title: Selective inhibition of embryonic development in starfish by long-chain alkyl derivatives of UMP, TMP and AMP.
abstract: Nucleoside analogs have been evaluated as useful tools for the investigation of the mechanism of cell differentiation. We thus examined the effects of nucleoside 5'-alkylphosphates (1-10) on the morphogenetic development of starfish embryos. These nucleotide derivatives were all permissive for their development up to the blastula stage, but the derivatives with lauryl side chain selectively inhibited one of the following stages into bipinnaria larvae. Among them, uridine 5'-laurylphosphate (2) inhibited gastrulation of the blastula, as is the case with the antibiotic tunicamycin, suggesting its inhibitory activity on sulfated and non-sulfated glycoprotein syntheses. Unexpectedly, adenosine 5'-laurylphosphate (8) was evaluated as a novel class of inhibitor that can arrest the embryos exactly at the late gastrula stage, absolutely inhibiting cell differentiation involved in the development of gastrointestinal tract. This is the first report on the appearance of biological activity due to the structural modification of a naturally-occurring molecule, which is critical to the morphogenetic development of multicellular organisms.
authors: Department of Biology and Geosciences, Graduate School of Science, Osaka City University, Osaka 558-8585, Japan. tanakato@sci.osaka-cu.ac.jp
authors: Toshio
authors: T
authors: Tanaka
authors: Akira
authors: A
authors: Ogita
authors: Yoshinosuke
authors: Y
authors: Usuki
authors: Ken-ichi
authors: K
authors: Fujita
mesh_terms: D000249:Adenosine Monophosphate / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D036703:Blastula / Q000187:drug effects / Q000196:embryology; D004625:Embryo, Nonmammalian / Q000187:drug effects / Q000196:embryology; D047108:Embryonic Development / Q000187:drug effects; D005775:Gastrula / Q000187:drug effects / Q000196:embryology; D015394:Molecular Structure; D013215:Starfish / Q000187:drug effects / Q000196:embryology; D013938:Thymidine Monophosphate / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D014542:Uridine Monophosphate / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D013938:Thymidine Monophosphate; D000249:Adenosine Monophosphate; D014542:Uridine Monophosphate