Investigating lipophilicity of boron dipyrromethenes using experimental and computational approaches

• Published in: Chemical Data Collections Vol. 51; p. 101129
• Main Authors: Horetski, Matvey S., Chylik, Yuliya A., Shkumatov, Vladimir M.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.06.2024
• Subjects: BODIPY; Electronic structure calculations; Fragment-based methods; Lipophilicity; Molecular surface area; Fragment-based methods; Molecular surface area; BODIPY; Lipophilicity; Electronic structure calculations
• ISSN: 2405-8300; 2405-8300
• DOI: 10.1016/j.cdc.2024.101129

•Facile modifications offer a convenient approach to modulate BODIPY lipophilicity.•LogP3 and ALogPS show accuracy in predicting BODIPY 1-octanol/water partitioning.•The type of SMILES notation can impact the accuracy of fragment-based methods.•Boron atom contributes to polar molecular surface area of BODIPY dyes. BODIPY fluorescent dyes is a versatile class of molecules with a wide spectrum of applications, particularly in biological imaging and sensing. For these applications, lipophilicity is a critical factor that influences the compound's solubility, biodistribution, and biological interactions. This study investigated the synthesis and lipophilicity characterization of a series of BODIPY fluorescent dyes. The lipophilicity of the compounds was determined by high-performance liquid chromatography and compared to the predictions of theoretical methods. The results demonstrated the effectiveness of some fragment-based methods in BODIPY's lipophilicity calculation. The role of hydrophobic surface area in molecular lipophilicity was also investigated. The findings of this study provide insights into the structure-property relationships of BODIPY dyes and can be used to design derivatives with desired lipophilicity for specific applications. [Display omitted]