Two Dipeptide-Bound Pyrralines with Ile or Ala: A Study on Their Synthesis, Transport across Caco-2 Cell Monolayers, and Interaction with Aminopeptidase N,Journal of Agricultural and Food Chemistry

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Two Dipeptide-Bound Pyrralines with Ile or Ala: A Study on Their Synthesis, Transport across Caco-2 Cell Monolayers, and Interaction with Aminopeptidase N
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2021-09-07 , DOI: 10.1021/acs.jafc.1c03773
Haiping Qi ₁ , Zhenhui Zhang ₁ , Xia Zhang ₁ , Bing Li ₁ , Lin Li _{1,

2}

Affiliation

In this study, pyrralylisoleucine (Pyrr-Ile) and pyrralylalanine (Pyrr-Ala), two dipeptide-bound pyrralines with different C-termini were synthesized as the representatives of dietary advanced glycation end products (dAGEs). The structures of Pyrr-Ile and Pyrr-Ala were characterized by high-resolution mass spectrometry, nuclear magnetic resonance, and Fourier transform infrared spectroscopy. Then, the transport of Pyrr-Ile and Pyrr-Ala across intestinal epithelial cells was investigated using Caco-2 cell monolayers, and their interaction with aminopeptidase N (APN) was analyzed. The results showed that the apparent permeability coefficient (P_app) of Pyrr-Ala was (14.1 ± 2.26) × 10^–7 cm·s^–1 calculated by free pyrraline, while the P_app values of Pyrr-Ile were (32.4 ± 5.35) × 10^–7 and (19.1 ± 1.46) × 10^–7 cm·s^–1 when they were, respectively, calculated according to their dipeptide-bound or free form. Both Pyrr-Ala and Pyrr-Ile were potential substrates of APN, and their hydrolysis by APN may make the intact transmembrane transport of Pyrr-Ala and Pyrr-Ile more difficult, especially for Pyrr-Ala. Besides, the occurrence of product inhibition in hydrolysis of Pyrr-Ile was possible. Pyrr-Ile and Pyrr-Ala were different in P_app values and transport forms, which suggested that the C-terminus may play an important role in their transport across the Caco-2 cell monolayers. In addition, the results highlight the intact transmembrane transport of dipeptide-bound pyrraline.

中文翻译：

两种与 Ile 或 Ala 结合的二肽吡咯啉：关于它们的合成、跨 Caco-2 细胞单层转运以及与氨肽酶 N 相互作用的研究

在这项研究中，合成了两种具有不同 C 端的二肽结合吡咯啉作为膳食晚期糖基化终产物 (dAGEs) 的代表吡咯基异亮氨酸 (Pyrr-Ile) 和吡咯基丙氨酸 (Pyrr-Ala)。Pyrr-Ile 和 Pyrr-Ala 的结构通过高分辨率质谱、核磁共振和傅里叶变换红外光谱进行了表征。然后，使用 Caco-2 细胞单层研究了 Pyrr-Ile 和 Pyrr-Ala 跨肠上皮细胞的转运，并分析了它们与氨肽酶 N (APN) 的相互作用。结果表明，按游离吡咯啉计算，Pyrr -Ala的表观渗透系数（P _app）为（14.1±2.26）×10 ^–7 cm·s ^–1，而PPyrr-Ile 的_app值分别为 (32.4 ± 5.35) × 10 ^–7和 (19.1 ± 1.46) × 10 ^–7 cm·s ^–1，分别根据其二肽结合形式或游离形式计算。Pyrr-Ala 和 Pyrr-Ile 都是 APN 的潜在底物，它们被 APN 水解可能使 Pyrr-Ala 和 Pyrr-Ile 的完整跨膜转运更加困难，尤其是 Pyrr-Ala。此外，Pyrr-Ile 水解过程中可能出现产物抑制。Pyr-Ile 和 Pyrr-Ala 在P _{app 中}是不同的值和运输形式，这表明 C 端可能在它们跨 Caco-2 细胞单层的运输中起重要作用。此外，结果突出了二肽结合吡咯啉的完整跨膜转运。

更新日期：2021-09-22

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