Please use this identifier to cite or link to this item:
https://ptsldigital.ukm.my/jspui/handle/123456789/499650Full metadata record
| DC Field | Value | Language |
|---|---|---|
| dc.contributor.advisor | Yang Farina Abdul Aziz, Prof. Dr. | - |
| dc.contributor.author | Naqeebullah (P52750) | - |
| dc.date.accessioned | 2023-10-13T09:33:28Z | - |
| dc.date.available | 2023-10-13T09:33:28Z | - |
| dc.date.issued | 2014-10-16 | - |
| dc.identifier.other | ukmvital:80654 | - |
| dc.identifier.uri | https://ptsldigital.ukm.my/jspui/handle/123456789/499650 | - |
| dc.description | Hydroxamic acids and dithiocarbamates are highly versatile chelating agents to main group metals and play an active role in living systems. These ligands can stabilize a variety of oxidation states and coordination geometries. The hydroxamic acids have been synthesized by the reaction of o- and p-substituted chloride with N-methyl-,phenyl- and tolylhydroxylamine in the presence of sodium hydrogen carbonate. The dithiocarbamate ligands were prepared by the reaction of p-substituted Nmethylbenzylamine with carbon disulfide and sodium hydroxide. A series of di- and triorganotin(IV) hydroxamate and dithiocarbamate complexes of the general formula RnSn [o- and p-XC6H4CONR'O] and RnSn [p-XC6H4CH2NR'CS2] (where n = 2, 3;R= CH3, C4H9 and C6H5; X= OCH3, NO2, Br, I and F; R'= CH3, C6H5 and p-CH3C6H4) were obtained. The derivatives were characterized by elemental analysis (C, H, N, S and Sn), spectroscopic methods (IR, 1H, 13C and 119Sn NMR) and single crystal X-ray diffraction studies. In the di- and triorganotin (IV) hydroxamate complexes, the hydroxamate moiety is coordinated to the tin centre as a bidentate ligand. The absence of the broad peak due to (OH) in the IR and NMR spectra of the complexes, which initially appeared at 3239-3084 cm-1 and 8.5-10.5 ppm, respectively suggested deprotonation of the hydroxyl proton. The X-ray studies were in full concurrence with the IR and NMR spectral evidences. The di- and triorganotin(IV) hydroxamate complexes are hexa- and penta-coordinated with a distorted octahedral geometry and distorted trigonal bipyramidal geometry. The thioureide band was found in all the chelated dithiocarbamates and the tin sulfur coordination is further supported by the presence of new medium to weak absorptions in the infrared spectra. The X-ray diffraction data illustrated that the dithiocarbamate anion acts as monodentate and anisobidentate ligands, and the geometry at tin is best described as a distorted tetrahedron as well as distorted trigonal bipyramidal. The cytotoxic activity against various cell lines was assayed by the MTT method, where all the tested organotins induced a dose dependent anti-proliferative effect toward the K562, Jurkat, HepG2, HCT116 and L929 upon treatment for 24 h. The triphenyltin(IV) complexes showed the highest cytotoxic effect whereas the dimethyltin(IV) complexes have little or no cytotoxic effect. The dibutyl- and diphenyltin(IV) complexes showed moderate cytotoxic activities. Moreover, the four dibutyltin(IV) hydroxamate complexes were also evaluated by comet assay to illustrate the DNA damage.,Asid hidroksamik dan ditiokarbamat merupakan ligan yang serba boleh bertindak terhadap logam kumpulan utama dan memainkan peranan yang penting dalam sistem kehidupan. Ligan ini dapat menstabilkan pelbagai keadaan pengoksidaan dan geometri koordinatan. Asid hidroksamik telah disintesis melalui tindak balas di antara kumpulan penukar ganti o- dan p-klorida dengan N-metil-, fenil- dan tolilhidroksilamina dengan kehadiran natrium hidrogen karbonat. Ligan ditiokarbamat pula dihasilkan melaui tindak balas di antara kumpulan penukarganti N-metilbenzilamina dengan karbon disulfida dan natrium hidroksida. Satu siri kompleks di- dan triorganotimah(IV) hidroksimat serta ditiokarbamat dengan formula umum RnSn [odan p-XC6H4CONR'O] dan RnSn [p-XC6H4CH2NR'CS2] (dimana n= 2, 3; R= CH3,C4H9 dan C6H5; X= OCH3, NO2, Br, I dan F; R'= CH3, C6H5 dan p-CH3C6H4) berjaya disintesis. Pencirian dilakukan menggunakan analisis unsur (C, H, N S dan Sn), kaedah spektroskopi (IR, 1H, 13C dan 119Sn RMN) dan pembelauan sinar-X hablur tunggal. Bagi kompleks hidroksimat di- dan triorganotimah(IV), moeiti hidroximat telah terkoodinat kepada logam tengah secara bidentat. Penyahproton (OH) berlaku dalam pembentukan kompleks apabila terdapat kehilangan puncak resonans OH pada spektrum IR dan RMN ligan bebas masing-masing pada julat sekitar 3239-3084 cm-1 dan 8.5-10.5 ppm. Kajian sinar-X adalah sangat menyokong hasil spectrum daripada IR dan NMR. Kompleks hidroksimat di- dan triorgano-timah(IV) terkoordinat