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Isoquinoline-1,3,4-trione derivatives inactivate caspase-3 by generation of reactive oxygen species.

Du JQ, Wu J, Zhang HJ, Zhang YH, Qiu BY, Wu F, Chen YH, Li JY, Nan FJ, Ding JP, Li J
J Biol Chem 283 30205-15 (2008)
Related entries: 3deh, 3dei, 3dek

Cited: 33 times
EuropePMC logo PMID: 18768468

Abstract

Caspase-3 is an attractive therapeutic target for treatment of diseases involving disregulated apoptosis. We report here the mechanism of caspase-3 inactivation by isoquinoline-1,3,4-trione derivatives. Kinetic analysis indicates the compounds can irreversibly inactivate caspase-3 in a 1,4-dithiothreitol (DTT)- and oxygen-dependent manner, implying that a redox cycle might take place in the inactivation process. Reactive oxygen species detection experiments using a chemical indicator, together with electron spin resonance measurement, suggest that ROS can be generated by reaction of isoquinoline-1,3,4-trione derivatives with DTT. Oxygen-free radical scavenger catalase and superoxide dismutase eliciting the inactivation of caspase-3 by the inhibitors confirm that ROS mediates the inactivation process. Crystal structures of caspase-3 in complexes with isoquinoline-1,3,4-trione derivatives show that the catalytic cysteine is oxidized to sulfonic acid (-SO(3)H) and isoquinoline-1,3,4-trione derivatives are bound at the dimer interface of caspase-3. Further mutagenesis study shows that the binding of the inhibitors with caspase-3 appears to be nonspecific. Isoquinoline-1,3,4-trione derivative-catalyzed caspase-3 inactivation could also be observed when DTT is substituted with dihydrolipoic acid, which exists widely in cells and might play an important role in the in vivo inactivation process in which the inhibitors inactivate caspase-3 in cells and then prevent the cells from apoptosis. These results provide valuable information for further development of small molecular inhibitors against caspase-3 or other oxidation-sensitive proteins.

Reviews - 3dej mentioned but not cited (1)

  1. Small Molecule Active Site Directed Tools for Studying Human Caspases. Poreba M, Szalek A, Kasperkiewicz P, Rut W, Salvesen GS, Drag M. Chem Rev 115 12546-12629 (2015)

Articles - 3dej mentioned but not cited (9)

  1. Isoquinoline-1,3,4-trione derivatives inactivate caspase-3 by generation of reactive oxygen species. Du JQ, Wu J, Zhang HJ, Zhang YH, Qiu BY, Wu F, Chen YH, Li JY, Nan FJ, Ding JP, Li J. J Biol Chem 283 30205-30215 (2008)
  2. Kaempferol mitigates Endoplasmic Reticulum Stress Induced Cell Death by targeting caspase 3/7. Abdullah A, Ravanan P. Sci Rep 8 2189 (2018)
  3. Aloin induced apoptosis by enhancing autophagic flux through the PI3K/AKT axis in osteosarcoma. He J, Zhang W, Zhou X, Yan W, Wang Z. Chin Med 16 123 (2021)
  4. Baicalein Alleviates Osteoarthritis Progression in Mice by Protecting Subchondral Bone and Suppressing Chondrocyte Apoptosis Based on Network Pharmacology. Yi N, Mi Y, Xu X, Li N, Zeng F, Yan K, Tan K, Kuang G, Lu M. Front Pharmacol 12 788392 (2021)
  5. Application of the Movable Type Free Energy Method to the Caspase-Inhibitor BindingAffinity Study. Xue S, Liu H, Zheng Z. Int J Mol Sci 20 E4850 (2019)
  6. Neutrophil Immunomodulatory Activity of Nerolidol, a Major Component of Essential Oils from Populus balsamifera Buds and Propolis. Schepetkin IA, Özek G, Özek T, Kirpotina LN, Kokorina PI, Khlebnikov AI, Quinn MT. Plants (Basel) 11 3399 (2022)
  7. The Mechanism and Experimental Validation of Forsythoside A in the Treatment of Male Infertility Were Analyzed Based on Network Pharmacology and Molecular Docking. Ma Z, Liu X, Lu H, Li H, Gao R, Wen R, Tang Z, Yin H, He Y, Yang H. Evid Based Complement Alternat Med 2022 7723358 (2022)
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  1. Photo-induced cycloaddition reactions of α-diketones and transformations of the photocycloadducts. Huang C, Zheng M, Xu J, Zhang Y. Molecules 18 2942-2966 (2013)

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  5. Design, synthesis and evaluation of 1,2-benzisothiazol-3-one derivatives as potent caspase-3 inhibitors. Liu D, Tian Z, Yan Z, Wu L, Ma Y, Wang Q, Liu W, Zhou H, Yang C. Bioorg Med Chem 21 2960-2967 (2013)
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  14. Facile synthesis of spiroisoquinolines based on photocycloaddition of isoquinoline-1,3,4-trione with oxazoles. Huang C, Yu H, Miao Z, Zhou J, Wang S, Fun HK, Xu J, Zhang Y. Org Biomol Chem 9 3629-3631 (2011)
  15. Molecular insight into the role of the leucine residue on the L2 loop in the catalytic activity of caspases 3 and 7. Kang HJ, Lee YM, Jeong MS, Kim M, Bae KH, Kim SJ, Chung SJ. Biosci Rep 32 305-313 (2012)
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