gupta SS Karki S Bhattacharya S Rathinasamy S Thangavel 2004 Synthesis, anticancer and antibacterial activity of some novel mononuclear Ru(II) complexes Chem Pharm Bull (Tokyo) 52 178 185 10.1248/cpb.52.178 (Pubitemid 41656749)
29. National Committee for Clinical Laboratory Standards (2003) Methods for dilution antimicrobial susceptibility test for bacteria that grow aerobically-sixth edition: approved standard M7-A6. NCCLS, Wayne
30. M Navarro OA Corona I Colmenares E Marchan 2006 Ruthenium polypyridyl complexes: synthesis, characterization and biological activity on Leishmania (L) mexicana Lett Drug Des Discov 3 454 458 10.2174/157018006778194826 (Pubitemid 44371977)
31. CCL Pereira M Nolasco SS Braga FA Almeida Paz P Ribeiro-Claro M Pillinger IS Gonçalves 2007 A combined theoretical-experimental study of the inclusion of niobocene dichloride in native and permethylated beta-cyclodextrins Organometallics 26 4220 4228 (Pubitemid 47310052)
32. 2 = 2,2?--biimidazole) and their cytotoxic action against K1735-M2 metastatic cells Organometallics 27 4948 4956
33. Ž Petrovski SS Braga AM Santos SS Rodrigues IS Gonçalves M Pillinger FE Kühn CC Romão 2005 Synthesis and characterization of the inclusion compound of a ferrocenyldiimine dioxomolybdenum complex with heptakis-2,3,6-tri-O-methyl-beta-cyclodextrin Inorg Chim Acta 358 981 988
34. Ž Petrovski SS Braga SS Rodrigues CCL Pereira IS Gonçalves M Pillinger C Freire CC Romão 2005 Synthesis of ferrocenyldiimine metal carbonyl complexes and an investigation of the Mo adduct encapsulated in cyclodextrin New J Chem 29 347 354 (Pubitemid 40320522)
35. Z Petrovski M de Matos SS Braga CCL Pereira ML Matos IS Gonçalves M Pillinger PM Alves CC Romão 2008 Synthesis, characterization and antitumor activity of 1,2-disubstituted ferrocenes and cyclodextrin inclusion complexes J Organomet Chem 693 675 684
36. M Reiher G Brehm S Schneider 2004 Assignment of vibrational spectra of 1,10-phenanthroline by comparison with frequencies and Raman intensities from density functional calculations J Phys Chem A 108 734 742
37. L Ronconi PJ Sadler 2007 Using coordination chemistry to design new medicines Coord Chem Rev 251 1633 1648 10.1016/j.ccr.2006.11.017
38. W Saenger 1980 Cyclodextrin inclusion-compounds in research and industry Angew Chem Int Ed Engl 19 344 362 10.1002/anie.198003441
39. ©. Bruker AXS, Madison, Wisconsin
40. TM Santos J Madureira BJ Goodfellow MGB Drew J Pedrosa de Jesus V Félix 2001 Interaction of ruthenium(II)-dipyridophenazine complexes with CT-DNA: effects of the polithioether ancillary ligands Met-Based Drugs 8 125 136 (Pubitemid 33034713)
41. Serli B, Zangrando E, Gianferrara T, Scolaro C, Dyson PJ, Bergamo A, Alessio E (2005) Is the aromatic fragment of piano-stool Ruthenium compounds an essential feature for anticancer activity? The development of new Ru-II-[9]aneS(3) analogues. Eur J Inorg Chem 3423-3434. doi: 10.1002/ejic.200500210
42. Sheldrick GM (1997a) SHELXS-97, program for crystal structure solution. University of Göttingen
43. Sheldrick GM (1997b) SHELXL-97, program for crystal structure refinement. University of Göttingen
44. Sheldrick GM (1998) SADABS v.2.01 Bruker/Siemens area detector absorption correction program. Bruker AXS, Madison
45. GM Sheldrick 2008 A short history of SHELX Acta Cryst A 64 112 122
46. J Szejtli 1998 Introduction and general overview of cyclodextrin chemistry Chem Rev 98 1743 1753 10.1021/cr970022c (Pubitemid 128633435)
47. RP Veregin CA Fyfe RH Marchessault MG Taylor 1987 Correlation of C-13 chemical-shifts with torsional angles from high-resolution, C-13 CP-MAS NMR studies of crystalline cyclomalto-oligosaccharide complexes, and their relation to the structures of the starch polymorphs Carbohydr Res 160 41 56
48. (Pubitemid 41509143)