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Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin

Yıl 2017, Cilt: 21 Sayı: 2, 330 - 337, 01.05.2017

Deniz Çıkla Yılmaz Mürşit Pekin

Öz

In this study, the stability constants of the copper(II) and
aluminium(III) complexes of quercetin were determined
potentiometrically by using Calvin-Bjerrum and Irwing Rossotti
methods. The protonation constants of quercetin were found:
logK1 = 11.15±0.118, logK2 = 10.42±0.144, logK3 = 9.44±0.162,
logK4 = 8.28±0.151. For copper complex formation constant
was found by Irwing-Rossotti method: logK1 = 19.92±0.367 and
for aluminium complex complex: logK1 = 23.02±0.459. From
the results, the components of quercetin / metal complexes are
given as 1/1 both copper(II) and aluminium(III).
A reversed phase high pressure liquid chromatographic method
was developed for the metal complexes which were prepared
according to potentiometric results with the ratio quercetin /
metal =1/1. Mobile phase was 0.01 M HClO4 / 8.33 x 10-5 M
quercetin in Methanol (40/60), column was XTerra RP18, 5 μm,
4.6 x 150 mm , detector was Diode Array Detector at λ = 373 ve
421 nm (band width 4nm).

Anahtar Kelimeler

Flavonoid-metal complexes quercetin complexes biologically active ligands antioxidants flavonoids

Kaynakça

  • 1. Amic D, Davidovic-Amic D, Beslo D, Rastija V, Lucic B,Trinajstic N. SAR and QSAR of the antioxidant activity offlavonoids. Curr Med Chem 2007;14: 827-452.
  • 2. George VC, Dellaire G, Rupasinghe HPV. Plant flavonoidsin cancer chemoprevention: Role in genome stability. J NutrBiochem 2017;45: 1-14.
  • 3. Corradini E, Foglia P, Giansanti P, Gubbiotti R, Samperi R,Lagana A. Flavonoids: Chemical properties and analyticalmethodologies of identification and quantitation in foods andplants. Nat Prod Res 2011;25: 469-95.
  • 4. Ravishankar D, Rajora AK, Greco F, Osborn HMI. Flavonoidsas prospective compounds for anti-cancer therapy. Int JBiochem Cell Biol 2013;45: 2821-31.
  • 5. Spoerlein C, Mahal K, Schmidt H, Schobert R. Effects ofchrysin, apigenin, genistein and their homoleptic copper(II)complexes on the growth and metastatic potential of cancercells. J Inorg Biochem 2013;127: 107-15.
  • 6. Frezza M, Hindo S, Chen D, Davenport A, Schmitt S, TomcoD, Dou QP. Novel metals and metal complexes as platformsfor cancer therapy. Curr Pharm Des 2010;16: 1813-25.
  • 7. Kostova I, Balkansky S. Metal complexes of biologically activeligands as potential antioxidants. Curr Med Chem 2013;20:4508-39.
  • 8. Mladenka P, Macakova K, Filipsky T, Zatloukalova L, JahodarL, Bovicelli P, Silvestri IP, Hrdina R, Saso L. In vitro analysisof iron chelating activity of flavonoids. J Inorg Biochem2011;105: 693-701.
  • 9. Samsonowicz M, Regulska E. Spectroscopic study of molecularstructure, antioxidant activity and biological effects of metalhydroxyflavonol complexes. Spectrochim Acta A Mol BiomolSpectrosc 2017;173: 757-71.
  • 10. Jabeen E, Janjua NK, Ahmed S, Murtaza I, Ali T, HameedS. Radical scavenging propensity of Cu2+, Fe3+ complexes offlavonoids and in-vivo radical scavenging by Fe3+-primuletin.Spectrochim Acta A Mol Biomol Spectrosc 2017;171: 432-8.
  • 11. de Souza RFV, De Giovani WF. Antioxidant properties ofcomplexes of flavonoids with metal ions. Redox Rep 2004;9:97-104.
  • 12. Cornard JP, Merlin JC. Spectroscopic and structural study ofcomplexes of quercetin with Al(III). J Inorg Biochem 2002;92:19-27.
  • 13. Fernandez MT, Mira ML, Florencio MH, Jennings KR. Ironand copper chelation by flavonoids: An electrospray massspectrometry study. J Inorg Biochem 2002;92:105-11.
  • 14. Ikeda NEA, Novak EM, Maria DA, Velosa AS, Pereira RMS.Synthesis, characterization and biological evaluation ofRutin-zinc(II) flavonoid -metal complex. Chem Biol Interact2015;239: 184-91.
  • 15. Petkovic M, Petrovic B, Savic J, Bugarcic ZD, Dimitric-Markovic J, Momic T, Vasic V. Flavonoids as matrices for MALDI-TOF mass spectrometric analysis of transition metalcomplexes. Int J Mass Spectrom 2010;290: 39-46.
  • 16. Lian H-Z, Kang Y-F, Yasin A, Bi S-P, Shao D-L, Chen Y-J, DaiL-M, Tian L-C. Determination of aluminum in environmentaland biological samples by reversed-phase high-performanceliquid chromatography via pre-column complexation withmorin. J Chromatogr A 2003;993: 179-85.
  • 17. Timerbaev AR, Tsoi IG, Petrukhin OM. Mathematicalsimulation of complex chromatographic systems: A simulationmodel of reversed-phase liquid chromatography of metalchelates. Anal Chim Acta 1992;269: 229-38.
  • 18. Irving, H. M., Rossotti, H. S. Methods for computing successivestability constants from experimental formation curves. JChem Soc 1953; 3397-3405.
  • 19. Irving, H. M., Rossotti, H. S. The calculation of formationcurves of metal complexes from pH-titration curves in mixedsolvents. J Chem Soc 1954; 2904-10.
  • 20. Dilli S, Haddad PR, Htoon AK. Further studies ofdiethyldithiocarbamate complexes by high-performanceliquid chromatography. J Chromatogr, 1990;500: 313-28.

