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Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi ve Termal Bozunmasının Belirlenmesi

Year 2019, , 1899 - 1908, 31.07.2019

Nilüfer Öksüz Ersin Orhan

https://doi.org/10.29130/dubited.568949

Abstract

Bu çalışmada [Ru4(p-cymene)4(μ2-NՈN)2(μ4-OOՈOO)2][CF3SO3)4]
(NՈN = Bütilen-1,4-bisbenzimidazol (bbim)) genel formülüne sahip biyolojik
aktif tetranükleer aren rutenyum kompleks bileşiği, Ru2(p-cymene)2 (μ4-OOՈOO)Cl2
(OOՈOO = 5,8-dioxido-1,4-naphtoquinonato (donq))'nun gümüş
triflorometansülfonat ile reaksiyona sokulması, ardından karşılık gelen NՈN
bağlayıcılarının eklenmesi ile hazırlanmıştır. Biyolojik aktif aren rutenyum
bileşiği IR, UV-VIS, 1H, 13C NMR spektroskopisi ve ESI-MS
spektrometresi dahil standart tekniklerle karakterize edildi. Aren rutenyum
bileşiğinin termal bozunma ölçüm verileri incelendi. Bu ölçümler
Termogravimetrik analiz (TGA) ve Diferansiyel termal analiz (DTA) teknikleri ile
yapıldı.

Keywords

Aren rutenyum Bisbenzimidazol Supramoleküler kimya Termal bozulma

Supporting Institution

Düzce Üniversitesi

Project Number

2017.05.03.600 ve 2017.05.03.620

Thanks

Bu çalışma Düzce Üniversitesi Bilimsel Araştırma Projeleri tarafından desteklenmiştir (Proje no: 2017.05.03.600 ve 2017.05.03.620)

