Department of Organic Chemistry, University of Chemical Technology and Metallurgy, 1756 Sofia, Bulgaria.
Department of Analytical Chemistry, University of Chemical Technology and Metallurgy, 1756 Sofia, Bulgaria.
Molecules. 2022 Jul 26;27(15):4770. doi: 10.3390/molecules27154770.
Some new N- and C-modified biomolecular peptide analogues of both VV-hemorphin-5 and VV-hemorphin-7 with varied amino acids (Cys, Glu, His), 1-adamantanecarboxylic acid, and niacin (nicotinic acid) were synthesized by solid-phase peptide synthesis-Fmoc (9-fluorenylmethoxy-carbonyl) chemistry and were characterized in water solutions with different pH using spectroscopic and electrochemical techniques. Basic physicochemical properties related to the elucidation of the peptide structure at physiological pH have been also studied. The results showed that the interaction of peptide compounds with light and electricity preserves the structural and conformational integrity of the compounds in the solutions. Moreover, textile cotton fibers were modified with the new compounds and the binding of the peptides to the surface of the material was proved by FTIR and SEM analysis. Washing the material with an alkaline soap solution did not show a violation of the modified structure of the cotton. Antiviral activity against the human respiratory syncytial virus (HRSV-S2) and human adenovirus serotype 5 (HAdV-5), the antimicrobial activity against and used as model bacterial strains and cytotoxic effect of the peptide derivatives and modified cotton textile material has been evaluated. Antimicrobial tests showed promising activity of the newly synthesized compounds against the used Gram-positive and Gram-negative bacteria. The compounds C-V, H-V, AC-V, and AH-V were found slightly more active than NH7C and NCH7. The activity has been retained after the deposition of the compounds on cotton fibers.
一些新的 N-和 C-修饰的生物分子肽类似物,包括 VV-hemorphin-5 和 VV-hemorphin-7,具有不同的氨基酸(半胱氨酸、谷氨酸、组氨酸)、1-金刚烷羧酸和烟酸(烟酰胺酸),通过固相肽合成-Fmoc(9-芴甲氧羰基)化学合成,并在不同 pH 值的水溶液中使用光谱和电化学技术进行了表征。还研究了与阐明生理 pH 值下肽结构相关的基本物理化学性质。结果表明,肽化合物与光和电的相互作用在溶液中保持了化合物的结构和构象完整性。此外,新化合物对棉纤维进行了修饰,并通过 FTIR 和 SEM 分析证明了肽与材料表面的结合。用碱性肥皂溶液洗涤材料不会破坏棉的修饰结构。对人呼吸道合胞病毒(HRSV-S2)和人腺病毒 5 型(HAdV-5)的抗病毒活性,以及作为模型细菌株的 和 的抗菌活性,以及肽衍生物和修饰的棉纺织品的细胞毒性进行了评估。抗菌试验表明,新合成的化合物对所使用的革兰氏阳性和革兰氏阴性细菌具有有希望的活性。化合物 C-V、H-V、AC-V 和 AH-V 被发现比 NH7C 和 NCH7 略具有更高的活性。化合物在沉积在棉纤维上后仍保留活性。