Bioactive Heteroleptic Bismuth(V) Complexes: Synthesis, Structural Analysis and Binding Pattern Validation
Sohaila Andleeb
Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Search for more papers by this authorCorresponding Author
Imtiaz-ud-Din
Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Correspondence
Prof. Imtiaz-ud-Din, Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan.
Email: [email protected]
Dr. Muhammad Khawar Rauf, Office of Research, Innovation and Commercialization, Quaid-I-Azam University Islamabad 45320, Pakistan.
Email: [email protected]
Search for more papers by this authorCorresponding Author
Muhammad Khawar Rauf
Office of Research, Innovation and Commercialization, Quaid-I-Azam University, Islamabad, 45320 Pakistan
Correspondence
Prof. Imtiaz-ud-Din, Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan.
Email: [email protected]
Dr. Muhammad Khawar Rauf, Office of Research, Innovation and Commercialization, Quaid-I-Azam University Islamabad 45320, Pakistan.
Email: [email protected]
Search for more papers by this authorSyed Sikander Azam
Computational Biology Lab, National Center for Bioinformatics, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Search for more papers by this authorIhsan-ul Haq
Department of Pharmacy, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Search for more papers by this authorMuhammad Nawaz Tahir
Department of Chemistry, University of Sargodha, Sargodha, 40100 Pakistan
Search for more papers by this authorSajjad Ahmad
Computational Biology Lab, National Center for Bioinformatics, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Search for more papers by this authorSohaila Andleeb
Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Search for more papers by this authorCorresponding Author
Imtiaz-ud-Din
Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Correspondence
Prof. Imtiaz-ud-Din, Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan.
Email: [email protected]
Dr. Muhammad Khawar Rauf, Office of Research, Innovation and Commercialization, Quaid-I-Azam University Islamabad 45320, Pakistan.
Email: [email protected]
Search for more papers by this authorCorresponding Author
Muhammad Khawar Rauf
Office of Research, Innovation and Commercialization, Quaid-I-Azam University, Islamabad, 45320 Pakistan
Correspondence
Prof. Imtiaz-ud-Din, Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan.
Email: [email protected]
Dr. Muhammad Khawar Rauf, Office of Research, Innovation and Commercialization, Quaid-I-Azam University Islamabad 45320, Pakistan.
Email: [email protected]
Search for more papers by this authorSyed Sikander Azam
Computational Biology Lab, National Center for Bioinformatics, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Search for more papers by this authorIhsan-ul Haq
Department of Pharmacy, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Search for more papers by this authorMuhammad Nawaz Tahir
Department of Chemistry, University of Sargodha, Sargodha, 40100 Pakistan
Search for more papers by this authorSajjad Ahmad
Computational Biology Lab, National Center for Bioinformatics, Quaid-i-Azam University, Islamabad, 45320 Pakistan
Search for more papers by this authorAbstract
Heteroleptic triorganobismuth (V) complexes of general formula, R3Bi(OOCR')2 (1–7), where R = C6H5 (1–3), p-CH3C6H4 (4–7) and R' = 3,5-Cl2C6H3 (1, 5); 3,4,5-(OCH3)3C6H2 (2, 6); 3-CH3C6H4 (3,7); 2-OH-3-OCH3C6H3 (4) have been synthesized and fully characterized by FT-IR, 1H &13C NMR spectroscopy, single crystal X-ray crystallography and elemental analysis. The molecular geometry observed for the compounds is predominantly distorted trigonal bipyramidal, the fact which was subsequently authenticated through X-ray analyses for (1–4). All the synthesized compounds have been bio-assayed for antileishmanial (Leishmania tropica KWH23) and Jack beans urease inhibitory activity, and human Lymphocytes were used to measure the general toxicity. Of these, (4) proved to be highly effective against the target species (Leishmania tropica KWH23), while being non-toxic towards the mammalian cells at levels below 0.74 μgmL−1, making it highly promising drug candidate. The high activities for (2, 4, and 6) against Jack beans Urease as compared to the reference standard demonstrate their significance in searching of therapeutic agents in future programs. The significant binding score of (2&4) against H. pylori in molecular docking studies further revealed their importance in future drug discovery processes.
CONFLICT OF INTEREST
There are no conflicts of interest to declare.
