Prevention of benzene-induced genotoxicity in bone marrow and lung cells: Superiority of polyphenolic acetates to polyphenols

Archives of Toxicology

Volumn 85, Issue 9, 2011, Pages 1141-1150

  Kumar, Ajit ^a   Sushama, Anupam ^a   Rohil, Vishwajeet ^a   Manral, Sushma ^a   Gangopadhyay, Sukanya ^a   Prasad, Ashok K ^b   Raj, Hanumantharao G ^a   Parmar, Virender S ^b  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF DELHI   (India)

Author keywords

Benzene; Calreticulin transacetylase; Genotoxicity; Micronuclei; Polyphenolic acetates

Indexed keywords

3,3' METHYLENE BIS (4,7,8 TRIHYDROXYCOUMARIN); 3,3' METHYLENE BIS 4,7,8 TRIACETOXYCOUMARIN; 7 ACETOXY 2 METHYL 3 ACETYLCHROMONE; 7,8 DIACETOXY 4 METHYLCOUMARIN; 7,8 DIACETOXY 4 PHENYLCOUMARIN; 7,8 DIHYDROXY 4 METHYLCOUMARIN; 7,8 DIHYDROXY 4 PHENYLCOUMARIN; BENZENE; CALRETICULIN; CYTOCHROME P450; ELLAGIC ACID; ETHOXYRESORUFIN DEETHYLASE; MIXED FUNCTION OXIDASE; MONOACETOXY COUMARIN; PENTOXYRESORUFIN DEALKYLASE; POLYPHENOL ACETATE DERIVATIVE; POLYPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BONE MARROW CELL; CATALYSIS; CELL ISOLATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG MEGADOSE; DRUG SPECIFICITY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MODIFICATION; ENZYME SPECIFICITY; GENOTOXICITY; LOW DRUG DOSE; LUNG ALVEOLUS CELL; LUNG LAVAGE; MALE; MICRONUCLEUS; NONHUMAN; PREVENTION; PRIORITY JOURNAL; RAT;

ACETATES; ACETYLATION; ANIMALS; BENZENE; BONE MARROW CELLS; BRONCHOALVEOLAR LAVAGE FLUID; CELLS, CULTURED; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP2B1; LUNG; MALE; MICRONUCLEI, CHROMOSOME-DEFECTIVE; MICROSCOPY, FLUORESCENCE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; MUTAGENS; POLYPHENOLS; RATS; RATS, WISTAR;

RATTUS;

EID: 80052752985     PISSN: 03405761     EISSN: 14320738     Source Type: Journal    
DOI: 10.1007/s00204-011-0646-9     Document Type: Article

References (50)

