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Some N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted) ureido/thioureido]benzenesulfonamides as carbonic anhydrase I and II inhibitors

Year 2017, Volume: 21 Issue: 1, 89 - 95, 25.08.2016

Sevda Türk Fatih Tok Hülya Çelik Sevgi Karakuş Hayrunnisa Nadaroğlu Bedia Koçyiğit-kaymakçıoğlu Kaan Küçükoğlu

https://doi.org/10.12991/marupj.259885

Abstract

In the present study, N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substitue)ureido] benzenesulfonamide (1-9) and N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substitue) thioureido]benzenesulfonamide (10-14) derivatives were synthesized from 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide (Sulfamethizole). All new compounds were characterized by elemental analysis and various spectroscopic methods (FTIR, 1H-NMR and MS). These new sulfonamide derivatives were investigated as inhibitors of carbonic anhydrase especially human carbonic anhydrase I and II. The new compounds showed higher activity against the human cytosolic CA I (IC50 values 0.095-15.65 nM) and CA II            (IC50 values 0.057-17.95 nM) in comparison with the clinically used CAI inhibitor acetazolamide.

Keywords

Carbonic anhydrase inhibitors sulfonamide sulfamethizole urea and thiourea

References

  • Leppialmi M, Koistinen P, Savolainen ER, Hannuksela J, Parkkila AK, Niemelä O, Pastoreková S, Pastorek J, Waheed A, Sly WS, Parkkila S, Rajaniemi H. The expression of carbonic anhydrase II in hematological malignancies. Clin Cancer Res 2002; 8: 2240-5.
  • Demir Y, Demir N, Yıldırm S, Nadaroğlu H, Karaosmanoğlu M, Bakan E. The Activities of Carbonic Anhydrase and Alkaline Phosphatase In Ancient Human Bones. Purification and Characterization of Outer Peripheral, Cytosolic, Inner Peripheral, and Integral CA. Prep Biochem Biotech 2001; 31: 291-304.
  • Demir N, Demir Y, Nadaroğlu H. Carbonic Anhydrase from Bovine Bone. Prep Biochem Biotech 2001; 31: 33-48.
  • Shah GN, Emmett DH, Grubb JH, Migas MC, Fleming RE, Waheed A, Sly WS. Mitochondrial carbonic anydrase CA VB: Differences in tissue distribution and pattern of evolution from those of CA VA suggest distinct physiological roles. Proc Natl Acad Sci USA 2000; 97: 1677-82.
  • Demir Y, Nadaroğlu H, Demir N. Purification and Characterization of Carbonic Anhydrase From Bovine Stomach And Inhibitory Effects Of Some Chemical Substances On Enzyme Activities. J Enzym Inhib Med Chem 2005; 20: 75-80.
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012; 27: 759-72.
  • Supuran CT. Carbonic anhydrases - an overview. Curr Pharm Des 2008; 14: 603-14.
  • Supuran CT. Carbonic anydrase inhibitors. Bioorg Med Chem Lett 2010; 20: 3467-74.
  • Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007; 15: 4336-50.
  • Hilvo M, Tolvanen M, Clark A, Shen BR, Shah GN, Waheed A, Halmi P, Hanninen M, Hamalainen JM, Vihinen M, Sly WS, Parkkila S. Characterization of CA XV, a new GPI-anchored form of carbonic anydrase. Biochem J 2005; 392: 83-92.
  • Supuran CT. Carbonic anydrases: Novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008; 7: 168-81.
  • Supuran CT. Diuretics: From classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr Pharm Design 2008; 14: 641-48.
  • Zolnowska B, Slawinski J, Pogorzelska A, Chojnacki J, Vullo D, Supuran CT. Carbonic anhydrase inhibitors: synthesis, and molecular structure of novel series N-substituted-N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII. Eur J Med Chem 2014; 71: 135-47.
  • Arslan A, Demir H, Arslan H. Investigating catalase and carbonic anhydrase enzyme activities and levels of certain trace elements and heavy metals in patients with primary and metastatic hepatic carcinoma. J Cancer Ther 2013; 4: 1373-81.
  • Haapasalo J, Nordfords K, Järvelä S, Bragge H,Rantala I, Parkkila AK, Haapasalo H, Parkkila S. Carbonic anhydrase II in the endothelium of glial tumors: A potential target for therapy. Neuro Oncol 2007; 9: 308-13.
  • Ibrahim DA, Lasheen DS, Zaky MY, Ibrahim AW, Vullo D, Ceruso M, Supuran CT, Ella DA. Design and synthesis of benzothiazole-6-sulfonamides acting as highly potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem 2015; 23: 4989-99.
  • Supuran CT, Scozzafava A. Carbonic anhydrae inhibitors: Aromatic sulfonamides and disulfonamides act as efficient tumor growth inhibitors. Eur J Med Chem 2000; 35: 867-74.

