Novel Genistein Derivatives Induce Cell Death and Cell Cycle Arrest Through Different Mechanisms

REFERENCES

• Adlercreutz , C H , Goldin , B R , Gorbach , S L , Hockerstedt , K A Watanabe , S . 1995 . Soybean phytoestrogen intake and cancer risk . J Nutr , 125 : 757 – 770 .
   PubMed Web of Science ®Google Scholar
• Knight , D C and Eden , J A . 1994 . A review of the clinical effect of phytoestrogens . Obstet Gynecol , 87 : 897 – 904 .
   Web of Science ®Google Scholar
• Lampe , J W , Nishino , Y , Ray , R M , Wu , C Li , W . 2007 . Plasma isoflavones and fibrocystic breast conditions and breast cancer among women in Shanghai, China . Cancer Epidemiol Biomarkers Prev , 16 : 2579 – 2586 .
   PubMed Web of Science ®Google Scholar
• Adlercreutz , H , Markkanen , H and Watanabe , S . 1993 . Plasma concentration of phyto-oestrogens in Japanese men . Lancet , 342 : 1209 – 1210 .
   PubMed Web of Science ®Google Scholar
• Mills , P K , Beeson , W L , Phillips , R L and Fraser , G E . 1989 . Cohort study of diet lifestyle and prostate cancer in Adventist men . Cancer , 64 : 598 – 604 .
   PubMed Web of Science ®Google Scholar
• Nagata , C , Takatsuka , N , Kawakami , N and Shimizu , H . 2002 . A prospective cohort study of soy produkt intake and stomach cancer death . Br J Cancer , 87 : 31 – 36 .
   PubMed Web of Science ®Google Scholar
• Messina , M J , Persky , V , Setchell , K D and Barnes , S . 1994 . Soy intake and cancer risk: a review of the in vitro and in vivo data . Nutr Cancer , 21 : 113 – 131 .
   PubMed Web of Science ®Google Scholar
• Shimazu , T , Inoue , M , Sasazuki , S , Iwasaki , M Sawada , N . 2010 . Isoflavone intake and risk of lung cancer: a prospective cohort study in Japan . Am J Clin Nutr , 91 : 722 – 728 .
   PubMed Web of Science ®Google Scholar
• Schabath , M B , Hernandez , L M , Wu , X , Pillow , PC Spitz , MR . 2005 . Dietary phytoestrogens and lung cancer risk . JAMA , 294 : 1493 – 1504 .
   PubMed Web of Science ®Google Scholar
• Horn-Ross , P J , Hoggat , K J and Lee , M M . 2002 . Phytoestrogens and thyroid cancer risk. Cancer Epidemiol . Biomarkers Prev , 11 : 43 – 49 .
   PubMed Web of Science ®Google Scholar
• Alhasan , S A , Aranha , O and Sarkar , F H . 2001 . Genistein elicits pleiotropic molecular effects on head and neck cancer cell . Clin Cancer Res , 7 : 4174 – 4181 .
   PubMed Web of Science ®Google Scholar
• Severson , R K , Nomura , A M , Grove , J S and Stemmermann , G N . 1989 . A prospective study of demographics, diet, and prostate cancer among men of Japanese ancestry in Hawaii . Cancer Res , 49 : 1857 – 1860 .
   PubMed Web of Science ®Google Scholar
• Akiyama , T , Ishida , J , Nakagawa , S , Ogawara , H Watanabe , S I . 1987 . Genistein, a specific inhibitor of tyrosine-specific protein kinases . J Biol Chem , 262 : 5592 – 5595 .
   PubMed Web of Science ®Google Scholar
• Bandele , O J and Osheroff , N . 2007 . Bioflavonoids as poisons of human topoisomerase IIα and IIα . Biochemistry , 46 : 6097 – 6108 .
   PubMed Web of Science ®Google Scholar
• Su , S J , Yeh , T M , Chuang , W J , Ho , C L Chang , K L . 2005 . The novel targets for anti-angiogenesis of genistein on human cancer cells . Biochemical Pharmacology , 69 : 307 – 318 .
   PubMed Web of Science ®Google Scholar
• Banerjee , S , Li , Y , Wang , Z and Sarkar , F H . 2008 . Multi-targeted therapy of cancer by genistein . Cancer Letters , 269 : 226 – 242 .
