Influence of amino acid sequence in a peptidic Cu+-responsive luminescent probe inspired by the copper chaperone CusF†,Organic & Biomolecular Chemistry

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Influence of amino acid sequence in a peptidic Cu+-responsive luminescent probe inspired by the copper chaperone CusF†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-07-20 00:00:00 , DOI: 10.1039/c8ob01044g
A. Roux _{1,

2,

3,

4,

5} , M. Isaac _{1,

2,

3,

4,

5} , V. Chabert _{1,

2,

3,

4,

5} , S. A. Denisov _{2,

6,

7,

8,

9} , N. D. McClenaghan _{2,

6,

7,

8,

9} , O. Sénèque _{1,

2,

3,

4,

5}

Affiliation

Copper(I) is a soft metal ion that plays an essential role in living organisms and Cu⁺-responsive probes are required to detect Cu⁺ ions in physiological conditions and understand its homeostasis as well as the diseases associated with its misregulation. In this article, we describe a series of cyclic peptides, which are structurally related to the copper chaperone CusF, and that behave as Cu⁺-repsonsive probes. These peptide probes comprise the 16-amino acid loop of CusF cyclized by a β-turn inducer dipeptide and functionalized by a Tb³⁺ complex for its luminescence properties. The mechanism of luminescence enhancement relies on the modulation of the antenna effect between a tryptophan residue and the Tb³⁺ ion within the probe when Cu⁺ forms a cation–π interaction with the tryptophan. Here, we investigate the influence of the amino acid sequence of these cyclic peptides on the copper-induced modulation of Tb³⁺ emission and show that the rigid β-turn inducer Aib-D-Pro and insertion of the Tb³⁺ complex close to its tryptophan antenna are required to obtain turn-on Cu⁺ responsive probes. We also show that the amino acid sequence, especially the number and position of proline residues has a significant impact on metal-induced luminescence enhancement and metal-binding constant of the probes.

中文翻译：

铜伴侣CusF †激发的肽性Cu ⁺响应发光探针中氨基酸序列的影响

铜（I）是一种软金属离子，在活生物体中起着至关重要的作用，需要使用Cu ⁺响应探针在生理条件下检测Cu ⁺离子并了解其稳态以及与其失调相关的疾病。在本文中，我们描述了一系列环状肽，这些环状肽在结构上与铜分子伴侣CusF有关，并且表现为Cu ⁺ -探针。这些肽探针包含一个由CusF的16个氨基酸组成的环，该环被β转角诱导剂二肽环化，并被Tb ³⁺复合物官能化，从而具有发光特性。发光增强的机制依赖于色氨酸残基和Tb之间的天线效应的调节当Cu⁺与色氨酸形成阳离子-π相互作用时，探针中的³⁺离子。在这里，我们研究了这些环状肽的氨基酸序列对铜诱导的Tb³⁺发射的调节的影响，并表明刚性β-转角诱导剂Aib- D -Pro和Tb³⁺复合物的插入接近需要使用其色氨酸天线才能获得开启的Cu⁺响应探针。我们还表明，氨基酸序列，尤其是脯氨酸残基的数量和位置，对金属诱导的发光增强和探针的金属结合常数具有重大影响。

更新日期：2018-07-20

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