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Articles

Pharmacologically bio-relevant N-functionalized homo-binuclear macrocyclic complexes: synthesis, spectral studies, biological screening, HSA binding, and molecular docking

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Pages 413-430 | Received 21 May 2018, Accepted 24 Aug 2019, Published online: 18 Sep 2019

References

  • (a) Böttger, U. A.; O’Sullivan, B.; Ziemer, B.; Schumann, H.; Mögge, C.; Weißhoff, H. Eur. J. Inorg. Chem. 2004, 2004(19), 3852–3864; (b) Koval I. A.; Selmeczi, K.; Belle, C.; Philouze, C.; Saint-Aman, E.; Gautier-Luneau, I.; Schuitema, A. M.; Vliet, M. V.; Gamez, P.; Roubeau, O.; Lüken, M.; Krebs, B.; Luta, M.; Spek, A. L.; Pierre, J. L.; Reedijk, J. Chem -Eur. J. 2006, 12(23), 6138–6150; (c) Lehn, J. M. Angew. Chem. Int. Ed. Engl. 1988, 27(1), 89–112; (d) Lin, Y. C.; Misra, T. K.; Lu, T. H.; Joseph, M. S.; Chung, C. S. Eur. J. Inorg. Chem. 2006, 2006(5), 994–1005; (e) Tandon, S. S.; Bunge, S. D.; Thompson, L. K. Chem. Commun. 2007, 8, 798–800; (f) Ragunathan, K. G.; Schneider, H. J. Angew. Chem. Int. Ed. Engl. 1996, 35, 1219–1221; (g) Verani, C. N.; Rentschler, E.; Weyhermüller, T.; Bill, E.; Chaudhuri, P. Dalton Trans. 2000, 3, 251–258; (h) Vigato, P. A.; Tamburini, S.; Fenton D. E. Coord. Chem. Rev. 1990, 106, 25–170.
  • (a) Fernandez, M.; Basitida, R.; Macias, A.; Valencia, L.; Lourido, P. Polyhedron 2006, 25 (3), 783–792; (b) Jouad, E. M.; Riou, A.; Allian, M.; Khan, M. A.; Bouet, G. M. Polyhedron 2001, 20, 67–74.
  • Naik, A. D.; Annigeri, S. M.; Gangadharmath, U. B.; Revankar, V. K.; Mahale, V. B. J. Inclusion Phenom. Macro. Chem. 2002, 43, 291–297. DOI:10.1023/A:1021289104845.
  • Lindoy, L. F. The chemistry of macrocyclic ligand complexes. Cambridge University Press: Cambridge, 1989.
  • Chandra, S.; Gupta, N.; Gupta, R. Spectrochim. Acta A Mol. Biomol. Spectrosc.. 2006, 63, 587–593. DOI:10.1016/j.saa.2005.06.005.
  • Dospil, G.; Schatz, J. Tetrahedron. Lett. 2001, 42, 7837–7840. DOI:10.1016/S0040-4039(01)01688-4.
  • (a) Salavati-Niasari, M.; Amiri, A. Transition Met. Chem. 2006, 31 (2), 157–162; (b) Siddiqi, K. S.; Khan, S.; Nami, S. A. A.; El-ajaily, M. M. Spectrochim. Acta A 2007, 67(34), 995–1002. DOI:10.1016/j.saa.2006.09.019.
