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Platin ve Bakır Temelli N-Heterosiklik Karben (NHC) Komplekslerinin Antikanser Özellikleri ve Etki Mekanizmaları

Year 2019, , 713 - 724, 28.06.2019
https://doi.org/10.17798/bitlisfen.480144

Abstract

Metal-N-Heterosiklik Karben (M-NHC) kompleksleri
uzun yıllardır organometalik kimyada katalitik aktivite gösteren bileşikler
olarak ön plana çıkmaktadırlar. Son yıllarda bu bileşiklerin biyolojik
özelliklerini ön plana çıkaran çalışmalar yoğun ilgi görmektedir. Kanser
çağımızın önemli bir hastalığı olup tedavisinde kullanılacak ilaçların keşfi
oldukça önemlidir. Bu nedenle M-NHC komplekslerinin antikanser özellikleri ile
ilgili çalışmalar önem kazanmıştır. Antikanser etki gösteren platin ve bakır
temelli M-NHC kompleksleri, bu komplekslerin en önemli olanlarındandır. NHC’lere
bağlı bulunan sübstitüentlerin değiştirilmesi ile M-NHC komplekslerinin antikanser
aktiviteleride değişmektedir. Bu bileşiklerin antikanser etki mekanizmaları DNA
mutasyonları ve Reaktif Oksijen Türleri (ROT)‘nden oluşur. Bununla beraber
M-NHC komplekslerinin antikanser etki mekanizmalarını tam olarak ortaya koyacak
ve yeni sentezlenecek komplekslere yol gösterecek çalışmalara ihtiyaç vardır.

References

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Year 2019, , 713 - 724, 28.06.2019
https://doi.org/10.17798/bitlisfen.480144

