4-Oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in 10T1/2 cells

Advances in Experimental Medicine and Biology

Volumn 387, Issue , 1996, Pages 121-128

  Stahl, Wilhelm ^a   Hanusch, Michael ^a   Sies, Helmut ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 OXOISOTRETINOIN; 4 OXORETINOIC ACID; ACETONE; CANTHAXANTHIN; CAROTENOID; CONNEXIN 43; GLYCERALDEHYDE 3 PHOSPHATE DEHYDROGENASE; MESSENGER RNA; RETINOID; TETRAHYDROFURAN;

ANIMAL CELL; CELL COMMUNICATION; CELL JUNCTION; CONFERENCE PAPER; CONTROLLED STUDY; DECOMPOSITION; DRUG STRUCTURE; EMBRYO; FIBROBLAST; MOUSE; NONHUMAN; PRIORITY JOURNAL;

EID: 0029776882     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4757-9480-9_17     Document Type: Conference Paper

References (17)

1. Bertram, J.S., Pung, A., Churley, M., Kappock, T.J., Wilkins, L.R. and Cooney, R.V. (1991). Diverse carotenoids protect against chemically induced neoplastic transformation. Carcinogenesis 12, 671-678.
2. Beyer, E.C., Paul, D.L. and Goodenough, D.A. (1990). Connexin family of gap junction proteins. Membrane Biol. 116, 187-194.
3. Chomszynsky, P. and Sacchi, N. (1987). Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol chloroform extraction. Anal. Biochem. 162, 156-159.
4. Handelman, G.J., van Kuijk, F.J.G.M., Chatterjee, A. and Krinsky, N.I. (1991). Characterization of products formed during the autoxidation of β-carotene. Free Rad. Biol. Med. 10, 427-437.
5. Hanusch, M., Stahl, W., Schulz, W., and Sies, H. (1995). Induction of gap junctional communication by 4-oxoretinoic acid generated from its precursor canthaxanthin. Arch. Biochem. Biophys. 317, 423-428
6. Hossain, M.Z., Wilkens, L.R., Mehta, P.P., Loewenstein, W.R. and Bertram, J.S. (1989). Enhancement of gap junctional communication by retinoids correlates with their ability to inhibit neoplastic transformation. Carcinogenesis 10, 1743-1748.
7. Levin, A.A., Sturzenbecker, L.J., Kazmer, S., Bosakowski, T., Huselton, C., Allenby, G., Speck, J., Kratzeisen, C., Rosenberger, M., Lovey, A. and Grippo, J.F. (1992). 9-cis Retinoic acid stereoisomer binds and activates the nuclear receptor RXR α. Nature 355, 359-361.
8. Mehta, P.P., Bertram, J.S., and Loewenstein, W.R. (1989). The action of retinoids on cellular growth correlates with their action on gap junctional communication. J. Cell Biol. 108, 1053-1065.
9. Nikawa, T., Schulz, W.A., van den Brink, C.E., Hanusch, M., van der Saag, P., Stahl, W. and Sies, H. (1995). Efficacy of all-trans β-carotene, canthaxanthin, and all-trans-, 9-cis, and 4-oxoretinoic acids in inducing differentiation of an F9 embryonal carcinoma RAR-β-lacZ reporter cell line. Arch. Biochem. Biophvs., 316, 665-672.
10. Oarada, M., Stahl, W. and Sies, H. (1993). Cellular levels of all-trans β-carotene under the influence of 9-cis β-carotene in FU-5 rat hepatoma cells. Biol. Chem. Hoppe-Seyler 374, 1075-1081.
11. Pijnappel, W.W.M., Hendriks, H.F.J., Folkers, G.E., van den Brink, C.E., Dekker, E.J., Edelenbosch, C., van der Saag, P.T. and Durston, A.J. (1993). The retinoid ligand 4-oxo-retinoic acid is a highly active modulator of positional specification. Nature 366, 340-344.
12. Pung, A., Rundhaug, J.E., Yoshizawa, C.N. and Bertram, J.S. (1988). β-Carotene and canthaxanthin inhibit chemically- and physically-induced neoplastic transformationin 10T1/2 cells. Carcinogenesis 9, 1533-1539.
13. Rushin, W.G., Catignani, G.L. and Schwartz, S.J. (1990). Determination of β-carotene and its cis-isomers in serum. Clin. Chem. 36, 1986-1989.
14. Sundquist, A.R., Hanusch, M., Stahl, W. and Sies, H. (1993a). Cis/trans isomerization of carotenoids by the triplet carbonyl source 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane. Photochem. Photobiol. 57, 785-791
15. Sundquist, A.R., Stahl, W., Steigel, A. and Sies, H. (1993b). Separation of retinoic acid all-trans, mono-cis, and poly-cis isomers by reversed phase high-performance liquid chromatography. J. Chromatography 637, 201-205.
16. Wang, X.D., Krinsky, N.I., Benotti, P.N. and Russell, R.M. (1994). Biosynthesis of 9-cis retinoic acid from 9-cis β-carotene in human intestinal mucosa in vitro. Arch. Biochem. Biophys. 313, 150-155.
17. Zhang, L.X., Cooney, R.V. and Bertram, J.S. (1991). Carotenoids enhance gap junctional communication and inhibit lipid peroxidation in C3H/10T1/2 cells: Relationship to their cancer chemopreventive action. Carcinogenesis 12, 2109-2114.