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Synthesis and Characterization of New Trimethoprim-Formazan Derivatives with Studying Them against Breast Cancer Cells

Hussein Mejbel Azeez, Nagham Mahmood Aljamali

Abstract


Trimethoprim is considered one of the very important pharmaceutical drugs in the field of medical drugs, so we linked the trimethoprim drug with the formazan compound to increase its importance in treating cancerous tumors and reduce the size of the tumor and thus the importance of the prepared derivative increased more than the original medicine. In this study, we started from reaction of trimethoprim with hydrazine to yield hydrazo-trimethoprim which after that reacted with some different aldehydes to form imine-trimethoprim, then the last reaction with diazonium salt to form trimethoprim drug-formazan derivatives. All drug-derivatives examined by spectroscopic techniques such as (FT. IR, H1NMR, C13 HNMR) to improve chemical structures for active groups and environments, other measurements, and some other chemical characterizations such as melting point and thin layer chromatography (TLC), in addition to the biomechanical test (MTT) against Breast Cancer Cells.


Keywords


Trimethoprim (TMP), Imine, azo, drug, MTT, formazan, Bioactive, cancer, breast cancer

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References


Abass, Amina M., Ahmed Ahmed. "Synthesis and application of trimethoprim selective electrodes." RJLBPCS 3.2 (2017): 146-156.‏

Crillin, Elizabeth. Trimethoprim use for urinary tract infection and risk of adverse outcomes in older patients: cohort study. Bmj, 2018.‏

Biagi, M. Activity of Cefiderocol alone and in combination with levofloxacin, minocycline, polymyxin B, or trimethoprim-sulfamethoxazole against multidrug-resistant Stenotrophomonas maltophilia. Antimicrobial agents and chemotherapy, 2020.

Nagham Mahmood Aljamali.,"Review on (Azo, Formazane, Sulfazane)-Compounds", International Journal of Innovations in Scientific Engineering., 2019, Vol. No. 10, Jul-Dec., 19-45.

Nagham Mahmood Aljamali., "The Various Preparation Methods in Synthetic Chemistry".,1 Edt., Evincepub Publishing house, 2019., ISBN :978-93-88277-82-2.

Nagham Mahmood Aljamali. "Reactions and Mechanisms"., 1 Edt., IJMRA Publication, 2018.,ISBN: 978- 93-87176-25-6.

Nagham Mahmood Aljamali. "Experimental Methods for Preparation of Mannich Bases, Formazan, Normal and Cyclic Sulfur Compounds", 1st edition Evince pub Publishing House;2018, ISBN: 978-93-87905-19-1.

Nagham Mahmood Aljamali., "Alternative Methods in Organic Synthesis".,1th–Edition, Eliva Press SRL, 2020., ISBN: 9798680201176.

Nagham Mahmood Aljamali, Tabark Emad Al-Faham., Synthesis, Identification, Chromatographic Studying of Formazane –Phenylenediamine Derivatives., Annals of R.S.C.B., ISSN:1583-6258, Vol. 25, Issue 4, 2021.

Nagham Mahmood Aljamali, (2015). Review in Azo Compounds and its Biological Activity. Biochem Anal Biochem, 4, 169., doi:10.4172/2161-1009.1000169.

Nagham Mahmood Aljamali. 2016. "Synthesis and Biological Study of Hetero (Atoms and Cycles) Compounds", Der Pharma Chemica, 8,6, 40-48.

Chen Y, Yang Y, Miller ML, Shen D, Shertzer HG, Stringer KF, Wang B, Schneider SN, Nebert DW, Dalton TP (May 2007). "Hepatocyte-specific Gclc deletion leads to rapid onset of steatosis with mitochondrial injury and liver failure". Hepatology. 45(5): 1118–28. doi:10.1002/hep.21635. PMID 17464988.

Sies H (1999). "Glutathione and its role in cellular functions". Free Radical Biology & Medicine. 27 (9–10): 916–21. doi:10.1016/S0891-5849(99)00177-X. PMID 10569624.

Mestaf M, Nawfel Muhammed Baqer Muhsin., NeuroQuantology, 2019.,17,11, 11-16.,10.14704/nq.2019. 17.11.NQ19108.

Nagham Mahmood Aljamali.,Synthesis of Antifungal Chemical Compounds from Fluconazole with (Pharma-Chemical) Studying, Research journal of Pharmaceutical, biological and chemical sciences, 2017, 8 (3), 564 -573.

Mehta SL, Manhas N, Raghubiz R. Molecular targets in cerebral ischemia for developing novel therapeutics. Brain Res Rev. 2007;54:34–66.

Mieaad M, Nagham Mahmood Aljamali, Wassan Ala Shubber., Sabreen Ali Abdalrahman."New Azomethine- Azo Heterocyclic Ligands Via Cyclization of Ester"., Research Journal of Pharmacy and Technology, 2018, 11,6, 2555-2560., DOI : 10.5958/0974-360X. 2018. 00472.9.

