|
|
γ-谷氨酰转肽酶促氧化作用在肿瘤进展和顺铂耐药中的研究进展
|
Abstract:
γ-谷氨酰转移酶(Gamma-glutamyl transferase, GGT)是参与谷胱甘肽代谢的关键酶，在恶性肿瘤中通常过表达。GGT在肿瘤细胞中的诱导、表达等过程十分复杂。早期的研究主要集中在GGT的细胞抗氧化防御功能，近年来GGT的促氧化活性逐渐被发现。GGT的促氧化剂可以调节细胞功能，如增殖/凋亡平衡，在肿瘤进展和耐药性方面具有明显而重要的意义。本文对近期关于γ-谷氨酰转移酶在肿瘤进展和顺铂耐药中的研究进行综述。
Gamma-glutamyl transferase (GGT) is a key enzyme involved in glutathione metabolism, whose expression is often significantly increased in human malignancies. The induction and expression of GGT in tumor cells are very complex. Early studies on GGT focused on antioxidant defense function. In recent years, the pro oxidative activity of GGT has been gradually found which can regulate cell function such as proliferative/apoptotic balance with great significance in tumor progression and drug resistance. This paper reviews the recent research on Gamma-glutamyl transferase in tumor progression and cisplatin resistance.
| [1] | 乔杰, 宋艳红. 谷氨酰转肽酶的研究进展[J]. 医学理论与实践, 2019, 32(5): 651-653. |
| [2] | Lim, J.S., Yang, J.H., Chun, B.Y., et al. (2004) Is Serum Gamma-Glutamyltransferase Inversely Associated with Serum Antioxidants as a Marker of Oxidative Stress? Free Radical Biology and Medicine, 37, 1018-1023.
https://doi.org/10.1016/j.freeradbiomed.2004.06.032 |
| [3] | Pastore, A., Federici, G., Bertini, E., et al. (2003) Analysis of Glutathione: Implication in Redox and Detoxification. Clinica Chimica Acta, 333, 19-39. https://doi.org/10.1016/S0009-8981(03)00200-6 |
| [4] | Corti, A., Franzini, M., Paolicchi, A., et al. (2010) Gamma-Glutamyltransferase of Cancer Cells at the Crossroads of Tumor Progression, Drug Resistance and Drug Targeting. Anticancer Research, 30, 1169-1181. |
| [5] | Whitfield, J.B. (2001) Gamma Glutamyl Transferase. Critical Reviews in Clinical Laboratory Sciences, 38, 263-355.
https://doi.org/10.1080/20014091084227 |
| [6] | Pompella, A., De Tata, V., Paolicchi, A., et al. (2006) Expression of Gamma-Glutamyltransferase in Cancer Cells and Its Significance in Drug Resistance. Biochemical Pharmacology, 71, 231-238.
https://doi.org/10.1016/j.bcp.2005.10.005 |
| [7] | Pompella, A., Corti, A., Paolicchi, A., et al. (2007) Gamma-Glutamyltransferase, Redox Regulation and Cancer Drug Resistance. Current Opinion in Pharmacology, 7, 360-366. https://doi.org/10.1016/j.coph.2007.04.004 |
| [8] | Dilda, P.J., Ramsay, E.E., Corti, A., et al. (2008) Metabolism of the Tumor Angiogenesis Inhibitor 4-(N-(S-Glutathi- onylacetyl)Amino) Phenylarsonous Acid. Journal of Biological Chemistry, 283, 35428-35434.
https://doi.org/10.1074/jbc.M804470200 |
| [9] | Roomi, M.W., Gaal, K., Yuan, Q.X., et al. (2006) Preneoplastic Liver Cell Foci Expansion Induced by Thioacetamide Toxicity in Drug-Primed Mice. Experimental and Molecular Pathology, 81, 8-14.
