New Boric Acid Derivative with Some of Its Complexes and Study the Biological and Anticancer Activity

Authors

DOI:

https://doi.org/10.30526/38.1.3418

Keywords:

Trimethoprim, boric acid, cobalt complex, nickel complex, platinum complex

Abstract

A new ligand (5-(2-benzamido-N-methylacetamido)-4-((3,4,5-trimethoxycyclohexa-1,3-dien-1-yl) methyl) pyrimidine-2-yl) amino)boric acid was synthesized by the reaction of trimethoprim amide derivative with boric acid, as well as its metal complexes with Co (II), Ni (II), and Pt (IV). Spectral methods such as Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, and proton nuclear magnetic resonance (1H-NMR) spectra, along with thermal analysis (TG/DTA), elemental analysis (CHN), and melting point, were used to characterize the synthesized compounds. This study conducted additional examinations for metal complexes, including molar conductivity, magnetic susceptibility, chloride, and metal content. All synthesized complexes have octahedral geometry; cobalt and nickel complexes are nonelectrolytes, while platinum complexes are electrolytic. This study tested all the synthesized compounds as antibacterial and antifungal agents against Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albican. Additionally, this study tested the new ligand and its platinum complexes as anticancer agents against adenocarcinoma human cells (A549). Thus study have achieved positive outcomes for every complex's antibacterial, antifungal, and anticancer properties.

Author Biographies

  • Alaa Abdullah Majeed, Department of Chemistry, College of Sciences, University of Baghdad, Baghdad, Iraq

    .

  • Asmaa Mohammed Noori, Department of Chemistry, College of Sciences, University of Baghdad

    .

References

1. Falagas ME, Vardakas KZ, Roussos NS. Trimethoprim/sulfamethoxazole for Acinetobacter spp.: A review of current microbiological and clinical evidence. Int J Antimicrob Agents. 2015; 46(3):231–241. https://doi.org/10.1016/j.ijantimicag.2015.04.002.

2. Maddileti D, Swapna B, Nangia A. Tetramorphs of the antibiotic drug trimethoprim: Characterization and stability. Crystal Growth & Design. 2015; 15(4):1745–1756. https://doi.org/10.1021/cg501772t.

3. Singh AK, Kumar S, Vinayak M. Recent development in antihyperalgesic effect of phytochemicals: anti-inflammatory and neuro-modulatory actions. IR. 2018; 67(8):633–654. https://doi.org/10.1007/s00011-018-1156-5.

4. Singh, S, Kumar, M, Potential therapeutic applications of trimethoprim-boric acid: A review. IJPS. 2019; 81(2):197–202. https://doi.org/10.1002/j.1875-9114.1981.tb03548.x.

5. Api AM, Belsito D, Biserta S, Botelho D, Bruze M, Burton GA, Buschmann J, Cancellieri MA, Dagli ML, Date M, Dekant W, Deodhar C, Fryer AD, Gadhia S, Jones L, Joshi K, Kumar M, Lapczynski A, Lavelle M, Lee I, Liebler DC, Moustakas H, Na M, Penning TM, Ritacco G, Romine J, Sadekar N, Schultz TW, Selechnik D, Siddiqi F, Sipes IG, Sullivan G, Thakkar Y, Tokura Y. RIFM fragrance ingredient safety assessment, ethyl lactate, CAS registry number 97-64-3. FCT. 2020; 146(1):111741. https://doi.org/10.1016/j.fct.2020.111741.

6. Ding R, Chen Y, Wang Q, Wu Z, Zhang X, Li B, Lin L. Recent advances in quantum dots-based biosensors for antibiotics detection. J Pharm Anal. 2022; 12(3):355-364. https://doi.org/10.1016/j.jpha.2021.08.002.

