Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents.

New monomethine, unsymmetrical styryl dyes consisting of benzothiazole and N-methylpiperazine or N-phenylpiperazine scaffolds were synthesized, and their binding affinities for different ds-polynucleotides and G-quadruplex were studied. Substitution of piperazine unit with methyl or phenyl group strongly influenced their binding modes, binding affinities, spectroscopic responses and antiproliferative activities. Compounds with N-methylpiperazine substituents showed a significant preference for AT-DNA polynucleotides and demonstrated AT-minor groove binding, which manifested in strong fluorescence increase, significant double helix stabilization, and positive induced circular dichroism spectra.

6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity.

The synthesis of novel 6-chloro/morpholino/amino/-9-sulfonylpurine derivatives was accomplished in two ways, either (i) involving the condensation reaction of 6-chloropurine with commercially available arylsulfonyl chlorides in acetone and the presence of aqueous KOH at 0 °C, followed by the substitution of C6-chlorine with morpholine, or (ii) employing a reversed synthetic approach where 6-morpholinopurine and commercially available adenine bases were reacted with the corresponding alkyl, 2-arylethene and arylsulfonyl chlorides giving the N9 sulfonylated products, the latter particularly used where prior nonselective sulfonylation was observed. In both approaches, the sulfonylation reaction occurred regioselectively at the purine N9 position lacking any concurrent N7 derivatives, except in the case of a smaller methyl substituent on SO and the free amino group at C6 of the purine ring. The tautomeric features of initial N9 unsubstituted purines, as well as stability trends among the prepared -9-sulfonylpurine derivates, were investigated using DFT calculations with an important conclusion that electron-donating C6 substituents are beneficial for the synthesis as they both promote the predominance of the desired N9 tautomers and help to assure the stability of the final products.

Synthesis, DNA/RNA-interaction and biological activity of benzo[k,l]xanthene lignans.

Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants - presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring - influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs.

Autofermentation of Chamomile Ligulate Flowers Promote Antitumor Effects in vitro.

In the frame of this paper, the enzyme-assisted hydrolysis coupled with ultrasound and Soxhlet extraction was applied in order to get extracts of chamomile ligulate flowers (CLF). Obtained extracts were characterized in terms to their apigenin and apigenin glucoside composition, as well as antiproliferative potential against tumour cells. Antioxidant activity was determined by two different assays based on different mechanisms showing that autofermented extracts have higher reduction potential.

Antiproliferative and proapoptotic activity of molecular copper(II) complex of N-1-tosylcytosine.

In an attempt to enhance the previously observed antiproliferative capacity of 1-(p-toluenesulfonyl)cytosine (N-1-tosylcytosine, ligand 1), its copper(II) complex (Cu(1-TsC-N3)Cl, complex 2) was prepared and tested in vitro on various carcinoma and leukemia cells. The comparative in vitro studies using the ligand 1, the complex 2, CuClx2HO salt (salt 3) and the 1:2 mixture of the salt 3 and ligand 1 (mixture 4) were performed on normal (WI38), human carcinoma (HeLa, CaCo2, MiaPaCa2, SW620), lymphoma (Raji) and leukemia (K562) cell lines. Significantly elevated concentration of the intracellular copper after treatment of K562 cells and HeLa cells during 2h with complex 2 (7.

Effect of Microwave-Assisted Extraction on the Phenolic Compounds and Antioxidant Capacity of Blackthorn Flowers.

This research was undertaken to investigate the influence of extraction parameters during microwave-assisted extraction on total phenolic content, total flavonoids, total hydroxycinnamic acids and total flavonols of blackthorn flowers as well as to evaluate the antioxidant capacity by two different methods (2,2-diphenyl-1-picrylhydrazyl free radical scavenging capacity and ferric reducing antioxidant power assays). The investigated extraction parameters were: solvent type and volume fraction of alcohol in solvent (50 and 70% aqueous solutions of ethanol and methanol), extraction time (5, 15 and 25 min) and extraction temperature (40, 50 and 60 °C) controlled by microwave power of 100, 200 and 300 W. Multivariate analysis of variance (MANOVA) was used to evaluate the differences at a 95% confidence level (p≤0.

New quinoline-arylamidine hybrids: Synthesis, DNA/RNA binding and antitumor activity.

Four series of new hybrid molecules with 7-chloroquinoline and arylamidine moieties joined through the rigid -O- (groups I (2a-g) and II (5a-g)) or flexible -NH-CH-CH-O- (groups III (8a-g) and IV (10a-g)) linker were synthesized, and their DNA/RNA binding properties and cytotoxic activity were tested, against several human cancer lines. The compounds and their interaction with DNA and RNA were studied by UV-Vis and CD spectroscopy. The obtained results showed that the binding affinity of the investigated compounds increases proportionally with the increase of the length and number of groups able to form hydrogen bonds with ds-polynucleotides.

The impact of α-hydrazino acids embedded in short fluorescent peptides on peptide interactions with DNA and RNA.

A series of novel hydrazino-based peptidomimetics and analogues comprising N-terminal lysine and C-terminal phenanthridinyl-l-alanine were prepared. The presented results demonstrate the up to now unknown possibility to finely modulate peptide interactions with DNA/RNA by α-hydrazino group insertion and how the different positioning of two α-hydrazino groups in peptides controls binding to various double stranded and single stranded DNA and RNA. All peptidomimetics bind with 1-10 micromolar affinity to ds-DNA/RNA, whereby the binding mode is a combination of electrostatic interactions and hydrophobic interactions within DNA/RNA grooves.

An efficient synthesis of pyridoxal oxime derivatives under microwave irradiation.

Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%-94%) were obtained in acetone in very short reaction times (3-5 min) as well as in the solvent-free procedure (42%-78%) in very short reaction times (7-10 min) too.

N-(o-chlorophenyl)-2,5-dimethylpyrrole-3-carbaldehyde.

Crystal structure analysis of the title compound, C(13)H(12)ClNO, reveals three crystallographically independent molecules in the asymmetric unit. The main conformational difference between these molecules is the orientation of the phenyl rings with respect to the pyrrole rings. The coplanar arrangement of the aldehyde groups attached to the pyrrole rings influences the pyrrole-ring geometry.

Ferrocene compounds. XXXVIII. Dimethyl ferrocene-1,1'-dicarboxylate.

In the title compound, [Fe(C(7)H(7)O(2))(2)], the cyclopentadienyl rings and the two attached methoxycarbonyl groups, in an anti arrangement, form an extended pi-conjugated system. The Fe-C distances range from 2.035 (3) to 2.