Synthesis of New Organoselenium Compounds: Characterization and Biological Studies

Authors

  • Nimra Naz Organometallic & Coordination Chemistry Laboratory, Department of Chemistry, University of Agriculture Faisalabad
  • Saima Saqib Government Postgraduate College for Women, Samanabad-Lahore, Pakistan
  • Rizwan Ashraf Department of Chemistry, University of Agriculture Faisalabad, Pakistan
  • Muhammad Irfan Majeed Department of Chemistry, University of Agriculture Faisalabad-38040, Pakistan
  • Muhammad Adnan Iqbal Organometallic & Coordination Chemistry Laboratory, Department of Chemistry, University of Agriculture Faisalabad

DOI:

https://doi.org/10.20450/mjcce.2020.1912

Keywords:

Selenium, N-Heterocyclic Carbenes, Biological

Abstract

Two new organoselenium analogs, (3,3'-(1,2-phenylenebis(methylene))bis(2-selenoxo-2,3-dihydro-1H-imidazole-3,1-diyl))bis(methylene) dibenzoate (III) and 3,3'-(1,2-phenylenebis(methylene))bis(1-benzyl-1H-imidazole-2(3H)-selenone) (V), were derived from newly synthesized organic salts 1,1'-(1,2-phenylenebis(methylene))bis(3-(2-phenoxyacetyl)-1H-imidazol-3-ium) chloride (II) and 1,1'-(1,2-phenylenebis(methylene))bis(3-benzyl-1H-imidazol-3-ium) chloride (IV), and each was characterized by various analytical techniques, such as Fourier-Transform Infrared Spectroscopy (FT-IR), UV–visible, and Nuclear Magnetic Resonance (NMR) spectroscopy, as well as Ultra-high performance liquid chromatography mass spectrometry/Photodiode array (UHPL-MS/PDA). All synthesized compounds were tested for their antioxidant and anticancer potential. Very good radical scavenging results were obtained for salts II and IV, with cell viability values of 84.6±3.5 and 56.7±5.5%, respectively, compared to their organoselenium adducts. All synthesized products showed significant activity against MCF-7 breast cancer cells, but compounds II and III showed better results, with cell viability values of 40.5±2.0% and 34.4±1.5%, respectively.

Author Biographies

Nimra Naz, Organometallic & Coordination Chemistry Laboratory, Department of Chemistry, University of Agriculture Faisalabad

MPhil Student

Saima Saqib, Government Postgraduate College for Women, Samanabad-Lahore, Pakistan

Miss Saima Saqib is Lecturer at Government Postgraduate College Lahore

Rizwan Ashraf, Department of Chemistry, University of Agriculture Faisalabad, Pakistan

Mr. Rizwan has submitted his PhD thesis for evaluation.

Muhammad Irfan Majeed, Department of Chemistry, University of Agriculture Faisalabad-38040, Pakistan

Dr. M. Irfan Majeed is Assistant Professor at UAF

Muhammad Adnan Iqbal, Organometallic & Coordination Chemistry Laboratory, Department of Chemistry, University of Agriculture Faisalabad

Dr. Iqbal was born in Punjab-Pakistan in April 1984. He completed his schooling and college education at city Faisalabad-Pakistan and bachelor degree in chemistry at university of the Punjab-Lahore-Pakistan in August 2007. He completed his masters (M.phil) in environmental sciences at college of earth and environmental science, University of the Punjab, Lahore  in 2010 and in parallel served as Lecturer of chemistry at Minhaj University Lahore till July 2010. He then joined Universiti Sains Malaysia, Penang-Malaysia in July 2010 for MS leading to PhD study in Dr. Rosenani A. Haque’s laboratory on a fellowship. He completed his PhD in organometallic chemistry in April 2014 and got an opportunity of postdoctoral fellowship at the same research laboratory. During his Ph.D studies Dr. Iqbal visited University of Western Australia, Perth, Australia on a research attachment at Professor Murray Baker’s research Laboratory. He finally joined University of Agriculture Faisalabad in September 2015 as assistant professor. Currently, he has established an organometallic and coordination chemistry laboratory at UAF community college, Faisalabad-Pakistan. His research interests include synthesis of metallodrugs. Dr. Iqbal has published more than 70 research and review articles in international journals, a book on organometallic chemistry and three book chapters. He is managing editor of two reputable research journals, Science International and Angiotherapy. He has organized several workshops, Seminars and duties as coordinator for postgraduate classes in chemistry at PARS campus for two years and also acted as convener to the coordinators at PARS.

References

S. C. Sau, P. K. Hota, S. K. Mandal, M. Soleilhav-oup, G. Bertrand, Stable abnormal N-heterocyclic car-benes and their applications, Chem. Soc. Rev., 49, 1233–1252 (2020).

D. Zhu, L. Chen, H. Fan, Q. Yao, S. Zhu, Recent pro-gress on donor and donor–donor carbenes, Chem. Soc. Rev., 49, 908–950 (2020).

M. Fevre, J. Pinaud, Y. Gnanou, J. Vignolle, D. Taton, N-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer syn-thesis, Chem. Soc. Rev., 42, 2142–2172 (2013).

