NSAID-Based Coordination Compounds for Biomedical Applications: Recent Advances and Developments
Abstract
:1. Introduction
2. History and Applications of Metallodrugs
2.1. Biometal−NSAID Complexes: A Few Coordination Topics
2.1.1. Copper(II) Complexes of NSAIDs
2.1.2. Cobalt(II) Complexes of NSAIDs
2.1.3. Nickel(II) Complexes of NSAIDs
2.1.4. Manganese(II) Complexes of NSAIDs
2.1.5. Zinc(II) Complexes of NSAIDs
Chemical Formula | NSAID | Chemical Structure | Biological Activity | Ref. | |
---|---|---|---|---|---|
NSAID Ligand | NSAID Coordinating Group | ||||
[Cu(asa)(aroy)(H2O)2] (a) | Aspirin | Acetylated salicylate | (proposed structure) | Weaker antimicrobial activity comparing to free aspirin. | [86] |
[Cu(difl)2(py)2] (b) | Diflunisal | Non-acetylated salicylate | Moderate to strong DNA and albumin binding. | [83] | |
[Cu(nap)(tpy)Cl] (c) | Naproxen | Propionic acid | Hydrolytic DNA cleavage. Moderated cytotoxicity in a human breast cancer cell line (MCF-7). | [84] | |
[Cu(dicl)2(temed)] (d) | Diclofenac | Acetate | Significant reversible affinity for BSA, higher than the free NSAID sodium diclofenac. | [85] | |
[Cu(Hmel)2(dmf)] (e) | Meloxicam | Enolic acid | Possible beneficial effects as anticancer agent due to its anti-proliferative activity. | [87] | |
[Cu(tolf)2(py)2(MeOH)2] (f) | Tolfenamic acid | Anthranilate | Tight binding affinity to BSA and HSA. Scavenging activity (against hydroxyl and superoxide radicals) stronger than free tolfenamic acid. | [88] | |
[Cu(cxb)2Cl2] (g) | Celecoxib | Coxib | (proposed structure) | Inhibitory activity against Cyclooxygenase II. | [89] |
Chemical Formula | NSAID | Chemical Structure | Biological Activity | Ref. | |
---|---|---|---|---|---|
NSAID Ligand | NSAID Coordinating Group | ||||
[Co(asa)(Haroy)(H2O)Cl] (a) | Aspirin | Acetylated salicylate | (proposed structure) | Weaker antimicrobial activity comparing to free aspirin. | [86] |
[Co(difl)2(MeOH)4] (b) | Diflunisal | Non-acetylated salicylate | Radical scavenging ability and DNA and albumin binding. | [90] | |
[Co(nap)2(py)2(H2O)2] (c) | Naproxen | Propionic acid | Good binding affinity to BSA and HSA and to DNA. High scavenging activity against hydroxyl and superoxide radicals. | [91] | |
[Co(dicl)2(py)2(H2O)2] (d) | Diclofenac | Acetate | Antioxidant activity, DNA binding. | [19] | |
[Co(Hmel)2(EtOH)2] (e) | Meloxicam | Enolic acid | DNA biding and photocleavage of pUC57 plasmid DNA. | [92] | |
[Co(tolf)2(bipyam)] (f) | Tolfenamic acid | Anthranilate | Good binding affinity to BSA and HSA and higher affinity to bind DNA comparing to free tolfenamic acid. | [93] | |
[Co(cxb)2Cl2] (g) | Celecoxib | Coxib | (proposed structure) | Inhibitory activity against cyclooxygenase II | [89] |
Chemical Formula | NSAID | Chemical Structure | Biological Activity | Ref. | |
---|---|---|---|---|---|
NSAID Ligand | NSAID Coordinating Group | ||||
[Ni(asa)(aroy)(H2O)2] (a) | Aspirin | Acetylated salicylate | (proposed structure) | Weaker antimicrobial activity comparing to free aspirin. | [86] |
[Ni(difl)2(MeOH)4] (b) | Diflunisal | Non-acetylated salicylate | Albumin and DNA interaction, antioxidant activity. | [31] | |
[Ni(nap)2(phen)(H2O)] (c) | Naproxen | Propionic acid | Significant affinity for BSA and HSA, DNA-binding and antioxidant activity. | [94] | |