1. BJ Dean 1988 Recent findings on the genetic toxicology of benzene, toluene, xylenes and phenols Mutat Res 154 153 181 (Pubitemid 16229479)
2. NJ Desai S Sethna 1957 Synthesis of some 4-hydroxycoumarin derivatives J Org Chem 22 388 390 10.1021/jo01355a010 1:CAS:528:DyaG1cXhtFWisg%3D%3D
3. BS Dwarkanath VK Jain 1985 Enhancement of the radiation damage by 2-deoxy-d-glucose in organ cultures of brain tumors Indian J Med Res 82 266 268 (Pubitemid 16254349)
4. BS Dwarkanath N Kapur S Chandna JS Adhikari S Singh V Jain 1998 Radiomodifying effect of the DNA ligand Hoechest in transformed mammalian cells Trends Radiat Cancer Bio 29 81 89
5. JR Elliot-Middleton C Kandaswami TC Theoharides 2000 The effects of plant flavonoids on mammalian cells: implications for inflammation, heart diseases and cancer Pharmacol Rev 52 673 751
6. GL Erexson JL Wilmer WH Steinhagen AD Klingerman 1986 Induction of cytogenetic damage in rodents after short-term inhalation of benzene Environ Mutagen 8 29 40 3943496 10.1002/em.2860080104 1:CAS:528:DyaL28XhsVelurw%3D (Pubitemid 16173589)
7. BD Goldstein 1977 Hematoxicity in humans J Toxicol Environ Health Suppl 2 69 105 342717 1:STN:280:DyaE1c7htFGnsg%3D%3D
8. WF Greenlee JD Sun JS Bus 1981 A proposed mechanism of benzene toxicity: formation of reactive intermediates from polyphenol metabolites Toxicol Appl Pharmacol 59 187 195 7256763 10.1016/0041-008X(81)90189-7 1:CAS:528: DyaL3MXkslCrtbo%3D (Pubitemid 11064644)
9. 1 activation in human liver microsomes by naringenin and other flavonoids Carcinogenesis 11 2275 2279 2265479 10.1093/carcin/11.12.2275 1:CAS:528:DyaK3MXhtlOrsrs%3D
10. JR Halpert JY Jaw LJ Cornfield C Balfour EA Mash 1989 Selective inactivation of rat liver cytochromes P-450 by 21-Chlorinated steroids Drug Metab Dispos 17 26 31 2566465 1:CAS:528:DyaL1MXhs12jtLc%3D (Pubitemid 19058159)
11. JA Heddle 1973 A rapid in vivo test for chromosomal damage Mutat Res 18 187 190 4351282 1:CAS:528:DyaE3sXktlyrtrs%3D
12. S Hernberg M Savilanti K Ahlman S Asp 1966 Prognostic aspects of benzene poisoning Br J Ind Med 23 204 209 5946130 1:STN:280:DyaF287ntVSmtA%3D%3D
13. P Khurana R Kumari P Vohra A Kumar Seema G Gupta HG Raj BS Dwarakanath VS Parmar D Saluja M Bose A Vij NK Chaudhary JS Adhikari YK Tyagi E Kohli 2005 Acetoxy drug: protein transacetylase catalyzed activation of human platelet nitric oxide synthase by polyphenolic peracetates Bioorg Med Chem 14 575 583 16214347 10.1016/j.bmc.2005.08.044
14. E Kohli M Gaspari HG Raj VS Parmar J Vander Greef G Gupta R Kumari AK Prasad S Goel G Pal YK Tyagi SC Jain N Ahmed AC Watterson CE Olsen 2002 Establishment of the enzymatic protein acetylation independent of acetyl CoA: Recombinant glutathione S-transferase 3-3 is acetylated by a novel membrane-bound transacetylase using 7, 8-diacetoxy-4-methylcoumarin as acetyl donor FEBS Lett 530 139 142 12387881 10.1016/S0014-5793(02)03445-2 1:CAS:528:DC%2BD38XnvVOrsro%3D (Pubitemid 35248200)
15. 1-induced genotoxicity by quercetin and quercetin pentaacetate Bioorg Med Chem Lett 12 2579 2582 12182864 10.1016/S0960-894X(02)00478-X 1:CAS:528:DC%2BD38XmsVWjtbs%3D (Pubitemid 35245285)
