Dipeptide self-assembly into water-channels and gel biomaterial

被引:11
作者
Bellotto, Ottavia [1 ]
Pierri, Giovanni [2 ]
Rozhin, Petr [1 ]
Polentarutti, Maurizio [3 ]
Kralj, Slavko [4 ,5 ]
D'Andrea, Paola [6 ]
Tedesco, Consiglia [2 ]
Marchesan, Silvia [1 ]
机构
[1] Univ Trieste, Chem Pharm Sc Dept, Via Giorgieri 1, I-34127 Trieste, Italy
[2] Univ Salerno, Dept Chem & Biol Zambelli, Via Giovanni Paolo II 132, I-84084 Fisciano, SA, Italy
[3] Elettra Sincrotrone Trieste, SS 114 km 163-5, I-34149 Trieste, Italy
[4] Jozef Stefan Inst, Mat Synth Dept, Jamova 39, Ljubljana 1000, Slovenia
[5] Univ Ljubljana, Dept Pharmaceut Technol, Fac Pharm, Askerceva 7, Ljubljana 1000, Slovenia
[6] Univ Trieste, Dept Life Sci, Via L Giorgieri 5, I-34127 Trieste, Italy
关键词
PEPTIDE; MICROTUBES;
D O I
10.1039/d2ob00622g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dipeptides are convenient building blocks for supramolecular gel biomaterials that can be produced on a large scale at low cost and do not persist in the environment. In the case of unprotected sequences, hydrophobicity is a key requirement to enable gelation, with Phe-Phe standing out for its self-assembling ability. Conversely, more hydrophilic sequences such as homochiral dipeptides Phe-Val and Val-Phe neither fibrillate nor gel aqueous buffers and their crystal structures reveal amphipathic layers. In this work, we test emerging rules for the design of self-assembling dipeptides using heterochiral Phe-Val and Val-Phe. Each dipeptide is characterized by H-1- and C-13-NMR, LC-MS, circular dichroism, infrared and Raman spectroscopies, rheology, electron microscopy, and single-crystal X-ray diffraction. In particular, d-Phe-l-Val is the first heterochiral dipeptide to self-assemble into supramolecular water-channels whose cavity is defined by four peptide molecules arranged head-to-tail. This minimalistic sequence is devoid of amyloid character as probed by thioflavin T fluorescence and it displays excellent biocompatibility in vitro. The dataset provided, through comparison with the literature, significantly advances the definition of molecular design rules for minimalistic unprotected dipeptides that self-assemble into water-channels and biocompatible gels, to assist with the future development of supramolecular biomaterials with fine control over nanomorphological features for a variety of applications.
引用
收藏
页码:6211 / 6218
页数:8
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