Decavanadate-Bearing Guanidine Derivatives Developed as Antimicrobial and Antitumor Species

• Published in: International journal of molecular sciences 2023-12, Vol.24 (24), p.17137
• Main Authors: Dumitrescu, Andreea, Maxim, Catalin, Badea, Mihaela, Rostas, Arpad Mihai, Ciorîță, Alexandra, Tirsoaga, Alina, Olar, Rodica
• Format: Article
• Language: English
• Subjects: antimicrobial; Biological activity; Cancer; Cytotoxicity; decavanadate; DFT calculations; Drug resistance; Gram-positive bacteria; guanidine; guanylurea; Hydrogen bonds; Insulin; Melanoma; Reactive oxygen species; Severe acute respiratory syndrome coronavirus 2
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms242417137

To obtain biologically active species, a series of decavanadates (Hpbg) [H V O ]·6H O ( ) (Htbg) [H V O ]·6H O; ( ) (Hgnd) (Hgnu) [V O ]; ( ) (Hgnu) [V O ]·2H O; and ( ) (pbg = 1-phenyl biguanide, tbg = 1-( -tolyl)biguanide, gnd = guanidine, and gnu = guanylurea) were synthesized and characterized by several spectroscopic techniques (IR, UV-Vis, and EPR) as well as by single crystal X-ray diffraction. Compound ( ) crystallizes in space group -1 while ( ) and ( ) adopt the same centrosymmetric space group 21/n. The unusual signal identified by EPR spectroscopy was assigned to a charge-transfer π(O)→d(V) process. Both stability in solution and reactivity towards reactive oxygen species (O and OH·) were screened through EPR signal modification. All compounds inhibited the development of , , , and bacterial strains in a planktonic state at a micromolar level, the most active being compound ( ). However, the experiments conducted at a minimal inhibitory concentration (MIC) indicated that the compounds do not disrupt the biofilm produced by these bacterial strains. The cytotoxicity assayed against A375 human melanoma cells and BJ human fibroblasts by testing the viability, lactate dehydrogenase, and nitric oxide levels indicated compound ( ) as the most active in tumor cells.