7. Frei A, Zuegg J, Elliott AG, Baker M, Braese S, Brown C, Chen F, Dowson CG, Dujardin G, Jung N, King AP, Mansour AM, Massi JM, Moat KJ, Mohamed HA, Renfrew AK, Rutledge PJ, Sadler PJ, Todd MH, Willans CE, Wilson JJ, Cooper MA, and Mark Blaskovich AT. Metal complexes as a promising source for new antibiotics. Chem Sci. 2020; 11(10):2627–2639. https://doi.org/10.1039/c9sc06460e.

8. Al-Adilee KJ, Abedalrazaq KA, Al-Hamdiny ZM. Synthesis and spectroscopic properties of some transition metal complexes with new azo-dyes derived from thiazole and imidazole. Asian J Chem. 2013; 25(18):10475–10481. https://doi.org/10.14233/ajchem.2013.15735.

9. Farrell N. Metal complexes as drugs and chemotherapeutic agents. In: Elsevier eBooks. 2003. p. 809–840. https://doi.org/10.1016/b0-08-043748-6/09021-6.

10. Desiatkina O, Johns SK, Anghel N, Boubaker G, Hemphill A, Furrer J, Paunescu, E. Synthesis and antiparasitic activity of new conjugates—organic drugs tethered to trithiolato-bridged dinuclear ruthenium (II)–arene complexes. Inorganics. 2021; 9(8):59. https://doi.org/10.3390/inorganics9080059.

11. Majeed AA, Khaleel AMN. Evaluation the anticancer and biological activity by new amide compound of trimethoprim with some of its complexes. CJES. 2024; 22(1):9-22. https://doi.org/10.22124/cjes.2023.7323.

12. Altahan MA, Beckett MA, Coles SJ, Horton PN, Jones CL. Synthesis and characterization of a tertiary amine: boric acid (1:1) co-crystal and a neutral zwitterionic diamine pentaboron adduct. Inorganica Chimica Acta. 2022; 539:120998. https://doi.org/10.1016/j.ica.2022.120998.

13. Arkhipenko S, Sabatini MT, Batsanov AS, Karaluka V, Sheppard TD, Rzepa HS, Whiting A. Mechanistic insights into boron-catalysed direct amidation reactions. Chem Sci. 2018; 9(4):1058–1072. https://doi.org/10.1039/c7sc03595k.

14. Chiu CH, Chen CT, Cheng MH, Pao LH, Wang C, Wan GH. Use of urinary hippuric acid and o-/p-/ m-methyl hippuric acid to evaluate surgical smoke exposure in operating room healthcare personnel. Ecotoxicol Environ Saf. 2021; 217:112231. https://doi.org/10.1016/j.ecoenv.2021.112231.

15. Shihab HM, Khaleel AMN. Synthesis of new homogeneous amino acids compound with boron and some of its metal complexes.‏ Chem Methodol. 2023;7(2):137-155. https://doi:10.22034/chemm.2023.363773.1613.

16. Abdul-Ghani AJ, Khaleel AM. Synthesis and characterizations of amide and Schiff base derived from n-substituted isatins and their complexes with some metal ions. JCP. 2009: 1458-1471. https://doi.org/10.1155/2009/413175.

17. Abdul-Ghani AJ, Khaleel AMN. Synthesis and characterization of new Schiff bases derived from n (1)-substituted isatin with dithiooxamide and their Co(II), Ni(II), Cu(II), Pd(II), and Pt(IV) complexes. Bioinorganic Chemistry and Applications. 2009; 413175:1-12. https://doi.org/10.1155/2009/413175.

18. Khaleel AMN, Jaafar MI. Synthesis and characterization of boron and 2-aminophenol schiff base ligands with their Cu(II) and Pt(IV) complexes and evaluation as antimicrobial agents. Orient J Chem. 2017; 33(5):2394–2404. https://doi.org/10.13005/ojc/330532.

19. Drevenšek P, Košmrlj J, Giester G, Skauge T, Sletten E, Sepčić K, Turel I. X-Ray crystallographic, NMR and antimicrobial activity studies of magnesium complexes of fluoroquinolones– racemic ofloxacin and its S-form, levofloxacin. Journal of Inorganic Biochemistry. 2006; 100(11):1755–1763. https://doi.org/10.1016/j.jinorgbio.2006.06.011.

