p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

Amaç: Farmakolojik olarak ilgi çekici özelliklere sahip rutenyum komplekslerinin gelişimine katkıda bulunmak amacıyla tiyosemikarbazon (TSC) içeren üç yeni mononükleer rutenyum(II)-aren kompleksleri sentezlendi. Yöntemler: Rutenyum(II)-aren dimeri [{RuCl(?-Cl)(?-p-simen)}2] (1) sırasıyla TSC1-3 (1:2 molar oranda) ile metanol içerisindeki reaksiyonu sonucu p-simen içeren konformasyonel olarak rijit yarı-sandviç Ru(II)-aren kompleksleri; [(?6-p-simen)Ru(TSC1-?3O,N,S)]Cl (I), [(?6-p-simen)Ru(Cl)(TSC2-?2N,S)]Cl (II), ve [(?-p-simen)Ru(Cl)(TSC3-?2N,S)]Cl (III) bileşikleri sentezlendi. Kompleks I, II ve III'ün moleküler yapıları elementel analiz teknikleri ve 1H NMR, Fourier transform infrared (FT-IR), UV-vis uygulamaları ile elde edilen spektroskopik veriler temelinde aydınlatıldı. Sentezlenen üç rutenyum(II)-aren kompleksinin in vitro antimikrobiyal aktivitesi disk difüzyon metodu ile değerlendirildi. Bulgular: Spektroskopik veriler TSC1'in kompleks I'de tiyon sülfür atomu, fenolik oksijen atomu ve azometin azot atomu üzerinden üç-dişli ligant olarak metale bağlanırken, TSC2 ve TSC3'ün kompleks II ve III'te tiyon sülfür atomu ve imin azot (C=N) atomu üzerinden çift-dişli ligant olarak merkezi metal atomuna bağlandığını ortaya koymuştur. Gözlemlenen antimikrobiyal aktivite sonuçları komplekslerin Gram-pozitif bakteri suşlarının büyümelerini etkin bir biçimde inhibe ettiğini göstermiştir. Sonuç: TSC1-3 içeren yeni mononükleer rutenyum(II)-aren kompleksleri başarılı bir biçimde sentezlendi ve moleküler yapıları spektroskopik yöntemlerle belirlendi. Bütün rutenyum(II)-aren kompleksleri Gram-negatif bakterilerden ziyade Gram-pozitif bakterilere karşı yüksek antimikrobiyal aktivite gösterdi.

Objective: Thiosemicarbazone (TSC) containing three new mononuclear ruthenium(II)-arene complexes were synthesized so as to contribute to the development of ruthenium complexes with pharmacologically attracted properties. Conclusion: The TSC1-3 containing ruthenium(II)-arene complexes were successfully synthesized and their molecular structures were also determined by the spectroscopic methods. All ruthenium(II)-arene complexes showed higher antibacterial activities against Gram-positive bacterial strains than the Gram-negative ones

