Terahertz and Raman Spectroscopic Investigation of Anti-tuberculosis Drug-Drug Cocrystallization Involving 4-aminosalicylic Acid and Pyrazinamide

Zhang, Ziming; Fang, Jiyuan; Bo, Yanhua; Xue, Jingling; Liu, Jianjun; Hong, Zhi; Du, Yong

doi:10.1016/j.molstruc.2020.129547

Cited by 14 publications

(3 citation statements)

References 38 publications

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“…However, it is reported that 40% of patients have reported nongouty polyarthralgia as a side effect (E ´vora et al, 2011). Cocrystals of pyrazinamide with 3-hydroxybenzoic acid (Wang et al, 2019), adipic acid, sebacic acid, trans-aconitic acid, citric acid (Wang et al, 2015) and 4-aminosalicylic acid (Zhang et al, 2021) were reported to alter the physicochemical properties. Complexes of PYZ were also reported with improved biological activities (Ali et al, 2019;Quaresma et al, 2021;Stenger-Smith et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

New cocrystals of heterocyclic drugs: structural, antileishmanial, larvicidal and urease inhibition studies

Murtaza

Khan

Farooq

et al. 2023

Acta Crystallogr C Struct Chem

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Many heterocycles have been developed as drugs due to their capacity to interact productively with biological systems. The present study aimed to synthesize cocrystals of the heterocyclic antitubercular agent pyrazinamide (PYZ, 1, BCS III) and the commercially available anticonvulsant drug carbamazepine (CBZ, 2, BCS class II) to study the effect of cocrystallization on the stability and biological activities of these drugs. Two new cocrystals, namely, pyrazinamide–homophthalic acid (1/1) (PYZ:HMA, 3) and carbamazepine–5-chlorosalicylic acid (1/1) (CBZ:5-SA, 4), were synthesized. The single-crystal X-ray diffraction-based structure of carbamazepine–trans-cinnamic acid (1/1) (CBZ:TCA, 5) was also studied for the first time, along with the known cocrystal carbamazepine–nicotinamide (1/1) (CBZ:NA, 6). From a combination drug perspective, these are interesting pharmaceutical cocrystals to overcome the known side effects of PYZ (1) therapy, and the poor biopharmaceutical properties of CBZ (2). The purity and homogeneity of all the synthesized cocrystals were confirmed by single-crystal X-ray diffraction, powder X-ray diffraction and FT–IR analysis, followed by thermal stability studies based on differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Detailed intermolecular interactions and the role of hydrogen bonding towards crystal stability were evaluated quantitatively via Hirshfeld surface analysis. The solubility of CBZ at pH 6.8 and 7.4 in 0.1 N HCl and H2O were compared with the values of cocrystal CBZ:5-SA (4). The solubility of CBZ:5-SA was found to be significantly improved at pH 6.8 and 7.4 in H2O. All the synthesized cocrystals 3–6 exhibited a potent urease inhibition (IC50 values range from 17.32 ± 0.89 to 12.3 ± 0.8 µM), several times more potent than standard acetohydroxamic acid (IC50 = 20.34 ± 0.43 µM). PYZ:HMA (3) also exhibited potent larvicidal activity against Aedes aegypti. Among the synthesized cocrystals, PYZ:HMA (3) and CBZ:TCA (5) were found to possess antileishmanial activity against the miltefosine-induced resistant strain of Leishmania major, with IC50 values of 111.98 ± 0.99 and 111.90 ± 1.44 µM, respectively, in comparison with miltefosine (IC50 = 169.55 ± 0.20 µM).

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Section: Introductionmentioning

confidence: 99%

New cocrystals of heterocyclic drugs: structural, antileishmanial, larvicidal and urease inhibition studies

Murtaza

Khan

Farooq

et al. 2023

Acta Crystallogr C Struct Chem

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“…Most of the studies of cocrystals relating to INH above are implemented by a few traditional ways such as differential scanning calorimetry (DSC), X-ray diffraction (XRD), which are time-consuming in some cases or not detailed enough about the structures of molecules and the influence of intra-molecular and/or inter-molecular interactions within the cocrystals [ 22 ]. Thus, the vibrational spectroscopy including Fourier transformation infrared (FTIR), Raman and the emerging terahertz (THz) spectroscopy with high sensitivity and selectivity [ 23 , 24 ], providing a wealth of information about the structure of molecules, intra-molecular and/or inter-molecular interactions [ 25 ], is considered to be beneficial to solid-state characterization.…”

