A mini-review and perspective on multicyclic peptide mimics of antibodies
- Corresponding author: Wu Chuanliu, chlwu@xmu.edu.cn
Citation:
Liu Weidong, Wu Chuanliu. A mini-review and perspective on multicyclic peptide mimics of antibodies[J]. Chinese Chemical Letters,
;2018, 29(7): 1063-1066.
doi:
10.1016/j.cclet.2018.03.015
A. Bradbury, A. Pluckthun, Nature 518(2015) 27-29.
doi: 10.1038/518027a
M. Baker, Nature 521(2015) 274-276.
doi: 10.1038/521274a
J. Bordeaux, A.W. Welsh, S. Agarwal, et al., Biotechniques 48(2010) 197-209.
doi: 10.2144/000113382
A.L.J. Marschall, S. Dubel, T. Boldicke, Mabs 7(2015) 1010-1035.
doi: 10.1080/19420862.2015.1076601
M. Akishiba, T. Takeuchi, Y. Kawaguchi, et al., Nat. Chem. 9(2017) 751-761.
doi: 10.1038/nchem.2779
P. Holliger, P.J. Hudson, Nat. Biotechnol. 23(2005) 1126-1136.
doi: 10.1038/nbt1142
H.K. Binz, P. Amstutz, A. Pluckthun, Nat. Biotechnol. 23(2005) 1257-1268.
doi: 10.1038/nbt1127
J. Lofblom, F.Y. Frejd, S. Stahl, Curr. Opin. Biotech. 22(2011) 843-848.
doi: 10.1016/j.copbio.2011.06.002
T. Wurch, A. Pierre, S. Depil, Trends Biotechnol. 30(2012) 575-582.
doi: 10.1016/j.tibtech.2012.07.006
K. Skrlec, B. Strukelj, A. Berlec, Trends Biotechnol. 33(2015) 408-418.
doi: 10.1016/j.tibtech.2015.03.012
C. Tiede, R. Bedford, S.J. Heseltine, et al., Elife 6(2017) e24903.
C.J. White, A.K. Yudin, Nat. Chem. 3(2011) 509-524.
doi: 10.1038/nchem.1062
C. Heinis, T. Rutherford, S. Freund, G. Winter, Nat. Chem. Biol. 5(2009) 502-507.
doi: 10.1038/nchembio.184
Y. Hamuro, M.C. Calama, H.S. Park, A.D. Hamilton, Angew. Chem. Int. Ed. 36(1997) 2680-2683.
doi: 10.1002/(ISSN)1521-3773
H.K. Cui, Y. Guo, Y. He, et al., Angew. Chem. Int. Ed. 52(2013) 9558-9562.
doi: 10.1002/anie.v52.36
K. Hu, H. Geng, Q.Z. Zhang, et al., Angew. Chem. Int. Ed. 55(2016) 8013-8017.
doi: 10.1002/anie.201602806
T.A. Hill, N.E. Shepherd, F. Diness, D.P. Fairlie, Angew. Chem. Int. Ed. 53(2014) 13020-13041.
doi: 10.1002/anie.201401058
R.U. Kadam, J. Juraszek, B. Brandenburg, et al., Science 358(2017) 496-502.
doi: 10.1126/science.aan0516
T.A. Whitehead, Science 358(2017) 450-451.
doi: 10.1126/science.aap9608
M. Favre, K. Moehle, L.Y. Jiang, B. Pfeiffer, J.A. Robinson, J. Am. Chem. Soc. 121(1999) 2679-2685.
doi: 10.1021/ja984016p
W.V. Williams, T. Kieberemmons, J. Vonfeldt, M.I. Greene, D.B. Weiner, J. Biol. Chem. 266(1991) 5182-5190.
