1H, 13C and 15N NMR spectra of ciprofloxacin

Zięba, Andrzej; Maślankiewicz, Andrzej; Sitkowski, Jerzy

doi:10.1002/mrc.1468

Cited by 23 publications

(16 citation statements)

References 9 publications

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“…3. Obtained results are in good agreement with previously published data for these fluoroquinolones in the zwitter-ion or free base form (17,24,25).…”

Section: Computation and Data Processingsupporting

confidence: 91%

Effects of substituents on the NMR features of basic bicyclic ring systems of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters

Takač¹

2010

Acta Pharmaceutica

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In the present study, the NMR spectroscopic features of trovafloxacin (TVA) mesylate, pefloxacin (PFX) mesylate dihydrate and ciprofloxacin (CIP) hydrochloride monohydrate were studied in DMSO-d 6 solution with the aim of investigating the effects of substituents and the type of salt on the NMR parameters of basic bicyclic fluoroquinolone and fluoronaphthyridone ring systems. For this purpose, the 1 H-and 13 C-one-and two-dimensional homo-and heteronuclear NMR methods were used. The analysis of 1 H-and 13 C-NMR spectra confirmed the structures of investigated fluoroquinolone salts. Relationships between 1 H-and 13 C-NMR chemical shifts of fluoronaphthyridone and fluoroquinolone ring systems, calculated molecular descriptors (MDs) and drug-likeness scores (DLSs), computed for monoprotonic cations of investigated fluoroquinolone salts (TVAH + , PFXH + and CIPH + ), were also explored. The topological polar surface area (TPSA), the parameter of lipophilicity (miLogP), the relative molecular mass (M r ) and the volume (V) of computed molecular descriptors (MDs), as well as the G protein-coupled receptor ligand-likeness (GPCR ligand-ls), the ion channel ligand-likeness (ICL-ls), the kinase inhibitor-likeness (KI-ls) and the nuclear receptor ligand-likeness (NRL-ls) were used in this study. The 1 H-NMR chemical shifts of protons in COOH, H5 and NH n + , as well as 13 C-NMR chemical shifts of C4, C5 and C11 shown to be good parameters in exploration of property-property and property-drug-likeness relationships for investigated fluoroquinolone salts. Thus, collinear relationships of 1 H-NMR chemical shifts of protons in COOH, H5 and NH n + with TPSA and miLogP, as well as with GPCR ligand-ls, KI-ls and NRL-ls were revealed (d, ppm H in COOH vs. TPSA, d, d, ppm H5 vs.

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“…3. Obtained results are in good agreement with previously published data for these fluoroquinolones in the zwitter-ion or free base form (17,24,25).…”

Section: Computation and Data Processingsupporting

confidence: 91%

Effects of substituents on the NMR features of basic bicyclic ring systems of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters

Takač¹

2010

Acta Pharmaceutica

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“…The crystal structure of ciprofloxacin alone showed that the cyclopropane ring is located almost perpendicular to the plane of the chinolon ring [16,17]. This fixed position of the cyclopropane ring could be the same in the HSA [14]. Therefore, the binding groove of HSA would fit to a band of atoms starting from H5, extending to the carboxylate and ending with H2 and one face of the cyclopropane ring (Ha/Ha ).…”

Section: Resultsmentioning

confidence: 95%

“…Because the solubility is decreased when compared to acidic conditions [11], ciprofloxacin has been typically analysed by NMR under non-physiological conditions (acidic D 2 O, DMSO [12][13][14]). As a comparison the proton chemical shifts of this study and of Sakai et al [15] are shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Characterization of the binding epitope of ciprofloxacin bound to human serum albumin

Fick

Reinscheid

2006

Journal of Pharmaceutical and Biomedical Analysis

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“…nm aer modication may be attributed to the formation of aggregated structures. 35 The peak at 2.8 ppm corresponds to the methylene group of GA. 25,31 To support this observation, DLS measurements on CDs and CDGAC were carried out.…”

Section: Resultsmentioning

confidence: 99%

Functionalized carbon dots enable simultaneous bone crack detection and drug deposition

et al. 2014

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Recently, carbon dots (CDs) have become one of the most sought nanomaterials for biological applications owing to their excellent fluorescence, chemical inertness and biocompatibility. This article depicts the generation of a fluorescent nano probe using CDs for viewing bone cracks and simultaneous drug delivery to the cracked or infected sites. Water soluble polyethylene glycol diamine capped CDs were conjugated with glutamic acid (GA), a calcium targeting ligand, and ciprofloxacin as an antibacterial model drug. Physicochemical characterizations, cytotoxicity evaluation, haemolysis and antibacterial activity studies of the synthesized probe and its ability to target onto bone are demonstrated. Our results indicate that there is significant scope in developing functionalized CDs as theranostic agents.

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¹H, ¹³C and ¹⁵N NMR spectra of ciprofloxacin

Abstract: 1H NMR assignment, including the values of delta(H) and J(H,H) for the cyclopropane moiety, and 13C NMR and 15N NMR spectral data for ciprofloxacin are presented.

Cited by 23 publications

References 9 publications

Effects of substituents on the NMR features of basic bicyclic ring systems of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters

Effects of substituents on the NMR features of basic bicyclic ring systems of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters

Characterization of the binding epitope of ciprofloxacin bound to human serum albumin

Functionalized carbon dots enable simultaneous bone crack detection and drug deposition

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