L. Benhamou, E. Chardon, G. Lavigne, Sp. Bellemin-Laponnaz, V. Cesar, Synthetic routes to N-heterocyclic carbene precursors, Chem. Rev., 111, 2705–2733 (2011).

L. Falivene, L. Cavallo, Theoretical NMR spectrosco-py of N-heterocyclic carbenes and their metal com-plexes, Coord. Chem. Rev., 344, 101–114 (2017).

M. Elsherbini, W. S. Hamama, H. H. Zoorob, Recent advances in the chemistry of selenium-containing het-erocycles: five-membered ring systems, Coord. Chem. Rev., 312, 149–177 (2016).

H-J. Sun, B. Rathinasabapathi, B. Wu, J. Luo, L-P. Pu, L.Q. Ma, Arsenic and selenium toxicity and their in-teractive effects in humans, Environ. Int. 69, 148–158 (2014).

A. G. Vogt, G. T. Voss, R. L. de Oliveira, J. J. Paltian, L. F. Duarte, D. Alves et al. Organoselenium group is critical for antioxidant activity of 7-chloro-4-phenyl-selenyl-quinoline, Chem. Biol. Interact., 282, 7–12 (2018).

A. Ecker, R. S. da Silva, M. M. dos Santos, D. Ardis-son-Araújo, O. E. Rodrigues, J. B. T. da Rocha et al., Safety profile of AZT derivatives: Organoselenium moieties confer different cytotoxic responses in fresh human erythrocytes during in vitro exposures, J. Trace Elem. Med. Biol., 50, 240–248 (2018).

J. Fernández-Lodeiro, M. F. Pinatto-Botelho, A. A. Soares-Paulino, A. C. Gonçalves, B. A. Sousa, C. Princival et al., Synthesis and biological properties of selenium-and tellurium-containing dyes, Dyes Pigm., 110, 28–48 (2014).

N. N. Kharabayev, Quantum chemical simulation of hexa-, penta- and tetracoordination modes in stereoi-somers of the Co(II) and Ni(II) bis(ligand) complexes based on (N,O,S(Se))-tridentate azomethines, Russ. J. Coord. Chem., 45, 573–584 (2019).

DOI: 10.1134/s1070328419080050.

M. S. Gularte, J. M. Anghinoni, L. Abenante, G. T. Voss, R. L. de Oliveira, R. A. Vaucher et al., Synthesis of chitosan derivatives with organoselenium and or-ganosulfur compounds: Characterization, antimicrobi-al properties and application as biomaterials, Carbo-hydr. Polym., 219, 240–250 (2019).

G. Spengler, M. Gajdács, M. A. Marć, E. Domínguez-Álvarez, C. Sanmartín, Organoselenium compounds as novel adjuvants of chemotherapy drugs — a promis-ing approach to fight cancer drug resistance, Mole-cules., 24, 336–338 (2019).

Z. Chen, H. Lai, L. Hou, T. Chen, Rational design and action mechanisms of chemically innovative orga-noselenium in cancer therapy, Chem. Commun., 56, 179–196 (2020).

A. R. Patra, S. Hajra, R. Baral, S. Bhattacharya, Use of selenium as micronutrients and for future anticancer drug: a review. Nucl. 2019, 1–12 (2019).

DOI: 10.1007/s13237-019-00306-y

M. Adly, E. Gedawy, A. El-Malah, F. El-Telbany, Synthesis and anticancer activity of certain seleno-phene derivatives, Russ. J. Org. Chem., 55, 1189–1196 (2019).

E. Fragoso, R. Azpiroz, P. Sharma, G. Espinosa-Pérez, F. Lara-Ochoa, A. Toscano et al., New organoseleni-um compounds with intramolecular Se⋯ O/Se⋯ H in-teractions: NMR and theoretical studies, J. Mol. Struct. 1155, 711–719 (2018).

A. Kamal, M. A. Iqbal, H. N. Bhatti, Therapeutic ap-plications of selenium-derived compounds, Rev. In-org. Chem., 38, 49–76 (2018).

B. Shojadoost, R. R. Kulkarni, A. Yitbarek, A. Laursen, K. Taha-Abdelaziz, T. N. Alkie et al., Dietary selenium supplementation enhances antiviral immuni-ty in chickens challenged with low pathogenic avian influenza virus subtype H9N2, Vet. Immunol. Im-munopathol., 207, 62–68 (2019).

P. Chakraborty, S. S. Roy, A. Basu, S. Bhattacharya, Sensitization of cancer cells to cyclophosphamide therapy by an organoselenium compound through ROS-mediated apoptosis, Biomed. Pharmacother., 84, 1992–1999 (2016).

R. A. Haque, M. A. Iqbal, F. Mohamad, M. R. Razali, Antibacterial and DNA cleavage activity of carbonyl functionalized N-heterocyclic carbene-silver (I) and selenium compounds, J. Mol. Struct. 1155, 362–370 (2018).

A. Kamal, V. M. Nazari, M. Yaseen, M. A. Iqbal, M. B. K. Ahamed, A. S. A. Majid et al., Green synthesis of selenium-N-heterocyclic carbene compounds: Evaluation of antimicrobial and anticancer potential, Bioorg. Chem., 90, 103042 (2019).

