Stepwise surface functionalization of graphite/graphene oxide with maleic anhydride and o-phenylenediamine: Spectroscopic structure characterization, cytotoxic activity towards HeLa cells and molecular docking analysis
Journal of Molecular Structure, cilt.1375, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1375
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.molstruc.2026.146892
- Dergi Adı: Journal of Molecular Structure
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC, Academic Search Ultimate (EBSCO), Engineering Source (EBSCO)
- Anahtar Kelimeler: Cytotoxic activity, Graphene oxide, HeLa cells, In silicostudy, Maleic anhydride, o-Phenylenediamine, Surface functionalization
- Sivas Cumhuriyet Üniversitesi Adresli: Evet
Özet
Graphite (G) and graphene oxide (GO) have attracted considerable interest as versatile carbon platforms for surface functionalization and molecular conjugation in biomedical applications. In this study, G and GO surfaces were sequentially functionalized with maleic anhydride (MA) and o-phenylenediamine (o-PDA) to construct novel hybrid conjugated systems. The modification strategy involved a two-step surface functionalization process in which MA was first grafted onto graphene surfaces, followed by nucleophilic ring-opening reactions between the anhydride groups and o-PDA, leading to the formation of amide-linkages. The resulting G-MA, GO-MA, G-MA/o-PDA and GO-MA/o-PDA conjugated materials were synthesized using charge-transfer complexes (CTCs). The spectroscopic analyses confirmed the stepwise functionalization of the graphene frameworks with o-PDA using Fourier transform infrared (FTIR), proton nuclear magnetic resonance (¹HNMR), and transmission electron microscopy (TEM). TEM revealed changes to the graphene surface after modification, indicating the presence of certain components. The synthesized materials were evaluated against HeLa cervical cancer cells and the IC50 values were determined. The GO-MA/o-PDA conjugate exhibited enhanced cytotoxic activity compared with GO and GO-MA, also were evaluated against human thymidylate synthase using molecular docking. A progressive increase in binding affinity was observed upon functionalization with GO-MA/o-PDA showing the strongest interaction (−12.4 kcal/mol) and enhanced interaction diversity. Docking simulations reveal that o-PDA surface functionalization enhances binding behaviour and provides structural insights supporting the observed cytotoxic activity, with functionalization facilitating improved exploration of binding pockets. In conclusion, sequential surface functionalization provides an effective strategy for constructing graphene-based conjugates with potential relevance for further optimization and development in anticancer applications.