Molecular structures of new ciprofloxacin derivatives

Tomišić, Zrinka Banić; Krajačić, Mirjana Bukvić; Višnjevac, Aleksandar; Kojić‐Prodić, Biserka

doi:10.1016/s0022-2860(02)00062-5

Cited by 9 publications

(2 citation statements)

References 17 publications

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“…It should be noted that, under these conditions, the separation of berberine derivatives from reactions was simple because the products were soluble in polar aprotic solvents, thus distinguishing them from the berberrubine. Concerning the synthesis of the berberine-ciprofloxacin conjugate (referred as berberine derivative 4 ), the first step of its synthesis was the derivatization of ciprofloxacin to its acylated form (Scheme 4) [51,52]. Prepared carbonyl chloride of ciprofloxacin was further mixed with berberrubine and the reaction was microwave irradiated to produce the berberine derivative 4 in 31% yield (Scheme 5).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Activity of Novel 9-O-Substituted Berberine Derivatives

Milata

Svedova

Barbieriková

et al. 2019

IJMS

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Berberine is a bioactive isoquinoline alkaloid derived from many plants. Although berberine has been shown to inhibit growth and induce apoptosis of several tumor cell lines, its poor absorption and moderate activity hamper its full therapeutic potential. Here, we describe the synthesis of a series of 9-O-substituted berberine derivatives with improved antiproliferative and apoptosis-inducing activities. An analysis of novel berberine derivatives by EPR spectroscopy confirmed their similar photosensitivity and analogous behavior upon UVA irradiation as berberine, supporting their potential to generate ROS. Improved antitumor activity of novel berberine derivatives was revealed by MTT assay, by flow cytometry and by detection of apoptotic DNA fragmentation and caspase-3 activation, respectively. We showed that novel berberine derivatives are potent inhibitors of growth of HeLa and HL-60 tumor cell lines with IC50 values ranging from 0.7 to 16.7 µM for HL-60 cells and 36 to >200 µM for HeLa cells after 48 h treatment. Further cell cycle analysis showed that the observed inhibition of growth of HL-60 cells treated with berberine derivatives was due to arresting these cells in the G2/M and S phases. Most strikingly, we found that berberine derivative 3 (9-(3-bromopropoxy)-10-methoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a] isoquinolin-7-ylium bromide) possesses 30-fold superior antiproliferative activity with an IC50 value of 0.7 µM and 6-fold higher apoptosis-inducing activity in HL-60 leukemia cells compared to berberine. Therefore, further studies are merited of the antitumor activity in leukemia cells of this berberine derivative.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Activity of Novel 9-O-Substituted Berberine Derivatives

Milata

Svedova

Barbieriková

et al. 2019

IJMS

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“…The 4-quinolone originates from 1,8-naphythyridine precursor-nalidixic acid, discovered in the early 1960s (Tomišic et al, 2002;Lesher et al, 1962;Foroumadi et al, 2007). In the 1980s quinolones containing fluorine atoms (Koga et al, 1980;Sanders, 1988) were introduced.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluations of enoxacin carboxamide derivatives

et al. 2009

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The present work deals with the synthesis of various enoxacin analogues via nucleophilic substitution of 3-carboxylic acid moiety of the drug by aromatic amines. The free carboxylic group was utilized in the formation of amides and the effect of functional group exchange on different biological activities of the parent was evaluated. The structure of these derivatives was established by various spectroscopic techniques and mass spectrometry. The derivatives were evaluated as antibacterial agents against a series of Gram-positive and Gram-negative bacteria whereby some of them displayed considerably improved antimicrobial profile against Gram-negative test strains. Additionally unlike enoxacin, the derivatives were also found to modulate oxidative burst response of phagocytes exhibiting moderate to significant inhibitory activity.

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