A pH-Sensitive Peptide-Containing Lasso Molecular Switch

被引:38
作者
Clavel, Caroline [1 ]
Fournel-Marotte, Karine [1 ]
Coutrot, Frederic [1 ]
机构
[1] Univ Montpellier 2, IBMM UMR CNRS UM1 UM2 5247, Inst Biomol Max Mousseron, Supramol Machines & ARchitectures Team, F-34095 Montpellier 5, France
关键词
1]rotaxane; lasso; molecular switch; self-entanglement; peptide; MICROCIN J25; ROTAXANES; INTERLOCKING; MATURATION; STABILITY; RELEASE; STATION; AZIDE;
D O I
10.3390/molecules180911553
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of a peptide-containing lasso molecular switch by a self-entanglement strategy is described. The interlocked [1] rotaxane molecular machine consists of a benzometaphenylene[25]crown-8 (BMP25C8) macrocycle surrounding a molecular axle. This molecular axle contains a tripeptidic sequence and two molecular stations: a N-benzyltriazolium and a pH-sensitive anilinium station. The tripeptide is located between the macrocycle and the triazolium station, so that its conformation can be tailored depending on the shuttling of the macrocycle from one station to the other. At acidic pH, the macrocycle resides around the anilinium moiety, whereas it shuttles around the triazolium station after deprotonation. This molecular machinery thus forces the lasso to adopt a tightened or a loosened conformation.
引用
收藏
页码:11553 / 11575
页数:23
相关论文
共 50 条
[41]   Preparation of T-2 toxin-containing pH-sensitive liposome and its antitumor activity [J].
Dong, Yuan ;
Meng, Guixian ;
Guo, Jian ;
Yin, Moli ;
Xu, Huijing ;
Li, Yujie ;
Zhu, Jie ;
Zhu, Wenhe ;
Li, Mingguang ;
Li, Yan ;
Wang, Huiyan .
MOLECULAR MEDICINE REPORTS, 2020, 22 (05) :4423-4431
[42]   Recent strategies to develop pH-sensitive injectable hydrogels [J].
Thambi, Thavasyappan ;
Jung, Jae Min ;
Lee, Doo Sung .
BIOMATERIALS SCIENCE, 2023, 11 (06) :1948-1961
[43]   pH-sensitive nanoparticles for improving the oral bioavailability of cyclosporine A [J].
Dai, JD ;
Nagai, T ;
Wang, XQ ;
Zhang, T ;
Meng, M ;
Zhang, Q .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2004, 280 (1-2) :229-240
[44]   Influence of a pH-sensitive polymer on the structure of monoolein cubosomes [J].
Kluzek, Monika ;
Tyler, Arwen I. I. ;
Wang, Shiqi ;
Chen, Rongjun ;
Marques, Carlos M. ;
Thalmann, Fabrice ;
Seddon, John M. ;
Schmutz, Marc .
SOFT MATTER, 2017, 13 (41) :7571-7577
[45]   pH-sensitive nanocarriers for curcumin delivery in cancer therapy [J].
Mohammadzadeh, Vahideh ;
Zirak, Mohammad Reza ;
Khah, Seyedeh Maryam Hosseini ;
Kamali, Hossein ;
Jaafari, Mahmoud Reza .
JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, 2021, 66
[46]   Novel PEGylated pH-sensitive polymeric hollow microspheres [J].
Bilalis, Panayiotis ;
Boukos, Nikos ;
Kordas, George .
MATERIALS LETTERS, 2012, 67 (01) :180-183
[47]   Recovery of gold nanoparticles using pH-sensitive microgels [J].
Lazim, Azwan Mat ;
Eastoe, Julian ;
Bradley, Melanie ;
Trickett, Kieran ;
Mohamed, Azmi ;
Rogers, Sarah E. .
SOFT MATTER, 2010, 6 (09) :2050-2055
[48]   Magnetic and pH-sensitive nanoparticles for antitumor drug delivery [J].
Yu, Shufang ;
Wu, Guolin ;
Gu, Xin ;
Wang, Jingjing ;
Wang, Yinong ;
Gao, Hui ;
Ma, Jianbiao .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2013, 103 :15-22
[49]   Preparation of pH-Sensitive Dextran Nanoparticle for Doxorubicin Delivery [J].
Wang, Bi ;
Liu, Peng ;
Shi, Bihua ;
Gao, Jihua ;
Gong, Ping .
JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY, 2015, 15 (04) :2613-2618
[50]   Mucoadhesive and pH-Sensitive Thiolated Eudragit Microspheres for Oral Delivery of Pasteurella multocida Antigens Containing Dermonecrotoxin [J].
Islam, Mohammad Ariful ;
Jiang, Hu-Lin ;
Quan, Ji-Shan ;
Arote, Rohidas B. ;
Kang, Mi-Lan ;
Yoo, Han-Sang ;
Yun, Cheol-Heui ;
Choi, Yun-Jaie ;
Cho, Chong-Su .
JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY, 2011, 11 (05) :4174-4181