二肽与荧光染料的缀合增强了其对人肠Caco-2细胞中二肽转运蛋白（PEPT1）的亲和力。,Bioconjugate Chemistry

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二肽与荧光染料的缀合增强了其对人肠Caco-2细胞中二肽转运蛋白（PEPT1）的亲和力。
Bioconjugate Chemistry ( IF 4.0 ) Pub Date : 1999 Jan-Feb , DOI: 10.1021/bc980049i
Hiroshi Abe ₁ , Momoko Satoh ₁ , Seiji Miyauchi ₁ , Satoshi Shuto ₁ , Akira Matsuda ₁ , Naoki Kamo ₁

Affiliation

小肠中的二肽转运蛋白具有非常宽的底物特异性，因此该转运蛋白有时可作为肽样化合物的载体。我们已经合成了在Val-Lys或Lys-Sar中的Lys的ε-氨基缀合的二肽类似物，与荧光化合物如异硫氰酸荧光素和香豆素-3-羧酸。通过测量表达二肽转运蛋白PEPT1的人肠上皮细胞系Caco-2的单层细胞内积累来检查这些肽类似物的摄取。动力学分析和解偶联剂（质子体）或通过Gly-Sar（PEPT1的良好底物之一）添加的影响表明，荧光二肽被被动扩散吸收。相反，这些类似物显着抑制了Caco-2细胞对Gly-Sar的吸收。在本文合成的荧光类似物中，Val-Lys（Flu）是最有效的针对Gly-Sar摄取的竞争性抑制剂，其抑制常数为5 microM。该值是有史以来报告的值中最小的：Val-Lys（Flu）对PEPT1的亲和力在有报道的化学品中最高。指出了基材疏水部分的重要性。

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Conjugation of dipeptide to fluorescent dyes enhances its affinity for a dipeptide transporter (PEPT1) in human intestinal Caco-2 cells.

Dipeptide transporters in small intestine have a very wide substrate specificity, so that the transporter sometimes serves as a carrier for peptide-like compounds. We have synthesized dipeptide analogues conjugated at an epsilon-amino group of Lys in Val-Lys or Lys-Sar with fluorescent compounds such as fluorescein isothiocyanate and coumarin-3-carboxylic acid. Uptakes of these peptide analogues were examined by measuring intracellular accumulations into monolayers of the human intestinal epithelial cell line Caco-2 expressing the dipeptide transporter PEPT1. Kinetic analysis and effects of addition either of uncoupler (protonophore) or by Gly-Sar, one of the good substrates of PEPT1, revealed that fluorescent dipeptides were taken up by passive diffusion. In contrast, these analogues remarkably inhibited the Gly-Sar uptake by Caco-2 cells. Among the fluorescent analogues synthesized in this paper, Val-Lys(Flu) was the most potent competitive inhibitor against the Gly-Sar uptake with an inhibition constant of 5 microM. This value is the smallest among those ever reported: Val-Lys(Flu) has the highest affinity for PEPT1 among chemicals ever reported. The importance of the hydrophobic part of the substrate was pointed out.

更新日期：2017-01-31

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