233
Views
27
CrossRef citations to date
0
Altmetric
Original Articles

Binding to Protein by Isothiocyanates: A Potential Mechanism for Apoptosis Induction in Human Nonsmall Lung Cancer Cells

&
Pages 12-20 | Received 18 Jul 2008, Accepted 22 Jul 2008, Published online: 10 Nov 2008

REFERENCES

  • Jiao , D , Smith , T J , Yang , C S , Pittman , B Desai , D . 1997 . Chemopreventive activity of thiol conjugates of isothiocyanates for lung tumorigenesis . Carcinogenesis , 18 : 2143 – 2147 .
  • Yang , Y M , Conaway , C C , Chiao , J W , Wang , C X Amin , S . 2002 . Inhibition of benzo(a)pyrene-induced lung tumorigenesis in A/J mice by dietary N-acetylcysteine conjugates of benzyl and phenethyl isothiocyanates during the postinitiation phase is associated with activation of mitogen-activated protein kinases and p53 activity and induction of apoptosis . Cancer Res , 62 : 2 – 7 .
  • Conaway , C C , Wang , C X , Pittman , B , Yang , Y M Schwartz , J E . 2005 . Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice . Cancer Res , 5 : 548 – 557 .
  • Sticha , K R , Kenney , P M , Boysen , G , Liang , H Su , X . 2002 . Effects of benzyl isothiocyanate and phenethyl isothiocyanate on DNA adduct formation by a mixture of benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung . Carcinogenesis , 23 : 1433 – 1439 .
  • Fowke , J H , Chung , F L , Jin , F , Qi , D Cai , Q . 2003 . Urinary isothiocyanate levels, brassica, and human breast cancer . Cancer Res , 63 : 3980 – 3986 .
  • London , S J , Yuan , J M , Chung , F L , Gao , Y T Coetzee , G A . 2000 . Isothiocyanates, glutathione S-transferase M1 and T1 polymorphisms, and lung-cancer risk: a prospective study of men in Shanghai, China . Lancet , 356 : 724 – 729 .
  • Seow , A , Yuan , J M , Sun , C L , Van DenBerg , D Lee , H P . 2002 . Dietary isothiocyanates, glutathione S transferase polymorphisms and colorectal cancer risk in the Singapore Chinese Health Study . Carcinogenesis , 23 : 2055 – 2061 .
  • Zhang , Y and Talalay , P . 1998 . Mechanism of differential potencies of isothiocyanates as inducers of anticarcinogenic Phase 2 enzymes . Cancer Res , 58 : 4632 – 4639 .
  • Singh , S V , Srivastava , S K , Choi , S , Lew , K L Antosiewicz , J . 2005 . Sulforaphane-induced cell death in human prostate cancer cells is initiated by reactive oxygen species . J Biol Chem , 280 : 19911 – 19924 .
  • Conaway , C C , Yang , Y M and Chung , F L . 2002 . Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans . Curr Drug Metab , 3 : 233 – 255 .
  • Hecht , S S . 2000 . Inhibition of carcinogenesis by isothiocyanates . Drug Metab Rev , 32 : 395 – 411 .
  • Moreno , R L , Goosen , T , Kent , U M , Chung , F L and Hollenberg , P F . 2001 . Differential effects of naturally occurring isothiocyanates on the activities of cytochrome P450 2E1 and the mutant P450 2E1 T303A . Arch Biochem Biophys , 391 : 99 – 110 .
  • von Weymarn , L B , Chun , J A and Hollenberg , P F . 2006 . Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers . Carcinogenesis , 27 : 782 – 790 .
  • Dinkova-Kostova , A T , Holtzclaw , W D , Cole , R N , Itoh , K Wakabayashi , N . 2002 . Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants . Proc Natl Acad Sci USA , 99 : 11908 – 11913 .
  • Eggler , A L , Liu , G , Pezzuto , J M , van Breemen , R B and Mesecar , A D . 2005 . Modifying specific cysteines of the electrophile-sensing human Keap1 protein is insufficient to disrupt binding to the Nrf2 domain Neh2 . Proc Natl Acad Sci USA , 102 : 10070 – 10075 .
  • Hong , F , Freeman , M L and Liebler , D C . 2005 . Identification of sensor cysteines in human Keap1 modified by the cancer chemopreventive agent sulforaphane . Chem Res Toxicol , 18 : 1917 – 1926 .
  • Yang , Y M , Jhanwar-Uniyal , M , Schwartz , J , Conaway , C C Halicka , H D . 2005 . N-acetylcysteine conjugate of phenethyl isothiocyanate enhances apoptosis in growth-stimulated human lung cells . Cancer Res , 65 : 8538 – 8547 .
