Irreversible binding of an anticancer compound (BI-94) to plasma proteins

Xenobiotica

Volumn 45, Issue 10, 2015, Pages 858-873

  Gautam, Nagsen ^a   Thakare, Rhishikesh ^a   Rana, Sandeep ^b   Natarajan, Amarnath ^b   Alnouti, Yazen ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

Glutathione; irreversible protein binding; isotopic filtering; LC MS MS; N acetylcysteine

Indexed keywords

ACETYLCYSTEINE; ANTINEOPLASTIC AGENT; BENZOFURAZAN DERIVATIVE; BI 94; BICARBONATE; BUFFER; CARBONIC ACID; CYSTEINE; GLUTATHIONE; HUMAN SERUM ALBUMIN; METHANOL; NUCLEOPHILE; PLASMA PROTEIN; SODIUM HYDROXIDE; UNCLASSIFIED DRUG; WATER; NSC228148; OXADIAZOLE DERIVATIVE; SERUM ALBUMIN; SULFONE;

ACIDIFICATION; ACIDITY; ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG STABILITY; HAPLORHINI; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; NUCLEOPHILICITY; PH; PLASMA; RAT; SUBSTITUTION REACTION; ANIMAL; BAGG ALBINO MOUSE; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; METABOLISM; TANDEM MASS SPECTROMETRY;

ACETYLCYSTEINE; ANIMALS; ANTINEOPLASTIC AGENTS; BLOOD PROTEINS; DRUG STABILITY; GLUTATHIONE; HUMANS; HYDROGEN-ION CONCENTRATION; MALE; MICE, INBRED BALB C; MOLECULAR STRUCTURE; OXADIAZOLES; SERUM ALBUMIN; SULFONES; TANDEM MASS SPECTROMETRY;

EID: 84940557888     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2015.1025250     Document Type: Article

References (71)