S.Y. Chen, I.R. Rebollo, S.A. Buth, et al., J. Am. Chem. Soc. 135(2013) 6562-6569.
doi: 10.1021/ja400461h
M.J. Feige, L.M. Hendershot, J. Buchner, Trends Biochem. Sci. 35(2010) 189-198.
doi: 10.1016/j.tibs.2009.11.005
K.E. Tiller, P.M. Tessier, Annu. Rev. Biomed. Eng. 17(2015) 191-216.
doi: 10.1146/annurev-bioeng-071114-040733
I.R. Rebollo, C. Heinis, Methods 60(2013) 46-54.
doi: 10.1016/j.ymeth.2012.12.008
R. Maini, S. Umemoto, H. Suga, Curr. Opin. Chem. Biol. 34(2016) 44-52.
doi: 10.1016/j.cbpa.2016.06.006
K. Deyle, X.D. Kong, C. Heinis, Acc. Chem. Res. 50(2017) 1866-1874.
doi: 10.1021/acs.accounts.7b00184
J. Wilbs, S.J. Middendorp, C. Heinis, ChemBioChem 17(2016) 2299-2303.
doi: 10.1002/cbic.v17.24
V. Baeriswyl, H. Rapley, L. Pollaro, et al., ChemMedChem 7(2012) 1173-1176.
doi: 10.1002/cmdc.v7.7
P. Timmerman, J. Beld, W.C. Puijk, R.H. Meloen, ChemBioChem 6(2005) 821-824.
doi: 10.1002/cbic.v6:5
S.Y. Chen, D. Bertoldo, A. Angelini, F. Pojer, C. Heinis, Angew. Chem. Int. Ed. 53(2014) 1602-1606.
doi: 10.1002/anie.201309459
C.E. Schafmeister, J. Po, G.L. Verdine, J. Am. Chem. Soc. 122(2000) 5891-5892.
doi: 10.1021/ja000563a
L. Mendive-Tapia, S. Preciado, J. Garcia, et al., Nat. Commun. 6(2015) 7160.
doi: 10.1038/ncomms8160
Y.H. Lau, Y.T. Wu, M. Rossmann, et al., Angew. Chem. Int. Ed. 54(2015) 15410-15413.
doi: 10.1002/anie.201508416
G.J. Hilinski, Y.W. Kim, J. Hong, et al., J. Am. Chem. Soc.136(2014) 12314-12322.
doi: 10.1021/ja505141j
H. Jo, N. Meinhardt, Y.B. Wu, et al., J. Am. Chem. Soc. 134(2012) 17704-17713.
doi: 10.1021/ja307599z
Y.X. Wang, D.H.C. Chou, Angew. Chem. Int. Ed. 54(2015) 10931-10934.
doi: 10.1002/anie.201503975
C.M.B.K. Kourra, N. Cramer, Chem. Sci. 7(2016) 7007-7012.
doi: 10.1039/C6SC02285E
K. Chua, E. Fung, E.D. Micewicz, et al., Angew. Chem. Int. Ed. 57(2018) 501-505.
doi: 10.1002/anie.201709127
W.D. Liu, Y.W. Zheng, X.D. Kong, et al., Angew. Chem. Int. Ed. 56(2017) 4458-4463.
doi: 10.1002/anie.201610942
J.H. Wang, M.R. Zha, Q.R. Fei, et al., Chem. Eur. J. 23(2017) 15150-15155.
doi: 10.1002/chem.201703139
A.M. Davis, A.T. Plowright, E. Valeur, Nat. Rev. Drug Discov. 16(2017) 681-698.
doi: 10.1038/nrd.2017.146
A.R.M. Bradbury, S. Sidhu, S. Dubel, J. McCafferty, Nat. Biotechnol. 29(2011) 245-254.
doi: 10.1038/nbt.1791
C. Heinis, G. Winter, Curr. Opin. Chem. Biol. 26(2015) 89-98.
doi: 10.1016/j.cbpa.2015.02.008
K.A. Noren, C.J. Noren, Methods 23(2001) 169-178.