https://doi.org/10.1016/j.yexmp.2006.02.006 |
| [10] | Borud, O., Mortensen, B., Mikkelsen, I.M., et al. (2000) Regulation of Gamma-Glutamyltransferase in Cisplatin-Re- sistant and -Sensitive Colon Carcinoma Cells after Acute Cisplatin and Oxidative Stress Exposures. International Journal of Cancer, 88, 464-468. https://doi.org/10.1002/1097-0215(20001101)88:3<464::AID-IJC20>3.0.CO;2-F |
| [11] | Mikkelsen, I.M., Huseby, N.E., Visvikis, A., et al. (2002) Activation of the Gamma-Glutamyltransferase Promoter 2 in the Rat Colon Carcinoma Cell Line CC531 by Histone Deacetylase Inhibitors Is Mediated Through the Sp1 Binding Motif. Biochemical Pharmacology, 64, 307-315. https://doi.org/10.1016/S0006-2952(02)01116-4 |
| [12] | Daubeuf, S., Duvoix, A., Wellman-Rousseau, M., et al. (2004) Phorbol Ester Regulation of the Human Gamma-Glu- tamyltransferase Gene Promoter. Biochemical and Biophysical Research Communications, 313, 300-307.
https://doi.org/10.1016/j.bbrc.2003.11.121 |
| [13] | Zhang, H., Liu, H., Iles, K.E., et al. (2006) 4-Hydroxynonenal Induces Rat Gamma-Glutamyl Transpeptidase Through Mitogen-Activated Protein Kinase-Mediated Electrophile Response Element/nuclear Factor Erythroid 2-Related Factor 2 Signaling. The American Journal of Respiratory Cell and Molecular Biology, 34, 174-181.
https://doi.org/10.1165/rcmb.2005-0280OC |
| [14] | Pandur, S., Pankiv, S., Johannessen, M., et al. (2007) Gamma-Glutamyltransferase Is Upregulated after Oxidative Stress through the Ras Signal Transduction Pathway in Rat Colon Carcinoma Cells. Free Radical Research, 41, 1376-1384.
https://doi.org/10.1080/10715760701739488 |
| [15] | Daubeuf, S., Accaoui, M.J., Pettersen, I., et al. (2001) Differential Regulation of Gamma-Glutamyltransferase MRNAs in Four Human Tumour Cell Lines. Biochimica et Biophysica Acta, 1568, 67-73.
https://doi.org/10.1016/S0304-4165(01)00201-X |
| [16] | Bouman, L., Sancéau, J., Rouillard, D., et al. (2002) Gamma-Glutamyl Transpeptidase Expression in Ewing’s Sarcoma Cells: Up-Regulation by Interferons. Biochemical Journal, 364, 719-724. https://doi.org/10.1042/bj20011854 |
| [17] | Reuter, S., Schnekenburger, M., Cristofanon, S., et al. (2009) Tumor Necrosis Factor Alpha Induces Gamma-Gluta- myltransferase Expression Via Nuclear Factor-KappaB in Cooperation with Sp1. Biochemical Pharmacology, 77, 397- 411. https://doi.org/10.1016/j.bcp.2008.09.041 |
| [18] | Murata, J., Ricciardi-Castagnoli, P., Dessous L’Eglise Mange, P., et al. (1997) Microglial Cells Induce Cytotoxic Effects toward Colon Carcinoma Cells: Measurement of Tumor Cytotoxicity with a Gamma-Glutamyl Transpeptidase Assay. International Journal of Cancer, 70, 169-174.
https://doi.org/10.1002/(SICI)1097-0215(19970117)70:2<169::AID-IJC6>3.0.CO;2-V |
| [19] | Tsutsumi, M., Sakamuro, D., Takada, A., et al. (1996) Detection of a Unique Gamma-Glutamyl Transpeptidase Messenger RNA Species Closely Related to the Development of Hepatocellular Carcinoma in Humans: A New Candidate for Early Diagnosis of Hepatocellular Carcinoma. Hepatology, 23, 1093-1097.
