Phosphorus–nitrogen compounds: part 30. Syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes
The gradual Cl replacement reactions of NN ( 1–3 ) or NO spirocyclic monoferrocenyl cyclotriphosphazenes ( 4 and 5 ) with the potassium salt of 4-hydroxy-3-methoxybenzaldehyde (potassium vanillinate) resulted in the mono ( 1a–5a ), geminal ( gem - 1b–5b ), non-geminal ( cis - 5b and trans -1b–4b ),...
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Published in | Journal of biological inorganic chemistry Vol. 20; no. 1; pp. 165 - 178 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Berlin/Heidelberg
Springer Berlin Heidelberg
01.01.2015
|
Subjects | |
Online Access | Get full text |
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Summary: | The gradual Cl replacement reactions of NN (
1–3
) or NO spirocyclic monoferrocenyl cyclotriphosphazenes (
4
and
5
) with the potassium salt of 4-hydroxy-3-methoxybenzaldehyde (potassium vanillinate) resulted in the mono (
1a–5a
), geminal (
gem
-
1b–5b
), non-geminal (
cis
-
5b
and
trans
-1b–4b
), tri (
1c
,
3c–5c
) and tetra-vanillinato-substituted phosphazenes (
1d–5d
). All the phosphazene derivatives have stereogenic P-center(s), except tetra-substituted ones. The vanillinatophosphazenes have reversible voltammograms with one-electron anodic and cathodic peaks which are attributed to ferrocenyl redox probe. The structures of the new phosphazene compounds were determined by FTIR, MS,
1
H,
13
C{
1
H} and
31
P{
1
H} NMR spectral data. The solid-state structure of
cis
-5b
was examined by single-crystal X-ray diffraction techniques. In addition, the compounds were tested in HeLa cancer cell lines using MTT assay. The 12 phosphazene derivatives were screened for antimicrobial activity, and
3c
was very effective against
S. aureus
even at 4.88 µM concentration, taking into account the MIC values. Besides, interactions between the phosphazenes and pBR322 plasmid DNA were also investigated.
Graphical Abstract
The vanillinato cyclotriphosphazenes containing pendant monoferrocenyl arms were obtained. Some of the phosphazenes were tested against HeLa cancer cells. The new phosphazenes were screened for antimicrobial activity, and interactions between the phosphazenes and pBR322 plasmid DNA were evaluated. The spectral characterizations of all the phosphazenes were presented. |
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ISSN: | 0949-8257 1432-1327 |
DOI: | 10.1007/s00775-014-1223-5 |