secara heksa- dan penta- dalam geometri oktahedral terherot dan trigonal bipiramidal terherot. Moeiti thiouride dalam kesemua ditiokarbamat terkelat dan koordinat timah sulfur telah disokong oleh kemunculan jalur serapan lemah dalam spectrum IR. Data pembelauan sinar-X menggambarkan bahawa anion ditiokarbamat bertindak sebagai monodentate dan anisobidentate ligan dan mempunyai geometri tetrahedron terherot dan juga trigonal bipiramidal terherot. Aktiviti sitotoksik terhadap pelbagai jenis sel telah dinilai menggunakan kaedah MTT iaitu ujian dilakukan tehadap dos yang menyebabkan kesan anti-proliferik ke atas Jurkat, K562, HepG2, HCT116 and L929 dalam tempoh rawatan 24 jam. Ujian mendapati kompleks trifeniltimah(IV)mempunyai kesan sitotoksik tinggi manakala kesan sitotoksik bagi kompleks dimetiltimah(IV) adalah rendah dan tiada kesan toksik. Kompleks dibutil- dan difeniltimah(IV) menunjukkan kesan sitotoksik sederhana. Oleh itu empat kompleks hidroksamat dibutiltimah(IV) dinilai terhadap ujian komet untuk mengambarkan kesan kerosakan DNA.,Ph.D.,Hydroxamic acids and dithiocarbamates are highly versatile chelating agents to main group metals and play an active role in living systems. These ligands can stabilize a variety of oxidation states and coordination geometries. The hydroxamic acids have been synthesized by the reaction of o- and p-substituted chloride with N-methyl-,phenyl- and tolylhydroxylamine in the presence of sodium hydrogen carbonate. The dithiocarbamate ligands were prepared by the reaction of p-substituted Nmethylbenzylamine with carbon disulfide and sodium hydroxide. A series of di- and triorganotin(IV) hydroxamate and dithiocarbamate complexes of the general formula RnSn [o- and p-XC6H4CONR'O] and RnSn [p-XC6H4CH2NR'CS2] (where n = 2, 3;R= CH3, C4H9 and C6H5; X= OCH3, NO2, Br, I and F; R'= CH3, C6H5 and p-CH3C6H4) were obtained. The derivatives were characterized by elemental analysis (C, H, N, S and Sn), spectroscopic methods (IR, 1H, 13C and 119Sn NMR) and single crystal X-ray diffraction studies. In the di- and triorganotin (IV) hydroxamate complexes, the hydroxamate moiety is coordinated to the tin centre as a bidentate ligand. The absence of the broad peak due to (OH) in the IR and NMR spectra of the complexes, which initially appeared at 3239-3084 cm-1 and 8.5-10.5 ppm, respectively suggested deprotonation of the hydroxyl proton. The X-ray studies were in full concurrence with the IR and NMR spectral evidences. The di- and triorganotin(IV) hydroxamate complexes are hexa- and penta-coordinated with a distorted octahedral geometry and distorted trigonal bipyramidal geometry. The thioureide band was found in all the chelated dithiocarbamates and the tin sulfur coordination is further supported by the presence of new medium to weak absorptions in the infrared spectra. The X-ray diffraction data illustrated that the dithiocarbamate anion acts as monodentate and anisobidentate ligands, and the geometry at tin is best described as a distorted tetrahedron as well as distorted trigonal bipyramidal. The cytotoxic activity against various cell lines was assayed by the MTT method, where all the tested organotins induced a dose dependent anti-proliferative effect toward the K562, Jurkat, HepG2, HCT116 and L929 upon treatment for 24 h. The triphenyltin(IV) complexes showed the highest cytotoxic effect whereas the dimethyltin(IV) complexes have little or no cytotoxic effect. The dibutyl- and diphenyltin(IV) complexes showed moderate cytotoxic activities. Moreover, the four dibutyltin(IV) hydroxamate complexes were also evaluated by comet assay to illustrate the DNA damage | - |
| dc.language.iso | eng | - |
| dc.publisher | UKM, Bangi | - |
| dc.relation | Faculty of Science and Technology / Fakulti Sains dan Teknologi | - |
| dc.rights | UKM | - |
| dc.subject | Dithiocarbamates | - |
| dc.subject | Biological studies | - |
| dc.subject | Hydroxamic acids | - |
| dc.subject | Dissertations, Academic -- Malaysia | - |
| dc.subject | Universiti Kebangsaan Malaysia -- Dissertations | - |
| dc.title | Synthesis, characterization and biological studies of organotin(iv) complexes of hydroxamic acids and dithiocarbamates | - |
| dc.type | Theses | - |
| dc.format.pages | 283 | - |
| dc.identifier.callno | QD305.A7N346 2014 tesis | - |
| dc.identifier.barcode | 001335 | - |
| Appears in Collections: | Faculty of Science and Technology / Fakulti Sains dan Teknologi | |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| ukmvital_80654+SOURCE1+SOURCE1.0.PDF Restricted Access | 9.84 MB | Adobe PDF |  View/Open |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.