Kuersetinin Cu(II) ve Al(III) Komplekslerinin Potansiyometrik ve Kromatografik İncelenmesi

Yıl 2017, Cilt: 21 Sayı: 2, 330 - 337, 01.05.2017

Deniz Çıkla Yılmaz Mürşit Pekin

Öz

Bu çalışmada, Kuersetinin bakır(II) ve alüminyum(III) ile

oluşturduğu komplekslerin kararlılık sabitleri Calvin-Bjerrum

ve Irwing-Rossotti yöntemleri kullanılarak potansiyometrik

yoldan tayin edildi. Kuersetin dissosiyasyon sabitleri

potansiyometrik yöntemle logK1 = 11.15±0.118, logK2 =

10.42±0.144, logK3 = 9.44±0.162, logK4 = 8.28±0.151 olarak

bulundu. Yine potansiyometrik olarak Irwing-Rossotti oluşum

sabitleri ise bakır(II) için logK1 = 19.92±0.367, alüminyum(III)

için logK1 = 23.02±0.459 olarak bulundu. Bakır(II) ve

alüminyum(III) komplekslerinin bileşimleri ligand/metal = 1/1

olarak bulundu.

Potansiyometrik sonuçlara dayanarak kuersetin/metal = 1/1

oranıyla hazırlanan kompleksler için ters fazlı yüksek basınçlı

sıvı kromatografisi ile tayin yöntemi gerçekleştirildi. Çalışmada

hareketli faz olarak 0.01 M HClO4 / 8.33 x 10-5 M Kuersetin

çözeltisi (Metanolde) (40/60), XTerra RP18, 5 μm, 4.6 x 150

mm özellikte kolon, λ = 373 ve 421 nm (bant genişliği 4nm)

kullanıldı.

Anahtar Kelimeler

Flavonoid-metal kompleksleri kuersetin kompleksleri biyolojik aktif ligandlar antioksidanlar flavonoidler