https://doi.org/10.1053/jhep.1996.v23.pm0008621139 |
| [20] | Sch？fer, C., Fels, C., Brucke, M., et al. (2001) Gamma-Glutamyl Transferase Expression in Higher-Grade Astrocytic Glioma. Acta Oncologica, 40, 529-535. |
| [21] | Paolicchi, A., Pompella, A., Tonarelli, P., et al. (1996) Gamma-Glutamyltranspeptidase Activity in Human Ovarian Carcinoma. Anticancer Research, 16, 3053-3058. |
| [22] | Hanigan, M.H., Frierson, Jr., H.F., Swanson, P.E. and De Young, B.R. (1999) Altered Expression of Gamma-Glutamyl Transpeptidase in Human Tumors. Human Pathology, 30, 300-305. https://doi.org/10.1016/S0046-8177(99)90009-6 |
| [23] | Prezioso, J.A., Wang, N., Duty, L., et al. (1993) Enhancement of Pulmonary Metastasis Formation and Gamma-Glu- tamyltranspeptidase Activity in B16 Melanoma Induced by Differentiation in Vitro. Clinical & Experimental Metastasis, 11, 263-274. https://doi.org/10.1007/BF00121169 |
| [24] | Staudigl, C., Concin, N., Grimm, C., et al. (2015) Prognostic Relevance of Pretherapeutic Gamma-Glutamyltransferase in Patients with Primary Metastatic Breast Cancer. PLoS ONE, 10, Article ID: e0125317.
https://doi.org/10.1371/journal.pone.0125317 |
| [25] | 张义静, 马莎, 魏晋, 曹希亮, 陈伟, 祁岳坤. 肾癌患者术前血清γ-谷氨酰转肽酶水平与术后生存的相关性研究[J]. 肿瘤研究与临床, 2021, 33(9): 668-672. |
| [26] | Takemura, K., Board, P.G. and Koga, F. (2021) A Systematic Review of Serum γ-Glutamyltransferase as a Prognostic Biomarker in Patients with Genitourinary Cancer. Antioxidants, 10, Article No. 549.
https://doi.org/10.3390/antiox10040549 |
| [27] | Ozdemirler, G., Pabu？？uoglu, H., Bulut, T., et al. (1998) Increased Lipoperoxide Levels and Antioxidant System in Colorectal Cancer. Journal of Cancer Research and Clinical Oncology, 124, 555-559.
https://doi.org/10.1007/s004320050214 |
| [28] | Koenig, G. and Seneff, S. (2015) Gamma-Glutamyltransferase: A Predictive Biomarker of Cellular Antioxidant Inadequacy and Disease Risk. Disease Markers, 2015, Article ID: 818570. https://doi.org/10.1155/2015/818570 |
| [29] | Kunutsor, S.K., Apekey, T.A. and Seddoh, D. (2015) Gamma Glutamyltransferase and Metabolic Syndrome Risk: A Systematic Review and Dose-Response Meta-Analysis. International Journal of Clinical Practice, 69, 136-144.
https://doi.org/10.1111/ijcp.12507 |
| [30] | Hanigan, M.H. (1995) Expression of Gamma-Glutamyl Transpeptidase Provides Tumor Cells with a Selective Growth Advantage at Physiologic Concentrations of Cyst(e)ine. Carcinogenesis, 16, 181-185.
https://doi.org/10.1093/carcin/16.2.181 |
| [31] | Hochwald, S.N., Harrison, L.E., Rose, D.M., et al. (1996) Gamma-Glutamyl Transpeptidase Mediation of Tumor Glutathione Utilization in Vivo. Journal of the National Cancer Institute, 88, 193-197.
https://doi.org/10.1093/jnci/88.3-4.193 |
| [32] | Franzini, M., Corti, A., Lorenzini, E., et al. (2006) Modulation of Cell Growth and Cisplatin Sensitivity by Membrane Gamma-Glutamyltransferase in Melanoma Cells. European Journal of Cancer, 42, 2623-2630.