20. Siskos M, Choudhary M, Gerothanassis I. Hydrogen atomic positions of O–H•••O hydrogen bonds in solution and in the solid state: The synergy of quantum chemical calculations with 1H-NMR chemical shifts and x-ray diffraction methods. Molecules. 2017; 22(3):415. https://doi.org/10.3390/molecules22030415.

21. Abbas AK, Kadhim RS. Synthesis, spectroscopic, thermal and antibacterial assay for azothiobutric acidlig and Co (ΙΙ), Ni (ΙΙ) and Cu (ΙΙ) complexes. Annals of R.S.C.B. 2021; 25(6):5059-5073. http://annalsofrscb.ro/index.php/journal/article/view/6435.

22. Al-adely KJ, Dakhil HK, Karam FF. Preparation and spectral characterization of new azo imidazole ligand 2-[1-(2, 4-dichoro phenyl) azo]-α-amino-1H-imidazole-4-propionic acid and its complexes with Co (п), Ni (п), Cu (п), Pd (II) and Ag (I) ions. Al-Qadisiyah Journal of Pure Science. 2017;16(2):50-64.

23. Al-Jebouri GS, Noorikhaleel AM. Synthesis of new boron compounds with amoxicillin and some of its metal complexes with use them in antibacterial, assessment of hepatoprotictive and kidneyactivity, anticancer and antioxidant applications. AJPS. 2019; 12(3):1-9. http://dx.doi.org/10.22159/ajpcr.2019.v12i3.30912.

24. Khaleel AM. Synthesis and characterization of trihydro mono and dihydrobis (indole-3-acetic acid) borate ligands and some of their metal complexes. IJS. 2015; 56(4A):2762-2772.

25. Abdul-ghani AJ, Khaleel AM. Study of thermal stability of tetraphenanthroporphyrazine and somemetal complexes by thermogravimetric analysis. IJS. 2015; 56(1B):316-328. https://ijs.uobaghdad.edu.iq/index.php/eijs/article/view/10439.

26. Ali DN, Khaleel AM. Synthesis of new Schiff base of ciprofloxacin derivative with its Cu (ii), Pt (iv) complexes and evaluation of antibacterial activity. Biochem Cell Arch. 2020; 20(1):2441-2448. https://doi:10.35124/bca.2020.20.1.2441.

27. Gray JR. Conductivity analyzers and their application. In: Down, R.D. and Lehr, J.H., Eds., Environmental Instrumentation and Analysis Handbook, Wiley, New York, 2004: 491-510. https://doi.org/10.1002/0471473332.ch23.

28. Abbas NF, Abbas AK. Novel complexes of thiobarbituric acid–azo dye: structural, spectroscopic, biological activity and dying. Biochem Cell Arch. 2020; 20(1):2419-2433. https// doi:10.35124/bca.2020.20.1.2419

29. Jassim SA, Khaleel AM. Characterization and synthesis of new Schiff base compound from levofloxacin and L-cysteine with its Cu (II) and Pt (IV) complexes and estimation antibacterial and antifungal activities. Biochem Cell Arch. 2021; 21(1):2187-2195. https://connectjournals.com/03896.2021.21.2187.

30. Ali I, Wani WA, Saleem K. Empirical formulae to molecular structures of metal complexes by molar conductance. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry. 2013; 43(9):1162-1170. https://doi.org/10.1080/15533174.2012.756898.

Downloads

Published

20-Jan-2025

Issue

Section

Chemistry

How to Cite

[1]
Abdullah Majeed, A. and Mohammed Noori, A. 2025. New Boric Acid Derivative with Some of Its Complexes and Study the Biological and Anticancer Activity. Ibn AL-Haitham Journal For Pure and Applied Sciences. 38, 1 (Jan. 2025), 234–250. DOI:https://doi.org/10.30526/38.1.3418.