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Investigation effects of some anthraquinones on human paraoxonase 1 (hPON1)

Yıl 2019, Cilt: 21 Sayı: 2, 546 - 553, 28.06.2019
https://doi.org/10.25092/baunfbed.624457

Öz

The in vitro effects of the some dihydroxyanthraquinone derivates, anthrorufin, xanthopurpurin, chrysazin and chrysaphanol which are commonly used as anticancer antibiotics, on the activity of purified  serum paraoxonase 1 (PON1) (EC 3.1.8.1.) were investigated.  Paraoxonase 1 was purified from human blood serum 355,12 fold with 55 % yield with use of ammonium sulphate precipitation and Sepharose-4B-L-tyrozine-1-napthylamine HIC (hydrophobic interaction chromatography) coloumn in return.  Sodium Dodecyl Sulphate -polyacrylamide gel electrophoresis (SDS-PAGE) analysis of purified enzyme showed a single band belong to human serum PON1, 43 kDa.  The four anthraquinones inhibited PON activity strongly, with IC50 values for anthrorufin, xanthopurpurin, chrysazin and chrysaphanol of 73, 72.25, 75.19 and 105.53 M respectively.  Ki constants were determined 34.64, 39.51, 39.73 and 63.59 M, respectively.  All anthraquinones showed inhibition in competitive manner.

Teşekkür

The author thanks to the Balikesir University Biochemistry Research Laboratuary for the use of equipments and thanks to Prof. Dr. Oktay Arslan and Assoc. Prof. Dr. Nahit Gencer for their helpful and constructive suggestion.