References

  • [1] B. Rosenbeng, L. Vancamp, J. E. Trosko, and V. H. Mansour, “Nature,” Nature, vol. 222, pp. 285–286, 1969.
  • [2] E. Orhan, A. Garci, B. Therrien, "Coordination-driven self-assembly of arene ruthenium metalla-rectangles," Inorganica Chimica Acta, vol. 461, pp. 78–83, 2017.
  • [3] E. Orhan, A. Garci, T. Riedel, P. J. Dyson, B. Therrien, " Cytotoxicity of arene ruthenium metalla-rectangles incorporating bis-pyridyl diimide linkers," Journal of Organometallic Chemistry, vol. 815-816, pp. 53-58, 2016.
  • [4] M. Galanski, M. A. Jakupec, and B. K. Keppler, “Update of the Preclinical Situation of Anticancer Platinum Complexes : Novel Design Strategies and Innovative Analytical Approaches,” Curr. Med. Chem., vol. 12, pp. 2075–2094, 2005.
  • [5] E. Orhan, A. Garci, T. Riedel, M. Saudani, P. J. Dyson, B. Therrien, "Cytotoxic double arene ruthenium metalla-cycles that overcome cisplatin resistance," Journal of Organometallic Chemistry, vol. 803, pp. 39-44, 2016.
  • [6] C. S. Allardyce and P. J. Dyson, “Ruthenium in Medicine : Current Clinical Uses and Future Prospects,” Platin. Met. Rev., vol. 45, no. 2, pp. 62–69, 2001.
  • [7] I. Kostova, “Ruthenium Complexes as Anticancer Agents,” Curr. Med. Chem., vol. 13, pp. 1085–1107, 2006.
  • [8] C. S. Allardyce, A. Dorcier, C. Scolaro, and P. J. Dyson, “Development of organometallic (organo-transition metal) pharmaceuticals,” Bioorganometallic Chem., vol. 19, pp. 1–10, 2005.
  • [9] E. Orhan, A. Garci, B. Therrien, "Flexible arene ruthenium metalla-prisms," Inorganica Chimica Acta, vol. 438, pp. 5–9, 2015.
  • [10] A. Garci, J. P. Mbakidi, V. Chaleix, V. Sol, E. Orhan, B. Therrien, "Tunable Arene Ruthenium Metallaprisms to Transport, Shield, and Release Porphin in Cancer Cells," Organometallics, vol. 34, pp. 4138−4146, 2015.
  • [11] A. Garci, A. A. Dobrov, T. Riedel, E. Orhan, P. J. Dyson, V. B. Arion, B. Therrien, "Strategy to optimize the biological activity of arene ruthenium metalla-assemblies," Organometallics, vol. 33, pp. 3813−3822, 2014.
  • [12] A. A. Hummer et al., “X-ray absorption near edge structure spectroscopy to resolve the in vivo chemistry of the redox-active Indazolium trans - [ tetrachlorobis ( 1H- indazole ) ruthenate ( III )] ( KP1019 ),” J. Med. Chem., vol. 56, pp. 1182, 2013.
  • [13] G. Tamasi et al., “Synthesis , spectroscopic and DFT structural characterization of two novel ruthenium ( III ) oxicam complexes . In vivo evaluation of anti-in fl ammatory and gastric damaging activities,” J. Inorg. Biochem., vol. 134, pp. 25–35, 2014.
  • [14] G. Süss-Fink, “Water-soluble arene ruthenium complexes : From serendipity to catalysis and drug design,” J. Organomet. Chem., vol. 751, pp. 2–19, 2014.
  • [15] H. Küçükbay, S. Günal, E. Orhan, R. Durmaz, "Synthesis and antimicrobial activities of some transition metal benzimidazole complexes," Asian Journal of Chemistry, vol. 22, pp. 7376–7382, 2010.
  • [16] H. Küçükbay, R. Durmaz, E. Orhan, S. Günal, "Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds," Farmaco, vol. 58, pp. 431–437, 2003.
  • [17] Ü. Ergun, "ONO Ve ONNO Tipindeki Schiff Bazlarının Geçiş Metalleri Komplekslerinin Termal Bozunma Tepkimelerinde Kinetik Parametrelerinin Belirlenmesi ve Bazı Koordinasyon Bağ Enerjilerinin Hesaplanması, Doktora Tezi, Kimya ABD, Ankara Üniversitesi, Ankara, Türkiye, 2009.
  • [18] M. A. Bennett and A. K. Smith, “Arene Ruthenium ( II ) Complexes formed by Dehydrogenation of cyclo-hexadienes with ruthenium( III) trichloride,” pp. 233–241, 1974.
  • [19] N. P. E. Barry and B. Therrien, “Host-guest Chemistry in the Hexanuclear (arene)Ruthenium metalla-prismatic cage [Ru6(p-cymene)6(tpt)2(dhnq) 3]6+,” Eur. J. Inorg. Chem., vol. 6, pp. 4695–4700, 2009.
  • [20] H. Küçükbay, R. Durmaz, N. Okuyucu, S. Günal, and C. Kazaz, “ArzneimForschDrugRes Synthesis and Antibacterial Activities of New Bis-benzimidazoles,” Arzneim.-Forsch./Drug Res., vol. 54, no. 1, pp. 64–68, 2004.

Synthesis and Determination of Thermal Decomposition of Biological Active Arene Ruthenium Compound Containing Bisbenzimidazole Linker

Year 2019, , 1899 - 1908, 31.07.2019

Nilüfer Öksüz Ersin Orhan

https://doi.org/10.29130/dubited.568949

Abstract

In this study, [Ru4(p-cymene)4(μ-NՈN)2(μ4-OOՈOO)2][CF3SO3)4]
(NՈN = Butylene-1,4-bisbenzimidazole (bbim)) biologically active tetranuclear
arene complex compound, reacting Ru2(p-cymene)2(μ4- OOՈOO) Cl2  (OOՈOO = 5,8-dioxido-1,4-naphtoquinonato
(donq)) with silver trifluoromethanesulfonate, followed by the addition of the
corresponding NՈN linkers. The biologically active arene ruthenium compound was
characterized by standard techniques including IR, UV-VIS, 1H NMR, 13C
NMR spectroscopy and ESI-MS spectrometry. Thermal decomposition measurement
data of arene ruthenium compound were examined. These measurements were made by
Thermogravimetric analysis (TGA) and Differential thermal analysis (DTA)
techniques.