  • Xu , K and Thornalley , P J . 2001 . Signal transduction activated by the cancer chemopreventive isothiocyanates: cleavage of BID protein, tyrosine phosphorylation and activation of JNK . Br J Cancer , 84 : 670 – 673 .
  • Keum , Y S , Jeong , W S and Kong , A N . 2004 . Chemoprevention by isothiocyanates and their underlying molecular signaling mechanisms . Mutat Res , 555 : 191 – 202 .
  • Xiao , D , Choi , S , Lee , Y J and Singh , S V . 2005 . Role of mitogen-activated protein kinases in phenethyl isothiocyanate-induced apoptosis in human prostate cancer cells . Mol Carcinog , 43 : 130 – 140 .
  • Mi , L , Wang , X , Govind , G , Hood , B L Veenstra , T D . 2007 . The role of protein binding in induction of apoptosis by phenethyl isothiocyanate and sulforaphane in human non-small lung cancer cells . Cancer Res , 67 : 6409 – 6416 .
  • Mi , L , Xiao , Z , Hood , B L , Dakshanamurthy , S Wang , X . 2008 . Covalent binding to tubulin by isothiocyanates: a mechanism of cell growth arrest and apoptosis . J Biol Chem , 283 : 22136 – 22146 .
  • Tang , L and Zhang , Y . 2005 . Mitochondria are the primary target in isothiocyanate-induced apoptosis in human bladder cancer cells . Mol Cancer Ther , 4 : 1250 – 1259 .
  • Zhang , Y , Tang , L and Gonzalez , V . 2003 . Selected isothiocyanates rapidly induce growth inhibition of cancer cells . Mol Cancer Ther , 2 : 1045 – 1052 .
  • Jakubikova , J , Bao , Y and Sedlak , J . 2005 . Isothiocyanates induce cell cycle arrest, apoptosis and mitochondrial potential depolarization in HL-60 and multidrug-resistant cell lines . Anticancer Res , 25 : 3375 – 3386 .
  • Tseng , E , Scott-Ramsay , E A and Morris , M E . 2004 . Dietary organic isothiocyanates are cytotoxic in human breast cancer MCF-7 and mammary epithelial MCF-12A cell lines . Exp Biol Med , 229 : 835 – 842 .
  • Bonnesen , C , Eggleston , I M and Hayes , J D . 2001 . Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines . Cancer Res , 61 : 6120 – 6130 .
  • Compton , M M . 1992 . A biochemical hallmark of apoptosis: internucleosomal degradation of the genome . Cancer Metastasis Rev , 11 : 105 – 119 .
  • Kulms , D , Poppelmann , B , Yarosh , D , Luger , T A Krutmann , J . 1999 . Nuclear and cell membrane effects contribute independently to the induction of apoptosis in human cells exposed to UVB radiation . Proc Natl Acad Sci USA , 96 : 7974 – 7979 .
  • Zhang , R , Loganathan , S , Humphreys , I and Srivastava , S K . 2006 . Benzyl isothiocyanate-induced DNA damage causes G2/M cell cycle arrest and apoptosis in human pancreatic cancer cells . J Nutr , 136 : 2728 – 2734 .
  • Andelová , H , Rudolf , E and Cervinka , M . 2007 . In vitro antiproliferative effects of sulforaphane on human colon cancer cell line SW620 . Acta Medica (Hradec Kralove) , 50 : 171 – 176 .
  • Singh , S V , Herman-Antosiewicz , A , Singh , A V , Lew , K L Srivastava , S K . 2004 . Sulforaphane-induced G2/M phase cell cycle arrest involves checkpoint kinase 2-mediated phosphorylation of cell division cycle 25C . J Biol Chem , 279 : 25813 – 25822 .
  • Conaway , C C , Jiao , D and Chung , F L . 1996 . Inhibition of rat liver cytochrome P450 isozymes by isothiocyanates and their conjugates: a structure-activity relationship study . Carcinogenesis , 17 : 2423 – 2427 .
  • von Weymarn , L B , Chun , J A , Knudsen , G A and Hollenberg , P F . 2007 . Effects of eleven isothiocyanates on P450 2A6- and 2A13-catalyzed coumarin 7-hydroxylation . Chem Res Toxicol , 20 : 1252 – 1259 .
  • Cowan , N . 1984 . “ Tubulin genes and the diversity of microtubule function ” . In Oxford Surveys on Eukaryotic Genes , Edited by: Maclean , N . Oxford, , England : University of Oxford Press .
  • Lowe , J , Li , H , Downing , K H and Nogales , E . 2001 . Refined structure of alpha beta-tubulin at 3.5 A resolution . J Mol Biol , 313 : 1045 – 1057 .
  • Britto , P J , Knipling , L , Mcphie , P and Wolff , J . 2005 . Thiol-disulphide interchange in tubulin: kinetics and the effect on polymerization . Biochem J , 389 : 549 – 558 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.