[Ni(dicl)(Hdicl)(Hpko)2](dicl) CH3OH•0.6H2O (d) | Diclofenac | Acetate | DNA and albumin binding. | [99] | |
[Ni(Hmel)2(H2O)2]•2H2O (e) | Meloxicam | Enolic acid | (theoretical structure) | Greater antibacterial activity than free meloxicam. | [100] |
[Νi(tolf)2(bipy)(CH3OH)2] (f) | Tolfenamic acid | Anthranilate | Significant affinity to bind BSA and HSA. Potent scavenging activity of hydroxyl and superoxide radicals. Better DNA binder comparing to free tolfenamic acid. | [101] | |
[Ni(cxb)2Cl2] (g) | Celecoxib | Coxib | (proposed structure) | Inhibitory activity against cyclooxygenase II. | [89] |
Chemical Formula | NSAID | Chemical Structure | Biological Activity | Ref. | |
---|---|---|---|---|---|
NSAID Ligand | NSAID Coordinating Group | ||||
[{Mn(asa)(nic)}2(H2O)Cl]Cl•2H2O (a) | Aspirin | Acetylated salicylate | (proposed structure) | Comparing to standard (ascorbic acid) similar antioxidant activities were observed for the Mn(II) complex and both free drugs. | [102] |
[Mn(nap)2(py)2(H2O)2] (b) | Naproxen | Propionic acid | Selective scavenging activity of hydroxyl and superoxide radicals. Binds tighter to CT-DNA than the corresponding free NSAID and exhibits significant affinity to BSA and HSA. | [95] | |
[Mn3(dicl)6(phen)2(MeOH)] (c) | Diclofenac | Acetate | Higher binding affinities to BSA and HSA comparing to those of free sodium diclofenac. Significant ability to scavenge ABTS and hydroxyl radicals. Potent inhibitory activity of soybean lipoxygenase. | [103] | |
[Mn(Hmel)(Gly)(H2O)2]•5H2O (d) | Meloxicam | Enolic acid | (DFT–optimized geometry) | No antifungal activity against A. niger, but antibacterial activities comparing to amoxycillin/clavulanic and cetaxime (antibacterial agents). | [104] |
[Mn(tolf)2(phen)(H2O)] (e) | Tolfenamic acid | Anthranilate | High scavenging activity against superoxide and hydroxyl radicals. It can also inhibit the activity of soybean lipoxygenase and shows tight binding affinity for BSA and HAS. | [96] |
Chemical Formula | NSAID | Chemical Structure | Biological Activity | Ref. | |
---|---|---|---|---|---|
NSAID Ligand | NSAID Coordinating Group | ||||
[Zn(asa)2] (a) | Aspirin | Acetylated salicylate | No crystal structure has been published to the best of our knowledge. | After oral administration to rats it caused a decrease in blood glucose levels, and type-2 diabetes-induced damage in rat cardiac tissue was alleviated. This complex also showed a better post-ischemic myocardial dysfunction- preventing effect than free aspirin. | [105,106,107] |
[Zn(difl)2(bipy)] (b) | Diflunisal | Non-acetylated salicylate | The complex is a more active radical scavenger and lipooxigenase inhibitor than free diflunisal. The complex also binds strongly to albumins. | [62] | |
[Zn(nap)2(N3)2]Na2 (c) | Naproxen | Propionic acid | The complex shows antibacterial activity against Gram-positive (S. aureus) and Gram-negative (E. coli) bacterial strains. | [80] | |
[Zn2(dicl)4(nic)2] (d) | Diclofenac | Acetate | Improved solubility of the complex in comparision with free NSAID. The complex probably interacts with the grooves of the secondary structure of CT-DNA by electrostatic attraction. | [97] | |
[Zn(Hmel)2(EtOH)2] (e) | Meloxicam | Enolic acid | The complex may interact with DNA through an electrostatic mode and promoted the photo cleavage of a plasmid DNA. | [92] | |