https://doi.org/10.1016/j.ejca.2006.04.016 |
| [33] | Ruoso, P. and Hedley, D.W. (2004) Inhibition of Gamma-Glutamyl Transpeptidase Activity Decreases Intracellular Cysteine Levels in Cervical Carcinoma. Cancer Chemotherapy and Pharmacology, 54, 49-56.
https://doi.org/10.1007/s00280-004-0776-3 |
| [34] | Corti, A., Belcastro, E., Dominici, S., et al. (2020) The Dark Side of Gamma-Glutamyltransferase (GGT): Pathogenic Effects of An ‘antioxidant’ Enzyme. Free Radical Biology & Medicine, 160, 807-819.
https://doi.org/10.1016/j.freeradbiomed.2020.09.005 |
| [35] | Spear, N. and Aust, S.D. (1994) Thiol-Mediated NTA-Fe(III) Reduction and Lipid Peroxidation. Archives of Biochemistry and Biophysics, 312, 198-202. https://doi.org/10.1006/abbi.1994.1299 |
| [36] | Stark, A.A., Russell, J.J., Langenbach, R., et al. (1994) Localization of Oxidative Damage by a Glutathione-Gamma- Glutamyl Transpeptidase System in Preneoplastic Lesions in Sections of Livers from Carcinogen-Treated Rats. Carcinogenesis, 15, 343-348. https://doi.org/10.1093/carcin/15.2.343 |
| [37] | Stark, A.A. and Glass, G.A. (1997) Role of Copper and Ceruloplasmin in Oxidative Mutagenesis Induced by the Glutathione-Gamma-Glutamyl Transpeptidase System and by Other Thiols. Environmental and Molecular Mutagenesis, 29, 63-72. https://doi.org/10.1002/(SICI)1098-2280(1997)29:1<63::AID-EM9>3.0.CO;2-E |
| [38] | Corti, A., Duarte, T.L., Giommarelli, C., et al. (2009) Membrane Gamma-Glutamyl Transferase Activity Promotes Iron-Dependent Oxidative DNA Damage in Melanoma Cells. Mutation Research, 669, 112-121.
https://doi.org/10.1016/j.mrfmmm.2009.05.010 |
| [39] | Drozdz, R., Parmentier, C., Hachad, H., et al. (1998) Gamma-Glutamyltransferase Dependent Generation of Reactive Oxygen Species from a Glutathione/Transferrin System. Free Radical Biology & Medicine, 25, 786-792.
https://doi.org/10.1016/S0891-5849(98)00127-0 |
| [40] | Toyokuni, S., Okamoto, K., Yodoi, J., et al. (1995) Persistent Oxidative Stress in Cancer. FEBS Letters, 358, 1-3.
https://doi.org/10.1016/0014-5793(94)01368-B |
| [41] | Sen, C.K. (1998) Redox Signaling and the Emerging Therapeutic Potential of Thiol Antioxidants. Biochemical Pharmacology, 55, 1747-1758. https://doi.org/10.1016/S0006-2952(97)00672-2 |
| [42] | Maellaro, E., Dominici, S., Del Bello, B., et al. (2000) Membrane Gamma-Glutamyl Transpeptidase Activity of Melanoma Cells: Effects on Cellular H2O2 Production, Cell Surface Protein Thiol Oxidation and NF-Kappa B Activation Status. Journal of Cell Science, 113, 2671-2678. https://doi.org/10.1242/jcs.113.15.2671 |
| [43] | Dominici, S., Visvikis, A., Pieri, L., et al. (2003) Redox Modulation of NF-KappaB Nuclear Translocation and DNA Binding in Metastatic Melanoma. The Role of Endogenous and Gamma-Glutamyl Transferase-Dependent Oxidative Stress. Tumori Journal, 89, 426-433. https://doi.org/10.1177/030089160308900416 |
| [44] | Foyer, C.H., Wilson, M.H. and Wright, M.H. (2018) Redox Regulation of Cell Proliferation: Bioinformatics and Redox Proteomics Approaches to Identify Redox-Sensitive Cell Cycle Regulators. Free Radical Biology & Medicine, 122, 137-149. https://doi.org/10.1016/j.freeradbiomed.2018.03.047 |
| [45] | Perego, P., Paolicchi, A., Tongiani, R., et al. (1997) The Cell-Specific Anti-Proliferative Effect of Reduced Glutathione Is Mediated by Gamma-Glutamyl Transpeptidase-Dependent Extracellular Pro-Oxidant Reactions. International Journal of Cancer, 71, 246-250.