Kaynakça

  • 1. Amic D, Davidovic-Amic D, Beslo D, Rastija V, Lucic B,Trinajstic N. SAR and QSAR of the antioxidant activity offlavonoids. Curr Med Chem 2007;14: 827-452.
  • 2. George VC, Dellaire G, Rupasinghe HPV. Plant flavonoidsin cancer chemoprevention: Role in genome stability. J NutrBiochem 2017;45: 1-14.
  • 3. Corradini E, Foglia P, Giansanti P, Gubbiotti R, Samperi R,Lagana A. Flavonoids: Chemical properties and analyticalmethodologies of identification and quantitation in foods andplants. Nat Prod Res 2011;25: 469-95.
  • 4. Ravishankar D, Rajora AK, Greco F, Osborn HMI. Flavonoidsas prospective compounds for anti-cancer therapy. Int JBiochem Cell Biol 2013;45: 2821-31.
  • 5. Spoerlein C, Mahal K, Schmidt H, Schobert R. Effects ofchrysin, apigenin, genistein and their homoleptic copper(II)complexes on the growth and metastatic potential of cancercells. J Inorg Biochem 2013;127: 107-15.
  • 6. Frezza M, Hindo S, Chen D, Davenport A, Schmitt S, TomcoD, Dou QP. Novel metals and metal complexes as platformsfor cancer therapy. Curr Pharm Des 2010;16: 1813-25.
  • 7. Kostova I, Balkansky S. Metal complexes of biologically activeligands as potential antioxidants. Curr Med Chem 2013;20:4508-39.
  • 8. Mladenka P, Macakova K, Filipsky T, Zatloukalova L, JahodarL, Bovicelli P, Silvestri IP, Hrdina R, Saso L. In vitro analysisof iron chelating activity of flavonoids. J Inorg Biochem2011;105: 693-701.
  • 9. Samsonowicz M, Regulska E. Spectroscopic study of molecularstructure, antioxidant activity and biological effects of metalhydroxyflavonol complexes. Spectrochim Acta A Mol BiomolSpectrosc 2017;173: 757-71.
  • 10. Jabeen E, Janjua NK, Ahmed S, Murtaza I, Ali T, HameedS. Radical scavenging propensity of Cu2+, Fe3+ complexes offlavonoids and in-vivo radical scavenging by Fe3+-primuletin.Spectrochim Acta A Mol Biomol Spectrosc 2017;171: 432-8.
  • 11. de Souza RFV, De Giovani WF. Antioxidant properties ofcomplexes of flavonoids with metal ions. Redox Rep 2004;9:97-104.
  • 12. Cornard JP, Merlin JC. Spectroscopic and structural study ofcomplexes of quercetin with Al(III). J Inorg Biochem 2002;92:19-27.
  • 13. Fernandez MT, Mira ML, Florencio MH, Jennings KR. Ironand copper chelation by flavonoids: An electrospray massspectrometry study. J Inorg Biochem 2002;92:105-11.
  • 14. Ikeda NEA, Novak EM, Maria DA, Velosa AS, Pereira RMS.Synthesis, characterization and biological evaluation ofRutin-zinc(II) flavonoid -metal complex. Chem Biol Interact2015;239: 184-91.
  • 15. Petkovic M, Petrovic B, Savic J, Bugarcic ZD, Dimitric-Markovic J, Momic T, Vasic V. Flavonoids as matrices for MALDI-TOF mass spectrometric analysis of transition metalcomplexes. Int J Mass Spectrom 2010;290: 39-46.
  • 16. Lian H-Z, Kang Y-F, Yasin A, Bi S-P, Shao D-L, Chen Y-J, DaiL-M, Tian L-C. Determination of aluminum in environmentaland biological samples by reversed-phase high-performanceliquid chromatography via pre-column complexation withmorin. J Chromatogr A 2003;993: 179-85.
  • 17. Timerbaev AR, Tsoi IG, Petrukhin OM. Mathematicalsimulation of complex chromatographic systems: A simulationmodel of reversed-phase liquid chromatography of metalchelates. Anal Chim Acta 1992;269: 229-38.
  • 18. Irving, H. M., Rossotti, H. S. Methods for computing successivestability constants from experimental formation curves. JChem Soc 1953; 3397-3405.
  • 19. Irving, H. M., Rossotti, H. S. The calculation of formationcurves of metal complexes from pH-titration curves in mixedsolvents. J Chem Soc 1954; 2904-10.
  • 20. Dilli S, Haddad PR, Htoon AK. Further studies ofdiethyldithiocarbamate complexes by high-performanceliquid chromatography. J Chromatogr, 1990;500: 313-28.
Toplam 20 adet kaynakça vardır.

Ayrıntılar

Konular Sağlık Kurumları Yönetimi
Bölüm Makaleler
Yazarlar

Deniz Çıkla Yılmaz

Mürşit Pekin

Yayımlanma Tarihi 1 Mayıs 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 21 Sayı: 2

Kaynak Göster

APA Çıkla Yılmaz, D., & Pekin, M. (2017). Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin. Marmara Pharmaceutical Journal, 21(2), 330-337.
AMA Çıkla Yılmaz D, Pekin M. Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin. J Res Pharm. Mayıs 2017;21(2):330-337.
Chicago Çıkla Yılmaz, Deniz, ve Mürşit Pekin. “Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin”. Marmara Pharmaceutical Journal 21, sy. 2 (Mayıs 2017): 330-37.
EndNote Çıkla Yılmaz D, Pekin M (01 Mayıs 2017) Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin. Marmara Pharmaceutical Journal 21 2 330–337.
IEEE D. Çıkla Yılmaz ve M. Pekin, “Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin”, J Res Pharm, c. 21, sy. 2, ss. 330–337, 2017.
ISNAD Çıkla Yılmaz, Deniz - Pekin, Mürşit. “Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin”. Marmara Pharmaceutical Journal 21/2 (Mayıs 2017), 330-337.
JAMA Çıkla Yılmaz D, Pekin M. Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin. J Res Pharm. 2017;21:330–337.
MLA Çıkla Yılmaz, Deniz ve Mürşit Pekin. “Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin”. Marmara Pharmaceutical Journal, c. 21, sy. 2, 2017, ss. 330-7.
Vancouver Çıkla Yılmaz D, Pekin M. Potentiometric and Chromatographic Study of Cu(II) and Al(III) Complexes of Quercetin. J Res Pharm. 2017;21(2):330-7.

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