Karbonik anhidraz I ve II inhibitörü olan bazı N-(5-metil- 1,3,4-tiyadiazol-2-il)-4-[(3-sübstitüe)üreido/tiyoüreido] benzensülfonamitler

Year 2017, Volume: 21 Issue: 1, 89 - 95, 25.08.2016

Sevda Türk Fatih Tok Hülya Çelik Sevgi Karakuş Hayrunnisa Nadaroğlu Bedia Koçyiğit-kaymakçıoğlu Kaan Küçükoğlu

https://doi.org/10.12991/marupj.259885

Abstract

Bu çalışmada
N-(5-metil-1,3,4-tiyadiazol-2-il)-4-[(3-sübstitüe)  üreido]benzensülfonamit ve
N-(5-metil-1,3,4-tiyadiazol-2-  il)-4-[(3-sübstitüe)tiyoüreido]benzensülfonamit
türevleri  4-amino-N-(5-metil-1,3,4-tiyadiazol-2-il)benzensülfonamitten  (sülfametizol) hareketle sentez edildi. Bütün
yeni bileşiklerin  yapıları elemental
analiz ve çeşitli spektroskopik yöntemler 
(FTIR, 1H-NMR ve MS) yardımıyla aydınlatıldı. Bu yeni  sülfonamit türevlerinin, özellikle insan
karbonik anhidraz  I ve II olmak üzere, karbonik
anhidraz inhibitor etkileri  incelendi.
Bileşiklerin klinikte kullanılan asetazolamide kıyasla  insan sitozolik CA I (IC50 değerleri
0.144-15.65 nM) ve CA II  (IC50 değerleri
0.109-17.95 nM) inhibisyon değerleri ile daha 
yüksek aktivite gösterdikleri tespit edildi.  

Keywords

Karbonik anhidraz inhibitörleri sülfonamit sülfametizol üre ve tiyoüre

References

  • Leppialmi M, Koistinen P, Savolainen ER, Hannuksela J, Parkkila AK, Niemelä O, Pastoreková S, Pastorek J, Waheed A, Sly WS, Parkkila S, Rajaniemi H. The expression of carbonic anhydrase II in hematological malignancies. Clin Cancer Res 2002; 8: 2240-5.
  • Demir Y, Demir N, Yıldırm S, Nadaroğlu H, Karaosmanoğlu M, Bakan E. The Activities of Carbonic Anhydrase and Alkaline Phosphatase In Ancient Human Bones. Purification and Characterization of Outer Peripheral, Cytosolic, Inner Peripheral, and Integral CA. Prep Biochem Biotech 2001; 31: 291-304.
  • Demir N, Demir Y, Nadaroğlu H. Carbonic Anhydrase from Bovine Bone. Prep Biochem Biotech 2001; 31: 33-48.
  • Shah GN, Emmett DH, Grubb JH, Migas MC, Fleming RE, Waheed A, Sly WS. Mitochondrial carbonic anydrase CA VB: Differences in tissue distribution and pattern of evolution from those of CA VA suggest distinct physiological roles. Proc Natl Acad Sci USA 2000; 97: 1677-82.
  • Demir Y, Nadaroğlu H, Demir N. Purification and Characterization of Carbonic Anhydrase From Bovine Stomach And Inhibitory Effects Of Some Chemical Substances On Enzyme Activities. J Enzym Inhib Med Chem 2005; 20: 75-80.
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012; 27: 759-72.
  • Supuran CT. Carbonic anhydrases - an overview. Curr Pharm Des 2008; 14: 603-14.
  • Supuran CT. Carbonic anydrase inhibitors. Bioorg Med Chem Lett 2010; 20: 3467-74.
  • Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007; 15: 4336-50.
  • Hilvo M, Tolvanen M, Clark A, Shen BR, Shah GN, Waheed A, Halmi P, Hanninen M, Hamalainen JM, Vihinen M, Sly WS, Parkkila S. Characterization of CA XV, a new GPI-anchored form of carbonic anydrase. Biochem J 2005; 392: 83-92.
  • Supuran CT. Carbonic anydrases: Novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008; 7: 168-81.
  • Supuran CT. Diuretics: From classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr Pharm Design 2008; 14: 641-48.
  • Zolnowska B, Slawinski J, Pogorzelska A, Chojnacki J, Vullo D, Supuran CT. Carbonic anhydrase inhibitors: synthesis, and molecular structure of novel series N-substituted-N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII. Eur J Med Chem 2014; 71: 135-47.
  • Arslan A, Demir H, Arslan H. Investigating catalase and carbonic anhydrase enzyme activities and levels of certain trace elements and heavy metals in patients with primary and metastatic hepatic carcinoma. J Cancer Ther 2013; 4: 1373-81.
  • Haapasalo J, Nordfords K, Järvelä S, Bragge H,Rantala I, Parkkila AK, Haapasalo H, Parkkila S. Carbonic anhydrase II in the endothelium of glial tumors: A potential target for therapy. Neuro Oncol 2007; 9: 308-13.
  • Ibrahim DA, Lasheen DS, Zaky MY, Ibrahim AW, Vullo D, Ceruso M, Supuran CT, Ella DA. Design and synthesis of benzothiazole-6-sulfonamides acting as highly potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem 2015; 23: 4989-99.
  • Supuran CT, Scozzafava A. Carbonic anhydrae inhibitors: Aromatic sulfonamides and disulfonamides act as efficient tumor growth inhibitors. Eur J Med Chem 2000; 35: 867-74.
There are 17 citations in total.

