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Öğe Phosphorus-nitrogen compounds Part 32. Structural and thermal characterizations, antimicrobial and cytotoxic activities, and in vitro DNA binding of the phosphazenium salts(Springer, 2016) Akbas, Huseyin; Okumus, Aytug; Karadag, Ahmet; Kilic, Zeynel; Hokelek, Tuncer; Koc, L. Yasemin; Turk, MustafaThe salicylic acid salts of fully substituted mono(4-fluorobenzyl)spirocyclotriphosphazenes (10-15) were prepared. The structures of these phosphazenium salts (10a-15a) were determined by elemental analyses, FTIR and H-1, C-13{H-1}, P-31{H-1} NMR techniques. The crystal structure of 14a was verified by X-ray diffraction analysis. The thermal properties of the salts were investigated using TG/DTA and DSC instruments. The results obtained from DSC indicated that the melting temperatures and latent heats of the compounds were in the ranges of 107.76-143.04 A degrees C and 41.64-69.73 J g(-1), respectively. The thermal stabilities of the phosphazenium salts (10a-15a) are found to be different, but they have a similar decomposition mechanism. The compounds 14a and 15a exhibit noticeable cytotoxic activity against DLD-1 cancer cells, and they seem to be good candidates for being anticancer agents. All of the compounds have an antimicrobial effect on bacterial and yeast strains within the ranges of 312-625 A mu M (bacterial strains) and 19.5-312 A mu M (yeast strains). It is found that compounds 13a-15a were most effective against yeast strains. Moreover, interactions between the salts and pBR322 plasmid DNA show that 14a and 15a cleave the DNA and decrease the intensity of form I. BamHI and HindIII digestion results demonstrate that the compounds are not bound with G/G and A/A nucleotides, respectively.Öğe Phosphorus-nitrogen compounds part 33: in vitro cytotoxic and antimicrobial activities, DNA interactions, syntheses, and structural investigations of new mono(4-nitrobenzyl)spirocyclotriphosphazenes(Springer, 2016) Okumus, Aytug; Akbas, Huseyin; Kilic, Zeynel; Koc, L. Yasemin; Acik, Leyla; Aydin, Betul; Dal, HakanThe condensation reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with N-alkyl-N'-mono(4-nitrobenzyl)diamines (1-3), NO2PhCH2NH(CH2) (n) NHR1 (R-1 = CH3 or C2H5), led to the formation of the mono(4-nitrobenzyl)spirocyclotriphosphazenes (4-6). The tetra-pyrrolidino (4a-6a), piperidino (4b-6b), and 1,4-dioxa-8-azaspiro[4,5]decaphosphazenes (4c-6c) were prepared from(for) the reactions of partly substituted compounds (4, 5, and 6) with excess pyrrolidine, piperidine, and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), respectively. The partly substituted geminal (4d and 5d) and cis-morpholino (6d) phosphazenes were isolated from the reactions of excess morpholine in boiling THF and o-xylene, but the expected fully substituted compounds were not obtained. The structures of all the phosphazene derivatives were determined by elemental analyses, MS, FTIR, H-1, C-13{H-1}, P-31{H-1} NMR, HSQC, and HMBC techniques. The crystal structures of 4, 6, 4a, and 5a were verified by X-ray diffraction analysis. In addition, in vitro cytotoxic activities of fully substituted phosphazenes (4a-6c) against HeLa cervical cancer cell lines (ATCC CCL-2) and the compounds 4a and 4c against breast cancer cell lines (MDA-MB-231) and L929 fibroblast cells were evaluated, respectively. Apoptosis effect was determined by MDA-MB-231 cancer cell lines and fibroblast cells. The MIC values of the compounds were in the ranges of 9.8-19.5 A mu M. The compounds 6, 5a, 6a, 5b, and 6d have greater MIC activity against bacterial and yeast strain. The investigation of DNA binding with the phosphazenes was studied using plasmid DNA. The phosphazene derivatives inhibit the restriction endonuclease cleavage of plasmid DNA by BamHI and HindIII enzymes. BamHI and HindIII digestion results demonstrate that the compounds bind with G/G and A/A nucleotides.