Supporting Information
| Filename | Description |
|---|---|
| aoc5061-sup-0001-Table_S1.docxWord 2007 document , 49.5 KB |
TABLE S1 Crystallographic and structural refinement data for complexes (1–4) TABLE S2 Selected bond lengths (Å) and angles (°) for complexes (1–4) |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1R. Mohan, Nat. Chem. 2010, 2, 336.
- 2O. Rohr, Ind. Lubr. Tribol. 2002, 54, 153.
- 3Y. Yang, R. Ouyang, L. Xu, N. Guo, W. Li, K. Feng, L. Ouyang, Z. Yang, S. Zhou, Y. Miao, J. Coord. Chem. 2015, 68, 379.
- 4P. Domenico, L. Baldassarri, P. E. Schoch, K. Kaehler, M. Sasatsu, B. A. Cunha, Antimicrob. Agents Chemother. 2001, 45, 1417.
- 5H. Zhu, Y. Li, R. Qiu, L. Shi, W. Wu, S. Zhou, Biomaterials 2012, 33, 3058.
- 6Y. Fang, C. Peng, R. Guo, L. Zheng, J. Qin, B. Zhou, M. Shen, X. Lu, G. Zhang, X. Shi, Analyst 2013, 138, 3172.
- 7R. Sushma, I. C. Tewari, World Res. J. Appl. Med. Chem. 2011, 1, 24.
- 8J. O'Neill, Expert Opin. Invest. Drugs 2008, 17, 297.
- 9(a)P. C. Andrews, G. B. Deacon, R. L. Ferrero, Dalton Trans. 2009, 6377. (b)L. Zhang, S. B. Mulrooney, A. F. K. Leung, Y. Zeng, B. B. C. Ko, R. P. Hausinger, H. Sun, BioMetals 2006, 19, 503.
- 10M. Busse, E. Border, P. C. Junk, R. L. Ferrero, P. C. Andrews, Dalton Trans. 2014, 43, 17980.
- 11B. J. Marshall, J. R. Warren, E. D. Blincow, M. Phillips, C. S. Goodwin, R. Murray, S. J. Blackbourn, T. E. Waters, C. R. Sanderson, Lancet 1988, 332, 1437.
10.1016/S0140-6736(88)90929-4 Google Scholar
- 12G. Sachs, D. Weeks, Y. Wen, D. R. Scott, E. A. Marcus, Y. Wen, S. Singh, J. Feng, G. Sachs, D. Weeks, Y. Wen, T. A. Krulwich, G. Sachs, E. Padan, Physiology. 2005, 20, 429.
- 13D. M. Keogan, B. Twamley, D. Fitzgerald-Hughes, D. M. Griffith, Dalton Trans. 2016, 45, 11008.
- 14S. T. C. Eey, M. J. Lear, Org. Lett. 2010, 12, 5510.
- 15M. L. N. Rao, V. Venkatesh, D. N. Jadhav, Eur. J. Org. Chem. 2010, 2010, 3945.
- 16H. Steinberg, D. R. Gardner, Y. S. Lee, P. Jarillo-Herrero, Nano Lett. 2010, 10, 5032.
- 17W. Chai, F. Yang, W. Yin, S. You, K. Wang, W. Ye, Dalton Trans. 2019, 48, 1906.
- 18M. Nawaz, J. Photochem. Photobiol., a 2017, 332, 326.
- 19N. Liang, M. Wang, L. Jin, S. Huang, W. Chen, M. Xu, Appl. Mater. Interfaces. 2014, 6, 11698.
- 20I. Bulimestru, S. Shova, N. Popa, P. Roussel, F. Capet, R. N. Vannier, N. Djelal, L. Burylo, J. P. Wignacourt, A. Gulea, K. H. Whitmire, Chem. Mater. 2014, 26, 6092.
- 21A. M. Preda, W. B. Schneider, M. Rainer, T. Rüffer, D. Schaarschmidt, H. Lang, M. Mehring, Dalton Trans. 2017, 46, 8269.
- 22D. Imtiaz ud, M. Mazhar, S. Ali, S. Dastgir, K. C. Molloy, M. F. Mahon, Appl. Organomet. Chem. 2003, 17, 781.
