Citation: Hongmei Yu, Baoxi Zhang, Meiju Liu, Cheng Xing, Guorong He, Li Zhang, Ningbo Gong, Yang Lu, Guanhua Du. Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers[J]. Chinese Chemical Letters, ;2024, 35(5): 109032. doi: 10.1016/j.cclet.2023.109032 shu

Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers

Hongmei Yu ^{a, 1} ,
Baoxi Zhang ^{a, 1} ,
Meiju Liu ^a ,
Cheng Xing ^a ,
Guorong He ^b ,
Li Zhang ^a ,
Ningbo Gong ^{a, *,} ,
Yang Lu ^{a, *,} ,
Guanhua Du ^b

a.
Beijing Key Laboratory of Polymorphic Drugs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Beijing City Key Laboratory of Drug Target Identification and Drug Screening, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

gnb@imm.ac.cn

luy@imm.ac.cn

Received Date: 16 February 2023
Revised Date: 1 August 2023
Accepted Date: 31 August 2023
Available Online: 4 September 2023

Figures(8)

The virtual cocrystal screening approach based on molecular electrostatic potential surface (MEPS) maps is a fast and feasible computational method to estimate the probability of cocrystal formation by calculating the difference in the interaction site pairing energies of monomers and that of their assemblies prior to experimental screening. In this paper, we report 12 cocrystal forms of temozolomide with mono-, di-, and trihydroxy benzoic acids, namely, 3-hydroxy-, 2,4-dihydroxy-, 2,5-dihydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, and 3,4,5-trihydroxy-benzoic acids, as well as benzoic acid, as pharmaceutical coformers for the first time. 10 single crystals out of the 12 cocrystal forms were obtained and unequivocally determined by single-crystal X-ray diffraction, which clarified spatial arrangements, molecular conformations, and supramolecular synthons. MEPS further gains some insights into the sites of hydrogen bonding interactions for exploring combination patterns in these assemblies. Modulated stability of TMZ was successfully achieved by cocrystallization with these acids.
- Virtual,
- Cocrystal,
- Temozolomide,
- Supramolecular synthon,
- Phenolic acid,
- Stability
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