  • (a) Develay, S.; Tripier, R.; Bernier, N.; Baccon M. L.; Patinec, V.; Serratrice, G.; Handel, H. Dalton Trans. 2007, 10, 1038–1046; (b) Gao, J.; Reibenspies, J. H.; Zingaro, R. A.; Woolley, F. R.; Martell, A. E.; Cleafield, A. Inorg. Chem. 2005, 44 (2), 232–241; (c) Kaden, T. A. Coord. Chem. Rev. 1999, 190–192, 371–389; (d) Liang, X.; Parkinson, J. A.; Weish, M.; Gould, R. O.; Paisey, S. J.; Park, H. S.; Hunter, T. M.; Blindauer, C. A.; Parsons, S.; Sadler, P. J. J. Am. Chem. Soc. 2002, 124 (31), 9105–9112; (e) Salavati-Niasari, M. J. Mol. Catal. 2007, 272 (1–2) (A), 207–212; (f) Zafar, H.; Kareem, A.; Sherwani, A.; Mohammad, O.; Khan, T. A. J. Mol. Struct. 2015, 1079, 337–346;
  • (a) Sandhanamalar, D.; Vedanayaki, S.; Rajavel, R. Int. J. Pharmacy. Tech. 2012, 4(1), 4018–4031; (b) Sandhanamalar, D.; Vedanayaki, S.; Rajavel, R. Int. J. Inorg. Bioinorg. Chem. 2011, 2 (1), 5–10.
  • (a) Chattopadhyay, T.; Banu, K. S.; Banerjee, A.; Ribas, J.; Majee, A.; Nethaji, M.; Das, D. J. Mol. Struct. 2007, 833 (1–3), 13–22; (b) Sougandi, I.; Mahalakshmi, R.; Kannappan, R.; Rajendiran, T. M.; Venkatesan, R.; Rao P. S. Trans. Met. Chem. 2002, 27(5), 512–519. DOI:10.1023/A:1015639514842.
  • (a) Mahalakshmi, N.; Rajavel, R. Arab. J. Chem. 2014, 7 (4), 509–517; (b) Raman, N.; Sakthivel, A.; Jeyamurugan, R. J. Coord. Chem. 2010, 63 (6), 1080–1096; (c) Shakir, M.; Abbasi, A.; Azam, M.; Khan, A. U. Spectrochim. Acta A 2011, 79 (5), 1866–1875.
  • Ang, W. H.; Daldini, E.; Juillerat-Jeanneret, L.; Dyson, P. Strategy to Tether Organometallic Ruthenium-Arene Anticancer Compounds to Recombinant Human Serum Albumin. Inorg. Chem. 2007, 46, 9048–9050. DOI:10.1021/ic701474m.
  • (a) Fard, F. J.; Khoshkhoo, Z. M.; Mirtabatabaei, H.; Housaindokht, M. R.; Jalal, R.; Hosseini, H. E.; Bozorgmehr, M. R.; Esmaeili, A. A.; Khoshkholgh, M. J. Spectrochim. Acta A 2012, 97, 74–82; (b) Shahabadi, N.; Maghsudi, M. J. Mol. Struct. 2009, 929 (1–3), 193–199.
  • Hall, M. L.; Hall, H. L.; Kier, L. B. Methods for Predicting the Affinity of Drugs and Drug-Like Compounds for Human Plasma Proteins: A Review. CAD. 2009, 5, 90–105. DOI:10.2174/157340909788451946.
  • Komatsu, T.; Ohmichi, N.; Zunszain, P. A.; Curry, S.; Tsuchida, E. J. Am. Chem. Soc. 2004, 126, 14304–14305. DOI:10.1021/ja046022t.
  • Chuang, V. T. G.; Kragh-Hansen, U.; Otagiri, M. Pharm. Res. 2002, 19, 569–577. DOI:10.1023/a:1015396825274.
  • Sirelkhatim, A.; Mahmud, S.; Seeni, A.; Kaus, N. H. M.; Ann, L. C.; Bakhori, S. K. M.; Hasan, H.; Mohamad, D. Review on Zinc Oxide Nanoparticles: Antibacterial Activity and Toxicity Mechanism. Nanomicro. Lett. 2015, 7, 219–242. DOI:10.1007/s40820-015-0040-x.
  • El-Gammal, O. A.; Rakha, T. H.; Metwally, H. M.; Abu El-Reash, G. M. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 127, 144–156. DOI:10.1016/j.saa.2014.02.008.
