Sains Malaysiana 49(8)(2020): 1891-1904

http://dx.doi.org/10.17576/jsm-2020-4908-11

Isatin Endowed Metal Chelates as Antibacterial and Antifungal Agents

(Isatin Pembawa Logam Pengkelat sebagai Agen Anti-Bakteria dan Anti-Kulat)

SEHER KHALID¹, SAJJAD HUSSAIN SUMRRA*² & ZAHID HUSSAIN CHOHAN³

¹Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan

²Department of Chemistry, University of Gujrat, Gujrat 50700, Pakistan

³Department of Chemistry, University College of Management & Sciences, Khanewal 58150, Pakistan

Diserahkan: 17 November 2019/Diterima: 3 April 2020

ABSTRACT

A new series of 5-chloroindoline-2,3-dione (isatin) derived ligands (L¹)-(L⁴) were prepared by reacting isatin with various diamines such as ethane-1,2-diamine, propane-1,3-diamine, butane-1,4-diamine, and benzene-1,2-diamine in an equimolar ratio to give 3-[(2-aminoethyl)imino]-5-chloro-1,3-dihydro-2H-indol-2-one (L¹), 3-[(3-aminopropyl)imino]-5-chloro-1,3-dihydro-2H-indol-2-one (L²), 3-[(4-aminobutyl)imino]-5-chloro-1,3-dihydro-2H-indol-2-one (L³) and 3-[(2-aminophenyl)imino]-5-chloro-1,3-dihydro-2H-indol-2-one (L⁴). All ligands acted as tridentate possessing three active sites, isatin-O, azomethine-N, and amino-N for binding with the metal atoms. The structures of the isatin based Schiff bases were elucidated through their spectral (infrared, ultraviolet, nuclear magnetic resonance, and mass spectra), physical (melting point and solubility) and analytical (C, N, H %) data. The prepared ligands were reacted with Co(II), Ni(II), Cu(II), and Zn(II) transition metals in 1:2 molar ratio (metal:ligand) to form their complexes. IR, UV, NMR, conductance, magnetic moment, and elemental analysis was used to characterize the metal complexes. Metals based isatins were evaluated for their in-vitro antimicrobial properties against selected fungal and bacterial species. The anti-bacterial and anti-fungal results showed the metal chelates to be more biologically active than their parent uncomplexed ligands.

Keywords: Antibacterial and antifungal activity; isatin transition metal(II) complexes
 

ABSTRAK

Siri baru 5-kloroindolin-2,3-dione (isatin) ligan terbitan (L¹)-(L⁴) dihasilkan melalui tindak balas isatin dengan pelbagai diamina seperti etana-1,2-diamin, propana-1,3-diamin, butana-1,4-diamin dan benzena-1,2-diamin dalam nisbah ekuimolar untuk membentuk 3-[(2-aminoetil) imino]-5-kloro-1,3-dihidro-2H-indol-2-one (L¹), 3-[(3-aminopropil) imino]-5-kloro-1,3-dihidro-2H-indol-2-one (L²), 3-[(4-aminobutil) imino]-5-kloro-1,3-dihydro-2H-indol-2-one (L³) dan 3-[(2-aminofenil)imino]-5-kloro-1,3-dihidro-2H-indol-2-one (L⁴). Semua ligan bertindak sebagai tridentat yang mempunyai tiga tapak aktif, isatin-O, azometine-N dan amino-N dengan mengikat atom logam. Struktur isatin berasaskan bes Schiff dijelaskan melalui spektrumnya (inframerah, ultraungu, resonansi magnetik nuklear dan spektra jisim), fizikal (takat lebur dan kelarutan) dan data analisis (C, N, H%). Ligan tersebut juga bertindak balas dengan logam peralihan Co(II), Ni(II), Cu(II) dan Zn(II) dalam nisbah molar 1: 2 (logam: ligan) untuk membentuk kompleks mereka. IR, UV, NMR, konduktans, momen magnetik dan analisis unsur digunakan untuk mencirikan kompleks logam. Isatin berasaskan logam dinilaikan untuk sifat antimikrobnya secara in vitro terhadap beberapa spesies kulat dan bakteria terpilih. Hasil kajian anti-bakteria dan anti-kulat ini menunjukkan bahawa pengkelat logam adalah lebih aktif secara biologinya berbanding ligan induk yang bukan kompleks.

Kata kunci: Aktiviti antibakteria dan antikulat; kompleks logam(II) peralihan isatin

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