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

Yıl 2020, Cilt: 41 Sayı: 2, 413 - 418, 25.06.2020

Nabih Lolak Süleyman Akocak

https://doi.org/10.17776/csj.595463
Cited By: 3

Öz

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.

Anahtar Kelimeler

Sulfonamide Schiff base antioxidant anticholinesterase

Destekleyen Kurum

The Scientific and Technological Research Council of Turkey (TUBITAK)

Proje Numarası

215Z484, 315S103, and 216S907

Teşekkür

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

Kaynakça

  • [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

Yıl 2020, Cilt: 41 Sayı: 2, 413 - 418, 25.06.2020

Nabih Lolak Süleyman Akocak

https://doi.org/10.17776/csj.595463
Cited By: 3

Öz

Proje Numarası

215Z484, 315S103, and 216S907

Kaynakça

  • [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
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Natural Sciences
Yazarlar

Nabih Lolak 0000-0003-0578-2761

Süleyman Akocak 0000-0003-4506-5265

Proje Numarası 215Z484, 315S103, and 216S907
Yayımlanma Tarihi 25 Haziran 2020
Gönderilme Tarihi 23 Temmuz 2019
Kabul Tarihi 17 Nisan 2020
Yayımlandığı Sayı Yıl 2020Cilt: 41 Sayı: 2

Kaynak Göster

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

Cited By

Evaluation of cytotoxic, antifungal, and larvicidal activities of different bis‐sulfonamide Schiff base compounds
Journal of Biochemical and Molecular Toxicology
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DNA cleavage, cytotoxic and antioxidant properties of Cistus laurifolius L. extracts
Journal of the Indian Chemical Society
https://doi.org/10.1016/j.jics.2022.100569
In Silico Studies and DNA Cleavage, Antioxidant, Acetylcholinesterase, and Butyrylcholinesterase Activity Evaluation of Bis-Histamine Schiff Bases and Bis-Spinaceamine Substituted Derivatives
Pharmaceutical Chemistry Journal
https://doi.org/10.1007/s11094-022-02581-7