Abstract

References

  • 1. Matzingerand S., Fulscher M.P. 1995. Methyl substitution in carbenes. A theoretica prediction of the singlet-triplet energy separation of dimethylcarbene. Journal of Physical Chemistry, 99 (27): 10747-10751.
  • 2. Öfele K. 1968. 1,3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer Übergangsmetall-carben-komplex. Journal Organometallic Chemistry, 12, 42-43.
  • 3. Wanzlick H.W., Schönherr H.J. 1968. Direct Synthesis of a Mercury Salt‐Carbene Complex. Angewandte Chemie International Edition, 7(2): 141-142.
  • 4. Sarı Y., Aktaş A., Barut Celepci D., Gök Y., Aygün M. 2017. Synthesis, Characterization and Crystal Structure of New 2-Morpholinoethyl-Substituted Bis-(NHC)Pd(II) Complexes and the Catalytic Activity in the Direct Arylation Reaction. Catalysis Letter, 147(9): 2340–2351.
  • 5. Gök Y., Aktaş A., Erdoğan H., Sarı Y. 2018. New 4-vinylbenzyl-substituted bis(NHC)-Pd(II) complexes: Synthesis, characterization and the catalytic activity in the direct arylation reaction. Inorganica Chimica Acta. 471: 735–740.
  • 6. Erdoğan H., Aktaş A., Gök Y., Sarı Y. 2018. N-Propylphthalimide-substituted bis-(NHC)PdX2 complexes: synthesis, characterization and catalytic activity in direct arylation reactions. Transition Metal Chemistry, 43(1): 31–37.
  • 7. Aktaş A., Akkoç S., Gök Y. 2013. Palladium catalyzed Mizoroki–Heck and Suzuki–Miyaura reactions using naphthalenomethyl-substituted imidazolidin-2-ylidene ligands in aqueous media. Journal of Coordination Chemistry, 66(16): 2901-2909.
  • 8. Haque R.A., Choo S.Y., Budagumpi S., Iqbal M.A., Abdullah A.A. 2015. Silver(I) complexes of mono- and bidentate N-heterocyclic carbene ligands: Synthesis, crystal structures, and in vitro antibacterial and anticancer studies. European Journal of Medicinal Chemistry, 90: 82-92.
  • 9. Li Y., Tan C.-P., Zhang W., He L., Ji L.-N., Mao Z.-W. 2015. Phosphorescent iridium(III)-bis-N-heterocyclic carbene complexes as mitochondria-targeted theranostic and photodynamic anticancer agents. Biomaterials 39: 95-104.
  • 10. Arduengo III A.J., Harlow R.L., Kline M. 1991. A Stable Crystalline Carbene. Journal of the American Chemical society,113(1): 361-363.
  • 11. Nguyen M.T., Nguyenand T.L., Le H.T. 1999. Theoretical Study of Dithioformic Acid, Dithiohydroxy Carbene and Their Radica Cations:  Unimolecularand Assisted Rearrangements. The Journal of Physical Chemistry A, 103(29): 5758-5765.
  • 12. Kühl O. 2010. Functionalised N-Heterocyclic Carbene Complexes. John Wiley&Sons, 7-8.
  • 13. Kühl O. 2009. Sterically induced differences in N-heterocyclic carbene transition metal complexes. Coordination Chemistry Reviews, 253(21-22): 2481-2492.
  • 14. Cisnetti F., Gautier A. 2013. Metal/N‐Heterocyclic Carbene Complexes: Opportunities for the Development of Anticancer Metallodrugs. Angewandte Chemie International Edition, 52(46): 11976- 11978.
  • 15. Aktaş A., Keleştemur Ü., Gök Y., Balcıoğlu S., Ateş B., Aygün M. 2017. Synthesis, characterization, crystal structure, and antimicrobial studies of 2-morpholinoethyl-substituted benzimidazolium salts and their silver(I)-N-heterocyclic carbene complexes. Research on Chemical Intermediates, 43(11): 6379–6393.
  • 16. Savić N.D., Glišić B.Đ., Wadepohl H., Pavic A., Senerovic L., Nikodinovic-Runic J., Djurana M.I. 2016. Silver(I) complexes with quinazoline and phthalazine: synthesis, structural characterization and evaluation of biological activities. Medicinal Chemistry Communication, 7: 282–291.
  • 17. Krishnamoorthy P., Sathyadevi P., Butorac R.R., Cowley A.H., Bhuvanesh N.S.P., Dharmaraj N. 2012. Copper(I) and nickel(II) complexes with 1[thin space (1/6-em)]:[thin space (1/6-em)]1 vs. 1[thin space (1/6-em)]:[thin space (1/6-em)]2 coordination of ferrocenyl hydrazone ligands: Do the geometry and composition of complexes affect DNA binding/cleavage, protein binding, antioxidant and cytotoxic activities? Dalton Transactions, 41:4423–4436.
  • 18. Li Y., Liu G.-F., Tan C.-P., Ji L.-N., Mao Z.-W. 2014. Antitumor properties and mechanisms of mitochondria-targeted Ag(I) and Au(I) complexes containing N-heterocyclic carbenes derived from cyclophanes. Metallomics, 6:1460-1468.
  • 19. Çetinkaya B., Özdemir İ., Binbaştoğlu B., Günal S. 1999. Antibacterial and Antifungal Activities of Complexes of Ruthenium (II). Arzneimitteforschung, 49(6): 538-540.
  • 20. Aktaş A., Taslimi P., Gülçin İ., Gök Y. 2017. Novel NHC Precursors: Synthesis, Characterization, and Carbonic Anhydrase and Acetylcholinesterase Inhibitory Properties. Archiv der Pharmazie, 350, DOI:10.1002/ardp.201700045.
  • 21. Sarı Y., Aktaş A., Taslimi P., Gök Y., Gülçin İ. 2017. Novel N‐propylphthalimide‐ and 4‐vinylbenzyl‐substituted benzimidazole salts: Synthesis, characterization, and determination of their metal chelating effects and inhibition profiles against acetylcholinesterase and carbonic anhydrase enzymes. Journal of Biochemical and Molecular Toxicology, doi.org/10.1002/jbt.22009.
