Solubility, lipophilicity and membrane permeability of some fluoroquinolone antimicrobials

Blokhina, Svetlana V.; Sharapova, Angelica; Ol’khovich, Marina V.; Volkova, Тatyana V.; Perlovich, German L.

doi:10.1016/j.ejps.2016.07.016

Cited by 69 publications

(33 citation statements)

References 37 publications

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“…In the range from approximately 150°С to approximately 270°С, the sample mass is nearly persistent, and the mass lost (Δm) at 150°С (9.2%) almost coincides with that calculated at the assumption of 3 water molecules release (10.2%). The average value of the CfH melting temperature is equal to 270.0°С, and H 2 tba melts with the decomposition at 250.6°C . Thus, compound 1 is thermally more stable than H 2 tba.…”

Section: Resultsmentioning

confidence: 98%

Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties

Головнев

Мolokeev

Lesnikov

et al. 2017

J of Physical Organic Chem

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Ciprofloxacin (CfH, C 17 H 18 FN 3 O 3 ) crystallizes with 2-thiobarbituric (H 2 tba) and barbituric acid (H 2 ba) in the aqueous solution to yield salt CfH 2 (Htba)·3H 2 O (1), salt cocrystal CfH 2 (Hba)(H 2 ba)·3H 2 O (2), and salt CfH 2 (Hba)·H 2 O (3). The compounds are structurally characterized by the Xray single-crystal diffraction. The numerous intermolecular hydrogen bonds N-H⋯O and O-H⋯O formed by water molecules, Htba − /Hba − and CfH 2 + ions, and H 2 ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2. There are different π-π interactions in 1 to 3.The compounds have been characterized by powder X-ray diffraction, thermogravimetry/differential scanning calorimetry, and Fourier transform infrared spectroscopy. The compounds dehydration ends at 130°C to 150°C, and their oxidative decomposition is observed in the range of 250°C to 275°C. KEYWORDS barbituric and thiobarbituric acids, ciprofloxacin, infrared spectroscopy, salt cocrystal, thermal stability, X-ray diffraction Electronic supplementary information (ESI) available.

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Section: Resultsmentioning

confidence: 98%

Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties

Головнев

Мolokeev

Lesnikov

et al. 2017

J of Physical Organic Chem

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“…36,37 Levofloxacin is more lipophilic than ciprofloxacin. 38 So, it is predicted that levofloxacin achieved higher testicular concentration relative to blood than ciprofloxacin. The present study showed histopathological alterations in seminiferous tubules and interstitial tissues with ciprofloxacin and to a lesser extent levofloxacin.…”

Section: Discussionmentioning

confidence: 99%

Ciprofloxacin and levofloxacin adversely affect male infertility indicated by pharmacological, andrological and pathological evidence

Mokhimar

Kandiel²,

Amin

et al. 2020

Int J Basic Clin Pharmacol

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Background: Drug-induced reproductive organs toxicities is an important aetiology in investigation of male infertility. The aim is to study levofloxacin effect on male reproductive system in comparison to ciprofloxacin.Methods: Twenty-five male wister rats weighted 230±20 gm and aged 8 weeks were randomly divided into five groups of five. The first group received ciprofloxacin with dose 78.23 mg/kg/day in 2 doses (therapeutic dose). The second group received the double dose of the first group ciprofloxacin. The third group received levofloxacin with dose 39.11 mg/kg/day once daily (OD) (therapeutic dose). The Fourth group received the double dose of the third group levofloxacin. However, the fifth group served as a control and received normal saline with carboxymethylcellulose OD. All treatments were administered orally for 14 days. On the 15th day, blood samples and reproductive organs were obtained from all rats. Testicular tissues were prepared for genetic testing and chemical and microscopical examination.Results: Ciprofloxacin and levofloxacin negatively altered reproductive organ weights, sperm parameters and serum follicle stimulating hormone (FSH) and luteinizing hormone (LH) level (p<0.05). Additionally, serum testosterone level was significantly deceased in ciprofloxacin-treated group (the double dose) (p<0.05) relative to control. The difference between ciprofloxacin and levofloxacin was significant in seminal vesicle weight and serum LH and FSH level (p<0.05). Testicular histopathological changes were also found with the two drugs with different degrees. Effects of levofloxacin and ciprofloxacin were dose-dependent.Conclusions: Both ciprofloxacin and levofloxacin adversely affect andrological function that should be monitored and controlled during application of these drugs.

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“…Since the SPs are located in the sarcoplasm (soluble fraction of myocyte), they could be more accessible to the ROS promoted by those FQs with better diffusion across the sarcolemma. Then, considering the order of increasing polarity of these substances (NOR < CIPRO < DANO < ENRO < SARA) [29], the FQs such as NOR and CIPRO would have more difficulty permeating the sarcoplasm, while SARA, ENRO and DANO would permeate it more easily, explaining their high impact on the solubility of these proteins [28,[30][31][32][33][34][35][36][37].…”

Section: Yielding Of Protein Fractions Is Affected By Protein Oxidatimentioning

confidence: 99%

Residues of Fluoroquinolone Antibiotics Induce Carbonylation and Reduce In Vitro Digestion of Sarcoplasmic and Myofibrillar Beef Proteins

Lázaro

Méndez-Cuadro

Rodríguez-Cavallo

2020

Foods

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Although the impact of oxidation on human health has been of growing interest, the oxidation of proteins, major component of meat, has received little attention. This paper describes the in vitro effect of five fluoroquinolones (FQs) on carbonylation of sarcoplasmic and myofibrillar proteins of beef when found at concentrations close to the maximum residue limit (MRL). Samples were treated individually with the FQs, determining in each protein fraction the carbonyl index, protein content and oxidized proteins identification, using 2,4-dinitrophenyhydrazine (DNPH) alkaline assay, Western blot and Bradford methods, and mass spectrometry, respectively. Besides, the in vitro effect of these residues on gastric and duodenal digestion of proteins was evaluated. The carbonylation induced by FQs affected both protein fractions being significant with respect to the blank in 73.3% of cases. This damage was correlated with loss of solubility and digestibility, with sarcoplasmic proteins the most affected. Danofloxacin and enrofloxacin were the FQs with greatest oxidant effects, especially affecting glycolysis and glycogen proteins. Our results suggest that these residues induce irreversible oxidative damage on the main beef proteins and could affect their nutritional value.

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Solubility, lipophilicity and membrane permeability of some fluoroquinolone antimicrobials

Cited by 69 publications

References 37 publications

Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties

Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties

Ciprofloxacin and levofloxacin adversely affect male infertility indicated by pharmacological, andrological and pathological evidence

Residues of Fluoroquinolone Antibiotics Induce Carbonylation and Reduce In Vitro Digestion of Sarcoplasmic and Myofibrillar Beef Proteins

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