Keywords

Arene ruthenium Bisbenzimidazole Supramolecular chemistry Thermal decomposition

Project Number

2017.05.03.600 ve 2017.05.03.620

References

  • [1] B. Rosenbeng, L. Vancamp, J. E. Trosko, and V. H. Mansour, “Nature,” Nature, vol. 222, pp. 285–286, 1969.
  • [2] E. Orhan, A. Garci, B. Therrien, "Coordination-driven self-assembly of arene ruthenium metalla-rectangles," Inorganica Chimica Acta, vol. 461, pp. 78–83, 2017.
  • [3] E. Orhan, A. Garci, T. Riedel, P. J. Dyson, B. Therrien, " Cytotoxicity of arene ruthenium metalla-rectangles incorporating bis-pyridyl diimide linkers," Journal of Organometallic Chemistry, vol. 815-816, pp. 53-58, 2016.
  • [4] M. Galanski, M. A. Jakupec, and B. K. Keppler, “Update of the Preclinical Situation of Anticancer Platinum Complexes : Novel Design Strategies and Innovative Analytical Approaches,” Curr. Med. Chem., vol. 12, pp. 2075–2094, 2005.
  • [5] E. Orhan, A. Garci, T. Riedel, M. Saudani, P. J. Dyson, B. Therrien, "Cytotoxic double arene ruthenium metalla-cycles that overcome cisplatin resistance," Journal of Organometallic Chemistry, vol. 803, pp. 39-44, 2016.
  • [6] C. S. Allardyce and P. J. Dyson, “Ruthenium in Medicine : Current Clinical Uses and Future Prospects,” Platin. Met. Rev., vol. 45, no. 2, pp. 62–69, 2001.
  • [7] I. Kostova, “Ruthenium Complexes as Anticancer Agents,” Curr. Med. Chem., vol. 13, pp. 1085–1107, 2006.
  • [8] C. S. Allardyce, A. Dorcier, C. Scolaro, and P. J. Dyson, “Development of organometallic (organo-transition metal) pharmaceuticals,” Bioorganometallic Chem., vol. 19, pp. 1–10, 2005.
  • [9] E. Orhan, A. Garci, B. Therrien, "Flexible arene ruthenium metalla-prisms," Inorganica Chimica Acta, vol. 438, pp. 5–9, 2015.
  • [10] A. Garci, J. P. Mbakidi, V. Chaleix, V. Sol, E. Orhan, B. Therrien, "Tunable Arene Ruthenium Metallaprisms to Transport, Shield, and Release Porphin in Cancer Cells," Organometallics, vol. 34, pp. 4138−4146, 2015.
  • [11] A. Garci, A. A. Dobrov, T. Riedel, E. Orhan, P. J. Dyson, V. B. Arion, B. Therrien, "Strategy to optimize the biological activity of arene ruthenium metalla-assemblies," Organometallics, vol. 33, pp. 3813−3822, 2014.
  • [12] A. A. Hummer et al., “X-ray absorption near edge structure spectroscopy to resolve the in vivo chemistry of the redox-active Indazolium trans - [ tetrachlorobis ( 1H- indazole ) ruthenate ( III )] ( KP1019 ),” J. Med. Chem., vol. 56, pp. 1182, 2013.
  • [13] G. Tamasi et al., “Synthesis , spectroscopic and DFT structural characterization of two novel ruthenium ( III ) oxicam complexes . In vivo evaluation of anti-in fl ammatory and gastric damaging activities,” J. Inorg. Biochem., vol. 134, pp. 25–35, 2014.
  • [14] G. Süss-Fink, “Water-soluble arene ruthenium complexes : From serendipity to catalysis and drug design,” J. Organomet. Chem., vol. 751, pp. 2–19, 2014.
  • [15] H. Küçükbay, S. Günal, E. Orhan, R. Durmaz, "Synthesis and antimicrobial activities of some transition metal benzimidazole complexes," Asian Journal of Chemistry, vol. 22, pp. 7376–7382, 2010.
  • [16] H. Küçükbay, R. Durmaz, E. Orhan, S. Günal, "Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds," Farmaco, vol. 58, pp. 431–437, 2003.
  • [17] Ü. Ergun, "ONO Ve ONNO Tipindeki Schiff Bazlarının Geçiş Metalleri Komplekslerinin Termal Bozunma Tepkimelerinde Kinetik Parametrelerinin Belirlenmesi ve Bazı Koordinasyon Bağ Enerjilerinin Hesaplanması, Doktora Tezi, Kimya ABD, Ankara Üniversitesi, Ankara, Türkiye, 2009.
  • [18] M. A. Bennett and A. K. Smith, “Arene Ruthenium ( II ) Complexes formed by Dehydrogenation of cyclo-hexadienes with ruthenium( III) trichloride,” pp. 233–241, 1974.
  • [19] N. P. E. Barry and B. Therrien, “Host-guest Chemistry in the Hexanuclear (arene)Ruthenium metalla-prismatic cage [Ru6(p-cymene)6(tpt)2(dhnq) 3]6+,” Eur. J. Inorg. Chem., vol. 6, pp. 4695–4700, 2009.
  • [20] H. Küçükbay, R. Durmaz, N. Okuyucu, S. Günal, and C. Kazaz, “ArzneimForschDrugRes Synthesis and Antibacterial Activities of New Bis-benzimidazoles,” Arzneim.-Forsch./Drug Res., vol. 54, no. 1, pp. 64–68, 2004.
There are 20 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Nilüfer Öksüz This is me 0000-0002-1583-5524