Kaynakça

  • Aviram, M., Rosenblat, M., Bisgaier, CL., Newton, RS., Primo-Parmo, SL., La, Du BN. Paraoxonase inhibits high-density lipoprotein oxidation and preserves its functions. A possible peroxidative role for paraoxonase. Journal of Clinical Investigation 101, 1581–90 (1998)
  • Aybey, A. and Demirkan E., Inhibition of quorum sensing-controlled virulence factors in Pseudomonas aeruginosa by human serum paraoxonase. Journal of Medical Microbiology, 65, 105-113, (2016)
  • Mackness, M., and Mackness, B., Human paraoxonase-1 (PON1): Gene structure and expression, promiscuous activities and multiple physiological roles. Gene, 567, 12–21(2015)
  • Rajkovic, M.G., Rumora, L., Barisic, K., The paraoxonase 1, 2 and 3 in humans. Biochemical Medicine, 21, 122–130 (2011).
  • She Z.G, Zheng W, Wei Y.S, Chen H.Z, Wang A.B, Li H.L, et al. Human paraoxonase gene cluster transgenic overexpression represses atherogenesis and promotes atherosclerotic plaque stability in ApoE-null mice. Circulation Research 104,1160–8 (2009).
  • Draganov, D.I., Teiber, J.F., Speelman, A., Osawa, Y., Sunahara, R., La Du, B.N., Human paraoxonases (PON1, PON2 and PON3 are lactonases with overlapping and distinct substrate specificities. Journal of Lipid Research 46, 1239–1247 (2005).
  • Durrington, P.N., Mackness, B., Mackness, M.I., The hunt for nutritional and pharmacologicalmodulators of paraoxonase. Arteriosclerosis Thrombosis and Vascular Biology. 22, 1248–1250 (2012).
  • Agarwal SK, Singh SS, Verma S, et al. Antifungal activity of anthraquinone derivatives from Rheum emodi. Journal of Ethnopharmacology 72: 43–46 (2008)
  • Yen, G.C., Duh, P.D., and Chuang, D.Y., Antioxidant activity of anthraquinones and anthrone. Food Chemistry 70: 437–441. (2000)
  • William P, Sorribas A, and Howes MJR. Natural products as a source of Alzheimer’s drug leads. Natural Product Reports 28: 48–77. (2010)
  • Rossi, S., Tabolacci, C., Lentini, A., et al. Anthraquinones danthron and quinizarin exert antiproliferative and antimetastatic activity on murine B16-F10 melanoma cells. Anticancer Research 30(2): 445–449 (2010)
  • Sinan, S., Kockar, F., Arslan, O., Novel purification strategy for humanPON1 and inhibition of the activity by cephalosporin andaminoglikozide derived antibiotics. Biochimie 88:565–74 (2006).
  • Gan, K.N., Smolen A, Eckerson HW, La Du BN. Purification of human serum paraoxonase/arylesterase. Evidence for one esterase catalyzing both activities. Drug Metabolism Disposition 19:100–6 (1991).
  • Gencer, N., and Arslan, O., Purification human PON1Q192 and PON1R192 isoenzymes by hydrophobic interaction chromatography and investigation of the inhibition by metals. Journal of Chromatography B, 877:134–140 (2009).
  • Bradford, M.M., A rapid and sensitive method for the quantition of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry, 72:248–51(1976).
  • Laemmli, U.K., Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227:680–5 (1970).
  • Lineweaver H, Burk D, The determination of enzyme dissocation constants. Journal of American Chemical Society; 57:685 (1934).
  • Dilek, E., Caglar, S., Erdogan, K., Caglar, B., Sahin, O., Synthesis and characterization of four novel palladium(II) and platinum(II) complexes with 1-(2-aminoethyl) pyrrolidine, diclofenac and mefenamic acid: In vitro effect of these complexes on human serum paraoxanase1 activity. Journal of Biochemical and Molecular Toxicology. 32:4 (2018)
  • Alim, Z, Kilic D, Koksal Z, Beydemir S, Ozdemir H. Assessment of the inhibitory effects and molecular docking of some sulfonamides on human serum paraoxonase 1. Journal of Biochemical and Molecular Toxicology. 31:10 (2017).
  • Gençer N, Yavuz E. An alternative purification method for human serum paraoxonase 1 and its interaction with methidathion. Archives Physiology Biochemistry. 123(3):159-164 (2017).
  • Everett, C. Cogbill John H. Yoe Derivatives of anthrarufin, chrysazin and quinizarin as colorimetric reagents for boron. Analytica Chimica Acta; 12: 455-463 (1955).
  • Zhang, J; Yan, C; Wang, S; Hou, Y; Xue, G; Zhang, L Chrysophanol attenuates lead exposure-induced injury to hippocampal neurons in neonatal mice. Neural Regeneration Research. 9 (9): 924–30 (2014).
  • Chien, S., Wu Y., Chen Z., Yang, W., Naturally Occurring Anthraquinones: Chemistry and Therapeutic Potential in Autoimmune Diabetes Review Article, Evidence-Based Complementary and Alternative Medicine 13: 357-357 (2015).
  • Fotia, C., Avnet, S. Granchi, D., Baldini N., The Natural Compound Alizarin as an Osteotropic Drug for the Treatment of Bone Tumors, Journal of Orthopaedıc Research 1486-1492 (2012)

Bazı antrakinonların insan paraoksonaz 1 (hPON1) üzerine etkilerinin incelenmesi

Yıl 2019, Cilt: 21 Sayı: 2, 546 - 553, 28.06.2019
https://doi.org/10.25092/baunfbed.624457

Öz

Antikanser antibiyotikler olarak yaygın kullanılan bazı dihidroksiantrakinon türevlerinin (antrorufin, ksantopurpirin, krisazin ve krizofanol) saflaştırılmış serum paraoksonaz 1 (PON1) aktivitesi üzerine (EC 3.1.8.1) in vitro etkileri araştırıldı.  Paraoksonaz 1, insan kan serumundan 355,12 kat, % 55 verimle, amonyum sülfat çöktürmesi ve Sepharose 4B-L-tirozin-1-naftilamin hidrofobik etkileşim kromatografisi kullanılarak saflaştırılmıştır. Saflaştırılmış enzimin Sodyum Dodesil Sülfat-poliakrilamid jel elektroforezi (SDS-PAGE),  insan serum PON1’e ait 43 kDa'lık tek bant gösterdi.  Dört antrakinon bileşiği, PON1 aktivitesini, sırasıyla antrorufin, ksantopurpirin, krisazin ve krizofanol için 73, 72.25, 75.19 ve 105.53 M değerleri ile güçlü bir şekilde inhibe etmiştir.   Ki sabitleri sırasıyla 34.64, 39.51, 39.73 ve 63.59 M olarak bulunmuştur.   Tüm antrakinonlar yarışmalı bir şekilde inhibisyon göstermiştir.