[Zn3(tolf)6(CH3OH)2] (f) | Tolfenamic acid | Anthranilate | Good binding constants for BSA and HSA, suggesting a possible release from the serum albumin to the target cell. | [98] |
3. Biological Effects of the Metal Complexes
3.1. Anti-Tumor Activity
3.2. Antimicrobial Activity
3.3. Antioxidant Activity
4. Interactions with Biomolecules
4.1. Nucleic Acids
Interactions of Cu(II)/Co(II)/Ni(II)/Mn(II)/Zn(II)−NSAID Complexes with DNA
4.2. Proteins
Interactions of Cu(II)/Co(II)/Ni(II)/Mn(II)/Zn(II)−NSAID Complexes with Serum Albumins
5. Conclusions
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
References
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NSAIDs | Kb (M−1) | Cu(II) | Kb (M−1) | Co(II) | Kb (M−1) | Ni(II) | Kb (M−1) | Mn(II)/ Zn(II) | Kb (M−1) |
---|---|---|---|---|---|---|---|---|---|
Diflunisal (difl) | 3.08 (±0.15) × 103 | Cu(II)-difl | 7.36 (±0.11) × 104 | Co(II)-difl | 2.26 (±0.12) × 105 | Ni(II)-difl | 2.00 (±0.17) × 105 | - | - |
Naproxen (nap) | 2.67 (±0.22) × 104 | Cu(II)-nap | 2.24 (±0.25) × 105 | Co(II)-nap | 3.15 (±0.57) × 104 | Ni(II)-nap | 1.54 (±0.12) × 105 | Mn(II)-nap | 2.29 (±0.13) × 105 |
Diclofenac (dicl) | 3.16 (±0.14) × 104 | - | - | Co(II)-dicl | 6.41 (±2.04) × 105 | Ni(II)-dicl | 3.63 (±0.12) × 105 | - | - |
Meloxicam (melox) | 5.5 × 103 | - | - | Co(II)-melox | 1.15 × 104 | - | - | Zn(II)-melox | 5.34 × 104 |
Tolfenamic acid (tolf) | 5.00 (±0.10) × 104 | - | - | Co(II)-tolf | 6.78 (±0.50) × 105 | Ni(II)-tolf | 2.35 (±0.12) × 105 | - | - |
NSAIDs | K (M−1) | Cu(II) | K (M−1) | Co(II) | K (M−1) | Ni(II) | K (M−1) | Mn(II)/ Zn(II) | K (M−1) |
---|---|---|---|---|---|---|---|---|---|
Diflunisal (difl) | 1.22 (±0.07) × 105 | Cu(II)-difl | 7.36 (±0.11) × 104 | Co(II)-difl | 2.26 (±0.12) × 105 | Ni(II)-difl2 | 1.41 (±0.08) × 105 | Zn(II)-dilf2 | 9.94 (±0.35) × 105 |
Naproxen (nap) | 5.35 × 103 | - | - | Co(II)-nap | 3.15 (±0.57) × 104 | Ni(II)-nap2 | 2.73 (±0.25) × 104 | Mn(II)-nap2 | 6.50 (±0.30) × 104 |
Diclofenac (dicl) | 3.55 × 103 | Cu(II)-dicl | 2.23 (±0.09) × 103 | Co(II)-dicl | 6.41 (±2.04) × 105 | Ni(II)-dicl | 2.54 (±0.27) × 104 | Mn(II)-dicl | 1.86 (7) × 105 |
Tolfenamic acid (tolf) | 3.12 (±0.25) × 105 | Cu(II)-tolf | 4.16 (±0.24) × 105 | Co(II)-tolf | 6.78 (±0.50) × 105 | Ni(II)-tolf2 | 2.23 (±0.11) × 105 | Mn(II)-tolf2 | 3.56 (±0.13) × 105 |
Zn(II)-tolf | 4.12 × 105 |
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Santos, A.C.F.; Monteiro, L.P.G.; Gomes, A.C.C.; Martel, F.; Santos, T.M.; Ferreira, B.J.M.L. NSAID-Based Coordination Compounds for Biomedical Applications: Recent Advances and Developments. Int. J. Mol. Sci. 2022, 23, 2855. https://doi.org/10.3390/ijms23052855
Santos ACF, Monteiro LPG, Gomes ACC, Martel F, Santos TM, Ferreira BJML. NSAID-Based Coordination Compounds for Biomedical Applications: Recent Advances and Developments. International Journal of Molecular Sciences. 2022; 23(5):2855. https://doi.org/10.3390/ijms23052855
Chicago/Turabian StyleSantos, Ariana C. F., Luís P. G. Monteiro, Adriana C. C. Gomes, Fátima Martel, Teresa M. Santos, and Bárbara J. M. Leite Ferreira. 2022. "NSAID-Based Coordination Compounds for Biomedical Applications: Recent Advances and Developments" International Journal of Molecular Sciences 23, no. 5: 2855. https://doi.org/10.3390/ijms23052855