4-Hydroxyphenylmethylene hydantoin (PMH, 1), isolated from the Red Sea sponge Hemimycale Arabica, and δ-tocotrienol (3), isolated from the tocotrienol-rich fraction of palm oil, are important antimetastatic and antiproliferative natural products that proved effective against metastatic prostate and breast cancers, respectively. New fluorescent derivatives of PMH (2) and δ-tocotrienol (4) were synthesized by Steglich esterification. Both 2 and 4 retained good anti-migratory and antiproliferative activities, respectively. Fluorescent analogues 2 and 4 can be used for the identification of molecular targets of 1 and 3 in tumor cell cultures.
YuTZ, ZhaoYL, DingXS, FanDW, QianL, DongWK. (2007) Synthesis, crystal structure and photoluminescent behaviors of 3-(1H-benzotriazol-1-yl)-4-methyl-benzo[7,8]coumarin. Journal of Photochemistry and Photobiology, A: Chemistry, 188, 245–251;
5.
MuditM, KhanfarM, MuralidharanA, ThomasS, ShahGV, van SoestRWM, El SayedKA. (2009) Discovery, design, and synthesis of antimetastatic lead phenylmethylene hydantoins inspired by marine natural products. Bioorganic & Medicinal Chemistry, 17, 1731–1738;
6.
ShahGV, MuralidharanA, ThomasS, GokulgandhiM, MuditM, KhanfarM, El SayedKA. (2009) Identification of a small molecule class to enhance cell-cell adhesion and attenuate prostate tumor growth and metastasis. Molecular Cancer Therapeutics, 8, 509–520.
7.
NesaretnamK, AmbraR, SelvadurayKR. (2004) Tocotrienol-rich fraction from palm oil and gene expression in human breast cancer cells. Annals of the New York Academy of Sciences, 1031, 143–157;
8.
SylvesterPW, TheriaultA. (2003) Role of tocotrienols in the prevention of cardiovascular disease and breast cancer. Current Topics in Nutraceutical Research, 1, 121–136.
9.
SteglichW, HofleG. (1969) N,N-Dimethyl-4-pyridinamine, a very effective acylation catalyst. Angewandte Chemie International Edition, 8, 981;
10.
ZieglerFE, BergerGD. (1979) A mild method for the esterification of fatty acids. Synthetic Communications, 9, 539–543;
11.
EitenmillerR, LeeJ. (2004) Vitamin E: Food Chemistry, Composition, and Analysis.Marcel Dekker Inc., New York. 1–380;
12.
McIntyreBS, BriskiKP, GaborA, SylvesterPW. (2000) Antiproliferative and apoptotic effects of tocopherols and tocotrienols on preneoplastic and neoplastic mouse mammary epithelial cells. Proceedings of the Society for Experimental Biology and Medicine, 224, 292–301.