___

  • Klayman DL, Scovill JP, Bartosevich JF, Bruce J. 2- Acetylpyridine Pyridyl)ethyl]-3-thiosemicarbazides antimalarial agents. J Med Chem. 1983;26:35-9. https://doi.org/10.1021/jm00355a008 [1-(2- potential as
  • Atalay T, Akgemci EG. Thermodynamic studies of some complexes thiosemicarbazone. Turk J Chem. 1998;22:123-7. phenyl-3
  • Beraldo H, Gambino D. The wide pharmacological versatility of semicarbazones, thiosemicarbozones and their metal complexes. Mini-Rev Med Chem. 2004; 4: -9. https://doi.org/10.2174/1389557043487484
  • Garcia-Tojal J, Garcia-Orad A, Serra JL, et al. Synthesis and spectroscopic properties of copper(II) complexes derived thiosemicarbazone. Structure and biological activity of Cu(C6H6N3S2)2]. J Inorg Biochem. 1999;75:45-54. https://doi.org/10.1016/S0162-0134(99)00031-8
  • Haraguchi SK, Silva AA, Vidotti GJ, et al. Antitrypanosomal activity of novel benzaldehyde- thiosemicarbazone derivatives from kaurenoic acid. Molecules. 2011; 16: 1166 - 80. https://doi.org/ 3390/molecules16021166
  • Dimmock JR, McColl JM, Wonkol SL, Thayer RS, Hancock DS. Evaluation of the thiosemicarbazones of some aryl alkyl ketones and related compounds for anticonvulsant activities. Eur J Med Chem. 1991;26: -34. (91)90148-G https://doi.org/10.1016/0223
  • Sharma S, Athar F, Maurya MR, Azam, A. Copper(II) complexes with substituted thiosemicarbazones of thiophene-2-carboxaldehyde: Synthesis, characterization and antiamoebic activity against E. histolytica. Eur J Med 1016/j.ejmech.2005.05.013 https://doi.org/
  • Singh S, Bharti N, Mohapatra PP. Chemistry and biology of synthetic and naturally occurring antiamoebic agents. Chem Rev. 2009;109:1900-47. https://doi.org/10.1021/cr068217k
  • Yildirim H, Guler E, Yavuz M, et al. Ruthenium (II) complexes of thiosemicarbazone: Synthesis, biosensor applications and evaluation as antimicrobial agents. Mater Sci Eng C. 2014;44:1-8. https://doi.org/ 1016/j.msec.2014.08.007
  • Castarlenas R, Vovard C, Fischmeister C, Dixneuf PH. Allenylidene-to-indenylidene arene-ruthenium complexes: A key step to highly active catalysts for olefin metathesis reactions. J Am Chem rearrangement 1021/ja0579762 in ;128:4079-89. https://doi.org/
  • Pampaloni G. Aromatic hydrocarbons as ligands. Recent advances in the synthesis, the reactivity and the applications of bis(?6-arene) complexes. Coord Chem Rev. j.ccr.2009.05.014 https://doi.org/10.1016/
  • Raja MU, Sindhuja E, Ramesh R. Arene ruthenium(II) p-chloroacetophenone complex mediated transfer hydrogenation of ketones. Inorg Chem Commun. 2010; 13: 1321 - 4. https://doi.org/10.1016/j.inoche.2010.07.026
  • Stringer T, Therrien B, Hendricks DT, Guzgay H, and Smith ruthenium(II) complexes: Synthesis, characterization and cytotoxicity. Inorg https://doi.org/10.1016/j.inoche.2011.03.041 ;14:956-60.
  • Beckford F, Dourth D, Shaloski Jr M, et al. Half- sandwich thiosemicarbazones: evaluation thiosemicarbazones)Cl]Cl complexes. J Inorg Biochem. ;105:1019-29. https://doi.org/10.1016/j.jinorgbio.2011.04.008 with Synthesis biological of
  • Allardyce CS, Dorcier A, Scolaro C, Dyson PJ. Development of organometallic (organo-transition metal) pharmaceuticals. Appl Organomet Chem. 2005;19:1-10. https://doi.org/10.1002/aoc.725
  • Ozturk N, Yaman PK, Yavuz M, Oter O, Timur S, Subasi E. Synthesis, structural characterization, oxygen sensitivity, and antimicrobial activity of ruthenium(II) carbonyl complexes with thiosemicarbazones. J Coord Chem. 2014;67:2688-700. 2014.948433
  • Bennett MA, Huang TN, Matheson TW, Smith AK. (?6- Hexamethylbenzene)ruthenium Synth. ch16 complexes. Inorg ;21:74-8. https://doi.org/10.1002/
  • Mandal SK, Chakravarty AR. Arene ruthenium complexes of N,N´- and N,O-donor schiff base ligands: An X-ray structure of [(?6-p-cymene) RuCl(C5,H4N-2- CH=NC6H4-p-Me)Cl·C6H6·H2O. Polyhedron. 1992;11: -7. https://doi.org/10.1016/S02775387(00)86017-9
  • Klayman DL, Bartosevich JF, Griffin TS, Mason CJ, Scovill JP. 2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents. J Med Chem. ;22:855-62. https://doi.org/10.1021/jm00193a020
  • Scovill JP. A facile synthesis of thiosemicarbazides and thiosemicarbazones by the transamination of 4- methyl-4-phenyl-3-thiosemicarbazide. Sulfur https://doi.org/10.1080/10426509108233920 ;60:15-9. Silicon Relat Elem.
  • Sampath K, Sathiyaraj S, Raja G, Jayabalakrishnan C. ruthenium(III) benzaldehyde 4-methyl-3-thiosemicarbazones with triphenylphosphine/triphenylarsine Synthesis, DNA binding, DNA cleavage, antioxidative and cytotoxic activity. J Mol Struct. 2013;1046:82-91. https://doi.org/10.1016/j.molstruc.2013.04.051 of co-ligands:
  • Manimaran A, Jayabalakrishnan C. DNA-binding, catalytic oxidation, C-C coupling reactions and antibacterial thiosemicarbazone complexes: Synthesis and spectral characterization. https://doi.org/10.1016/j.jare.2011.07.005 Ru(II) J Adv Res. ;3:233-43.
  • Natarajan K, Poddar RK, Agarwala U. Mixed complexes of ruthenium(III) and ruthenium(II) with triphenylphosphine or triphenylarsine and other ligands. J Inorg Nucl Chem. 1977;39:431-5. https://doi.org/10.1016/0022-1902(77)80056-0
  • Manivannan S, Prabhakaran R, Balasubramanian KP, Dhanabal V, Karvembu R, Chinnusamy V. Synthesis, spectral, electrochemical and catalytic studies of new Ru(III) tetradentate Schiff base complexes. Appl Organomet https://doi.org/10.1002/aoc.1318 ; : -
  • Kamalesu S, Swarnalatha K, Subramanian R, Muralidharan K, Gomathi S. Polypyridyl-hydrazone based Ruthenium(II) complexes: Spectral and computational analysis. Inorg Chim Acta. 2017;461:35- https://doi.org/10.1016/j.ica.2017.01.029
  • Beckford FA, Leblanc G, Thessing J, et al. Organometallic thiosemicarbazone ligands: Synthesis, structure and cytotoxicity of [(?6-p-cymene)Ru(NS)Cl]+ (NS = 9- anthraldehyde thiosemicarbazones. Inorg Chem Commun. 2009; 12: 1094-8. 1016/j.inoche.2009.08.034 complexes with https://doi.org/
  • Sivagamasundari M, Ramesh R. Luminescent property and catalytic activity of Ru(II) carbonyl complexes containing N, O donor of 2-hydroxy-1- naphthylideneimines. Spectrochim Acta Part A. 2007; :427-33. https://doi.org/10.1016/j.saa.2006.03.017
  • Krishna S, Miller LS. Host-pathogen interactions between the skin and Staphylococcus aureus. Curr Opin Microbiol. 2012;15:28-35. j.mib.2011.11.003
  • Schlecht LM, Peters BM, Krom BP, et al. Systemic Staphylococcus aureus infection mediated by Candida albicans hyphal invasion of mucosal tissue. Microbiology. 1099/mic.0.083485-0 https://doi.org/
  • Walsh SE, Maillard JY, Russel AD, Catrenich CE, Charbonneau DL, Bartolo RG. Activity and mechanisms of action of selected biocidal agents on Gram-positive and -negative bacteria. J Appl Microbiol. 2003;94:240- https://doi.org/10.1046/j.1365-2672.2003.01825.x
Dicle Tıp Dergisi-Cover
  • ISSN: 1300-2945
  • Yayın Aralığı: 4
  • Başlangıç: 1963
  • Yayıncı: Cahfer GÜLOĞLU
Sayıdaki Diğer Makaleler