Öğe Phosphorus-nitrogen compounds. Part 35. Syntheses, spectroscopic and electrochemical properties, and antituberculosis, antimicrobial and cytotoxic activities of mono-ferrocenyl-spirocyclotetraphosphazenes(Royal Soc Chemistry, 2016) Okumus, Aytug; Elmas, Gamze; Cemaloglu, Resit; Aydin, Betul; Binici, Arzu; Simsek, Hulya; Hokelek, TuncerThe reactions of octachlorocyclotetraphosphazene, N4P4Cl8, with N-alkyl-N-mono-ferrocenyldiamines, FcCH(2)NH(CH2)(n)NHR1 [n = 2, Fc = ferrocene, R-1 = Me (1); n = 2, R-1 = Et (2) and n = 3, R-1 = Me (3)], led to the formation of monoferrocenyl-spirocyclotetraphosphazenes (4-6). When the reactions were carried out with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5] decane (DASD), the fully substituted products (4a-6c) were obtained in high yields. The structures of all the phosphazene derivatives were characterized by MS, FTIR, H-1, C-13 and P-31 NMR, HSQC and HMBC techniques. The crystal structures of 4a and 5a were determined by X-ray crystallography. The electrochemically reversible one-electron oxidation of Fc redox centers was observed for cyclotetraphosphazenes. The fully substituted phosphazenes (4a-6c) were evaluated for their antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv, and compounds 4a-6a and 5c were found to be active. The antibacterial activities of phosphazenes 4a-6c against G(+) and G(-) bacteria and their antifungal activities against yeast strains were carefully scrutinized. The results indicate that compounds 4a-6a, 6b, 4c and 5c are very effective against yeast strains. The anticandidal activities of 6a and 6b make them promising anticandidal agents. The interactions of these compounds with plasmid DNA and their cytotoxic activity against L929 fibroblast and DLD-1 colon cancer cell lines were also investigated.Öğe Phosphorus-nitrogen compounds. Part 37. Syntheses and structural characterizations, biological activities of mono and bis(4-fluorobenzyl)spirocyclotetraphosphazenes(Royal Soc Chemistry, 2017) Elmas, Gamze; Okumus, Aytug; Sevinc, Pelin; Kilic, Zeynel; Acik, Leyla; Atalan, Mustafa; Hokelek, TuncerThe Cl substitution reactions of octachlorocyclotetraphosphazene, N4P4Cl8, with one equimolar amount of (4-fluorobenzyl)diamines (1-3) affords mono(4-fluorobenzyl) spirocyclotetraphosphazenes (4-6) as minor products. However, the reactions of N4P4Cl8 with two equimolar amounts of (4-fluorobenzyl) diamines (1-3) leads to the formation of mono (4-6), 2-trans-6-bis (7-9, as major products) and 2-cis-6-bis (4-fluorobenzyl) spirocyclotetraphosphazenes (10-12). The 2-cis-6-bis compounds (10 and 12) were separated and purified using column chromatography as minor products, whereas compound 11 could not be isolated. The mono-spiro (4-6) and 2-trans-6-bis-spiro (7-9) cyclotetraphosphazenes were reacted with excess pyrrolidine in THF to afford the fully substituted hexapyrrolidino (4a-6a) and tetra-pyrrolidino (7a-9a) products in high yield. Compound 9 was also reacted with piperidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD) to obtain the tetraamino products (9b, 9c and 9d), respectively, due to its very high yield. The elemental analyses, mass spectra (ESI-MS), Fourier transform infrared (FTIR) spectra, and H-1, C-13{H-1}, and P-31{H-1} NMR data of the cyclotetraphosphazenes were in agreement with the suggested structures. The molecular structures of 7, 9 and 12 were established by X-ray crystallography. The antibacterial activities of the compounds against G(+) and G(-) bacteria and their antifungal activities against yeast strains were scrutinized. The results indicated that 4a and 5a were the most active compounds, especially to yeast strains. In addition, it was found that the most active compound toward DNA was 8. The cytotoxic activities of the cyclotetraphosphazenes against L929 fibroblast and MCF-7 breast cancer cell lines were elucidated. Compound 8a exhibited the most toxic effects against both types of cells.