Synthesis of fluorescent and photoaffinity-labeled derivatives of bisphenol A and their inhibitory activity toward hypoxic expression of erythropoietin

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 18, 2007, Pages 5121-5124

  Maezawa, Nobuhiro ^a   Tsuchikawa, Hiroshi ^a   Katsumura, Shigeo ^a   Kubo, Tomoko ^a   Imaoka, Susumu ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

Bisphenol A; Fluorescence; Inhibition; Photoaffinity label; Synthesis

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; ERYTHROPOIETIN; FLUORESCENT DYE;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; HUMAN; HUMAN CELL; HYPOXIA; PHOTOAFFINITY LABELING; PROTEIN EXPRESSION; SYNTHESIS;

CELL HYPOXIA; ERYTHROPOIETIN; FLUORESCENT DYES; HUMANS; PHENOLS; PHOTOAFFINITY LABELS;

EID: 34547902101     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.07.007     Document Type: Article

References (17)

1. Safe S.H., Pallaroni L., Yoon K., Gaido K., Ross S., Saville B., and McDonnellc D. Reprod. Fertil. Dev. 13 (2001) 307
2. Oka T., Adati N., Shinkai T., Sakuma K., Nishimura T., and Kurose K. Biochem. Biophys. Res. Commun. 312 (2003) 877
3. Nishi K., Takai M., Morimune K., and Ohkawa H. Biosci. Biotechnol. Biochem. 67 (2003) 1358
4. Susan A.B., Ebert D.A., and Duncan W.P. J. Label. Compd. Radiopharm. 16 (1979) 579
5. Kubo T., Maezawa N., Osada M., Katsumura S., Funae Y., and Imaoka S. Biochem. Biophys. Res. Commun. 318 (2004) 1006
6. Ghosh, P. B.; Whitehouse, M. W. 1968, 108, 155.
7. Hashimoto M., and Hatanaka Y. Bioorg. Med. Chem. Lett. 16 (2006) 5998 and references cited therein
8. Kawasaki M., Kakuda H., Goto M., Kawabata S., and Kometani T. Tetrahedron: Asymmetry 14 (2003) 1529
9. Takamura M., Kakurai M., Yamada E., Fujita S., Yachi M., Takagi T., Isobe A., Hagisawa Y., Fujiwara T., and Yanagisawa H. Bioorg. Med. Chem. 12 (2004) 2419
10. - 505.2087, found 505.2092.
11. - 461.1825, found 461.1811.
12. Hatanaka Y., Hashimoto M., Kurihara H., Nakayama H., and Kanaoka Y. J. Org. Chem. 42 (1994) 826
13. Hatanaka Y., Hashimoto M., Nakayama H., and Kanaoka Y. Chem. Pharm. Bull. 42 (1994) 826
14. Shigenari T., Hakogi T., and Katsumura S. Chem. Lett. 33 (2004) 594
15. + 741.2624, found 741.2641.
16. + 685.1998, found 685.1977.
17. 2 balanced with a modulator incubator chamber (Napco 7101, Winchester, VA) or were incubated in a sealed 2.5-L box with an Anero Pack for cells. Hep3B cells were incubated for 6 h under hypoxia in the presence of BpA and derivatives (200-300 μM). Total RNA was extracted from Hep3B cells and a reaction mixture containing 1 μg of RNA and 200 U of reverse transcriptase was reacted according to the condition as follows: incubation for 10 min at 25 °C and 60 min at 42 °C, followed by heating for 10 min at 70 °C to stop the reaction. Polymerase chain reaction (PCR) was performed using a reaction mixture containing 10 pmol of each primer, 1.5 U of Ampli Taq, and 100 ng of cDNA according to the following protocol: 10 min at 96 °C and then 35 cycles of 30 s at 96 °C, 30 s at 56 °C, and 1 min at 72 °C. Primers for β-actin were 5′-CAAGAGATGGCCACGGCTGCT-3′ (sense) and 5′-TCCTTCTGCATCCTGTCGGCA-3′ (antisense). Primers for EPO were 5′-GCCAGAGGAACTGTCCAGAG-3′ (sense) and 5′-TTCTCCAGGTCATCCTGTCC-3′ (antisense). The cycle number is within the linear range of amplification. Bands of amplified DNA fragments on agarose gel were quantified by NIH Image.