Ceza İnfaz Kurumlarının Yönetim, Dış Koruma, Hükümlü ve Tutukluların Sevk ve Nakilleri ile Sağlık Hizmetlerinin Yürütülmesi Hakkındaki Protokolün Bir Olgu Sunumu Üzerinden Adli Tıbbi Değerlendirilmesi

Yaşar TIRAŞCI, CEM UYSAL, Aydın ALTINAL, Mustafa AKIN, Ubeydullah DURMAZ

Mikroenkapsüle edilen paratiroid hücrelerinin in-vitro optimizasyonu

Emrah YÜCESAN, Harun BASOGLU, Beyza GÖNCÜ, Nur ÖZTEN KANDAŞ, Yeliz Emine ERSOY, Fahri AKBAŞ, Erhan AYŞAN

Adneksiyal Torsiyonlu Hastaların Tanısında Mean Platelet Volümün Rolü Var mıdır?

ADNAN İNCEBIYIK, HACER UYANIKOĞLU

p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

MURAT YAVUZ, PELİN KÖSE YAMAN, Nurdan ÖZTÜRK, SUNA TİMUR, ELİF SUBAŞI

Yurtta Kalan Üniversiteli Kız Öğrencilerde Metabolik Sendrom Risk Faktörlerinin Değerlendirilmesi

MURAT AÇIK, FUNDA PINAR ÇAKIROĞLU

Kemik Kist Hidatik Hastalığı

YAVUZ PİRHAN, Necmi KURT

İntraartiküler propolis ekstraktının erişkin sıçanlarda deneysel osteoartrit tedavisinde etkinliği

GÖKÇEN KERİMOĞLU, MEHMET EMRE BAKİ, Kübra ÇAKIROĞLU AKBULUT

Azaltılmış Beyin Kaynaklı Nörotrofik Faktörün (BDNF), Fare Karaciğer ve Böbrek Dokusuna Apoptotik Etkileri

Berna TEZCAN, GÜLAY HACIOĞLU DERVİŞOĞLU, Selcen Aydın ABİDİN, İsmail ABİDİN

Huntington Hastalığında Dikkat Fonksiyonlarının Değerlendirilmesi

Murat GÜLTEKİN, Ayten EKİNCİ

Çoklu Primer Tümörler-Tek Merkez Deneyimi

Gökşen İMAMOĞLU İNANÇ, Tülay EREN, Süleyman ŞAHİN, Doğan YAZILITAŞ, MUSTAFA ALTINBAŞ, RAMAZAN ESEN, Ebru ÇILBIR, FATİH KARATAŞ, ÖZGÜR ÖMER YILDIZ, Pelin GÜMÜŞ