1. Ballard P, Rowland M. (2011). Correction for nonspecific binding to various components of ultrafiltration apparatus and impact on estimating in vivo rat clearance for a congeneric series of 5-ethyl,5-n-alkyl barbituric acids. Drug Metab Dispos 39:2165-8.
2. Banker MJ, Clark TH. (2008). Plasma/serum protein binding determinations. Curr Drug Metab 9:854-9.
3. Barre J, Chamouard JM, Houin G, Tillement JP. (1985). Equilibrium dialysis, ultrafiltration, and ultracentrifugation compared for determining the plasma-protein-binding characteristics of valproic acid. Clin Chem 31:60-4.
4. Cantor SB, Bell DW, Ganesan S, et al. (2001). BACH1, a novel helicaselike protein, interacts directly with BRCA1 and contributes to its DNA repair function. Cell 105:149-60.
5. Chan S, Gerson B. (1987). Free drug monitoring. Clin Lab Med 7: 279-87.
6. Chuang VT, Maruyama T, Otagiri M. (2009). Updates on contemporary protein binding techniques. Drug Metab Pharmacokinet 24:358-64.
7. Crampton MR, Lunn RE, Lucas D. (2003). Sigma-adduct formation and oxidative substitution in the reactions of 4-nitrobenzofurazan and some derivatives with hydroxide ions in water. Org Biomol Chem 1: 3438-43.
8. Dasgupta A. (2007). Usefulness of monitoring free (unbound) concentrations of therapeutic drugs in patient management. Clin Chim Acta 377:1-13.
9. Dubois N, Lapicque F, Maurice MH, et al. (1993). In vitro irreversible binding of ketoprofen glucuronide to plasma proteins. Drug Metab Dispos 21:617-23.
10. Enoch SJ, Ellison CM, Schultz TW, Cronin MT. (2011). A review of the electrophilic reaction chemistry involved in covalent protein binding relevant to toxicity. Crit Rev Toxicol 41:783-802.
11. Federici L, Lo Sterzo C, Pezzola S, et al. (2009). Structural basis for the binding of the anticancer compound 6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol to human glutathione s-transferases. Cancer Res 69: 8025-34.
12. Freed AL, Strohmeyer HE, Mahjour M, et al. (2008). pH control of nucleophilic/electrophilic oxidation. Int J Pharm 357:180-8.
13. Gabard B, Mascher H. (1991). Endogenous plasma N-acetylcysteine and single dose oral bioavailability from two different formulations as determined by a new analytical method. Biopharm Drug Dispos 12: 343-53.
14. Gautam N, Bathena SP, Chen Q, et al. (2013). Pharmacokinetics, protein binding and metabolism of a quinoxaline urea analog as an NFkappaB inhibitor in mice and rats by LC-MS/MS. Biomed Chromatogr 27:900-9.
15. Ghosh PB, Ternai B, Whitehouse MW. (1972). Potential antileukemic and immunosuppressive drugs. 3. Effects of homocyclic ring substitution on the in vitro drug activity of 4-nitrobenzo-2,1,3-oxadiazoles (4-nitrobenzofurazans) and their N-oxides (4-nitrobenzofuroxans). J Med Chem 15:255-60.
16. Howard ML, Hill JJ, Galluppi GR, McLean MA. (2010). Plasma protein binding in drug discovery and development. Comb Chem High Throughput Screen 13:170-87.
17. Hyneck ML, Smith PC, Munafo A, et al. (1988). Disposition and irreversible plasma protein binding of tolmetin in humans. Clin Pharmacol Ther 44:107-14.
18. Ito K, Iwatsubo T, Kanamitsu S, et al. (1998). Prediction of pharmacokinetic alterations caused by drug-drug interactions: metabolic interaction in the liver. Pharmacol Rev 50:387-412.
19. Jahn S, Faber H, Zazzeroni R, Karst U. (2012a). Electrochemistry/liquid chromatography/mass spectrometry to demonstrate irreversible binding of the skin allergen p-phenylenediamine to proteins. Rapid Commun Mass Spectrom 26:1415-25.
20. Jahn S, Faber H, Zazzeroni R, Karst U. (2012b). Electrochemistry/mass spectrometry as a tool in the investigation of the potent skin sensitizer p-phenylenediamine and its reactivity toward nucleophiles. Rapid Commun Mass Spectrom 26:1453-64.
21. Jenkins RE, Meng X, Elliott VL, et al. (2009). Characterisation of flucloxacillin and 5-hydroxymethyl flucloxacillin haptenated HSA in vitro and in vivo. Proteomics Clin Appl 3:720-9.
22. Jenkinson C, Jenkins RE, Maggs JL, et al. (2009). A mechanistic investigation into the irreversible protein binding and antigenicity of p-phenylenediamine. Chem Res Toxicol 22:1172-80.
23. Jinno F, Yoneyama T, Morohashi A, et al. (2011). Chemical reactivity of ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242) in vitro. Biopharm Drug Dispos 32:408-25.