DOI: https://doi.org/10.1016/j.bioorg.2019.103042

S. F. Jafari, M. B. Khadeer Ahamed, M. A. Iqbal, F. S. R. Al Suede, S. H. Khalid, R. A. Haque et al., In-creased aqueous solubility and proapoptotic activity of potassium koetjapate against human colorectal cancer cells, J. Pharm. Pharmacol., 66, 1394–1409 (2014).

R. A. Ammar, A-N. M. Alaghaz, M. E. Zayed, L. A. Al-Bedair, Synthesis, spectroscopic, molecular struc-ture, antioxidant, antimicrobial and antitumor behavior of Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes of O2N type tridentate chromone-2-carboxaldehyde Schiff's base ligand, J. Mol. Struct., 1141, 368–381 (2017).

S. B. Kedare, R. Singh, Genesis and development of DPPH method of antioxidant assay, J. Food Sci. Technol., 48, 412–422 (2011).

A. G. Heriot. Whither Anal Cancer?, Nature Publish-ing Group, 2020.

A. P. Thrift, H. B. El-Serag, Burden of gastric cancer. Clin. Gastroenterol. Hepatol., 18, 534–542 (2020).

R. L. Siegel, K. D. Miller, A. Jemal, Cancer statistics, 2020, CA: Ca-Cancer J. Clin., 70, 7–30 (2020).

DOI: 10.3322/caac.21590

J. Ferlay, I. Soerjomataram, R. Dikshit, S. Eser, C. Mathers, M. Rebelo et al., Cancer incidence and mor-tality worldwide: sources, methods and major patterns in GLOBOCAN 2012. Int. J. Cancer. 136, E359–E386 (2015).

M. Krstic, B. Petković, M. Milčić, D. Mišić, J. F. San-tibanez, Synthesis, characterization and biological study of new dinuclear zinc(II) and nickel(II) octaaza macrocyclic complexes, Maced. J. Chem. Chem. Eng. 38, 11 (2019). DOI: 10.20450/mjcce.2019.1599

M. Atif, H. N. Bhatti, R. A. Haque, M. A. Iqbal, M. B. Ahamed Khadeer, A. M. S. A Majid, Synthesis, struc-ture and anticancer activity of symmetrical and non-symmetrical silver(I)-N-heterocyclic carbene com-plexes, Appl. Biochem. Biotechnol., 2020.

DOI: 10.1007/s12010-019-03186-9

M. Yaqoob, S. Gul, N. F. Zubair, J. Iqbal, M. A. Iqbal, Theoretical calculation of selenium N-heterocyclic carbene compounds through DFT studies: Synthesis, characterization and biological potential. J. Mol. Struct. 1204, 127462 (2020).

DOI: https://doi.org/10.1016/j.molstruc.2019.127462.

M. A. Iqbal, R. A. Haque, S. F. Nasri, A. A. Majid, M. B. K. Ahamed, E. Farsi et al., Potential of silver against human colon cancer: (synthesis, characteriza-tion and crystal structures of xylyl (ortho, meta, & pa-ra) linked bis-benzimidazolium salts and Ag(I)-NHC complexes: In vitro anticancer studies). Chem. Cent. J. 7, 1–27 (2013).

M. Refat, S. Abdel-Hafez, Synthesis and spectroscopic studies of the new Ag (I) organoselenium complex. Russ. J. Gen. Chem. 86, 1151–1153 (2016).

F. Al-Khodir, Synthesis, spectroscopic interpretations, and antioxidant efficiency of two vital selenium com-plexes, Acta Phys. Pol., A. 132, 1265–1271 (2017).

A. M. Al‐Majid, S. Yousuf, M. I. Choudhary, F. Nahra, S. P. Nolan, Gold‐NHC complexes as potent bioactive compounds, Chemistry Select. 1, 76–80 (2016).

R. A. Haque, S. Y. Choo, S. Budagumpi, M. A. Iqbal, A. A.-A. Abdullah, Silver(I) complexes of mono- and bidentate N-heterocyclic carbene ligands: Synthesis, crystal structures, and in vitro antibacterial and anti-cancer studies, Eur. J. Med. Chem. 90, 82–92 (2015).

R. A. Haque, M. A. Iqbal, P. Asekunowo, A. A. Majid, M. B. K. Ahamed, M. I. Umar et al, Synthesis, struc-ture, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinu-clear Ag(I) N-heterocyclic carbene complexes (Part-II), Med. Chem. Res. 22, 4663–4676 (2013).

Se-NHC Selenones

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Published

2020-05-30

How to Cite

Naz, N., Saqib, S., Ashraf, R., Majeed, M. I., & Iqbal, M. A. (2020). Synthesis of New Organoselenium Compounds: Characterization and Biological Studies. Macedonian Journal of Chemistry and Chemical Engineering, 39(1), 1–10. https://doi.org/10.20450/mjcce.2020.1912

Issue

Vol. 39 No. 1 (2020)

Section

Organic Chemistry

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