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- 검색키워드
- 저자 : CheongCheon Lee (검색결과 3 건)
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Cocrystal Formation via Resorcinol-Urea Interactions: Naringenin and Carbamazepine
Lee, CheongCheon,Cho, A. Young,Yoon, Woojin,Yun, Hoseop,Kang, Jeong Won,Lee, Jonghwi The American Chemical Society 2019 CRYSTAL GROWTH AND DESIGN Vol.19 No.7
<P>Improving the stability, bioavailability, and processability of active pharmaceutical ingredients (APIs) has been the key research goal in the field of pharmaceutical crystallization. Cocrystallization has been considered as an effective route to achieve this goal, and intense research over decades has revealed cocrystals of many APIs. However, most cocrystal formers have been designed based primarily on their molecular interactions not their health benefits. Herein, we choose naringenin (N), a natural flavonoid, as a novel cocrystal former as it has many health efficacies and the ability to form specific interactions. At a 1:1 stoichiometric ratio, N successfully forms a cocrystal with carbamazepine (CBZ), whose plasma concentration is known to be improved by natural flavonoids such as N. The resorcinol functional group of N and the urea functional group of CBZ are connected through hydrogen bonds, and the improved stability of the cocrystal seems to originate from this structure. The melting temperature of the cocrystal is 262 °C, which is higher than those of CBZ and N, and the better stability of the cocrystal is further confirmed by the observation of enhanced hydration stability (up to 30 days at 93% RH). This novel strategy of cocrystallization using natural flavonoids could improve the commercialization potential of API cocrystals.</P><P>Natural flavonoids exhibit unique molecular interactions via resorcinol, pyrogallol, or catechol groups. We found that naringenin, which has a resorcinol group, could form a unique cocrystal with carbamazepine, which has a urea group. This presents a new direction for the development of drug cocrystals.</P> [FIG OMISSION]</BR>
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Molecular structures of flavonoid co-formers for cocrystallization with carbamazepine
CheongCheon Lee,Ju Hee Lim,A. Young Cho,Woojin Yoon,Hoseop Yun,Jeong Won Kang,Jonghwi Lee 한국공업화학회 2023 Journal of Industrial and Engineering Chemistry Vol.118 No.-
Flavonoids have numerous beneficial effects on human health, such as antioxidant capacity and immuneboostingeffects, which make them attractive cocrystal formers for drugs. Previously, a co-crystalbetween carbamazepine (CBZ) and naringenin, a flavonoid, was discovered, but no understanding onthe requirements of cocrystal formers was assessed. Herein, the structural requirement of flavonoidscocrystallization with CBZ was examined using eight different natural flavonoids with planar and bentstructures and 0–4 phenolic groups including the naringenin. The flavonoids without double bonds intheir heterocyclic rings (F1, P2, and N3) formed cocrystals with monoclinic unit cells and a 1:1 CBZ toflavonoid molecular ratio, whereas the flavonoids with double bonds (F1d, C2d, and A3d) did not formcocrystals. F1, P2, and N3 had geometrically bent structures, which enabled the formation of cocrystals. The phenolic groups of flavonoids play an essential role in cocrystal formation with CBZ, undergoingstrong intermolecular interactions. The flavonoid with no phenolic group, F0, could not form a cocrystal. For CF1, CP2, and CN3, the melting temperature, packing coefficient, and hydrogen bonding energy of thecocrystals increased as the number of phenolic groups increased. These results confirm that the phenolicgroups and molecular geometry of flavonoids are critical cocrystal forming factors.
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