  • Naveen, P.; Jain, R.; Kalaivani, P.; Shankar, R.; Dallemer, F.; Prabhakaran, R. New J. Chem. 2017, 41, 8885–8898. DOI:10.1039/C7NJ01273J.
  • Singh, B. K.; Prakash, A.; Rajour, H. K.; Bhojak, N.; Adhikari, D. Spectrochim. Acta A 2010, 76, 376–383. DOI:10.1016/j.saa.2010.03.031.
  • (a) Hathaway, B. J.; Underhill, A. E. J. Chem. Soc. 1961, 3091–3096; (b) Shakir, M.; Bano, N; Rauf, A; Kazmi, S; Alam, M. Inorg. Nano-Met. Chem. 2017, 47 (4), 576–590; (c) Svatos, G. F.; Curran, C.; Quagliano, J. V. J. Am. Chem. Soc. 1955, 77(23), 6159–6163.
  • (a) Djebbar-Sid, S.; Benali-Baitich. Transition Met. Chem. 1998, 23 (4), 443–447; (b) Bellamy, L.J. The Infrared Spectra of the Complex Molecules, 2nd ed.; Wiley Interscience: New York, 1970.
  • Shakir, M.; Abbasi, A.; Faraz, M.; Sherwani, A. J. Mol. Struct. 2015, 1102, 108–116. DOI:10.1016/j.molstruc.2015.08.061.
  • Burgess, K.; Lim, D.; Ho, K.-K.; Ke, C.-Y. J. Org. Chem. 1994, 59, 2179–2185. DOI:10.1021/jo00087a039.
  • Priya, N. P.; Arunachalam, S.; Manimaran, A.; Muthupriya, D.; Jayabalakrishnan, C. 2009, 72, 670–676. DOI:10.1016/j.saa.2008.10.028.
  • Lampman, G. M.; Pavia, D. L.; Kriz, G. S.; Vyvyan, J. R. Spectroscopy, 4th ed. Nelson Edu. Ltd.: USA, 2010.
  • (a) Kivelson, D.; Neiman, R. J. Chem. Phys. 1961, 35, 149–155; (b) Thirumavalavan, M.; Akilan, P.; Kandaswamy, M. Supramol. Chem. 2004, 16(7), 495–504. DOI:10.1080/10610270410001722349.
  • (a) Arun, T.; Packianathan, S.; Malarvizhi, M.; Antony, R.; Raman, N. J. Photochem. Photobiol. B 2015, 149, 93–102; (b) Balhahausen, J. Introduction to Ligand Field Theory, Mcgraw Hill: New York, 1984; (c) Ottaviani, M. F.; Bossmann, S. N.; Turro, J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116 (2), 661–671; (d) Philip, V.; Suni, V.; Kurup, M. R. P.; Nethaji, M. Polyhedron 2004, 23(7), 1225–1233.
  • Hathaway, B. J. Complex Chem. 1962, 57, 55–118.
  • (a) Hathaway, B. J.; Billing, D. E. Coord. Chem. Rev. 1970, 5(2), 143–207; (b) Kneubuhl, F. K. J. Chem. Phys. 1960, 33(4), 1074–1078.
  • Emara, A. A. A. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2010, 77, 117–125.
  • Bew, M. J.; Hathaway, B. J.; Fereday, R. J. J. Chem. Soc. Dalton Trans. 1972, 12, 1229–1237. DOI:10.1039/dt9720001229.
  • Matsumoto, J.; Suzuki, T.; Kajita, Y.; Masuda, H. Dalton Trans. 2012, 41, 4107–4117. DOI:10.1039/c2dt12056a.
  • Emara, A. A. A.; El-Sayed, B. A.; El-Sayed.; Ahmed, A. E. 2008, 69, 757–769. DOI:10.1016/j.saa.2007.05.028.
  • (a) Mabbs, F. E.; Machin, D. I. Magnetism and Transition Metal Complexes, Chapman and Hall: London, 1973; (b) Sreedaran, S.; Bharathi, K. S.; Rahiman, A. K.; Jagadish, L.; Kaviyarasan, V.; Narayanan, V. Polyhedron 2008, 27(13), 2931–2938. DOI:10.1016/j.poly.2008.06.025.
