A new calcium(II) complex of marbofloxacin showing much lower acute toxicity with retained antibacterial activity

Xie, Yanjie; Yu, Mengxin; Yang, Qi-Zhen; Liu, Yancheng; Liu, Ruixue; Dong, Jiaxin; Wu, Xiao-Ye; Guo, Rui-Feng; Pan, Yu-Xing; Chen, Zhen-Feng; Liang, Hong

doi:10.1016/j.jinorgbio.2019.110905

Cited by 10 publications

(11 citation statements)

References 47 publications

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“…The FT-IR spectra of MBF, MBF-FA-H 2 FA salt cocrystal, and MBF-MA salt are shown in Figure S4. The characteristic peaks of marbofloxacin appeared at 3428, 1725, and 1620 cm –1 , which were ascribed to the O–H stretching, CO stretching of carboxylic acids, and CO stretching of pyridinone, respectively, which is consistent with the results reported in the literature . It indicates that the −COOH group of the marbofloxacin portion is stable and no zwitterions were formed.…”

Section: Resultssupporting

confidence: 90%

“…The characteristic peaks of marbofloxacin appeared at 3428, 1725, and 1620 cm −1 , which were ascribed to the O−H stretching, C�O stretching of carboxylic acids, and C�O stretching of pyridinone, respectively, which is consistent with the results reported in the literature. 40 It indicates that the −COOH group of the marbofloxacin portion is stable and no zwitterions were formed. In the spectra of MBF-FA-H 2 FA salt cocrystal and MBF-MA salt, the absorption peaks for the C�O stretching vibration of carboxylic acids were seen to be displaced from 1725 to 1716 cm −1 and 1718 cm −1 , respectively, which may be the result from intramolecular or intermolecular interactions (hydrogen bonding).…”

Section: Powder X-ray Diffractionmentioning

confidence: 99%

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Salt Cocrystal and Salt of Marbofloxacin with Butenedioic Acid: Impact of cis–trans Isomerism of Coformer on the Conformation and Properties of Marbofloxacin

Li,

Zhang,

et al. 2024

Crystal Growth & Design

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Based on the study of the effect of positional isomerism of coformer functional groups on the cocrystallization and physicochemical properties of the active pharmaceutical ingredients, the impact of cis−trans isomeric butenedioic acid as coformers on the conformation, crystal structure, and its physicochemical properties of marbofloxacin was further explored. In this work, fumaric acid (FA) and maleic acid (MA) with different configurations were chosen as coformers to synthesize the pharmaceutical salt cocrystal (MBF-FA-H 2 FA) and salt (MBF-MA) of marbofloxacin (MBF), and their structures were fully characterized. Significant differences between the conformations of marbofloxacin in the salt cocrystal and in salt were found. In the salt cocrystal, the N atom of the piperazine group from marbofloxacin is coplanar with the pyridone ring, and the whole is straight like fumaric acid, whereas the marbofloxacin piperazine group in the salt is bent like the maleic acid configuration. Furthermore, the conformational variability of marbofloxacin in the salt cocrystal and the salt resulted in different crystal structures and opposite physicochemical properties. Notably, both multicomponent crystals have a surface hydrophilic intercalation structure. However, the salt cocrystal and salt exhibited different solubility and permeability. Specifically, the MBF-MA salt showed improved solubility and permeability, while the MBF-FA-H 2 FA salt cocrystal showed a decreased solubility and permeation rate compared to MBF. In addition, in vitro bacterial inhibitory activity assays indicated that the MBF-MA salt has stronger inhibitory activity against Gram-negative and Gram-positive bacterial strains than the MBF-FA-H 2 FA salt cocrystal and pure MBF.

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Section: Resultssupporting

confidence: 90%

Section: Powder X-ray Diffractionmentioning

confidence: 99%

Salt Cocrystal and Salt of Marbofloxacin with Butenedioic Acid: Impact of cis–trans Isomerism of Coformer on the Conformation and Properties of Marbofloxacin

Li,

Zhang,

et al. 2024

Crystal Growth & Design

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“…Furthermore, as we reported previously, to satisfy the electrical neutrality in each MB–Ln complex, any one of the four MB ligands could be protonated on the nitrogen atom. 32 However, it should be noted that this was based on the previous analysis and speculation on the crystallized complex, and the corresponding crystal structure analysis was merely based on theoretical hydrogenation (Fig. 4).…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, its significant antibacterial activity with decreased acute toxicity in mice was tested and confirmed, suggesting that metal complexes of MB should be further studied and developed. 32 In this study, we attempted to explore the lanthanide( iii ) complexes of MB, i.e. , MB–Ln, primarily considering the similar biological properties of lanthanide( iii ) to calcium( ii ).…”

Section: Introductionmentioning

confidence: 99%

Marbofloxacin combined with heavy rare-earth ions makes better candidates for veterinary drugs: crystal structure and bio-activity studies

Chen,

Liu,

Xie

et al. 2024

Dalton Trans.

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“…Age, which is often poorly reported, affects the physiological state and sensitivity to substance [39]. Four to eight weeks mice (18 ~ 30g) are often used in toxicity tests [40][41][42][43]. It is indicated that ICR, KM, and BALB/c mice (26 ~ 30 g) under the state of 8 ~ 10 weeks are equivalent to the human adulthood [44].…”

Section: Discussionmentioning

confidence: 99%

Improved Up-and-Down Procedure for Acute Toxicity Measurement With Reliable LD50 Verified by Typical Toxic Alkaloids and Modified Karber Method

Zhang

Huang

Liang

et al. 2021

Preprint

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Background: Up-and-down procedure (UDP) was recommended to replace traditional acute toxicity methods. However, it was limited due to the long experimental period (20 - 42 days). To improve UDP, an improved UDP method (iUDP) was developed by shortening observation time between sequence dosages. The aim of this study was to test the reliability of iUDP to provide a reliable method for the acute toxicity measurement of valuable or minor amount compounds. Methods: Oral median lethal dosage (LD50) of nicotine, sinomenine hydrochloride and berberine hydrochloride were measured both by iUDP and modified Karber method (mKM). Results: LD50 of the three alkaloids measured by iUDP with 23 mice were 32.71 ± 7.46, 453.54 ± 104.59, 2954.93 ± 794.88 mg/kg, respectively. LD50 of the three alkaloids measured by mKM with 240 mice were 22.99 ± 3.01, 456.56 ± 53.38, 2825.53 ± 1212.92 mg/kg, respectively. The average time consumed by the two methods were 22 days and 14 days respectively. Total grams of the alkaloids used by the two methods were 0.0082 and 0.0673 (nicotine), 0.114 and 1.24 (sinomenine hydrochloride), 1.9 and 12.7 (berberine hydrochloride). Conclusion: iUDP could replace mKM to detect acute toxicity of substances with comparable and reliable result. And it was suitable for valuable or minor amount substances.

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A new calcium(II) complex of marbofloxacin showing much lower acute toxicity with retained antibacterial activity

Cited by 10 publications

References 47 publications

Salt Cocrystal and Salt of Marbofloxacin with Butenedioic Acid: Impact of cis–trans Isomerism of Coformer on the Conformation and Properties of Marbofloxacin

Salt Cocrystal and Salt of Marbofloxacin with Butenedioic Acid: Impact of cis–trans Isomerism of Coformer on the Conformation and Properties of Marbofloxacin

Marbofloxacin combined with heavy rare-earth ions makes better candidates for veterinary drugs: crystal structure and bio-activity studies

Improved Up-and-Down Procedure for Acute Toxicity Measurement With Reliable LD50 Verified by Typical Toxic Alkaloids and Modified Karber Method

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