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Levofloxacin Cocrystal/Salt with Phthalimide and Caffeic Acid as Promising Solid-State Approach to Improve Antimicrobial Efficiency.

ABSTRACT: To overcome the issue of multidrug resistant (MDR) microbes, the exploration of ways to improve the antimicrobial efficiency of existing antibiotics is one of the promising approaches. In search of synthons with higher efficiency, in current investigations, cocrystal and amorphous salt of levofloxacin hemihydrate (LEV) were developed with phthalimide (PTH) and caffeic acid (CFA). New materials were characterized with the help of FT-IR, Raman spectroscopy, powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Shifting, attenuation, appearance/disappearance and broadening of bands were observed in the FT-IR and Raman spectra of the materials as evidence of the required product. The PXRD diffraction pattern observed for LEV-PTH indicated cocrystal while halo diffractogram of LEV-CFA revealed amorphous nature. DSC/TG analysis confirmed the hydrated nature of the cocrystal/salt. The dissolution rate and antimicrobial activity against selected strains, K.pneumonia, E. coli and S. typhi of parent drug and the new material were compared. The zone of inhibition (ZI) observed for 5 µg LEV-PTH was 30.4 + 0.36 (K. pneumonia), 26.33 + 0.35 (E. coli) and 30.03 + 0.25 mm (S. typhi) while LEV-CFA salt (5 µg) against the same strains inhibited 33.96 ± 0.25, 31.66 ± 0.35 and 27.93 ± 0.40 mm, respectively. These novel formulations enhance the dissolution rate as well as antibacterial efficiency and are expected to be potent against MDR bacterial strains.

SUBMITTER: Islam NU

PROVIDER: S-EPMC9220774 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Levofloxacin Cocrystal/Salt with Phthalimide and Caffeic Acid as Promising Solid-State Approach to Improve Antimicrobial Efficiency.

Islam Noor Ul NU Umar Muhammad Naveed MN Khan Ezzat E Al-Joufi Fakhria A FA Abed Shaymaa Najm SN Said Muhammad M Ullah Habib H Iftikhar Muhammad M Zahoor Muhammad M Khan Farhat Ali FA

Antibiotics (Basel, Switzerland) 20220613 6

To overcome the issue of multidrug resistant (MDR) microbes, the exploration of ways to improve the antimicrobial efficiency of existing antibiotics is one of the promising approaches. In search of synthons with higher efficiency, in current investigations, cocrystal and amorphous salt of levofloxacin hemihydrate (LEV) were developed with phthalimide (PTH) and caffeic acid (CFA). New materials were characterized with the help of FT-IR, Raman spectroscopy, powder X-ray diffraction (PXRD), differe ...[more]

PMID: 35740203

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Project description:The development of a new class of antibiotics to fight bacterial resistance is a time-consuming effort associated with high-cost and commercial risks. Thus, modification, conjugation or combination of existing antibiotics to enhance their efficacy is a suitable strategy. We have previously reported that the amphiphilic cyclic peptide [R?W?] had antibacterial activity with a minimum inhibitory concentration (MIC) of 2.97 µg/mL against Methicillin-resistant Staphylococcus aureus (MRSA). Herein, we hypothesized that conjugation or combination of the amphiphilic cyclic peptide [R?W?] with levofloxacin or levofloxacin-Q could improve the antibacterial activity of levofloxacin and levofloxacin-Q. Fmoc/tBu solid-phase chemistry was employed to synthesize conjugates of [R?W?K]-levofloxacin-Q and [R?W?K]-levofloxacin. The carboxylic acid group of levofloxacin or levofloxacin-Q was conjugated with the amino group of ?-alanine attached to lysine in the presence of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexa?uorophosphate (HBTU) and N,N-diisopropylethylamine (DIPEA) for 3 h to afford the products. Antibacterial assays were conducted to determine the potency of conjugates [R?W?K]-levofloxacin-Q and [R?W?K]-levofloxacin against MRSA and Klebsiella pneumoniae. Although levofloxacin-Q was inactive even at a concentration of 128 µg/mL, [R?W?K]-levofloxacin-Q conjugate and the corresponding physical mixture showed MIC values of 8 µg/mL and 32 µg/mL against MRSA and Klebsiella pneumonia, respectively, possibly due to the activity of the peptide. On the other hand, [R?W?K]-levofloxacin conjugate (MIC = 32 µg/mL and MIC = 128 µg/mL) and the physical mixture (MIC = 8 µg/mL and 32 µg/mL) was less active than levofloxacin (MIC = 2 µg/mL and 4 = µg/mL) against MRSA and Klebsiella pneumoniae, respectively. The data showed that the conjugation of levofloxacin with [R?W?K] significantly reduced the antibacterial activity compared to the parent analogs, while [R?W?K]-levofloxacin-Q conjugate was more significantly potent than levofloxacin-Q alone.

Dataset Information

Levofloxacin Cocrystal/Salt with Phthalimide and Caffeic Acid as Promising Solid-State Approach to Improve Antimicrobial Efficiency.

Publications

Levofloxacin Cocrystal/Salt with Phthalimide and Caffeic Acid as Promising Solid-State Approach to Improve Antimicrobial Efficiency.

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