Sains Malaysiana 47(6)(2018): 1199–1208

http://dx.doi.org/10.17576/jsm-2018-4706-15

Synthesis and Binding Behaviour of New Isomers of Bis-Thiourea

(Perilaku Sintesis dan Pengikatan Isomer-Isomer Baharu Bis-Tiourea)

IMRAN FAKHAR, BOHARI MUHAMMAD YAMIN, SAHILAH ABDUL MUTALIB

& SITI AISHAH HASBULLAH*

School of Chemical Sciences and Food Technology, Faculty of Science and Technology

Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

Received: 25 September 2017/Accepted: 22 January 2018

ABSTRACT

The two new symmetrical bis-thiourea compounds, 2,2'-[{(terephthaloylbis(azanediyl)bis (carbonothioyl)bis(azanediyl)} bis(4-methylpentanoicacid)] 1A and 2,2'-[{(isophthaloylbis (azanediyl)bis(carbonothioyl)bis(azanediyl)}bis(4- methylpentanoic acid)] 1B have been synthesized by reacting terephthaloyl/isophthaloyl chloride and L-leucine in high yields. Newly synthesized bis-thiourea derivatives were characterized using FTIR, 1D NMR, 2D NMR, MS spectrometry and Elemental analysis. Their binding properties with various cations were also carried out using UV-vis titration experiments. Both isomers exhibited effective binding against Ag⁺, Cu²⁺, Ni²⁺, Hg²⁺, Pb²⁺, Fe²⁺, and Fe³⁺ in the presence of other cations, such as Na⁺, Co²⁺, Cd²⁺, Zn²⁺, Mn²⁺, Mg²⁺, Ca²⁺, Sn²⁺, and Al³⁺. Stoichiometries of the host-guest complexation for both isomers were found to be 1:4 by plotting molar-ratio curves. Pearson Product moment correlation coefficient was in the range of 0.83-0.99 and nonlinear regression equation was used to calculate dissociation constant (Kd). Both compounds displayed weak antibacterial activities against gram-positive and gram negative bacteria. Cytotoxicity testing on CCD841 Normal human colon epithelial cell line showed that both compounds are non-toxic, with an IC50 value of 1.50 mg/mL.

Keywords: Bis-thiourea; binding studies; host-guest complexation; L-leucine

ABSTRAK

Dua sebatian baru bis-tiourea bersimetri, 2,2'- [{(tereptaloilbis (azanedil) bis (karbonotiol) bis (azanedil)} bis (4-metilpentanoik asid)] 1A dan 2,2' - [{(isoptaloibis (azanedil) bis (karbonotiol) bis (azanedil)} bis (4-metilpentanoik asid)] 1B telah disintesis melalui tindak balas antara tereptaloil/isoptaloil klorida dan L-leusin dengan peratusan hasil yang tinggi. Terbitan baru bis-tiourea ini dicirikan menggunakan FTIR, 1D NMR, 2D NMR, spektrometri SJ dan analisis jisim; unsur. Kedua-dua isomer menunjukkan pengikatan yang berkesan terhadap kation Ag⁺, Cu²⁺, Ni²⁺, Hg²⁺, Pb²⁺, Fe²⁺ dan Fe³⁺ dengan kehadiran kation Na⁺, Co²⁺, Cd²⁺, Zn²⁺, Mn²⁺, Mg²⁺, Ca²⁺, Sn²⁺ dan Al³⁺. Kompleks perumah-tetamu bagi kedua-dua isomer menunjukkan stoikiometri 1:4 yang dicerap melalui lengkung nisbah molar. Nilai pekali korelasi hasil Pearson berada dalam julat 0.83-0.99 dan persamaan regresi tak linear digunakan untuk mengira pemalar pengikatan (Kd). Kedua-dua sebatian ini menunjukkan aktiviti anti-bakteria yang lemah terhadap bakteria gram positif dan gram negatif. Ujian kesitoksikan terhadap sel epitelium manusia, CCD841 menunjukkan bahawa kedua-dua sebatian tersebut tidak toksik, dengan nilai IC50, 1.50 mg/mL.

Kata kunci: Bis-tiourea; kajian pengikatan; kompleks perumah-teteamu; L-leusin

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*Corresponding author; email: aishah80@ukm.edu.my