Hasaneen Kudhair Abdullabass, Aseel Mahmood Jawad, Nagham Mahmood Aljamali. Synthesis of drugs derivatives as inhibitors of cancerous cells., Biochem. Cell. Arch, Vol. 20 (2) – October 2020., DocID: https://connectjournals.com/03896.2020.20.5315.

Nagham Mahmood Aljamali, Imad Kareem Alwan Alsabri., Development of Trimethoprim Drug and Innovation of Sulfazane-Trimethoprim Derivatives as Anticancer Agents., Biomedical & Pharmacology Journal, March 2020.,Vol. 13,(2), p. 613-625., http://dx.doi.org/10.13005/bpj/1925

Nagham Mahmood Aljamali, Hussein Mejbel Azeez., Synthesis and Characterization of Some New Formazan - Cefixime and Study of Against Breast Cancer Cells., Annals of R.S.C.B., ISSN:1583-6258, Vol. 25, Issue 4, 2021.

Nagham Mahmood Aljamali, Asmaa Kefah Mahdi., Synthesis, Identification and Anticancer Studying of Heterocyclic- Mefenamic Drug via Thiosemicarbazide., Annals of R.S.C.B., ISSN:1583-6258, Vol. 25, Issue 4, 2021.

Hussein Ali Ahmed, Nagham Mahmood Aljamali., Preparation, Characterization, Antibacterial Study, Toxicity Study of New Phenylene diamine- Formazan Derivatives., Indian Journal of Forensic Medicine & Toxicology, April-June 2021, Vol. 15, No. 2.

Aseel Mahmood Jawad, Nagham Mahmood Aljamali.,"Innovation, Preparation of Cephalexin Drug Derivatives and Studying of (Toxicity & Resistance of Infection)"., International Journal of Psychosocial Rehabilitation, Vol. 24, Issue 04, 2020, 3754-3767.

Imad Kareem Alwan Alsabri, Hasaneen Kudhair Abdullabass, Nagham Mahmood Aljamali.,Invention of (Gluta.Sulfazane-Cefixime) Compounds as Inhibitors of Cancerous Tumors., Journal of Cardiovascular Disease Research, 2020,11, 2., 44-55., DOI: 10.31838/jcdr.2020.11.02.09.

Aseel Mahmood Jawad, Nagham Mahmood Aljamali, Saher Mahmood Jwad, Aseel M J, Saher M J., Development and Preparation of ciprofloxacin Drug Derivatives for Treatment of Microbial Contamination in Hospitals and Environment, Indian Journal of Forensic Medicine & Toxicology, 2020,14, 2, p:1115-1122.

Hussniya A. Aldifar, Mohammad F. Ali, Abdulrahim M. Khlafulla. Preparation and Characterization of Some of Formazan Derivatives. Research & Reviews: A Journal of Pharmacology. 2017.

Moussa, Shaaban H. "Tetrazolium/formazan test as an efficient method to determine fungal chitosan antimicrobial activity." Journal of Mycology 2013 (2013).‏

Tezcan, Habibe, Elif uzluk, and Mehmet Levent Aksu. "Electrochemical and spectroscopic properties of 1: 2 Ni complexes of 1, 3-substitued (CH3, OCH3) phenyl-5-phenylformazans. " Electrochimica acta 53.18 (2008): 5597-5607.‏

Nagham Mahmood Aljamali, Intisar Obaid Alfatlawi. "Synthesis of Sulfur Heterocyclic Compounds and Study of Expected Biological Activity", Research J. Pharm. and Tech., 2015, 8,9,1225-1242, DOI: 10.5958/0974-360X.2015.00224.3.

Nagham Mahmood Aljamali.; Saher Mahmood Jawd.; Zainab M J.; Intisar, Obaid. Alfatlawi.; 2017, "Inhibition activity of (Azo–acetyl acetone) on bacteria of mouth"., Research Journal of Pharmacy and Technology 10(6):1683-1686, DOI: 10.5958/0974-360X.2017.00297.9

Nagham Mahmood Aljamali., “(Synthesis, Investigation, Chromatography, Thermal)- Behavior of (Five, Seven)- Membered Ring with Azo and Anil Compounds”, Pak. J. Biotechnol.; 15(1): 219-239 (2018).

Shireen R. Rasool, Nagham Mahmood Aljamali, Ali Jassim Al-Zuhairi., Guanine substituted heterocyclic derivatives as bioactive compounds., Biochem. Cell. Arch. Vol. 20, Supplement 2, pp. 3651-3655, 2020., DocID: https://connectjournals.com/03896.2020.20.3651.

Nagham Mahmood Aljamali.,"Synthesis and Chemical Identification of Macro Compounds of (Thiazol and Imidazol)".,Research J. Pharm. and Tech,2015, 8,1,78-84., DOI: 10.5958/0974-360X.2015.00016.5.

