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1.
Org Lett ; 26(20): 4377-4382, 2024 May 24.
Article in English | MEDLINE | ID: mdl-38747558

ABSTRACT

The total synthesis of marine macrolide glycoside (-)-irijimaside A is described. Key to the synthesis is the convergent fragment assembly enabled by nickel/zirconocene-mediated one-pot reductive ketone coupling. At the last stage of the synthesis, Stille coupling and glycosylation led to the first total synthesis of (-)-irijimaside A.

2.
PLoS One ; 18(3): e0280421, 2023.
Article in English | MEDLINE | ID: mdl-36928065

ABSTRACT

A synthetic estrogen, diethylstilbestrol (DES), is known to cause adult vaginal carcinoma by neonatal administration of DES to mice. However, the carcinogenic process remains unclear. By Cap Analysis of Gene Expression method, we found that neonatal DES exposure up-regulated inflammatory Cxcl chemokines 2, 3, 5, and 7 located in the 5qE1 region in the vaginal epithelium of mice 70 days after birth. When we examined the gene expressions of these genes much earlier stages, we found that neonatal DES exposure increased these Cxcl chemokine genes expression even after 17 days after birth. It implies the DES-mediated persistent activation of inflammatory genes. Intriguingly, we also detected DES-induced non-coding RNAs from a region approximately 100 kb far from the Cxcl5 gene. The non-coding RNA up-regulation by DES exposure was confirmed on the 17-day vagina and continued throughout life, which may responsible for the activation of Cxcl chemokines located in the same region, 5qE1. This study shows that neonatal administration of DES to mice causes long-lasting up-regulation of inflammatory Cxcl chemokines in the vaginal epithelium. DES-mediated inflammation may be associated with the carcinogenic process.


Subject(s)
Chemokines, CXC , Diethylstilbestrol , Estradiol Congeners , Animals , Female , Mice , Animals, Newborn , Carcinogens/pharmacology , Diethylstilbestrol/adverse effects , Diethylstilbestrol/pharmacology , Epithelium/pathology , Estradiol Congeners/adverse effects , Estradiol Congeners/pharmacology , Vagina/metabolism , Vaginal Neoplasms/chemically induced , Chemokines, CXC/drug effects , Chemokines, CXC/metabolism
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