https://doi.org/10.1002/(SICI)1097-0215(19970410)71:2<246::AID-IJC20>3.0.CO;2-E |
| [46] | del Bello, B., Paolicchi, A., Comporti, M., et al. (1999) Hydrogen Peroxide Produced During Gamma-Glutamyl Transpeptidase Activity Is Involved in Prevention of Apoptosis and Maintainance of Proliferation in U937 Cells. The FASEB Journal, 13, 69-79. https://doi.org/10.1096/fasebj.13.1.69 |
| [47] | Giommarelli, C., Corti, A., Supino, R., et al. (2008) Cellular Response to Oxidative Stress and Ascorbic Acid in Melanoma Cells Overexpressing Gamma-Glutamyltransferase. European Journal of Cancer, 44, 750-759.
https://doi.org/10.1016/j.ejca.2008.02.010 |
| [48] | Corti, A., Raggi, C., Franzini, M., et al. (2004) Plasma Membrane Gamma-Glutamyltransferase Activity Facilitates the Uptake of Vitamin C in Melanoma Cells. Free Radical Biology & Medicine, 37, 1906-1915.
https://doi.org/10.1016/j.freeradbiomed.2004.08.015 |
| [49] | Shi, M., Gozal, E., Choy, H.A., et al. (1993) Extracellular Glutathione and Gamma-Glutamyl Transpeptidase Prevent H2O2-Induced Injury by 2,3-Dimethoxy-1,4-Naphthoquinone. Free Radical Biology & Medicine, 15, 57-67.
https://doi.org/10.1016/0891-5849(93)90125-E |
| [50] | Hochwald, S.N., Rose, D.M., Brennan, M.F., et al. (1997) Elevation of Glutathione and Related Enzyme Activities in High-Grade and Metastatic Extremity Soft Tissue Sarcoma. Annals of Surgical Oncology, 4, 303-309.
https://doi.org/10.1007/BF02303579 |
| [51] | Mares, V., Lisá, V., Malík, R., et al. (2003) Cisplatin Induced Gamma-Glutamyltransferase Up-Regulation, Hypertrophy and Differentiation in Astrocytic Glioma Cells in Culture. Histology and Histopathology, 18, 687-693. |
| [52] | Benlloch, M., Ortega, A., Ferrer, P., et al. (2005) Acceleration of Glutathione Efflux and Inhibition of Gamma-Glu- tamyltranspeptidase Sensitize Metastatic B16 Melanoma Cells to Endothelium-Induced Cytotoxicity. Journal of Biological Chemistry, 280, 6950-6959. https://doi.org/10.1074/jbc.M408531200 |
| [53] | Warren, B.S., Naylor, M.F., Winberg, L.D., et al. (1993) Induction and Inhibition of Tumor Progression. Proceedings of the Society for Experimental Biology and Medicine, 202, 19-15. https://doi.org/10.3181/00379727-202-43511B |
| [54] | Paolicchi, A., Lorenzini, E., Perego, P., et al. (2002) Extra-Cellular Thiol Metabolism in Clones of Human Metastatic Melanoma with Different Gamma-Glutamyl Transpeptidase Expression: Implications for Cell Response to Platinum-Based Drugs. International Journal of Cancer, 97, 740-745. https://doi.org/10.1002/ijc.10110 |
| [55] | Perego, P., Romanelli, S., Carenini, N., et al. (1998) Ovarian Cancer Cisplatin-Resistant Cell Lines: Multiple Changes Including Collateral Sensitivity to Taxol. Annals of Oncology, 9, 423-430. https://doi.org/10.1023/A:1008265012435 |
| [56] | Hanigan, M.H., Frierson Jr., H.F., Abeler, V.M., et al. (1999) Human Germ Cell Tumours: Expression of Gamma- Glutamyl Transpeptidase and Sensitivity to Cisplatin. British Journal of Cancer, 81, 75-79.