Kaynakça

  • Aviram, M., Rosenblat, M., Bisgaier, CL., Newton, RS., Primo-Parmo, SL., La, Du BN. Paraoxonase inhibits high-density lipoprotein oxidation and preserves its functions. A possible peroxidative role for paraoxonase. Journal of Clinical Investigation 101, 1581–90 (1998)
  • Aybey, A. and Demirkan E., Inhibition of quorum sensing-controlled virulence factors in Pseudomonas aeruginosa by human serum paraoxonase. Journal of Medical Microbiology, 65, 105-113, (2016)
  • Mackness, M., and Mackness, B., Human paraoxonase-1 (PON1): Gene structure and expression, promiscuous activities and multiple physiological roles. Gene, 567, 12–21(2015)
  • Rajkovic, M.G., Rumora, L., Barisic, K., The paraoxonase 1, 2 and 3 in humans. Biochemical Medicine, 21, 122–130 (2011).
  • She Z.G, Zheng W, Wei Y.S, Chen H.Z, Wang A.B, Li H.L, et al. Human paraoxonase gene cluster transgenic overexpression represses atherogenesis and promotes atherosclerotic plaque stability in ApoE-null mice. Circulation Research 104,1160–8 (2009).
  • Draganov, D.I., Teiber, J.F., Speelman, A., Osawa, Y., Sunahara, R., La Du, B.N., Human paraoxonases (PON1, PON2 and PON3 are lactonases with overlapping and distinct substrate specificities. Journal of Lipid Research 46, 1239–1247 (2005).
  • Durrington, P.N., Mackness, B., Mackness, M.I., The hunt for nutritional and pharmacologicalmodulators of paraoxonase. Arteriosclerosis Thrombosis and Vascular Biology. 22, 1248–1250 (2012).
  • Agarwal SK, Singh SS, Verma S, et al. Antifungal activity of anthraquinone derivatives from Rheum emodi. Journal of Ethnopharmacology 72: 43–46 (2008)
  • Yen, G.C., Duh, P.D., and Chuang, D.Y., Antioxidant activity of anthraquinones and anthrone. Food Chemistry 70: 437–441. (2000)
  • William P, Sorribas A, and Howes MJR. Natural products as a source of Alzheimer’s drug leads. Natural Product Reports 28: 48–77. (2010)
  • Rossi, S., Tabolacci, C., Lentini, A., et al. Anthraquinones danthron and quinizarin exert antiproliferative and antimetastatic activity on murine B16-F10 melanoma cells. Anticancer Research 30(2): 445–449 (2010)
  • Sinan, S., Kockar, F., Arslan, O., Novel purification strategy for humanPON1 and inhibition of the activity by cephalosporin andaminoglikozide derived antibiotics. Biochimie 88:565–74 (2006).
  • Gan, K.N., Smolen A, Eckerson HW, La Du BN. Purification of human serum paraoxonase/arylesterase. Evidence for one esterase catalyzing both activities. Drug Metabolism Disposition 19:100–6 (1991).
  • Gencer, N., and Arslan, O., Purification human PON1Q192 and PON1R192 isoenzymes by hydrophobic interaction chromatography and investigation of the inhibition by metals. Journal of Chromatography B, 877:134–140 (2009).
  • Bradford, M.M., A rapid and sensitive method for the quantition of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry, 72:248–51(1976).
  • Laemmli, U.K., Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227:680–5 (1970).
  • Lineweaver H, Burk D, The determination of enzyme dissocation constants. Journal of American Chemical Society; 57:685 (1934).
  • Dilek, E., Caglar, S., Erdogan, K., Caglar, B., Sahin, O., Synthesis and characterization of four novel palladium(II) and platinum(II) complexes with 1-(2-aminoethyl) pyrrolidine, diclofenac and mefenamic acid: In vitro effect of these complexes on human serum paraoxanase1 activity. Journal of Biochemical and Molecular Toxicology. 32:4 (2018)
  • Alim, Z, Kilic D, Koksal Z, Beydemir S, Ozdemir H. Assessment of the inhibitory effects and molecular docking of some sulfonamides on human serum paraoxonase 1. Journal of Biochemical and Molecular Toxicology. 31:10 (2017).
  • Gençer N, Yavuz E. An alternative purification method for human serum paraoxonase 1 and its interaction with methidathion. Archives Physiology Biochemistry. 123(3):159-164 (2017).
  • Everett, C. Cogbill John H. Yoe Derivatives of anthrarufin, chrysazin and quinizarin as colorimetric reagents for boron. Analytica Chimica Acta; 12: 455-463 (1955).
  • Zhang, J; Yan, C; Wang, S; Hou, Y; Xue, G; Zhang, L Chrysophanol attenuates lead exposure-induced injury to hippocampal neurons in neonatal mice. Neural Regeneration Research. 9 (9): 924–30 (2014).
  • Chien, S., Wu Y., Chen Z., Yang, W., Naturally Occurring Anthraquinones: Chemistry and Therapeutic Potential in Autoimmune Diabetes Review Article, Evidence-Based Complementary and Alternative Medicine 13: 357-357 (2015).
  • Fotia, C., Avnet, S. Granchi, D., Baldini N., The Natural Compound Alizarin as an Osteotropic Drug for the Treatment of Bone Tumors, Journal of Orthopaedıc Research 1486-1492 (2012)
Toplam 24 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Araştırma Makalesi
Yazarlar