Section: Introductionmentioning

confidence: 99%

Terahertz and Raman Spectroscopic Investigation of Monohydrate Cocrystal of Antitubercular Isoniazid with Protocatechuic Acid

Fang

Zhang

et al. 2021

Pharmaceutics

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Pharmaceutical cocrystal provides an alternative modification strategy for the formulation development of drugs owning to their potential ability to improve the physicochemical properties of active pharmaceutical ingredients (APIs) efficiently by changing inter-molecular interactions between raw materials. Isoniazid (INH) is an indispensable main drug for the treatment of tuberculosis, but its tablet formulation is unstable and prone to degradation. In the present study, the monohydrate cocrystal of INH and protocatechuic acid (PA) was prepared by solvent evaporation using PA as cocrystal former to optimize the properties of INH. The parent materials and corresponding 1:1 molar ratio INH-PA monohydrate cocrystal have been characterized by the terahertz time-domain (THz-TDS) and Raman spectroscopy. The THz absorption spectra displayed that there were obvious differences between the peaks of experimental cocrystal and the parent materials, and the same situation was found in Raman vibrational spectra. In addition, density functional theory (DFT) was applied to simulating and optimizing the structure of INH-PA monohydrate cocrystal and supplied corresponding vibrational modes. Our results provided a unique method to characterize the formation of INH-PA monohydrate cocrystal at the molecular-level and a lot of information about cocrystal structure and intra-molecular and/or inter-molecular hydrogen bond interactions in the emerging pharmaceutical cocrystal fields.

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“…Zhu et al used DFT to calculate the interaction between 5-ASA as a non-steroid anti-inflammatory drug and B12N12, AlB11N12, and GaB11N12 nanoclusters to find a new drug delivery system [17]. Zhang et al calculated the antitubercular drug-drug cocrystal structures of 4-ASA and pyrazinamide using DFT, and gave their terahertz and Raman spectral vibrational mode assignments [18].…”

mentioning

confidence: 99%

Qualitative and quantitative study of intermolecular weak interactions for aminosalicylic acid isomers by terahertz spectroscopy

Tang

et al. 2022

Int J of Quantum Chemistry

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In the field of chemical science, the development of new drugs, the formation of crystals and molecular clusters, and the optimization of drug safety and efficacy are all closely related to weak molecular interactions. In this paper, the salicylic drugs 4-aminosalicylic acid (4-ASA) and 5-aminosalicylic acid (5-ASA) are used as the research objects. First, the terahertz (THz) absorption spectra of the two isomers were measured in the range of .4-2.0 THz by terahertz time-domain spectroscopy (THz-TDS). Then the unit cells were calculated by using density functional theory (DFT). We found that the characteristic absorption peaks of the experimental spectra were basically consistent with the theoretical calculation. In addition, under the solvent model, the free energy of dissolution and the free energy of the systems were considered and calculated, and the results showed that solvation had a certain influence on the position and intensity of spectral absorption peaks. In order to further explore the origin of the characteristic absorption peaks, the vibrational properties of the unit cell model were analyzed using the potential energy distribution (PED) method. At the same time, the weak interactions of the system were qualitatively and quantitatively analyzed by interaction region indicator (IRI) and energy decomposition analysis based on forcefield (EDA-FF) methods, respectively. The results show that the absorption peaks of 4-ASA and 5-ASA are mainly derived from the vibration mode of dihedral angle torsion. The weak interactions in the 4-ASA are dominated by dispersion, while they are dominated by electrostatic and dispersion in the 5-ASA. Therefore, it is an effective way to identify isomers and study intermolecular weak interactions by using THz-TDS combined with PED, IRI, and EDA-FF.

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Terahertz and Raman Spectroscopic Investigation of Anti-tuberculosis Drug-Drug Cocrystallization Involving 4-aminosalicylic Acid and Pyrazinamide

Cited by 14 publications

References 38 publications

New cocrystals of heterocyclic drugs: structural, antileishmanial, larvicidal and urease inhibition studies

New cocrystals of heterocyclic drugs: structural, antileishmanial, larvicidal and urease inhibition studies

Terahertz and Raman Spectroscopic Investigation of Monohydrate Cocrystal of Antitubercular Isoniazid with Protocatechuic Acid

Qualitative and quantitative study of intermolecular weak interactions for aminosalicylic acid isomers by terahertz spectroscopy

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