Öğe Phosphorus-nitrogen compounds. part 38. Syntheses, characterizations, cytotoxic, antituberculosis and antimicrobial activities and DNA interactions of spirocyclotetraphosphazenes with bis-ferrocenyl pendant arms(Elsevier Science Sa, 2017) Elmas, Gamze; Okumus, Aytug; Cemaloglu, Resit; Kilic, Zeynel; Celik, Suheyla Pinar; Acik, Leyla; Hokelek, TuncerThe reactions of N4P4Cl8 (1), with two equimolar amounts of N-(1-ferrocenylmethyl)-N-methyl-propylenediamine gave the monoferrocenyl-spiro (as a byproduct), bisferrocenyl-2-trans-6-dispiro (2) and bisferrocenyl-2-cis-6-dispiro (3) cyclotetraphosphazenes. The 2-trans-6-dispiro (2) was reacted with excess monoamines to produce the tetraamino products (2a-2d). The one equimolar amount of the diamines and dialkoxides with 2 afforded the mono-diamino (2e and 2f) and mono-dialkoxy (2g and 2h) cyclotetraphosphazenes. Whereas, excess diamines and dialkoxides with 2 produced the bis-diamino (2i and 2j) and bis-dialkoxy (2k and 2l) bisferrocenyl-2-trans-6-dispirocyclotetraphosphazenes. The structures of the compounds were verified by elemental analyses, ESI-MS, FTIR, HSQC, HMBC, H-1, C-13, and P-31 NMR techniques. The molecular structures of 2 and 2b were established by X-ray crystallography. Compounds 2e and 2f have two stereogenic P-atoms. Additionally, the structures of 2i-2l containing tetraspiro rings in the skeletons look similar a propeller. The Fc groups of the cyclotetraphosphazenes were found to be redox active with two-reversible electron oxidations. The antimicrobial activity of the compounds was examined against some bacteria and yeast strains. The interactions of the compounds with DNA revealed that the compounds caused conformational changes even strand break on super-coiled DNA helix. Furthermore, the compounds (except 2, 2a and 2d) inhibited DNA restriction indicating compounds binding to A/A and G/G nucleotides of the DNA. The evaluations of the cytotoxic activity against L929 fibroblast and DLD-1 colon cancer cell lines were carried out. Some of the compounds were evaluated for antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv, and 2i and 2l displayed antituberculosis activity against H37Rv. (C) 2017 Elsevier B.V. All rights reserved.Öğe Phosphorus-nitrogen compounds. Part 42. The comparative syntheses of 2-cis-4-ansa(N/O) and spiro(N/O) cyclotetraphosphazene derivatives: spectroscopic and crystallographic characterization, antituberculosis and cytotoxic activity studies(Royal Soc Chemistry, 2019) Binici, Arzu; Okumus, Aytug; Elmas, Gamze; Kilic, Zeynel; Ramazanoglu, Nagehan; Acik, Leyla; Hokelek, TuncerThe reaction of N4P4Cl8 (1) with one equimolar amount of the sodium salt of an N/O donor-type bidentate ligand (2) afforded two kinds of derivatives, namely, mono-ferrocenyl-2-cis-4-dichloro-ansa- (2,4-ansa; 3) and mono-ferrocenyl-spiro- (spiro; 4) hexachlorocyclotetraphosphazenes. The reaction yield (35%) of 4 was significantly larger than that of 3 (14%). The 2,4-ansa compound (3) was reacted with excess secondary amines to produce 2-cis-4-dichloro-ansa-cyclotetraphosphazenes (3a-3d). On the other hand, the spiro compound (4) gave fully substituted mono-ferrocenyl-spiro-cyclotetraphosphazenes (4a-4d) with excess monoamines as well. The tetrameric phosphazene derivatives were characterized by ESI-MS and/or HRMS, FTIR, HSQC, HMBC, H-1, C-13, and P-31 NMR spectroscopy and X-ray crystallography (for 4). It is observed that the 2,4-ansa and spiro-cyclotetraphosphazenes have different thermal stabilities. Additionally, the CVs of the new mono-ferrocenyl pendant-armed cyclotetraphosphazenes revealed electrochemically reversible one-electron oxidation of the Fe-redox centre. The 2,4-ansa phosphazenes (3 and 3a-3d) have two different stereogenic P centers indicating that they are expected to be in racemic mixtures (RR'/SS'). The chiralities of 3a and 3c were investigated by chiral HPLC. The manuscript also deals with the antimicrobial activities against G(+)/G(-) bacteria and fungi, the interactions with plasmid DNA, the in vitro cytotoxic activities against L929 fibroblast and MCF7 breast cells, and the antituberculosis activities against Mycobacterium tuberculosis H37Rv of the cyclotetraphosphazenes.