doi: 10.1006/meth.2000.1118
A. Galan, L. Comor, A. Horvatic, et al., Mol. Biosyst. 12(2016) 2342-2358.
doi: 10.1039/C6MB00219F
Y. Yamagishi, I. Shoji, S. Miyagawa, et al., Chem. Biol. 18(2011) 1562-1570.
doi: 10.1016/j.chembiol.2011.09.013
B. Owens, Nat. Biotechnol. 35(2017) 602-603.
doi: 10.1038/nbt0717-602
M.L. Azoitei, B.E. Correia, Y.E.A. Ban, et al., Science 334(2011) 373-376.
doi: 10.1126/science.1209368
G. Bhardwaj, V.K. Mulligan, C.D. Bahl, et al., Nature 538(2016) 329-335.
doi: 10.1038/nature19791
A. Chevalier, D.A. Silva, G.J. Rocklin, et al., Nature 550(2017) 74-79.
S.C. Penchala, M.R. Miller, A. Pal, et al., Nat. Chem. Biol. 11(2015) 793-798.
doi: 10.1038/nchembio.1907
C. Rader, Nature 518(2015) 38-39.
doi: 10.1038/518038a
Hongmei Yu , Baoxi Zhang , Meiju Liu , Cheng Xing , Guorong He , Li Zhang , Ningbo Gong , Yang Lu , Guanhua Du . Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers. Chinese Chemical Letters, 2024, 35(5): 109032-. doi: 10.1016/j.cclet.2023.109032
Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO2 nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
Beitong Zhu , Xiaorui Yang , Lirong Jiang , Tianhong Chen , Shuangfei Wang , Lintao Zeng . A portable and versatile fluorescent platform for high-throughput screening of toxic phosgene, diethyl chlorophosphate and volatile acyl chlorides. Chinese Chemical Letters, 2025, 36(1): 110222-. doi: 10.1016/j.cclet.2024.110222
Qingyun Hu , Wei Wang , Junyuan Lu , He Zhu , Qi Liu , Yang Ren , Hong Wang , Jian Hui . High-throughput screening of high energy density LiMn1-xFexPO4 via active learning. Chinese Chemical Letters, 2025, 36(2): 110344-. doi: 10.1016/j.cclet.2024.110344
Chen Li , Ziyuan Zhao , Shouyun Yu . Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides. Chinese Chemical Letters, 2024, 35(6): 109128-. doi: 10.1016/j.cclet.2023.109128
Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
Weiyu Chen , Zenghui Li , Chenguang Zhao , Lisha Zha , Junfeng Shi , Dan Yuan . Enzyme-modulate conformational changes in amphiphile peptide for selectively cell delivery. Chinese Chemical Letters, 2024, 35(12): 109628-. doi: 10.1016/j.cclet.2024.109628
Xiaofang Luo , Ye Wu , Xiaokun Zhang , Min Tang , Feiye Ju , Zuodong Qin , Gregory J Duns , Wei-Dong Zhang , Jiang-Jiang Qin , Xin Luan . Peptide-based strategies for overcoming multidrug-resistance in cancer therapy. Chinese Chemical Letters, 2025, 36(1): 109724-. doi: 10.1016/j.cclet.2024.109724
Yanqi Wu , Yuhong Guan , Peilin Huang , Hui Chen , Liping Bai , Zhihong Jiang . Preparation of norovirus GII loop mediated isothermal amplification freeze-drying microsphere reagents and its application in an on-site integrated rapid detection platform. Chinese Chemical Letters, 2024, 35(9): 109308-. doi: 10.1016/j.cclet.2023.109308
Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994
Dake Liu , Shuyan Liu , Fanlei Hu , Zhongtang Li , Zhongjun Li . N-Glycosylated type Ⅱ collagen peptides as therapeutic saccharide vaccines for rheumatoid arthritis. Chinese Chemical Letters, 2024, 35(5): 108762-. doi: 10.1016/j.cclet.2023.108762
Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157