16. E Kohli M Gaspari HG Raj VS Parmar SK Sharma J Vander Greef R Kumar G Gupta Seema P Khurana YK Tyagi AC Watterson CE Olsen 2004 Acetoxy drug: protein transacetylase of buffalo liver-characterization and mass spectrometry of the acetylated protein product Biochim Biophys Acta 1698 55 66 15063315 1:CAS:528:DC%2BD2cXivVCqtr4%3D (Pubitemid 38446899)
17. P Kolachana VV Subrahmanyam KB Meyer L Zhang MT Smith 1993 Benzene and its phenolic metabolites produce oxidative DNA damage in HL60 cells in vitro and in the BM in vivo Cancer Res 53 1023 1026 8439949 1:CAS:528:DyaK3sXkt1amtLk%3D (Pubitemid 23087901)
18. A Kumar BK Singh R Tyagi SK Jain AK Prasad HG Raj RC Rastogi AC Watterson VS Parmar 2005 Mechanism of biochemical action of substituted 4-methylbenzopyran-2-one part-11: Comparison of the specificities of the acetoxy derivative of 4-methylcoumarin and 4-phenylcoumarin to acetoxycoumarins: protein transacetylase Bioorg Med Chem 13 4300 4305 15878663 10.1016/j.bmc.2005.04.023 1:CAS:528:DC%2BD2MXltVOnu78%3D (Pubitemid 40779400)
19. A Kumar BK Singh NK Sharma K Gyanda SK Jain YK Tyagi AS Baghel M Pandey SK Sharma AK Prasad SC Jain RC Rastogi HG Raj AC Watterson VS Parmar 2007 Specificities of acetoxy derivatives of coumarins, biscoumarins, chromones, flavones, isoflavones and xanthones for acetoxy drug:protein transacetylase Eur J Med Chem 42 447 455 17182154 10.1016/j.ejmech.2006.09.008 1:CAS:528: DC%2BD2sXktVens7c%3D (Pubitemid 46517779)
20. 1 in bone marrow and lung cells J Pharm Pharmacol 59 81 86 17227624 10.1211/jpp.59.1.0011 1:CAS:528:DC%2BD2sXksVOhsrg%3D (Pubitemid 46133046)
21. JG Lewis W Stewart DO Adams 1988 Role of oxygen radicals in induction of DNA damage by metabolites of benzene Cancer Res 48 4762 4765 2842037 1:CAS:528:DyaL1cXls1GntLw%3D
22. OH Lowry NJ Rosebrough AL Farr RJ Randall 1951 Protein measurement with Folin phenol reagent J Biol Chem 193 265 275 14907713 1:CAS:528: DyaG38XhsVyrsw%3D%3D
23. RA Lubet RT Mayer JW Cameron RW Nims MD Burke T Wolff FP Guengerich 1985 Dealkylation of pentoxyresorufin: a sensitive assay for the measuring induction of cytochrome(s) P-450 by phenobarbital and other xenobiotics in the rat Arch of Biochem Biophys 238 43 48 10.1016/0003-9861(85)90138-9 1:CAS:528: DyaL2MXitFKnsrs%3D (Pubitemid 16232407)
24. CA Luke RR Tice RT Drew 1985 Duration and regimen for induced micronuclei in the peripheral blood of mice exposed chronically to benzene Environ Mutagen 7 suppl. 3 29
25. JM Lunetta K Sgiyama MA Correia 1989 Secobarbital mediated inactivation of rat liver cytochrome P450b, a mechanistic reappraisal Mol Pharmacol 35 10 17 2913483 1:CAS:528:DyaL1MXhsVOlsLs%3D (Pubitemid 19048628)
26. AJ McMichael 1988 Carcinogenicity of benzene, toluene and xylene: epidemiological and experimental evidence IARC Sci Publ 85 3 18 3053447 1:CAS:528:DyaL1MXlt1eltg%3D%3D
27. M Michalak EF Corbett N Mesaeli K Nakamura M Opas 1999 Calreticulin: one protein, one gene, many functions Biochem J 344 281 292 10567207 10.1042/0264-6021:3440281 1:CAS:528:DC%2BD3cXltFCk (Pubitemid 30011581)