Başak Gökçe 0000-0001-8548-9703

Yayımlanma Tarihi 28 Haziran 2019
Gönderilme Tarihi 21 Kasım 2018
Yayımlandığı Sayı Yıl 2019 Cilt: 21 Sayı: 2

Kaynak Göster

APA Gökçe, B. (2019). Investigation effects of some anthraquinones on human paraoxonase 1 (hPON1). Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 21(2), 546-553. https://doi.org/10.25092/baunfbed.624457
AMA Gökçe B. Investigation effects of some anthraquinones on human paraoxonase 1 (hPON1). BAUN Fen. Bil. Enst. Dergisi. Haziran 2019;21(2):546-553. doi:10.25092/baunfbed.624457
Chicago Gökçe, Başak. “Investigation Effects of Some Anthraquinones on Human Paraoxonase 1 (hPON1)”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 21, sy. 2 (Haziran 2019): 546-53. https://doi.org/10.25092/baunfbed.624457.
EndNote Gökçe B (01 Haziran 2019) Investigation effects of some anthraquinones on human paraoxonase 1 (hPON1). Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 21 2 546–553.
IEEE B. Gökçe, “Investigation effects of some anthraquinones on human paraoxonase 1 (hPON1)”, BAUN Fen. Bil. Enst. Dergisi, c. 21, sy. 2, ss. 546–553, 2019, doi: 10.25092/baunfbed.624457.
ISNAD Gökçe, Başak. “Investigation Effects of Some Anthraquinones on Human Paraoxonase 1 (hPON1)”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 21/2 (Haziran 2019), 546-553. https://doi.org/10.25092/baunfbed.624457.
JAMA Gökçe B. Investigation effects of some anthraquinones on human paraoxonase 1 (hPON1). BAUN Fen. Bil. Enst. Dergisi. 2019;21:546–553.
MLA Gökçe, Başak. “Investigation Effects of Some Anthraquinones on Human Paraoxonase 1 (hPON1)”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 21, sy. 2, 2019, ss. 546-53, doi:10.25092/baunfbed.624457.
Vancouver Gökçe B. Investigation effects of some anthraquinones on human paraoxonase 1 (hPON1). BAUN Fen. Bil. Enst. Dergisi. 2019;21(2):546-53.