Ersin Orhan 0000-0002-5461-1005

Project Number 2017.05.03.600 ve 2017.05.03.620
Publication Date July 31, 2019
Published in Issue Year 2019

Cite

APA Öksüz, N., & Orhan, E. (2019). Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi ve Termal Bozunmasının Belirlenmesi. Duzce University Journal of Science and Technology, 7(3), 1899-1908. https://doi.org/10.29130/dubited.568949
AMA Öksüz N, Orhan E. Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi ve Termal Bozunmasının Belirlenmesi. DÜBİTED. July 2019;7(3):1899-1908. doi:10.29130/dubited.568949
Chicago Öksüz, Nilüfer, and Ersin Orhan. “Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi Ve Termal Bozunmasının Belirlenmesi”. Duzce University Journal of Science and Technology 7, no. 3 (July 2019): 1899-1908. https://doi.org/10.29130/dubited.568949.
EndNote Öksüz N, Orhan E (July 1, 2019) Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi ve Termal Bozunmasının Belirlenmesi. Duzce University Journal of Science and Technology 7 3 1899–1908.
IEEE N. Öksüz and E. Orhan, “Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi ve Termal Bozunmasının Belirlenmesi”, DÜBİTED, vol. 7, no. 3, pp. 1899–1908, 2019, doi: 10.29130/dubited.568949.
ISNAD Öksüz, Nilüfer - Orhan, Ersin. “Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi Ve Termal Bozunmasının Belirlenmesi”. Duzce University Journal of Science and Technology 7/3 (July 2019), 1899-1908. https://doi.org/10.29130/dubited.568949.
JAMA Öksüz N, Orhan E. Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi ve Termal Bozunmasının Belirlenmesi. DÜBİTED. 2019;7:1899–1908.
MLA Öksüz, Nilüfer and Ersin Orhan. “Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi Ve Termal Bozunmasının Belirlenmesi”. Duzce University Journal of Science and Technology, vol. 7, no. 3, 2019, pp. 1899-08, doi:10.29130/dubited.568949.
Vancouver Öksüz N, Orhan E. Bisbenzimidazol Bağlayıcı İçeren Biyolojik Aktif Aren Rutenyum Bileşiğinin Sentezi ve Termal Bozunmasının Belirlenmesi. DÜBİTED. 2019;7(3):1899-908.