28. QN Myrvik Q Leake B Fairsis 1961 Studies on pulmonary macrophases from the normal rabbit: a technique to procure them in high state of purity J Immunology 86 128 132 1:STN:280:DyaF3c%2Fks1yqsQ%3D%3D
29. Newmark HC (1996) Dietary phytochemicals in cancer prevention and treatment: advances in experimental medicine and biology, vol 401. American institute for cancer research; Plenum, New York
30. VS Parmar KS Bisht R Jain S Singh SK Sharma S Gupta S Malhotra OD Tyagi A Vardhan HN Pati 1996 Synthesis, antimicrobial and antiviral activities of novel polyphenolic compounds Indian J Chem 35B 220 232 1:CAS:528:DyaK28Xht1SgsLc%3D (Pubitemid 126476266)
31. S Pascoe D Gatehouse 1975 The use of simple heamatoxylin and eosin staining procedure to demonstrate micronuclei within rodent bone marrow Mutat Res 64 237 243
32. 1-DNA binding in vitro Bioorg Med Chem 4 2225 2228 9022986 10.1016/S0968-0896(96)00227-1 1:CAS:528:DyaK2sXhtVykt7s%3D (Pubitemid 27060235)
33. HG Raj VS Parmar SC Jain S Goel P Himinashu S Malhotra A Singh CE Olsen J Wengel 1998 Mechanism of biochemical action of substituted 4-methylbenzopyran- 2-ones. Part1: Dioxygenated 4-methylcoumarins as superb antioxidant and radical scavenging agents Bioorg Med Chem 6 833 839 9681149 10.1016/S0968-0896(98)00043- 1 1:CAS:528:DyaK1cXkvVOmtbc%3D (Pubitemid 28287285)
34. 1-DNA binding by the candidate antimutagen 7, 8-diacetoxy-4-methylcoumarin Bioorg Med Chem 6 1895 1904 9839019 10.1016/S0968-0896(98)00111-4 1:CAS:528:DyaK1cXntlOhtbk%3D (Pubitemid 28524243)
35. HG Raj VS Parmar SC Jain S Goel A Singh K Gupta V Rohil YK Tyagi HN Jha CE Olsen J Wengel 1999 Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part 4: Hyperbolic acti-vation of rat liver microsomal NADPH-cytochrome c reductase by the novel acetylator 7, 8-diacetoxy-4-methylcoumarin Bioorg Med Chem 7 369 373 10218830 10.1016/S0968-0896(98)00228-4 1:CAS:528:DyaK1MXit1equ7Y%3D (Pubitemid 29117101)
36. HG Raj VS Parmar SC Jain E Kohli N Ahmad S Goel YK Tyagi SK Sharma J Wengel CE Olsen 2000 Mechanism of biochemical action of substituted 4-methylbenzopyran-2-one. Part VII: Assay and characterization of 7, 8-diacetoxy-4-methylcoumarin: Protein transacetylase from rat liver microsomes based irreversible inhibition of cytosolic Glutathione S-transferase Bioorg Med Chem 8 1707 1712 10976517 10.1016/S0968-0896(00)00104-8 1:CAS:528: DC%2BD3cXkvVyksLg%3D (Pubitemid 30427235)
37. HG Raj E Kohli R Goswami S Goel RC Rastogi SC Jain J Wengel CE Olsen VS Parmar 2001 Mechanism of biochemical action of substituted benzopyran-2-ones. Part8: Acetoxycoumarin: protein transacetylase-specificity for aromatic nuclear acetoxy groups in proximity to the oxygen heteroatom Bioorg Med Chem 9 1085 1089 11377166 10.1016/S0968-0896(00)00328-X 1:CAS:528:DC%2BD3MXjslegu70%3D (Pubitemid 32453268)
38. HG Raj E Kohli V Rohil BS Dwarakanath VS Parmar S Malik JS Adhikari YK Tyagi S Goel K Gupta M Bose CE Olsen 2001 Acetoxy of 4-methylcoumarins confer differential protection from aflatoxinB1 -induced micronuclei and apoptosis in lung and bone marrow cells Mutat Res 494 31 40 11423343 1:CAS:528: DC%2BD3MXksVGqsLk%3D (Pubitemid 32566280)