  • Rahman, K. N. A.; Haribabu, J.; Balachandran, C.; Bhuvanesh, N. S. P.; Karvembu, R.; Sreekanth, A.Polyhedron 2017, 135, 26. DOI:10.1016/j.poly.2017.06.044.
  • Sathyanarayana, D. N. Electronic Absorption Spectroscopy and Related Techniques, Universities Press India Ltd.: Hyderabad, India, 2001.
  • Gaber, M.; Ayad, M. M.; Ayad, M. I. Thermochim. Acta 1991, 176, 21–29. DOI:10.1016/0040-6031(91)80256-I.
  • El-Ansary, A. L.; Abdel-Kader, N. S. Int. J. Inorg. Chem. 2012, 2012, 1–13. DOI:10.1155/2012/901415.
  • Bondet, V.; Williams, W. B.; Berset, C. LWT-Food Sci. Technol. 1997, 30, 609–615.
  • (a) Banerjee, S.; Chakravarty, A. R. Acc. Chem. Res. 2015, 48 (7), 2075–2083; (b) Shakir, M.; Bano, N.; Rauf, M. A.; Owais, M. J. Chem. Sci. 2017, 129(12), 1905–1920. DOI:10.1007/s12039-017-1398-8.
  • Corbin, B. D.; Seeley, E. H.; Raab, A.; Feldmann, J.; Miller, M. R.; Torres, V. J. K. L.; Anderson, B.; Dattilo, Dunman, M. P. M.; Gerads, R.; et al. Science 2008, 319, 962–965. DOI:10.1126/science.1152449.
  • Wang, X.; Yang, F.; Yang, W.; Yang, X. Chem. Commun. 2007, 42, 4419–4421. DOI:10.1039/b708662h.
  • Ahmad, R.; Mohsin, M.; Ahmad, T.; Sardar, M. J. Hazard. Mater. 2015, 283, 171–177. DOI:10.1016/j.jhazmat.2014.08.073.
  • Singh, S.; Bahadur, D. Colloids Surf. B Biointerfaces 2015, 133, 58–65. DOI:10.1016/j.colsurfb.2015.05.033.
  • Chiappori, F.; D'Ursi, P.; Merelli, I.; Milanesi, L.; Rovida, E. BMC Bioinf. 2009, 10, S3–S8. 1, DOI:10.1186/1471-2105-10-S12-S3.
  • Ganeshpandian, M.; Loganathan, R.; Suresh, E.; Riyasdeen, A.; Akbarsha, M. A.; Palaniandavar, M. Dalton Trans. 2014, 43, 1203–1219. DOI:10.1039/c3dt51641e.
  • Moriyama, Y.; Ohta, D.; Hachiya, K.; Mitsui, Y.; Takeda, K. J. Protein Chem. 1996, 15, 265–272.
  • Tabassum, S.; Al-Asbahy, W. M.; Afzal, M.; Arjmand, F. J. Photochem. Photobiol. B 2012, 114, 132–139. DOI:10.1016/j.jphotobiol.2012.05.021.
  • Yamasaki, K.; Maruyama, T.; Hansen, U. K.; Otagiri, M. Biochim. Biophys. Acta 1996, 1295, 147–157. DOI:10.1016/0167-4838(96)00013-1.
  • Hall, M. L.; Jorgensen, W. L.; Whitehead, L. J. Chem. Inf. Model. 2013, 53, 907–922. DOI:10.1021/ci3006098.
  • Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed., Plenum Press: New York. 1999.
  • Kazemi, Z.; Rudbari, H. A.; Mirkhani, V.; Sahihi, M.; Moghadam, M.; Tangestaninejad, S.; Baltork, I. M. J. Mol. Struct. 2015, 1096, 110–120. DOI:10.1016/j.molstruc.2015.04.033.