Details

Subjects Health Care Administration
Journal Section Articles
Authors

Sevda Türk This is me

Fatih Tok This is me

Hülya Çelik

Sevgi Karakuş

Hayrunnisa Nadaroğlu This is me

Bedia Koçyiğit-kaymakçıoğlu

Kaan Küçükoğlu

Publication Date August 25, 2016
Published in Issue Year 2017 Volume: 21 Issue: 1

Cite

APA Türk, S., Tok, F., Çelik, H., Karakuş, S., et al. (2016). Some N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted) ureido/thioureido]benzenesulfonamides as carbonic anhydrase I and II inhibitors. Marmara Pharmaceutical Journal, 21(1), 89-95. https://doi.org/10.12991/marupj.259885
AMA Türk S, Tok F, Çelik H, Karakuş S, Nadaroğlu H, Koçyiğit-kaymakçıoğlu B, Küçükoğlu K. Some N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted) ureido/thioureido]benzenesulfonamides as carbonic anhydrase I and II inhibitors. Marmara Pharm J. September 2016;21(1):89-95. doi:10.12991/marupj.259885
Chicago Türk, Sevda, Fatih Tok, Hülya Çelik, Sevgi Karakuş, Hayrunnisa Nadaroğlu, Bedia Koçyiğit-kaymakçıoğlu, and Kaan Küçükoğlu. “Some N-(5-Methyl-1,3,4-Thiadiazol-2-Yl)-4-[(3-Substituted) ureido/Thioureido]benzenesulfonamides As Carbonic Anhydrase I and II Inhibitors”. Marmara Pharmaceutical Journal 21, no. 1 (September 2016): 89-95. https://doi.org/10.12991/marupj.259885.
EndNote Türk S, Tok F, Çelik H, Karakuş S, Nadaroğlu H, Koçyiğit-kaymakçıoğlu B, Küçükoğlu K (September 1, 2016) Some N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted) ureido/thioureido]benzenesulfonamides as carbonic anhydrase I and II inhibitors. Marmara Pharmaceutical Journal 21 1 89–95.
IEEE S. Türk, “Some N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted) ureido/thioureido]benzenesulfonamides as carbonic anhydrase I and II inhibitors”, Marmara Pharm J, vol. 21, no. 1, pp. 89–95, 2016, doi: 10.12991/marupj.259885.
ISNAD Türk, Sevda et al. “Some N-(5-Methyl-1,3,4-Thiadiazol-2-Yl)-4-[(3-Substituted) ureido/Thioureido]benzenesulfonamides As Carbonic Anhydrase I and II Inhibitors”. Marmara Pharmaceutical Journal 21/1 (September 2016), 89-95. https://doi.org/10.12991/marupj.259885.
JAMA Türk S, Tok F, Çelik H, Karakuş S, Nadaroğlu H, Koçyiğit-kaymakçıoğlu B, Küçükoğlu K. Some N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted) ureido/thioureido]benzenesulfonamides as carbonic anhydrase I and II inhibitors. Marmara Pharm J. 2016;21:89–95.
MLA Türk, Sevda et al. “Some N-(5-Methyl-1,3,4-Thiadiazol-2-Yl)-4-[(3-Substituted) ureido/Thioureido]benzenesulfonamides As Carbonic Anhydrase I and II Inhibitors”. Marmara Pharmaceutical Journal, vol. 21, no. 1, 2016, pp. 89-95, doi:10.12991/marupj.259885.
Vancouver Türk S, Tok F, Çelik H, Karakuş S, Nadaroğlu H, Koçyiğit-kaymakçıoğlu B, Küçükoğlu K. Some N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted) ureido/thioureido]benzenesulfonamides as carbonic anhydrase I and II inhibitors. Marmara Pharm J. 2016;21(1):89-95.