Öğe Phosphorus-nitrogen compounds. Part 44. The syntheses of N,N-spiro bridged cyclotriphosphazene derivatives with (4-fluorobenzyl) pendant arms: Structural and stereogenic properties, DNA interactions, antimicrobial and cytotoxic activities(Elsevier Science Sa, 2019) Ozturk, Ezel; Okumus, Aytug; Kilic, Zeynel; Kilic, Adem; Kayalak, Hande; Acik, Leyla; Hokelek, TuncerIsopropylaminopentachlorocyclotriphosphazene, (N3P3Cl5(NHCHMe2) (1), containing a P-NH group in the alkyl-chain, gives the NN-spirobridged octachlorobiscyclotriphosphazene, [N3P3Cl4(NCHMe2)](2) (2), in the presence of NaH. The reactions of 2 with excess pyrrolidine result in the formation of the fully substituted bridged product 2a. The reactions of 2 with 1:1 and 1:2 equimolar amounts of N-(4-fluorobenzyl)N'methylethane-1,2-diamine and N-(4-fluorobenzyl)-N'methylpropane-1,3-diamine produce the (4-fluorobenzyl) pendant armed monospiro (2b and 2c) and dispiro (2f and 2g) products. These compounds react with excess pyrrolidine to form stable, fully substituted cyclotriphosphazenes (2d, 2e, 2h and 2i). The structures of 2a and 2f are determined by X-ray crystallography. The stereogenic properties of 2a and 2f having four potential stereogenic P-centers are investigated by crystallography. The monospiro (2b-2e) and dispiro (2f-2i) products have one and two equivalent chiral centers, respectively. The dispiro derivatives may have two meso (trans-trans and cis-cis) and two racemate (trans-cis and cis-trans) mixtures. However, the structure of 2f is found to be as trans-trans (meso) isomer. Besides, in vitro antimicrobial and cytotoxic activities of 2d and 2h are evaluated. The compounds exhibit significant growth inhibitory effects on E. coli and B. cereus bacteria. Compound 2d has high anticancer and apoptotic activities.Öğe Phosphorus-nitrogen compounds. Part 48. syntheses of the phosphazenium salts containing 2-pyridyl pendant arm: structural characterizations, thermal analysis, antimicrobial and cytotoxic activity studies(NATL INST SCIENCE COMMUNICATION-NISCAIR, 2020) Elmas, Gamze; Okumus, Aytug; Kilic, Zeynel; Ozbeden, Pelin; Acik, Leyla; Tunali, Beste Cagdas; Turk, MustafaThe phosphazenium salts (protic ionic liquids, PILs/protic molten salts, PMOSs) (6a-6d and 7a) of the free phosphazene bases (4a-4d and 5a) have been prepared by the reactions of the corresponding cyclotriphosphazenes with the bulky gentisic acid. The structures of the PMOS have been evaluated using the elemental analyses, FTIR, H-1, C-13{H-1} and P-31{H-1} NmR data. The molecular and crystal structures of 4a and 6c are established by X-ray crystallography. The thermal properties of the PMOS are determined using TG and DTA techniques. On the other hand, the antimicrobial activities of the free phosphazene bases (4a-4d and 5a-5d) and PMOSs (6a-6d and 7a) are screened against the selected bacteria and yeast strains. The antimicrobial activities of the free phosphazene bases and the PMOSs are compared. The interactions of the phosphazenes and their salts with plasmid DNA are elucidated by the agarose gel electrophoresis. The evaluations of the cytotoxic activities of these compounds are also studied against to L929 fibroblast and breast cancer cells (MDA-MB-231).Öğe Phosphorus-nitrogen compounds. Part 64. Comparative reactions of spiro and ansa (N/O) cyclotetraphosphazenes with bulky (4-fluorobenzyl) N/N and N/O donor type bidentate reagents: structure, stereogenic properties and cytotoxic activity studies(Royal Soc Chemistry, 2022) Elmas, Gamze; Binici, Arzu; Yakut, Mehtap; Okumus, Aytug; Kilic, Zeynel; Cosut, Bunyemin; Hokelek, TuncerThe reaction of octachlorocyclotetraphosphazene, N4P4Cl8 (1) (OCCP, tetramer), with an equimolar amount of sodium 3-(N-ferrocenylmethylamino)-1-propanoxide (L1) resulted in the formation of ferrocenyl-spiro-(2) and ferrocenyl-2-cis-4-dichloro-ansa-(3) cyclotetraphosphazenes. Both of the starting compounds were used to produce the new inorganic-organic hybrid multiheterocyclic-spiro