39. HG Raj S Malik VS Parmar E Kohli YK Tyagi V Rohil BS Dwarakanath JS Adhikari M Bose SC Jain CE Olsen 2001 Chemoprevention of benzene induced bone marrow and pulmonary genotoxicity Ter Car Mut 21 181 187 10.1002/1520-6866(2001) 21:2<181::AID-TCM7>3.0.CO;2-2 1:CAS:528:DC%2BD3MXhvVCgtrc%3D (Pubitemid 32199725)
40. HG Raj R Kumari Seema KM Muralidhar BS Dwarkanath RC Rastogi AK Prasad AC Watterson VS Parmar 2006 Novel function of calreticulin: Characterization of calreticulin as transacetylase-mediating protein acetylation independent of acetyl CoA using polyphenolic acetates Pure & Appl Chem 78 985 992 10.1351/pac200678050985 1:CAS:528:DC%2BD28XlvVOmsr4%3D
41. CB Rao G Subramanyan V Venkateswarlu 1959 Synthesis of chromones. II. Some derivatives of 7-Hydroxy-2-methylchromone J Org Chem 24 683 684 10.1021/jo01087a032 1:CAS:528:DyaF3cXhtVensrs%3D
42. ML Robertson DA Eastmond MT Smith 1991 Two benzene metabolites, catechol and hydroquinone, produce a synergistic induction of micronuclei and toxicity in cultured human lymphocytes Mutat Res 31 9 15
43. W Schmid 1975 The micronucleus test Mutat Res 31 9 15 48190 1:CAS:528:DyaE2MXhtVOjs7Y%3D
44. Seema R Kumari G Gupta D Saluja A Kumar S Goel YK Tyagi R Gulati A Vinocha KM Muralidhar BS Dwarkanath RC Rastogi VS Parmar SA Patkar HG Raj 2007 Characterization of protein transacetylase from human placenta as a signaling molecule calreticulin using polyphenolic peracetates as acetyl donors Cell Biochem Biophys 47 53 64 17420526 1:CAS:528:DC%2BD2sXkvFCmtbg%3D (Pubitemid 46570698)
45. I Singh E Kohli HG Raj K Gyanda SK Jain YK Tyagi G Gupta R Kumari A Kumar G Pal AK Prasad RC Rastogi CE Olsen SC Jain VS Parmar 2002 Mechanism of biochemical action substituted-4-methyl Benzopyran-2-ones. Part 9: Comparison of acetoxy-4-methylcoumarins and other polyphenolic acetates reveal the specificity acetoxy: drug protein transacetylase for pyran Carbonyl group in proximity to the oxygen heteroatom Bioorg Med Chem 10 4103 4111 12413864 10.1016/S0968-0896(02)00257-2 1:CAS:528:DC%2BD38Xot1egurs%3D (Pubitemid 36164711)
46. JA Styles CR Richardson 1984 Cytogenetic effects of benzene: dosimetric studies on rats exposed to benzene vapour Mutat Res 135 203 209 6708961 10.1016/0165-1218(84)90123-X 1:CAS:528:DyaL2cXhvVOjt7g%3D (Pubitemid 14151464)
47. R Synder CC Hedli 1996 An overview of benzene metabolism Environ Health Perspect 104 1165 1171 (Pubitemid 27046143)
48. A Tunek B Hogstedt T Olofsson 1982 Mechanism of benzene toxicity. Effects of benzene and benzene metabolites on bone marrow cellularity, number of granulopoietic stem cells and frequency of micronuclei in mice Chem Biol Interact 39 129 138 7060224 10.1016/0009-2797(82)90116-8 1:CAS:528: DyaL38XitFajs7w%3D (Pubitemid 12190610)
49. EC Vigliani A Forni 1976 Benzene and Leukemia Environ Res 11 122 127 767102 10.1016/0013-9351(76)90115-8 1:STN:280:DyaE287jvFGqug%3D%3D
50. MD Waters HF Stack AL Brady PHM Lohman L Haroun H Vainio 1988 Use of computerized data listing and activity profiles of genetic and related effects in the review of 195 compounds Mutat Res 205 295 312 3367921 10.1016/0165-1218(88)90024-9 1:CAS:528:DyaL1cXitFOgsbo%3D