- 23(a)S. Andleeb, S. L. Donaldson, D. E. Schipper, I. I. Loera Fernandez, I. ud Din, K. H. Whitmire, Eur. J. Inorg. Chem. 2017, 11, 1457. (b)I. I. Loera Fernandez, S. L. Donaldson, D. E. Schipper, S. Andleeb, K. H. Whitmire, Inorg. Chem. 2016, 55, 11560.
- 24P. C. Andrews, G. B. Deacon, P. C. Junk, I. Kumar, M. Silberstein, Dalton Trans. 2006, 40, 4852.
- 25(a)I. Rizvi, P. A. Singh, Int. J. Sci. Eng. Res. 2015, 6, 562. (b)P. C. Andrews, P. C. Junk, L. Kedzierski, Aust. J. Chem. 2013, 66, 1297.
- 26Y. C. Ong, V. L. Blair, L. Kedzierski, P. C. Andrews, Dalton Trans. 2014, 43, 12904.
- 27V. V. Sharutin, O. K. Sharutina, V. S. Senchurin, Russ. J. Inorg. Chem. 2013, 58, 1470.
- 28A. Luqman, V. L. Blair, R. Brammananth, P. K. Crellin, R. L. Coppel, P. C. Andrews, Chem. – Eur. J. 2014, 20, 14362.
- 29(a)H. Suzuki, N. Komatsu, T. Ogawa, T. Marafuji, T. Ikegami, Y. Matano, Organobismuth Chemistry, 1st ed., Elsevier Science, Amsterdam 2001. (b)T. Murafuji, T. Azuma, Y. Miyoshi, M. Ishibashi, A. F. M. M. Rahman, K. Migita, Y. Sugihara, Y. Mikata, Bioorg. Med. Chem. Lett. 2006, 16, 1510.
- 30A. Raheel, Imtiaz-ud-Din, S. Andleeb, S. Ramadan, M. N. Tahir, Appl. Organomet. Chem. 2017, 31, e3632.
- 31Y. C. Ong, V. L. Blair, L. Kedzierski, K. L. Tuck, P. C. Andrews, Dalton Trans. 2015, 44, 18215.
- 32S. Andleeb, Imtiaz-Ud-Din, M. K. Rauf, S. S. Azam, A. Badshah, H. Sadaf, A. Raheel, M. N. Tahir, S. Raza, RSC Adv. 2016, 6, 79651.
- 33R. N. Duffin, V. L. Blair, L. Kedzierski, P. C. Andrews, Dalton Trans. 2018, 47, 971.
- 34M. I. Ali, M. K. Rauf, A. Badshah, I. Kumar, C. M. Forsyth, P. C. Junk, L. Kedzierski, P. C. Andrews, Dalton Trans. 2013, 42, 16733.
- 35R. Mushtaq, M. K. Rauf, M. Bolte, A. Nadhman, A. Badshah, M. N. Tahir, M. Yasinzai, K. M. Khan, Appl. Organomet. Chem. 2017, 31, 1.
- 36W. L. F. Armarego, C. L. L. Chai, Purification of laboratory chemicals, Butterworth–Heinemann, London 2003.
10.1016/B978-075067571-0/50007-7 Google Scholar
- 37G. M. Sheldrick, Acta Crystallogr. Sect. A Found. Crystallogr. 2007, 64, 112.
- 38L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 568.
- 39M. Ahmed, H. Fatima, M. Qasim, B. Gul, Ihsan-ul-Haq, BMC Complement. Altern. Med. 2017, 17, 1.
- 40Atta-ur-Rahman, M. I. Choudhary, W. J. Thomesen, Bioassay Techniques for Drug Development, Harwood Academic Publishers, Amsterdam 2001.
10.4324/9780203304532 Google Scholar
- 41D. Kalemba, A. Kunicka, Curr. Med. Chem. 2003, 10, 813.
- 42G. Jones, P. Willett, R. C. Glen, A. R. Leach, R. Taylor, J. Mol. Biol. 1997, 267, 727.
- 43S. Ahmad, S. Raza, R. Uddin, S. S. Azam, J. Mol. Graphics Modell. 2017, 77, 72.
- 44E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt, E. C. Meng, T. E. Ferrin, J. Comput. Chem. 2004, 25, 1605.
- 45 Dassault Systems BIOVIA, Discovery Studio Visualizer, Dassault Sytems, San Diego, CA 2016.