and ansa cyclotetraphosphazenes. Spiro (2) was treated with excess N-(4-fluorobenzyl)-N'-ethyl-1,2-diaminoethane (L2) to give 2-trans-6-dispiro (trans-2a) and 2-trans-4-cis-6-trans-8-tetraspiro (tetraspiro-2a) cyclotetraphosphazenes. Spiro (2) was also reacted with excess sodium 3-(4-fluorobenzylamino)-1-propanoxide (L3) to produce 2-trans-6-dispiro (trans-2b), 2-cis-6-dispiro (cis-2b), 2-cis-4-trans-6-trispiro (trans-2c), 2-cis-4-dispiro-6-trispiro (cis-2c), 2-cis-4-dichloro-ansa-4-trans-6-spiro(N/O) (ansa-2b) and 2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/O) (ansa-2c). The reactions of 2,4-ansa (3) with excess L2 led to the formation of 2-cis-4-dichloro-ansa-2-trans-6-spiro(N/N) (trans-3a) and 2-cis-4-dichloro-ansa-2-cis-6-spiro(N/N) (cis-3a) cyclotetraphosphazenes. However, the reactions of 2,4-ansa (3) with excess L3 afforded monospiro {2-cis-4-dichloro-ansa-4-trans-6-spiro(N/O) (trans-3b) and 2-cis-4-dichloro-ansa-4-cis-6-spiro(N/O) (cis-3b)} and dispiro {2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/O) (trans-3c) and 2-cis-4-dichEoro-ansa-6-cis-8-dispiro(N/O) (cis-3c)}. The obtained products were characterized by spectroscopic techniques. The crystal structures of trans-2b and cis-3b were clarified by single crystal X-ray analysis. The products had stereogenic P-centres except for trans-2a, tetraspiro-2a, trans-2b and cis-2b. The stereogenic properties of tetrameric phosphazenes were evaluated by X-ray crystallography and chiral high performance liquid chromatography (HPLC) methods. The structure of cis-3b revealed the absolute configurations of the enantiomers (SS'R ''/RR'S ''). The broad HPLC peak of cis-3b indicates that it may exist as a resamate in solution. The cytotoxic activities of the cyclotetraphosphazenes were evaluated using an MTT assay against L929 mouse fibroblasts, A549 non-small lung cancer and Caco-2 colorectal adenocarcinoma cells. Compound cis-3b was found to be very effective in all cell lines up to 104.1 mu M.Öğe Syntheses, structural characterization and biological activities of spiro-ansa-spiro-cyclotriphosphazenes(Royal Soc Chemistry, 2015) Basterzi, Nisan Sevin; Kocak, Selen Bilge; Okumus, Aytug; Kilic, Zeynel; Hokelek, Tuncer; Celik, Omer; Aydin, BetulThe replacement reactions of the Cl-atoms in partly substituted spiro-ansa-spiro-cyclotriphosphazenes (7 and 8) with excess pyrrolidine, 4-(2-aminoethyl) morpholine, and 1,4-dioxa-8-azaspiro[4,5] decane in dry THF led to the formation of heterocyclic amine substituted cyclotriphosphazenes (9a-c and 10a-c). All cyclotriphosphazene derivatives were characterized by elemental analysis, FTIR, MS, 1D H-1, C-13 and P-31 NMR and 2D HSQC, and HMBC techniques, and the crystal structure of partly substituted cyclotriphosphazene 8 was verified by X-ray diffraction analysis. Cyclotriphosphazene derivatives (5-8, 9a-c, and 10a-c) were subjected to antimicrobial activity against seven clinic bacteria and one yeast strain, and the interactions of the phosphazenes with plasmid pBR322 DNA were investigated. Phosphazene derivatives [(5, 7, 8, 9b and 9c) and (10a and 10b)] caused a slight increase and substantial decrease in the mobility of form I DNA, respectively, while 9a caused retardation on gel. Cytotoxic, apoptotic and necrotic effects against L929 fibroblast and A549 lung cancer cells were also evaluated. While the highest toxic effect was obtained for 9a in L929 fibroblast cells and for 9c in A549 lung cancer cells at 100 mg mL(-1) concentration, the highest apoptotic effect was determined for 10a in L929 fibroblast cells and for 9a in A549 lung cancer cells at the same concentration. It was found that 9a and 10b exhibited the most necrotic effects against L929 fibroblast and A549 lung cancer cells, respectively. The toxic and necrotic effects of the phosphazenes against A549 lung cancer cells were greater than those against L929 fibroblast cells, whereas, the apoptotic effect of the compounds was greater in L929 fibroblast cells than in A549 lung cancer cells.
