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Biological evaluation of aromatic bis-sulfonamide Schiff bases as antioxidant, acetylcholinesterase and butyrylcholinesterase inhibitors

Year 2020, Volume: 41 Issue: 2, 413 - 418, 25.06.2020

Nabih Lolak Süleyman Akocak

https://doi.org/10.17776/csj.595463
Cited By: 4

Abstract

Aromatic/heterocyclic Schiff bases are one of the most investigated and studied scaffold for many pharmaceutical applications. For this reason, in the current work, a series of aromatic bis-sulfonamide Schiff bases (7-15) were re-synthesized by reacting aromatic bis-aldehydes and aromatic sulfonamides in ethanol and assayed for antioxidant properties by using different bioanalytical methods such as DPPH free radical scavenging assay, ABTS cation radical decolarization, cupric reducing antioxidant capacity (CUPRAC) and metal chelating methods. The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition profiles were also assessed. In general, the synthesized compounds showed weak antioxidant activity against all tested methods, but two compounds (12 and 15) showed good CUPRAC activity at 10, 25 and 50 µM concentrations. The weak inhibition potency was obtained against AChE and moderate activity was observed against BChE enzymes at 200 µM.

Keywords

Sulfonamide Schiff base antioxidant anticholinesterase

Supporting Institution

The Scientific and Technological Research Council of Turkey (TUBITAK)

Project Number

215Z484, 315S103, and 216S907

Thanks

This work was partially funded by The Scientific and Technological Research Council of Turkey (TUBITAK) with Grant nos. 215Z484, 315S103, and 216S907.