24. Joseph PR, Yuan Z, Kumar EA, et al. (2010). Structural characterization of BRCT-tetrapeptide binding interactions. Biochem Biophys Res Commun 393:207-10.
25. Kalgutkar AS, Didiuk MT. (2009). Structural alerts, reactive metabolites, and protein covalent binding: how reliable are these attributes as predictors of drug toxicity? Chem Biodivers 6:2115-37.
26. Kappus H, Bolt HM, Remmer H. (1973). Irreversible protein binding of metabolites of ethynylestradiol in vivo and in vitro. Steroids 22: 203-25.
27. Kerksick C, Willoughby D. (2005). The antioxidant role of glutathione and N-acetyl-cysteine supplements and exercise-induced oxidative stress. J Int Soc Sports Nutr 2:38-44.
28. Kessler U, Castagnolo D, Pagano M, et al. (2013). Discovery and synthesis of novel benzofurazan derivatives as inhibitors of influenza A virus. Bioorg Med Chem Lett 23:5575-7.
29. Kim H, Huang J, Chen J. (2007). CCDC98 is a BRCA1-BRCT domainbinding protein involved in the DNA damage response. Nat Struct Mol Biol 14:710-15.
30. Li F, Lu J, Ma X. (2011a). Profiling the reactive metabolites of xenobiotics using metabolomic technologies. Chem Res Toxicol 24: 744-51.
31. Li H, Grigoryan H, Funk WE, et al. (2011b). Profiling Cys34 adducts of human serum albumin by fixed-step selected reaction monitoring. Mol Cell Proteomics 10: M110 004606.
32. Liao S, Ewing NP, Boucher B, et al. (2012). High-throughput screening for glutathione conjugates using stable-isotope labeling and negative electrospray ionization precursor-ion mass spectrometry. Rapid Commun Mass Spectrom 26:659-69.
33. Liu X, Shen Q, Li J, et al. (2013). In silico prediction of cytochrome P450-mediated site of metabolism (SOM). Protein Pept Lett 20: 279-89.
34. Liu Z, Wu J, Yu X. (2007). CCDC98 targets BRCA1 to DNA damage sites. Nat Struct Mol Biol 14:716-20.
35. Lokesh GL, Rachamallu A, Kumar GD, Natarajan A. (2006). Highthroughput fluorescence polarization assay to identify small molecule inhibitors of BRCT domains of breast cancer gene 1. Anal Biochem 352:135-41.
36. Ma S, Subramanian R. (2006). Detecting and characterizing reactive metabolites by liquid chromatography/tandem mass spectrometry. J Mass Spectrom 41:1121-39.
37. Manke IA, Lowery DM, Nguyen A, Yaffe MB. (2003). BRCT repeats as phosphopeptide-binding modules involved in protein targeting. Science 302:636-9.
38. Masubuchi N, Makino C, Murayama N. (2007). Prediction of in vivo potential for metabolic activation of drugs into chemically reactive intermediate: correlation of in vitro and in vivo generation of reactive intermediates and in vitro glutathione conjugate formation in rats and humans. Chem Res Toxicol 20:455-64.
39. Meng X, Jenkins RE, Berry NG, et al. (2011). Direct evidence for the formation of diastereoisomeric benzylpenicilloyl haptens from benzylpenicillin and benzylpenicillenic acid in patients. J Pharmacol Exp Ther 338:841-9.
40. Meng X, Maggs JL, Usui T, et al. (2015). Auto-oxidation of isoniazid leads to isonicotinic-lysine adducts on human serum albumin. Chem Res Toxicol 28:51-8.
41. Michelet F, Gueguen R, Leroy P, et al. (1995). Blood and plasma glutathione measured in healthy subjects by HPLC: relation to sex, aging, biological variables, and life habits. Clin Chem 41:1509-17.
42. Mutlib A, Lam W, Atherton J, et al. (2005). Application of stable isotope labeled glutathione and rapid scanning mass spectrometers in detecting and characterizing reactive metabolites. Rapid Commun Mass Spectrom 19:3482-92.
43. Nakayama S, Atsumi R, Takakusa H, et al. (2009). A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding. Drug Metab Dispos 37:1970-7.
44. Nakayama S, Takakusa H, Watanabe A, et al. (2011). Combination of GSH trapping and time-dependent inhibition assays as a predictive method of drugs generating highly reactive metabolites. Drug Metab Dispos 39:1247-54.
45. Nassar AE, Lopez-Anaya A. (2004). Strategies for dealing with reactive intermediates in drug discovery and development. Curr Opin Drug Discov Dev 7:126-36.
46. Paliwal JK, Smith DE, Cox SR, et al. (1993). Stereoselective, competitive, and nonlinear plasma protein binding of ibuprofen enantiomers as determined in vivo in healthy subjects. J Pharmacokinet Biopharm 21:145-61.