   PubMed Web of Science ®Google Scholar
• Li , Y , Upadhyay , S , Bhuiyan , M and Sarkar , F H . 1999 . Induction of apoptosis in breast cancer cells MDA-MB-231 by genistein . Oncogene , 18 : 3166 – 3172 .
   PubMed Web of Science ®Google Scholar
• Li , Y , Achmed , F , Ali , S , Philip , P A Kucuk , O . 2005 . Inactivation of Nuclear Factor κB by soy isoflavone genistein contributes to increased apoptosis induced by chemotherapeutic agents in human cancer cells . Cancer Res , 65 : 6934 – 6942 .
   PubMed Web of Science ®Google Scholar
• Alhasan , S A , Ensley , J F and Sarkar , F H . 2000 . Genistein induced molecular changes in a squamous cell carcinoma of the head and neck cell line . Int J Oncol , 16 : 333 – 338 .
   PubMed Web of Science ®Google Scholar
• Natarajan , K , Manna , S K , Chaturvedi , M M and Aggarwal , B B . 1998 . Protein tyrosine kinase inhibitors block tumor necrosis factor-induced activation of nuclear factor-kappaB, degradation of IkappaBalpha, nuclear translocation of p65 and subsequent gene expression . Arch Biochem Biophys , 352 : 59 – 70 .
   PubMed Web of Science ®Google Scholar
• Casagrande , F and Karbon , J M . 2000 . p21CIP1 is dispensable for the G2 arrest caused by genistein in human melanoma cells . Exp Cell Res , 258 : 101 – 108 .
   PubMed Web of Science ®Google Scholar
• Davis , J N , Singh , B , Bhuiyan , M and Sarkar , F H . 1998 . Genistein induced upregulation of p21WAF1, downregulation of cyclin B, and induction of apoptosis in prostate cancer cells . Nutr Cancer , 32 : 123 – 131 .
   PubMed Web of Science ®Google Scholar
• Lian , F , Bhuiyan , M , Li , Y W , Wall , N Kraut , M . 1998 . Genistein-induced G2-M arrest, p21WAF1 upregulation, and apoptosis in a non-small-cell lung cancer cell line . Nutr Cancer , 31 : 184 – 191 .
   PubMed Web of Science ®Google Scholar
• Luo , H , Jiang , B H , King , S M and Chen , Y C . 2008 . Inhibition of cell growth and VEGF expression in ovarian cancer cells by flavonoids . Nutr Cancer , 60 : 800 – 809 .
   PubMed Web of Science ®Google Scholar
• Farina , H G , Pomieć , M , Alonso , D F and Gomez , D E . 2006 . Antitumor and antiangiogenic activity of soy isoflavone genistein in mouse model of melanoma and breast cancer . Oncology Reports , 16 : 885 – 891 .
   PubMed Web of Science ®Google Scholar
• Constantinou , A and Huberman , E . 1995 . Genistein as an inducer of tumor cell differentiation: possible mechanisms of action . Proc Soc Exp Biol Med , 208 : 109 – 115 .
   PubMed Web of Science ®Google Scholar
• Sanchez , Y , Amran , D , de Blas , E and Aller , P . 2009 . Regulation of genistein-induced differentiation in human acute myeloid leukemia cells (HL60, NB4) Protein kinase modulation and reactive oxygen species generation . Biochem Pharmacol , 77 : 384 – 396 .
   PubMed Web of Science ®Google Scholar
• Gossner , G , Choi , M , Tan , L , Fogoros , S and Griffith , K A . 2007 . Genistein-induced apoptosis and autophagocytosis in ovarian cancer cells . Gynecologic Oncology , : 23 – 30 .
   PubMed Web of Science ®Google Scholar
• Zava , D T and Duwe , G . 1997 . Estrogenic and antiproliferative properties of genistein and other flavonoids in human breast cancer cells in vitro . Nutr Cancer , 27 : 31 – 40 .
   PubMed Web of Science ®Google Scholar
• Ogawara , H , Akiyama , T , Watanabe , S , Ito , N Kobori , M . 1989 . Inhibiton of tyrosine protein kinase activity by synthetic isoflavones and flavones . J Antibiot , 42 : 340 – 343 .
   PubMed Web of Science ®Google Scholar
• Peterson , G . 1995 . Evaluation of the biochemical targets of genistein in tumor cells . J Nutr , 125 ( Suppl ) : 784 – 789 .
