Ketomethylene and methyleneamino pseudopeptide analogues of insect allatostatins inhibit juvenile hormone and vitellogenin production in the cockroach Blattella germanica.
Ketomethylene and methyleneamino pseudopeptide analogues of insect allatostatins inhibit juvenile hormone and vitellogenin production in the cockroach Blattella germanica.
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DOI：
10.1016/s0965-1748(97)00067-2
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发表时间：
1997-10
影响因子：
3.8
通讯作者：
M. Piulachs;L. Vilaplana;J. Bartolome;C. Carreño;D. Martín;R. González-Muñiz;R. Herranz;M. García-López;D. Andreu;X. Belles
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文献类型：
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作者：
M. Piulachs;L. Vilaplana;J. Bartolome;C. Carreño;D. Martín;R. González-Muñiz;R. Herranz;M. García-López;D. Andreu;X. Belles
对昆虫尿抑素的代谢研究表明，二肽 Leu-Tyr 可能是内肽酶的靶标。为了增加抗降解性，分别在尿抑素 Asp-Arg-Leu-Tyr-Ser-Phe-Gly-Leu-amide (BLAST-2) 的 Leu3-Tyr4 位置和 [Phe4]BLAST-2 的 Leu3-Phe4 位置引入亚甲基 Ψ[CH2NH] 和酮亚甲基 Ψ[COCH2] 肽键替代物。德国小蠊蟑螂体体外抑制保幼激素 (JH) 合成的测定表明，两种类似物对各自的模型肽具有相似的活性。进一步在体内测试了亚甲基氨基类似物作为JH合成的抑制剂，以及在体内和体外作为德国芽孢杆菌脂肪体产生卵黄蛋白原的抑制剂。体外测试时，该类似物的活性低于 BLAST-2，但体内测试时的活性高于 BLAST-2。
Metabolic studies on insect allatostatins have suggested that the dipeptide Leu-Tyr may be a target for endopeptidases. In order to increase resistance to degradation, methyleneamino Ψ[CH2NH] and ketomethylene Ψ[COCH2] peptide bond surrogates have been introduced at the position Leu3-Tyr4of the allatostatin Asp-Arg-Leu-Tyr-Ser-Phe-Gly-Leu-amide (BLAST-2), and Leu3-Phe4of [Phe4]BLAST-2, respectively. Assays of inhibition of juvenile hormone (JH) synthesis in vitro by corpora allata from the cockroach Blattella germanica showed that both analogues were similarly active to the respective model peptides. The methyleneamino analogue was further tested in vivo as an inhibitor of JH synthesis, and in vivo and in vitro as an inhibitor of vitellogenin production by the fat body of B. germanica. The analogue was less active than BLAST-2 when tested in vitro, but more active than it when tested in vivo.