47. Patridge EV, Eriksson ES, Penketh PG, et al. (2012). 7-Nitro-4-(phenylthio)benzofurazan is a potent generator of superoxide and hydrogen peroxide. Arch Toxicol 86:1613-25.
48. Pessetto ZY, Yan Y, Bessho T, Natarajan A. (2012). Inhibition of BRCT(BRCA1)-phosphoprotein interaction enhances the cytotoxic effect of olaparib in breast cancer cells: a proof of concept study for synthetic lethal therapeutic option. Breast Cancer Res Treat 134: 511-17.
49. Prakash C, Sharma R, Gleave M, Nedderman A. (2008). In vitro screening techniques for reactive metabolites for minimizing bioactivation potential in drug discovery. Curr Drug Metab 9:952-64.
50. Rappaport SM, Li H, Grigoryan H, et al. (2012). Adductomics: characterizing exposures to reactive electrophiles. Toxicol Lett 213: 83-90.
51. Ricci G, De Maria F, Antonini G, et al. (2005). 7-Nitro-2,1,3-benzoxadiazole derivatives, a new class of suicide inhibitors for glutathione S-transferases. Mechanism of action of potential anticancer drugs. J Biol Chem 280:26397-405.
52. Rubino FM, Pitton M, Di Fabio D, Colombi A. (2009). Toward an "omic" physiopathology of reactive chemicals: thirty years of mass spectrometric study of the protein adducts with endogenous and xenobiotic compounds. Mass Spectrom Rev 28:725-84.
53. Schmidt S, Gonzalez D, Derendorf H. (2010). Significance of protein binding in pharmacokinetics and pharmacodynamics. J Pharm Sci 99: 1107-22.
54. Schuhmacher J, Kohlsdorfer C, Buhner K, et al. (2004). High-throughput determination of the free fraction of drugs strongly bound to plasma proteins. J Pharm Sci 93:816-30.
55. Shibukawa A, Kuroda Y, Nakagawa T. (1999). High-performance frontal analysis for drug-protein binding study. J Pharm Biomed Anal 18: 1047-55.
56. Simeonov A, Yasgar A, Jadhav A, et al. (2008). Dual-fluorophore quantitative high-throughput screen for inhibitors of BRCT-phosphoprotein interaction. Anal Biochem 375:60-70.
57. Smith PC, McDonagh AF, Benet LZ. (1986). Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J Clin Invest 77: 934-9.
58. Sobhian B, Shao G, Lilli DR, et al. (2007). RAP80 targets BRCA1 to specific ubiquitin structures at DNA damage sites. Science 316: 1198-202.
59. Squellerio I, Caruso D, Porro B, et al. (2012). Direct glutathione quantification in human blood by LC-MS/MS: comparison with HPLC with electrochemical detection. J Pharm Biomed Anal 71: 111-18.
60. Tang W, Lu AY. (2010). Metabolic bioactivation and drug-related adverse effects: current status and future directions from a pharmaceutical research perspective. Drug Metab Rev 42:225-49.
61. Uetrecht J. (2003). Screening for the potential of a drug candidate to cause idiosyncratic drug reactions. Drug Discov Today 8:832-7.
62. Wang B, Matsuoka S, Ballif BA, et al. (2007). Abraxas and RAP80 form a BRCA1 protein complex required for the DNA damage response. Science 316:1194-8.
63. Wang L, Zhang YY, Liu FY, et al. (2014). Benzofurazan derivatives as antifungal agents against phytopathogenic fungi. Eur J Med Chem 80: 535-42.
64. Wen B, Fitch WL. (2009). Analytical strategies for the screening and evaluation of chemically reactive drug metabolites. Expert Opin Drug Metab Toxicol 5:39-55.
65. Xie F, Li BX, Broussard C, Xiao X. (2013). Identification, synthesis and evaluation of substituted benzofurazans as inhibitors of CREBmediated gene transcription. Bioorg Med Chem Lett 23:5371-5.
66. Yan Z, Caldwell G. (2004). Optimization in drug discovery: in vitro methods. Totowa, NJ: Humana Press.
67. Yang Y, Guan X. (2015). Rapid and thiol-specific high-throughput assay for simultaneous relative quantification of total thiols, protein thiols, and nonprotein thiols in cells. Anal Chem 87:649-55.
68. Yu X, Chini CC, He M, et al. (2003). The BRCT domain is a phosphoprotein binding domain. Science 302:639-42.
69. Yuan J, Yang DC, Birkmeier J, Stolzenbach J. (1995). Determination of protein binding by in vitro charcoal adsorption. J Pharmacokinet Biopharm 23:41-55.
70. Yuan Z, Kumar EA, Campbell SJ, et al. (2011a). Exploiting the P-1 pocket of BRCT domains toward a structure guided inhibitor design. ACS Med Chem Lett 2:764-7.
71. Yuan Z, Kumar EA, Kizhake S, Natarajan A. (2011b). Structure-activity relationship studies to probe the phosphoprotein binding site on the carboxy terminal domains of the breast cancer susceptibility gene 1. J Med Chem 54:4264-8.