   Google Scholar
• Zhang , T , Wang , F , Xu , H X , Yi , L Qin , Y . 2013 . Activation of nuclear factor erythroid 2-related factor 2 and PPARγ plays a role in the genistein-mediated attenuation of oxidative stress-induced endothelial cell injury . Br J Nutr , 109 : 223 – 235 .
   PubMed Web of Science ®Google Scholar
• Popiołkiewicz , J , Polkowski , K , Skierski , J S and Mazurek , A P . 2005 . In vitro toxicity evaluation in the development of new anticancer drugs: genistein glycosides . Cancer Lett , 229 : 67 – 75 .
   PubMed Web of Science ®Google Scholar
• Rusin , A. , Gogler , A. , Głowala-Kosińska , M. , Bochenek , D. Gruca , A. 2009 . Unsaturated genistein disaccharide glycoside as a novel agent affecting microtubules . Bioorganic & Medical Chemistry Letters , 19 : 4939 – 4943 .
   PubMed Web of Science ®Google Scholar
• Tchize Ndejouong , B LS , Sattler , I , Dahse , H M , Kothe , E and Hertweck , C . 2009 . Isoflavones with unusually modified B-rings and their evaluation as antiproliferative agents . Bioorganic & Medical Chemistry Letters , 19 : 6473 – 6476 .
   PubMed Web of Science ®Google Scholar
• Choi , J N , Kim , D , Choi , H K , Yoo , K M Kim , J . 2009 . 2’-hydroxylation of genistein enhanced antioxidant and antiproliferative activities in MCF-7 human breast cancer cells . J Microbiol Biotechnol , 19 : 1348 – 1254 .
   PubMed Web of Science ®Google Scholar
• Xiang , W S , Zhang , J , Wang , J D , Jiang , L Jiang , B . 2010 . Isolation and identyfication of chlorinated genistein from Actinoplanes sp. HBDN08 with antioxidant and antitumor activities . J Agric Food Chem , 58 : 1933 – 1938 .
   PubMed Web of Science ®Google Scholar
• Klein , R , Brown , D and Turnley , A M . 2007 . Phenoxodiol protects against cisplatin induced neurite toxicity In a PC-12 cell model . BMC Neuroscience , 8 : 61 – 67 .
   PubMed Web of Science ®Google Scholar
• Aguero , M F , Facchinetti , M M , Sheleg , Z and Senderowicz , A M . 2005 . Phenoxodiol, a novel isoflavone, induces G1 arrest by specific loss in cyclin-dependent kinase 2 activity by p53-independent induction of p21WAF1/CIP1 . Cancer , 106 : 599 – 608 .
   Google Scholar
• Okobira , T. , Miyoshi , K. , Uezu , K. , Samurai , K. and Shinkai , S. 2008 . Molecular dynamic studies of side chain effect on the beta-1,3-D-glucan triple helix in aqueous solution . Biomacromolecules , 9 : 783 – 788 .
   PubMed Web of Science ®Google Scholar
• Kony , D B , Damm , W , Stoll , S , van Gunsteren , W F and Hünenberger , P H . 2007 . Explicit-solvent molecular dynamics simulations of the polysaccharide Schizophyllan in water . Biophysical Journal , 93 : 442 – 455 .
   PubMed Web of Science ®Google Scholar
• Kubala , L , Ruzickova , J , Nickova , K , Sandula , J Ciz , M . 2003 . The effect of (1–3)-β-D-glucans, carboxymethyloglucan and Schisophillan on human leukocytes in vitro . Carbohydrate Research , 338 : 2835 – 2840 .
   PubMed Web of Science ®Google Scholar
• Yuguchi , Y , Kumagai , T , Wu , M , Hirotsu , T and Hosokawa , J . 2004 . Gelation of xyloglucan in water/alkohol systems . Cellulose , 11 : 203 – 208 .
   Web of Science ®Google Scholar
• Skehan , P , Storeng , R , Scudiero , D , Monks , A McMahon , J . 1990 . New colorimetric cytotoxicity assay for anticancer-drug screening . J Natl Cancer Inst , 82 : 1107 – 1112 .
   PubMed Web of Science ®Google Scholar
• Wietrzyk , J , Chodyński , M , Fitak , H , Wojdat , E Kutner , A . 2007 . Antitumor properties of diastereomeric and geometric analogs of vitamin D3 . Anticancer Drugs , 18 : 447 – 457 .