References

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  • [2] Sridhar, S.K., Saravanan, M., Ramesh, A., Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives, Eur. J. Med. Chem. 36 (2001), 615-625.
  • [3] Panneerselvam, P., Nair, R.R., Vijayalakshmi, G., Subramanian, E.H., Sridhar, S.K., Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents, Eur. J. Med. Chem., 40 (2005), 225-229.
  • [4] Lam, P.L., Lee, K.K.H., Kok, S.H.L., Gambari, R., Lam, K.H., Ho, C.L., Ma, X., Lo, Y.H., Wong, W.Y., Dong, Q.C., Bian, Z.X., Chui, C.H., Antifungal study of substituted 4-pyridylmethylene-4’-aniline Schiff bases, RSC Adv., 106 (2016), 104575-104581. [5] Nizami, G., Sayyed, R., Antimicrobial, electrochemical and thermodynamic studies of Schiff base complexes and their potential as anticarcinogenic and antitumor agents: A review, IOSR J. Appl.Chem., 10 (2017), 40-51.
  • [6] Raquel, S.A., Pessoa, C., Lourenco, M.C.S., de Souza, V.N.M., Lessa, A.J., Synthesis, Antitubercular and Anticancer activities of p-nitrophenylethylenediamine derived Schiff bases, Med. Chem. 13 (2017), 391-397.
  • [7] Dhar, D.N., Taploo, C.L., Schiff bases and their applications, J. Sci. Ind. Res. 41 (1982), 501-506.
  • [8] Gupta, S.D., Revathi, B., Mazaira, G.I., Galigniana, M.D., Subrahmanyam, C.V.S., Gowrishankar, N.L., Raghavendra, N.M., 2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead. Bioorg. Chem., 59 (2014), 97-105.
  • [9] Akocak, S., Lolak, N., Nocentini, A., Karakoc, G., Tufan, A., Supuran, C.T., Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors, Bioorg. Med. Chem., 25 (2017), 3093-3097.
  • [10] Durgun, M., Turkmen, H., Ceruso, M., Supuran, C.T., Synthesis of 4-sulfamoylphenyl-benzylamine derivatives with inhibitory activity against human carbonic anhaydrase isoforms I, II, IX and XII, Bioorg. Med. Chem., 24 (2016), 982-988.
  • [11] Sarikaya, B., Ceruso, M., Carta, F., Supuran, C.T., Inhibition of carbonic anhydrase isoforms I, II, IX ad XII with novel Schiff bases: Identification of selective inhibitors for the tumor-associated isoforms over the cytosolic ones, Bioorg. Med. Chem., 22 (2014), 5883-5890.
  • [12] Durgun M, Turkes C, Isik M, Demir, Y., Sakli, A., Kuru, A., Guzel, A., Beydemir, S., Akocak, S., Osman, S.M., AlOthman, Z., Supuran, C.T., Synthesis, characterization, biological evaluation, and in silico studies of novel series sulfonamide derivatives. J. Enzyme Inhib. Med. Chem. 35 (2020), doi:10.1080/14756366.2020.1746784.
  • [13] Akocak, S., Lolak, N., Vullo, D., Durgun, M., Supuran, C.T., Synthesis and biological evaluation of histamine Schiff bases as carbonic anhydrase I, II, IV, VII and IX activators, J. Enzyme Inhib. Med. Chem., 32 (2017), 1305-1312.
  • [14] Akocak, S., Lolak, N., Bua, S, Nocentini, A., Karakoc, G., Supuran, C.T., α-Carbonic anhydrases are strongly activated by spinaceamine derivatives, Bioorg. Med. Chem., 27 (2019), 800-804.
  • [15] Akocak, S., Lolak, N., Bua, S, Nocentini, A., Supuran, C.T., Activation of human α-Carbonic anhydrase isoforms I, II, IV and VII with bis-histamine Schiff bases and bis-spinaceamine substituted derivatives, J. Enzyme Inhib. Med. Chem., 34 (2019), 1193-1198.
  • [16] Blois, M.S., Antioxidant determinations by the use of a stable free radical, Nature, 181 (1958), 1199-1200.
  • [17] Pellegrini, R.R.N., Proteggente, A., Pannala, A., Yang, M., Rice-Evans, C., Antioxidant activity applying an improved ABTS radical cation decolorization assay, Free Rad. Bio. Med., 26 (1999), 1231-1237.
  • [18] Akocak, S., Boga, M., Lolak, N., Tuneg, M., Sanku, R.K.K.. Design, synthesis and biological evaluatuon of 1,3-diaryltriazene-substituted sulfonamides as antioxidant, acetylcholinesterase and butyrylcholinesterase inhibitors, J. Turk Chem. Soc. Sec. A: Chem., 6 (2019), 63-70.
  • [19] Dinis, T.C.P., Maderia, V.M.C., Almedia, L.M.., Action of phenolic derivatives (acetoaminophen, salycilate and 5-aminosalycilate) as inhibitors of membrane lipid preoxidation and as peroxyl radical scavengers, Arch. Biochem. Biophy., 315 (1994), 161-169.
  • [20] Akocak, S., Lolak, N., Tuneg, M., Boga, M., Antioxidant, acetylcholinesterase and butyrylcholinesterase inhibition profiles of histamine Schiff bases, J. Turk Chem. Soc. Sec. A: Chem., 6 (2019) 157-164.
  • [21] Apak, R., Guclu, K., Ozyurek, M., Karademir, S.E.. Novel total antioxidant capacity index for dietary polyphenols and vitamine C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC Method, J. Agric. Food Chem., 52 (2004), 7970-7981.
  • [22] Ellman, G.L., Courtney, K.D., Andres, V., Featherstone, R.M., A new and rapid colorimetric determination of acetylcholinesterase activity, Biochem. Pharmacol., 7 (1961), 88-95.
  • [23] Mohapatra, R.K., Das, P.K, Pradhan, M.K., Maihub, A.A., El-ajaily, M.M., Biological aspects of Schiff base-metal complexes derived from benzaldehydes: an overview, J. Iran. Chem. Soc. 15 (2018), 2193-2227.
  • [24] Al Zoubi, W., Al-Hamdani, A.A.S., Kaseem, M., Synthesis and antioxidant activities of Schiff bases and their complexes: a review, Appl. Organometal. Chem., 30 (2016), 810-817.
  • [25] Khan, M., Khan, M., Taha, M., Salar, U., Hameed, A., Ismail, N.H., Jamil, W., Saad, S.M., Perveen, S., Kashif, S.M., Synthesis of 4-amino-1,5-dimethyl-2-phenylpyrazolone derivatives and their antioxidant activity, J. Chem. Soc. Pak., 37 (2015), 802-810.
  • [26] Aslam, M., Anis, I., Mehmood, R., Iqbal, L., Iqbal, S., Khan, I., Chishti, M.S., Perveen, S., Synthesis and biological activities of 2-aminophenol-based Schiff bases and their structure-activity relationship, Med. Chem. Res., 25 (2016), 109-115