https://doi.org/10.1038/sj.bjc.6690653 |
| [57] | Zimmermann, T., Zeizinger, M. and Burda, J.V. (2005) Cisplatin Interaction with Cysteine and Methionine, a Theoretical DFT Study. Journal of Inorganic Biochemistry, 99, 2184-2196. https://doi.org/10.1016/j.jinorgbio.2005.07.021 |
| [58] | Paolicchi, A., Sotiropuolou, M., Perego, P., et al. (2003) Gamma-Glutamyl Transpeptidase Catalyses the Extracellular Detoxification of Cisplatin in a Human Cell Line Derived from the Proximal Convoluted Tubule of the Kidney. European Journal of Cancer, 39, 996-1003. https://doi.org/10.1016/S0959-8049(03)00067-4 |
| [59] | Jerremalm, E., Wallin, I., Yachnin, J., et al. (2006) Oxaliplatin Degradation in the Presence of Important Biological Sulphur-Containing Compounds and Plasma Ultrafiltrate. European Journal of Pharmaceutical Sciences, 28, 278-283.
https://doi.org/10.1016/j.ejps.2006.03.001 |
| [60] | Daubeuf, S., Leroy, P., Paolicchi, A., et al. (2002) Enhanced Resistance of HeLa Cells to Cisplatin by Overexpression of Gamma-Glutamyltransferase. Biochemical Pharmacology, 64, 207-216.
https://doi.org/10.1016/S0006-2952(02)01118-8 |
| [61] | Arany, I., Safirstein, R.L. (2003) Cisplatin Nephrotoxicity. Seminars in Nephrology, 23, 460-464.
https://doi.org/10.1016/S0270-9295(03)00089-5 |
| [62] | Zhang, L. and Hanigan, M.H. (2003) Role of Cysteine S-Conjugate Beta-Lyase in the Metabolism of Cisplatin. Journal of Pharmacology and Experimental Therapeutics, 306, 988-994. https://doi.org/10.1124/jpet.103.052225 |
| [63] | Hanigan, M.H., Lykissa, E.D., Townsend, D.M., et al. (2001) Gamma-Glutamyl Transpeptidase-Deficient Mice Are Resistant to the Nephrotoxic Effects of Cisplatin. The American Journal of Pathology, 159, 1889-1894.
https://doi.org/10.1016/S0002-9440(10)63035-0 |
| [64] | Hanigan, M.H., Gallagher, B.C., Taylor Jr., P.T., et al. (1994) Inhibition of Gamma-Glutamyl Transpeptidase Activity by Acivicin in Vivo Protects the Kidney from Cisplatin-Induced Toxicity. Cancer Research, 54, 5925-5929. |
| [65] | Townsend, D.M. and Hanigan, M.H. (2002) Inhibition of Gamma-Glutamyl Transpeptidase Or Cysteine S-Conjugate Beta-Lyase Activity Blocks the Nephrotoxicity of Cisplatin in Mice. Journal of Pharmacology and Experimental Therapeutics, 300, 142-148. https://doi.org/10.1124/jpet.300.1.142 |
| [66] | Wainford, R.D., Weaver, R.J., Stewart, K.N., et al. (2008) Cisplatin Nephrotoxicity Is Mediated by Gamma Glutamyltranspeptidase, Not Via a C-S Lyase Governed Biotransformation Pathway. Toxicology, 249, 184-193.