  • 22. Erdemir F., Barut Celepci D., Aktaş A., Taslimi P., Gök Y., Karabıyık H., Gülçin İ. 2018. 2-Hydroxyethyl substituted NHC precursors: Synthesis, characterization, crystal structure and carbonic anhydrase, α-glycosidase, butyrylcholinesterase, and acetylcholinesterase inhibitory properties. Journal of Molecular Structure 1155: 797-806.
  • 23. Türker F., Barut Celepci D., Aktaş A., Taslimi P., Gök Y., Aygün M., Gülçin İ. 2018. meta‐Cyanobenzyl substituted benzimidazolium salts: Synthesis, characterization, crystal structure and carbonic anhydrase, α‐glycosidase, butyrylcholinesterase, and acetylcholinesterase inhibitory properties. Archiv der Pharmazie, doi.org/10.1002/ardp.201800029.
  • 24. Behçet A., Çağlılar T., Barut Celepci D., Aktaş A., Taslimi P., Gök Y., Aygün M., Kaya R., Gülçin İ. 2018. Synthesis, characterization and crystal structure of 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl Substituted Benzimidazole Bromide Salts: Their inhibitory properties against carbonic anhydrase and acetylcholinesterase. Journal of Molecular Structure, 1170: 160-169.
  • 25. Ott I., Gust R. 2007. Preclinical and Clinical Studies on the Use of Platinum Complexes for Breast Cancer Treatment. Anti-Cancer Agents in Medicinal Chemistry, 7(16): 95–110.
  • 26. Gust R., Beck W., Jaouen G, Schönenberger H, 2009. Optimization of cisplatin for the treatment of hormone-dependent tumoral diseases: Part 2: Use of non-steroidal ligands. Coordination Chemistry Reviews, 253(21-22): 2760–2779.
  • 27. Berners-Price S.J. 2011. Activating Platinum Anticancer Complexes with Visible Light. Angewandte Chemie International Edition, 50(4): 804–805.
  • 28. Wedlock L.E., Berners-Price S.J. 2011. Recent Advances in Mapping the Sub-cellular Distribution of Metal-Based Anticancer Drugs. Australian Journal of Chemistry, 64(6): 692–704.
  • 29. Wheate N.J., Walker S., Craig G.E., Oun R. 2010. The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Transactions, 39: 8113–8127.
  • 30. Monneret C. 2011. Platinum anticancer drugs. From serendipity to rational design. Annales Pharmaceutiques Françaises, 69(6): 286–295.
  • 31. Rabik C.A. Dolan ME. 2007. Molecular mechanisms of resistance and toxicity associated with platinating agents. Cancer Treatment Reviews, 33(1): 9-23.
  • 32. Gust R., Beck W., Jaouen G., Schönenberger H. 2009. Optimization of cisplatin for the treatment of hormone dependent tumoral diseases: Part 1: Use of steroidal ligands. Coordination Chemistry Reviews, 253(21-22): 2742–2759.
  • 33. Tan S.J. Yan Y.K., Lee P.P., Lim K.H. 2010. Copper, gold and silver compounds as potential new anti-tumor metallodrugs. Future Medicinal Chemistry, 2(10): 1591-1608.
  • 34. Scott L.E., Orvig C. 2009. Medicinal Inorganic Chemistry Approaches to Passivation and Removal of Aberrant Metal Ions in Disease. Chemical Reviewes, 109(10): 4885-4910.
  • 35. Hindi K.M., Panzner M.J., Tessier C.A., Cannon C.L., Youngs W.J. 2009. The Medicinal Applications of Imidazolium Carbene−Metal Complexes. Chem. Rev., 109(8): 3859-3884.
  • 36. Gautier A., Cisnetti F. 2012. Advances in metal–carbene complexes as potent anti-cancer agents. Metallomics, 4: 23-32.
  • 37. Mercs L., Albrecht M. 2010. Beyond catalysis: N-heterocyclic carbene complexes as components for medicinal, luminescent, and functional materials applications. Chemical Society Reviews, 39(6): 1903-1912.
  • 38. Liu W., Gust R. 2013. Metal N-heterocyclic carbene complexes as potential antitumor metallodrugs. Chemical Society Reviews, 42(2): 755-773.
  • 39. Alves G., Morel L., El-Ghozzi M., Avignant D., Legeret B., Nauton L., Cisnetti F., Gautier A. 2011. A platinum Chugaev carbene complex as a potent anticancer agent. Chemical Communications, 47(27): 7830–7832.
  • 40. Sun R.W.-Y., Chow A.L.-F., Li X.-H., Yan J.J., Chui S.S.-Y., Che C.-M. 2011. Luminescent cyclometalated platinum(II) complexes containing N-heterocyclic carbene ligands with potent in vitro and in vivo anti-cancer properties accumulate in cytoplasmic structures of cancer cells, Chemical Science, 2: 728-736.
  • 41. Trachootham D., Alexandre J., Huang P. 2009. Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? Nature Reviews, 8: 579-591.
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There are 61 citations in total.

Details

Primary Language Turkish
Journal Section Corrigendum
Authors

Aydın Aktaş 0000-0001-8496-6782

Publication Date June 28, 2019
Submission Date November 7, 2018
Acceptance Date April 24, 2019
Published in Issue Year 2019

Cite

IEEE A. Aktaş, “Platin ve Bakır Temelli N-Heterosiklik Karben (NHC) Komplekslerinin Antikanser Özellikleri ve Etki Mekanizmaları”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 8, no. 2, pp. 713–724, 2019, doi: 10.17798/bitlisfen.480144.



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