Synthesis, spectral characterization and biological activities of Ag(I), Pt(IV) and Au(III) complexes with novel azo dye ligand (N, N, O) derived from 2-amino-6-methoxy benzothiazole

被引:48
作者
Kyhoiesh, Hussein Ali Kadhim [1 ]
Al-Adilee, Khalid J. [2 ]
机构
[1] Minist Educ, Directorate Educ Al Muthanna, Al Muthanna, Iraq
[2] Univ Al Qadisiyah, Coll Educ, Dept Chem, Diwaniya 1753, Iraq
关键词
Benzothiazole; MFE-296; Molecular docking; Antioxidant; Antimicrobial; XRD; TRANSITION-METAL-COMPLEXES; ANTIMICROBIAL ACTIVITY; THERMAL-STABILITY; CELL VIABILITY; DRUG DESIGN; CO(II); DERIVATIVES; ZN(II); CU(II); FE(III);
D O I
10.1007/s11696-022-02072-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The novel ligand 2-[2'-(6-methoxybenzothiazolyl)azo]-3,5-dimethyl benzoic acid (6-MBTAMB), derived from 2-amino-6-methoxy benzothiazole, has been used to synthesize a series of new metal complexes of Ag(I), Pt(IV) and Au(III). The metal complexes were characterized by elemental analyses (CHNS), molar conductivity, crystal structure (XRD), spectroscopic techniques: FT-IR, H-1 NMR, C-13 NMR, UV-Vis, mass spectra, thermal analysis (TG-DTA), FE-SEM and magnetic properties. Results confirmed that the azo dye ligand behaves a tridentate and coordinates to the metal ion via nitrogen atom of azomethine group of heterocyclic benzothiazole ring, nitrogen atom of the azo group which is the farthest of the benzothiazole molecule and carboxylic oxygen. Antimicrobial properties of all newly synthesized azo compounds are also demonstrated against bacterial pathogenic organisms and fungi. These complexes are more effective against bacteria and less effective against fungi compared to standard antibacterial drugs (novobiocin) and antifungal drugs (cycloheximide). By using the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging test, it was discovered that the complexes had good antioxidant properties. In addition, the (6-MBTAMB) and metal complexes were docked with the crystal structure of FGF Receptor 2 (FGFR2) kinase domain harboring the pathogenic gain of function K659E mutation identified in endometrial cancer using the molecular operating environment (MOE) module. In vitro studies on human endometrial cancer cell lines (MFE-296) as well as healthy human umbilical vein endothelial cells (HUVEC) show uptake of the intact compounds by the cancer cells and increased activity against the cancer cells. [GRAPHICS] .
引用
收藏
页码:2777 / 2810
页数:34
相关论文
共 103 条
  • [41] French, 1944, MAGNETOCHEMISTRY
  • [42] GAO F, 1995, J INORG BIOCHEM, V60, P61
  • [43] In vitro Cell Viability by CellProfiler® Software as Equivalent to MTT Assay
    Gasparini, Luciana S.
    Macedo, Nayana D.
    Pimentel, Elisangela F.
    Fronza, Marcio
    Junior, Valdemar L.
    Borges, Warley S.
    Cole, Eduardo R.
    Andrade, Tadeu U.
    Endringer, Denise C.
    Lenz, Dominik
    [J]. PHARMACOGNOSY MAGAZINE, 2017, 13 (50) : S365 - S369
  • [44] Synthesis of 2-(4-Propyloxyphenyl)benzothiazole
    Ha, Sie-Tiong
    Koh, Teck-Ming
    Ong, Siew-Teng
    Lee, Teck-Leong
    Sivasothy, Yasodha
    [J]. MOLBANK, 2009, (03)
  • [45] Habeeb, 2014, SYNTHESIS, V6
  • [46] Synthesis, characterization, pharmacological evaluation and molecular docking studies of benzothiazole azo derivatives
    Harisha, S.
    Keshavayya, Jathi
    Prasanna, S. M.
    Hoskeri, H. Joy
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2020, 1218
  • [47] A COMPUTATIONAL APPROACH PREDICTING CYP450 METABOLISM AND ESTROGENIC ACTIVITY OF AN ENDOCRINE DISRUPTING COMPOUND (PCB-30)
    Harris, Jason B.
    Eldridge, Melanie L.
    Sayler, Gary
    Menn, Fu-Min
    Layton, Alice C.
    Baudry, Jerome
    [J]. ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY, 2014, 33 (07) : 1615 - 1623
  • [48] DIAGNOSTIC MICROBIOLOGY OF BACTERIAL VAGINOSIS
    HILLIER, SL
    [J]. AMERICAN JOURNAL OF OBSTETRICS AND GYNECOLOGY, 1993, 169 (02) : 455 - 459
  • [49] L-Proline catalyzed one-pot synthesis of polysubstituted pyridine system incorporating benzothiazole moiety via sustainable sonochemical approach
    Ibrahim, Hamada Mohamed
    Arafa, Wael Abdelgayed Ahmed
    Behbehani, Haider
    [J]. RSC ADVANCES, 2018, 8 (66): : 37606 - 37617
  • [50] Cu(ii) complex with auxin (3-indoleacetic acid) and an aromatic planar ligand: synthesis, crystal structure, biomolecular interactions and radical scavenging activity
    Inci, Duygu
    Aydin, Rahmiye
    Zorlu, Yunus
    [J]. EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS, 2021, 50 (05): : 771 - 785