https://doi.org/10.1016/j.tox.2008.05.006 |
| [67] | Zunino, F., Pratesi, G., Micheloni, A., et al. (1989) Protective Effect of Reduced Glutathione against Cisplatin-Induced Renal and Systemic Toxicity and Its Influence on the Therapeutic Activity of the Antitumor Drug. Chemico-Biological Interaction, 70, 89-101. https://doi.org/10.1016/0009-2797(89)90065-3 |
| [68] | Bernareggi, A., Torti, L., Facino, R.M., et al. (1995) Characterization of Cisplatin-Glutathione Adducts by Liquid Chromatography-Mass Spectrometry. Evidence for Their Formation in Vitro but Not in Vivo after Concomitant Administration of Cisplatin and Glutathione to Rats ANC Cancer Patients. Journal of Chromatography B: Biomedical Sciences and Applications, 669, 247-263. https://doi.org/10.1016/0378-4347(95)00098-4 |
| [69] | Griffith, O.W. and Meister, A. (1979) Translocation of Intracellular Glutathione to Membrane-Bound Gamma-Glutamyl Transpeptidase as a Discrete Step in the Gamma-Glutamyl Cycle: Glutathionuria after Inhibition of Transpeptidase. Proceedings of the National Academy of Sciences of the United States of America, 76, 268-272.
https://doi.org/10.1073/pnas.76.1.268 |
| [70] | Lieberman, M.W., Wiseman, A.L., Shi, Z.Z., et al. (1996) Growth Retardation and Cysteine Deficiency in Gamma- Glutamyl Transpeptidase-Deficient Mice. Proceedings of the National Academy of Sciences of the United States of America, 93, 7923-7926. https://doi.org/10.1073/pnas.93.15.7923 |
| [71] | Larsson, A., Orrenius, S., Holmgren, A., Mannervik, B. and Meister, A. (1983) Metabolism and Transport of Glutathione and Other Gamma-Glutamyl Compounds. In: Larsson, A., Orrenius, S., Holmgren, A. and Mannervik, B., Eds, Functions of Glutathione: Biochemical, Toxicological and Clinical Aspects, Raven Press, New York, 1-22. |
| [72] | Heudi, O., Brisset, H., Cailleux, A., et al. (2001) Chemical Instability and Methods for Measurement of Cisplatin Adducts Formed by Interactions with Cysteine and Glutathione. International Journal of Clinical Pharmacology and Therapeutics, 39, 344-349. https://doi.org/10.5414/CPP39344 |
| [73] | Mena, S., Benlloch, M., Ortega, A., et al. (2007) Bcl-2 and Glutathione Depletion Sensitizes B16 Melanoma to Combination Therapy and Eliminates Metastatic Disease. Clinical Cancer Research, 13, 2658-2666.
https://doi.org/10.1158/1078-0432.CCR-06-2642 |
| [74] | Lherbet, C., Gravel, C. and Keillor, J.W. (2004) Synthesis of S-Alkyl L-Homocysteine Analogues of Glutathione and Their Kinetic Studies with Gamma-Glutamyl Transpeptidase. Bioorganic & Medicinal Chemistry Letters, 14, 3451- 3455. https://doi.org/10.1016/j.bmcl.2004.04.072 |
| [75] | Han, L., Hiratake, J., Kamiyama, A., et al. (2007) Design, Synthesis, and Evaluation of Gamma-Phosphono Diester Analogues of Glutamate as Highly Potent Inhibitors and Active Site Probes of Gamma-Glutamyl Transpeptidase. Biochemistry, 46, 1432-1447. https://doi.org/10.1021/bi061890j |
| [76] | King, J.B., West, M.B., Cook, P.F., et al. (2009) A Novel, Species-Specific Class of Uncompetitive Inhibitors of Gamma-Glutamyl Transpeptidase. Journal of Biological Chemistry, 284, 9059-9065.
https://doi.org/10.1074/jbc.M809608200 |