Maulucci G, Labate V, Mele M, Panieri E, Arcovito G, Galeotti T, Østergaard H, Winther JR, De Spirito M, Pani G (October 2008). "High-resolution imaging of redox signaling in live cells through an oxidation-sensitive yellow fluorescent protein". ScienceSignaling. 1 (43):pl3. doi:10.1126 /scisignal.143pl3.

M. N Abdmajed, Nagham Mahmood Aljamali., Preparation of Benzothiazole-Formazane Reagents and Studying of (Spectral, Thermal, Scanning Microscopy, Biological Evaluation)., International Journal of Pharmaceutical Research, 2021, Volume 13, Issue 1, Pages 4290-4300., DOI:https://doi.org/10.31838/ijpr/2021.13.01.641.

Rabab Mahdi Ubaid Mahmood, Nagham Mahmood Aljamali., Synthesis, Spectral Investigation and Microbial Studying of Pyridine-Heterocyclic Compounds., European Journal of Molecular & Clinical Medicine, 2020, Volume 7, Issue 11, Pages 4444-4453.

Miad Mohmed, Nagham Mahmood Aljamali, Sabreen Ali Abdalrahman., Wassan Ala Shubber., "Formation of Oxadiazole Derivatives Ligands from Condensation and Imination Reaction with References To Spectral Investigation, Thermal and Microbial Assay"., Biochem. Cell. Arch., 2018, 18, 1, pp. 847-853.

Nagham Mahmood Aljamali, Rabab Mahdi Ubaid Mahmood., Synthesis, Characterization of Diazepine-Bicycles System and Study of their Bio-Behavior., International Journal of Pharmaceutical Research, 2021, Volume 13, Issue 1, Pages 4225-4233.

Vanita S.; Supriya, M. "Development of furfuraldehyde formazans as potential antitubercular agents"., Der Pharma Chemica, 2016,8,18, 144-148.

Nour A., Suad S., Nagham Mahmood Aljamali., Synthesis, Characterization and Thermal Analysis for New Amoxil Ligands, Asian Journal of Chemistry; 31, 5, 1022-1026, (2019).

Rajaa Abdul Ameer Ghafil, Nour A Alrazzakb, Nagham Mahmood Aljamali., Synthesis of Triazole Derivatives via Multi Components Reaction and Studying of (Organic Characterization, Chromatographic Behavior, Chem-Physical Properties)., Egypt. J. Chem. Vol. 63, No. 11, pp. 4163 - 4174 (2020). DOI: 10.21608/EJCHEM.2020.23541.2399.

Ahmad, T; Kandil, F and Moustapha, M. Preparation and Characterization of Some New Azo Dyes, Azomethine Dyes and Heterocyclic-Schiff Bases Derivatives, AASCIT Journal of Chemistry, 2015, 2(2): 24-31.

Shinde, A. T; Deshmukh, N. J; Kottapalle G. D and Zangade.S.B.. Synthesis Antimicrobial Evaluation of Some New FluoroFormazans, Journal of Pure and Applied Chemistry Research, 2016,5 (2) 61-66.

Gurusamy M, Rejaul K, Nand M. J, Faruk A, Rajib H, Deepak K, and Tiewlasubon U. Synthesis and biological evaluation of formazan Derivatives, Journal of Advanced Pharmaceutical Technology & Research, 2016,1(4):396-400

Venkatesan, P., B. Anand, and P. Matheswaran. "Influence of formazan derivatives on corrosion inhibition of mild steel in hydrochloric acid medium." E-Journal of Chemistry 6.S1 (2009): S438-S444.‏

Nagham Mahmood Aljamali. 2014. Synthesis and Investigation of Formazane compounds (Azo– Imine) and their complexes, Asian J. Research Chem, 7 (2), 225-231.

Fei, Na; Sauter, Basilius; Gillingham, Dennis (2016). "The pK a of Brønsted acids controls their reactivity with diazo compounds". Chemical Communications. 52(47): 7501–7504.

Turkoglu, Gulsen, Halil Berber. "Novel formazan derivatives containing phenylsulfanyl and carbonyl units: synthesis, optical and electrochemical properties." RSC advances 6.98 (2016): 96065-96078.‏

Al-Atbi, Hala S., Bushra K. Al-Salami, and Iqbal J. Al-Assadi. "New azo-azomethine derivative of sulfanilamide: Synthesis, Characterization, Spectroscopic, Antimicrobial and Antioxidant activity study." Journal of Physics: Conference Series. Vol. 1294. No. 5. IOP Publishing, 2019.‏

Mohammed, Omar A., and Omar S. Dahham. "Synthesis, Characterization, and Study of Antibacterial Activity of Some New Formazan Dyes Derivatives, Derived from 2-Mercapto Benzoxazole." IOP Conference Series: Materials Science and Engineering. Vol. 454. No. 1. IOP Publishing, 2018.‏


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