  • Qais, F. A.; Abdullah, K. M.; Alam, M. M.; Naseem, I.; Ahmad, I. Int. J. Biol. Macromol. 2017, 97, 392–402. DOI:10.1016/j.ijbiomac.2017.01.022.
  • Li, M.; Huang, S.; Ye, C.; Xie, Y. Spectrochim. Acta A 2015, 150, 290–300. DOI:10.1016/j.saa.2015.05.064.
  • Li, H.; Wu, F.; Tan, J.; Wang, K.; Zhang, C.; Zheng, H.; Hu, F. J. Pharm. Biomed. Anal. 2016, 122, 21–28. DOI:10.1016/j.jpba.2016.01.040.
  • Laitinen, H.; Hytonen, V. P.; Nordlund, H. R.; Kuloma, M. S. Cell. Mol. Life Sci. 2006, 63, 2992–3017. DOI:10.1007/s00018-006-6288-z.
  • Kyropoulou, M.; Raptopoulou, C. P.; Psycharis, V.; Psomas, G. Polyhedron 2013, 61, 126–136. DOI:10.1016/j.poly.2013.05.043.
  • Matei, I.; Ionescu, S.; Hillebrand, M. J. Lumin .2011, 131, 1629–1635. DOI:10.1016/j.jlumin.2011.03.073.
  • Dhar, S.; Rana, D. K.; Pal, A.; Bhattacharya, S. C. J. Photochem. Photobiol. B, Biol. 2013, 129, 69–77. DOI:10.1016/j.jphotobiol.2013.09.007.
  • (a) Rehman, M. T.; Ahmed, S.; Khan, A.U. J. Biomol. Struct. Dyn. 2016, 34 (9), 1849–1864; (b) Wu, F. Y.; Xie, F. Y.; Wu, Y. M.; Hong, J. I. Spectrochim. Acta A 2008, 70(5), 1127–1133. DOI:10.1016/j.saa.2007.10.028.
  • (a) Ahmad, B.; Muteeb, G.; Alam, P.; Varshney, A.; Zaidi, N.; Ishtikhar, M.; Badr, G.; Mahmoud, M. H.; Khan, R. H. Int. J. Biol. Macromol. 2015, 75, 447–452; (b) Wang, Y. Q.; Wang, X. Y.; Wang, J.; Zhao, Y. M.; He, W. J.; Guo. Z. J. Inorg. Chem. 2011, 50(24), 12661–12668.
  • Varshney, A.; Ansari, Y.; Zaidi, N.; Ahmad, E.; Badr, G.; Alam, P.; Khan, R. H. Cell Biochem. Biophys. 2014, 70, 93–101. DOI:10.1007/s12013-014-9863-1.
  • Khosravi, I.; Hosseini, F.; Khorshidifard, M.; Sahihi, M.; Rudbari, H. A. J. Mol. Struct. 2016, 1119, 373–384. DOI:10.1016/j.molstruc.2016.04.094.
  • Paul, B. K.; Ghosh, N.; Mukherjee, S.  J. Phys. Chem. B 2015, 119, 13093–13102. DOI:10.1021/acs.jpcb.5b08147.
  • Sevilla, P.; Rivas, J. M.; García-Blanco, F.; García-Ramos, J. V.; Sánchez-Cortés, S. Biochim Biophys. Acta Proteins Proteomics 2007, 1774, 1359–1369. DOI:10.1016/j.bbapap.2007.07.022.
  • Gupta, R. K.; Sharma, G.; Pandey, R.; Kumar, A.; Koch, B.; Li, P. Z.; Xu, Q.; Pandey, D. S. Inorg. Chem. 2013, 52, 13984–13996. DOI:10.1021/ic401662d.
  • Rahnama, E.; Moghaddam, M. M.; Ahmadi, S. K.; Saberi, M. R.; Chamani, J. J. Biomol. Struct. Dyn. 2015, 33, 513–533. DOI:10.1080/07391102.2014.893540.

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