   PubMed Web of Science ®Google Scholar
• Reers , M , Smith , T W and Chen , L B . 1991 . J-aggregate formation of a carbocyanine as a quantitative fluorescent indicator of membrane potential . Biochemistry , 30 : 4480 – 4486 .
   PubMed Web of Science ®Google Scholar
• Kim , R , Emi , M , Tanabe , K , Uchida , Y and Arihiro , K . 2006 . The role of apoptotic or nonapoptotic cell heath in determining cellular response to anticancer treatment . EJSO , 32 : 269 – 277 .
   PubMed Web of Science ®Google Scholar
• Dixon , R A and Ferreira , D . 2002 . Genistein . Phytochem , 60 : 205 – 211 .
   PubMed Web of Science ®Google Scholar
• Shelnutt , S R , Cimino , C O , Wiggins , P A , Ronis , M JJ and Badger , T M . 2002 . Pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein in men and women after consumption of a soy beverage . Amer J Clin Nutr , 76 : 588 – 594 .
   PubMed Web of Science ®Google Scholar
• Simons , A L , Renouf , M , Murphy , P A and Hendrich , S . 2010 . Greater apparent absorption of flavonoids is associated with lesser human fecal flavonoid disappearance rates . J Agric Food Chem , 58 : 141 – 147 .
   PubMed Web of Science ®Google Scholar
• Booth , C , Hargreaves , D F , Hadfield , J A , McGown , A T and Potten , C S . 1999 . Isoflavones inhibit intestinal epithelial cell proliferation and induce apoptosis in vitro . Br J Cancer , 80 : 1550 – 1557 .
   PubMed Web of Science ®Google Scholar
• Uckun , F M , Narla , R K , Zeren , T , Yanishevski , Y Myers , D F . 1998 . In vitro toxivity, pharmacokinetics, and anticancer activity of genistein linked to recombinant human epidermal growth factor . Clin Cancer Res , 4 : 1125 – 1134 .
   PubMed Web of Science ®Google Scholar
• Ek , O , Yanishevski , Y , Zeren , T , Waurzyniak , B Gunther , R . 1998 . In vivo toxicity and pharmacokinetic features of B43(anti-CD19)-genistein immunoconjugate . Leuk Lymphoma , 30 : 389 – 394 .
   PubMed Web of Science ®Google Scholar
• Messinger , Y , Yanishevski , Y , Ek , O , Zeren , T Waurzyniak , B . 1998 . In vitro toxicity and pharmacokinetic features of B43 (anti-CD19)-genistein immunoconjugate in nonhuman primates . Clin Cancer Res , 4 : 165 – 170 .
   PubMed Web of Science ®Google Scholar
• Mazurek , A P , Kozerski , L , Sadlej , J , Kawęcki , R Bednarek , E . 1998 . Genistein complexes with amines: structure and properties . J Chem Soc Perkin Trans , 2 : 1223 – 1230 .
   Google Scholar
• Meng , Q H , Wahala , K , Adlercreutz , H and Tikkanen , M J . 1999 . Antiproliferative efficacy of lipophilic soy isoflavone phytoestrogens delivered by low density lipoprotein particles into cultured U937 cells . Life Sci , 65 : 1695 – 1705 .
   PubMed Web of Science ®Google Scholar
• Polkowski , K , Popiołkiewicz , J , Krzeczynski , P , Pucko , W Zegrocka-Stendel , O . 2004 . Cytostatic and cytotoxic activity of synthetic genistein glycosides against human cancer cell lines . Cancer Lett , 203 : 59 – 69 .
   PubMed Web of Science ®Google Scholar
• Rusin , A , Krawczyk , Z , Grynkiewicz , G , Gogler , A Zawisza-Puchałka , J . 2010 . Synthetic derivatives of genistein, their properties and possible application . Acta Biochim Pol , 57 : 23 – 34 .
   PubMed Web of Science ®Google Scholar
• Rusin , A , Zawisza-Puchałka , J , Kujawa , K , Gogler-Pigłowska , A Wietrzyk , A . 2011 . Synthetic conjugates of genistein affecting proliferation and mitosis of cancer cells . Bioorg Med Chem , 19 : 295 – 305 .
   PubMed Web of Science ®Google Scholar
• McCall , J L , Burich , R A and Mack , P C . 2010 . GCP, a genistein-rich compound, inhibits proliferation and induces apoptosis in lymphoma cell lines . Leuk Res , 34 ( 1 ) : 69 – 76 .
   PubMed Web of Science ®Google Scholar