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- Title
A family of amphiphilic dioxidovanadium(V) hydrazone complexes as potent carbonic anhydrase inhibitors along with anti-diabetic and cytotoxic activities.
- Authors
Ghosh, Chiranjit; Patra, Debashis; Bala, Niranjan; Majumder, Indira; Sepay, Nayim; Mukhopadhyay, Prabuddha; Das, Sukhen; Kundu, Rita; Drew, Michael G. B.; León, Armando Rafael; Ghosh, Tapas; Pradhan, Manik
- Abstract
A family of dioxidovanadium(V) complexes (1–4) of the type [Na(H2O)x]+[VVO2(HL1−4)]− (x = 4, 4.5 and 7) where HL2− represents the dianionic form of 2-hydroxybenzoylhydrazone of 2-hydroxyacetophenone (H2L1, complex 1), 2-hydroxy-5-methylacetophenone (H2L2, complex 2), 2-hydroxy-5-methoxyacetophenone (H2L3, complex 3) and 2-hydroxy-5-chloroacetophenone (H2L4, complex 4), have been synthesized and characterized by analytical and spectral methods. These complexes exhibited the potential abilities to suppress the erythrocytes carbonic anhydrase enzymatic activity in type 1 and type 2 diabetic patients (in vitro), promising antidiabetic activity against T2 diabetic mice (in vivo). They also exhibited significant cytotoxic activity against cervical cancer (SiHa) cells (in vitro) as the IC50 value of complexes 1, 2 and 4 is substantially lower than the value found for cisplatin while that of 3 is comparable and follow the order: 4 < 1 < 2 < 3 and can kill the cells by apoptosis via the generation of reactive oxygen species (ROS). The complexes are soluble both in water and octanol media and also non-toxic at working concentrations. The antidiabetic activity of these four complexes follows the order: 4 > 2 > 1 > 3 while both the carbonic anhydrase and cytotoxic activity follow the order: 4 > 1 > 2 > 3 suggesting that complex 4, containing electron withdrawing Cl atom is the most reactive while 3 with electron donating OCH3 group is the least reactive species. The molecular docking study on hCA-I and hCA-II demonstrates that complexes interact via hydrogen bonding as well as different types of π-stacking.
- Subjects
CARBONIC anhydrase inhibitors; CARBONIC anhydrase; REACTIVE oxygen species; HYDRAZONE derivatives; CISPLATIN; HYDROGEN bonding; MOLECULAR docking
- Publication
BioMetals, 2022, Vol 35, Issue 3, p499
- ISSN
0966-0844
- Publication type
Article
- DOI
10.1007/s10534-022-00384-7