Year 2020, Volume: 41 Issue: 2, 413 - 418, 25.06.2020

Nabih Lolak Süleyman Akocak

https://doi.org/10.17776/csj.595463
Cited By: 4

Abstract

Project Number

215Z484, 315S103, and 216S907

References

  • [1] Rani, A., Kumar, M., Khare, R., Tuli, H.S., Schiff bases as an antimicrobial agents: A review, J. Biol. Chem. Sci., 2 (2015), 62-91.
  • [2] Sridhar, S.K., Saravanan, M., Ramesh, A., Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives, Eur. J. Med. Chem. 36 (2001), 615-625.
  • [3] Panneerselvam, P., Nair, R.R., Vijayalakshmi, G., Subramanian, E.H., Sridhar, S.K., Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents, Eur. J. Med. Chem., 40 (2005), 225-229.
  • [4] Lam, P.L., Lee, K.K.H., Kok, S.H.L., Gambari, R., Lam, K.H., Ho, C.L., Ma, X., Lo, Y.H., Wong, W.Y., Dong, Q.C., Bian, Z.X., Chui, C.H., Antifungal study of substituted 4-pyridylmethylene-4’-aniline Schiff bases, RSC Adv., 106 (2016), 104575-104581. [5] Nizami, G., Sayyed, R., Antimicrobial, electrochemical and thermodynamic studies of Schiff base complexes and their potential as anticarcinogenic and antitumor agents: A review, IOSR J. Appl.Chem., 10 (2017), 40-51.
  • [6] Raquel, S.A., Pessoa, C., Lourenco, M.C.S., de Souza, V.N.M., Lessa, A.J., Synthesis, Antitubercular and Anticancer activities of p-nitrophenylethylenediamine derived Schiff bases, Med. Chem. 13 (2017), 391-397.
  • [7] Dhar, D.N., Taploo, C.L., Schiff bases and their applications, J. Sci. Ind. Res. 41 (1982), 501-506.
  • [8] Gupta, S.D., Revathi, B., Mazaira, G.I., Galigniana, M.D., Subrahmanyam, C.V.S., Gowrishankar, N.L., Raghavendra, N.M., 2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead. Bioorg. Chem., 59 (2014), 97-105.
  • [9] Akocak, S., Lolak, N., Nocentini, A., Karakoc, G., Tufan, A., Supuran, C.T., Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors, Bioorg. Med. Chem., 25 (2017), 3093-3097.
  • [10] Durgun, M., Turkmen, H., Ceruso, M., Supuran, C.T., Synthesis of 4-sulfamoylphenyl-benzylamine derivatives with inhibitory activity against human carbonic anhaydrase isoforms I, II, IX and XII, Bioorg. Med. Chem., 24 (2016), 982-988.
  • [11] Sarikaya, B., Ceruso, M., Carta, F., Supuran, C.T., Inhibition of carbonic anhydrase isoforms I, II, IX ad XII with novel Schiff bases: Identification of selective inhibitors for the tumor-associated isoforms over the cytosolic ones, Bioorg. Med. Chem., 22 (2014), 5883-5890.
  • [12] Durgun M, Turkes C, Isik M, Demir, Y., Sakli, A., Kuru, A., Guzel, A., Beydemir, S., Akocak, S., Osman, S.M., AlOthman, Z., Supuran, C.T., Synthesis, characterization, biological evaluation, and in silico studies of novel series sulfonamide derivatives. J. Enzyme Inhib. Med. Chem. 35 (2020), doi:10.1080/14756366.2020.1746784.
  • [13] Akocak, S., Lolak, N., Vullo, D., Durgun, M., Supuran, C.T., Synthesis and biological evaluation of histamine Schiff bases as carbonic anhydrase I, II, IV, VII and IX activators, J. Enzyme Inhib. Med. Chem., 32 (2017), 1305-1312.
  • [14] Akocak, S., Lolak, N., Bua, S, Nocentini, A., Karakoc, G., Supuran, C.T., α-Carbonic anhydrases are strongly activated by spinaceamine derivatives, Bioorg. Med. Chem., 27 (2019), 800-804.
