The gradually Cl replacement reactions of spirocyclic mono (1 and 2) and bisferrocenyl cyclotriphosphazenes (3–5) with the potassium salt of 4-hydroxy-3-methoxybenzaldehyde (potassium vanillinate) gave mono (1a–5a), geminal (gem-1b–5b), non-geminal (cis-1b, cis-5b and trans-2b–5b), tri (1c–5c) and tetra-substituted phosphazenes (1d–5d). Some phosphazenes have stereogenic P-center(s). The chirality of 4c was verified using chiral HPLC column. Electrochemical behaviors were influenced only by the number of ferrocene groups, but not the length of the amine chains and the substituent(s). The structures of the new phosphazenes were determined by FTIR, MS, 1H, 13C and 31P NMR, HSQC and HMBC spectral data. The solid-state structures of cis-1b and 4d were examined by single crystal X-ray diffraction techniques. The twelve phosphazene derivatives were screened for antimicrobial activity and the compounds 5a, cis-1b and 2c exhibited the highest antibacterial activity against G(+) and G(−) bacteria. In addition, it was found that overall gem-1b inhibited the growth of Mycobacterium tuberculosis. The compounds 1d, 2d and 4d were tested in HeLa cancer cell lines. Among these compounds, 2d had cytotoxic effect on HeLa cell in the first 48 h. Moreover, interactions between compounds 2a, gem-1b, gem-2b, cis-1b, 2c, 3c, 4c, 5c, 1d, 2d and 4d, and pBR322 plasmid DNA were investigated. -
Keywords: Ferrocenylphosphazenes; Spectroscopy; Crystal structure; Electrochemistry; Antituberculosis activity; HeLa cell line
Publication Name (dc.title) | Phosphorus-nitrogen compounds: Part 28. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing vanillinato and pendant ferrocenyl groups |
Author/s (dc.contributor.yazarlar) | Yasemin Tümer, Nuran Asmafiliz, Zeynel Kılıç, Tuncer Hökelek, L. Yasemin Koç, Leyla Açık, Mehmet Lütfi Yola, Ali Osman Solak, Yağmur Öner, Devrim Dündar, Makbule Yavuz |
Publication type (dc.type) | Makale |
Language (dc.language) | İngilizce |
Publication year (dc.date.issued) | 2013 |
National/International (dc.identifier.ulusaluluslararasi) | Uluslararası |
Source (dc.relation.journal) | Journal of Molecular Structure |
Volume/Issue (dc.identifier.volume) | 1049 |
Page (dc.identifier.startpage) | 112–124 |
ISSN/ISBN (dc.identifier.issn) | ISSN: 0022-2860 |
Publisher (dc.publisher) | Elsevier |
Databases (dc.contributor.veritaban) | Web of Science Core Collection |
Databases (dc.contributor.veritaban) | Sciencedirect |
Databases (dc.contributor.veritaban) | Scopus |
Index Type (dc.identifier.index) | SCI Expanded |
Index Type (dc.identifier.index) | Scopus |
Impact Factor (dc.identifier.etkifaktoru) | 2,011 / 2017-WOS / 5 Year: 1,784 |
Abstract (dc.description.abstract) | The gradually Cl replacement reactions of spirocyclic mono (1 and 2) and bisferrocenyl cyclotriphosphazenes (3–5) with the potassium salt of 4-hydroxy-3-methoxybenzaldehyde (potassium vanillinate) gave mono (1a–5a), geminal (gem-1b–5b), non-geminal (cis-1b, cis-5b and trans-2b–5b), tri (1c–5c) and tetra-substituted phosphazenes (1d–5d). Some phosphazenes have stereogenic P-center(s). The chirality of 4c was verified using chiral HPLC column. Electrochemical behaviors were influenced only by the number of ferrocene groups, but not the length of the amine chains and the substituent(s). The structures of the new phosphazenes were determined by FTIR, MS, 1H, 13C and 31P NMR, HSQC and HMBC spectral data. The solid-state structures of cis-1b and 4d were examined by single crystal X-ray diffraction techniques. The twelve phosphazene derivatives were screened for antimicrobial activity and the compounds 5a, cis-1b and 2c exhibited the highest antibacterial activity against G(+) and G(−) bacteria. In addition, it was found that overall gem-1b inhibited the growth of Mycobacterium tuberculosis. The compounds 1d, 2d and 4d were tested in HeLa cancer cell lines. Among these compounds, 2d had cytotoxic effect on HeLa cell in the first 48 h. Moreover, interactions between compounds 2a, gem-1b, gem-2b, cis-1b, 2c, 3c, 4c, 5c, 1d, 2d and 4d, and pBR322 plasmid DNA were investigated. - |
Abstract (dc.description.abstract) | Keywords: Ferrocenylphosphazenes; Spectroscopy; Crystal structure; Electrochemistry; Antituberculosis activity; HeLa cell line |
URL (dc.rights) | http://www.sciencedirect.com/science/article/pii/S0022286013005565 |
DOI (dc.identifier.doi) | 10.1016/j.molstruc.2013.06.036 |
Faculty / Institute (dc.identifier.fakulte) | Mühendislik Fakültesi |
Department (dc.identifier.bolum) | Kimya Mühendisliği Bölümü |
Author(s) in the Institution (dc.contributor.author) | Ali Osman SOLAK |
Kayıt No (dc.identifier.kayitno) | BL673D0979 |
Record Add Date (dc.date.available) | 2016-03-17 |
Notes (Publication year) (dc.identifier.notyayinyili) | 8 October 2013 |
Wos No (dc.identifier.wos) | WOS:000324784700014 |
Subject Headings (dc.subject) | ferrocenylphosphazenes |
Subject Headings (dc.subject) | spectroscopy |
Subject Headings (dc.subject) | crystal structure |
Subject Headings (dc.subject) | electrochemistry |
Subject Headings (dc.subject) | antituberculosis activity |
Subject Headings (dc.subject) | hela cell line |