  • [15] Akocak, S., Lolak, N., Bua, S, Nocentini, A., Supuran, C.T., Activation of human α-Carbonic anhydrase isoforms I, II, IV and VII with bis-histamine Schiff bases and bis-spinaceamine substituted derivatives, J. Enzyme Inhib. Med. Chem., 34 (2019), 1193-1198.
  • [16] Blois, M.S., Antioxidant determinations by the use of a stable free radical, Nature, 181 (1958), 1199-1200.
  • [17] Pellegrini, R.R.N., Proteggente, A., Pannala, A., Yang, M., Rice-Evans, C., Antioxidant activity applying an improved ABTS radical cation decolorization assay, Free Rad. Bio. Med., 26 (1999), 1231-1237.
  • [18] Akocak, S., Boga, M., Lolak, N., Tuneg, M., Sanku, R.K.K.. Design, synthesis and biological evaluatuon of 1,3-diaryltriazene-substituted sulfonamides as antioxidant, acetylcholinesterase and butyrylcholinesterase inhibitors, J. Turk Chem. Soc. Sec. A: Chem., 6 (2019), 63-70.
  • [19] Dinis, T.C.P., Maderia, V.M.C., Almedia, L.M.., Action of phenolic derivatives (acetoaminophen, salycilate and 5-aminosalycilate) as inhibitors of membrane lipid preoxidation and as peroxyl radical scavengers, Arch. Biochem. Biophy., 315 (1994), 161-169.
  • [20] Akocak, S., Lolak, N., Tuneg, M., Boga, M., Antioxidant, acetylcholinesterase and butyrylcholinesterase inhibition profiles of histamine Schiff bases, J. Turk Chem. Soc. Sec. A: Chem., 6 (2019) 157-164.
  • [21] Apak, R., Guclu, K., Ozyurek, M., Karademir, S.E.. Novel total antioxidant capacity index for dietary polyphenols and vitamine C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC Method, J. Agric. Food Chem., 52 (2004), 7970-7981.
  • [22] Ellman, G.L., Courtney, K.D., Andres, V., Featherstone, R.M., A new and rapid colorimetric determination of acetylcholinesterase activity, Biochem. Pharmacol., 7 (1961), 88-95.
  • [23] Mohapatra, R.K., Das, P.K, Pradhan, M.K., Maihub, A.A., El-ajaily, M.M., Biological aspects of Schiff base-metal complexes derived from benzaldehydes: an overview, J. Iran. Chem. Soc. 15 (2018), 2193-2227.
  • [24] Al Zoubi, W., Al-Hamdani, A.A.S., Kaseem, M., Synthesis and antioxidant activities of Schiff bases and their complexes: a review, Appl. Organometal. Chem., 30 (2016), 810-817.
  • [25] Khan, M., Khan, M., Taha, M., Salar, U., Hameed, A., Ismail, N.H., Jamil, W., Saad, S.M., Perveen, S., Kashif, S.M., Synthesis of 4-amino-1,5-dimethyl-2-phenylpyrazolone derivatives and their antioxidant activity, J. Chem. Soc. Pak., 37 (2015), 802-810.
  • [26] Aslam, M., Anis, I., Mehmood, R., Iqbal, L., Iqbal, S., Khan, I., Chishti, M.S., Perveen, S., Synthesis and biological activities of 2-aminophenol-based Schiff bases and their structure-activity relationship, Med. Chem. Res., 25 (2016), 109-115
There are 25 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Nabih Lolak 0000-0003-0578-2761

Süleyman Akocak 0000-0003-4506-5265

Project Number 215Z484, 315S103, and 216S907
Publication Date June 25, 2020
Submission Date July 23, 2019
Acceptance Date April 17, 2020
Published in Issue Year 2020Volume: 41 Issue: 2

Cite

APA Lolak, N., & Akocak, S. (2020). Biological evaluation of aromatic bis-sulfonamide Schiff bases as antioxidant, acetylcholinesterase and butyrylcholinesterase inhibitors. Cumhuriyet Science Journal, 41(2), 413-418. https://doi.org/10.17776/csj.595463

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