Design of a MCoTI-based cyclotide with angiotensin (1-7)-like activity

Molecules

Volumn 21, Issue 2, 2016, Pages

  Aboye, Teshome ^a   Meeks, Christopher J ^a   Majumder, Subhabrata ^b   Shekhtman, Alexander ^b   Rodgers, Kathleen ^a   Camarero, Julio A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

Angiotensin; Cyclotide; MAS1 receptor

Indexed keywords

ANGIOTENSIN I; ANGIOTENSIN I (1-7); CYCLOTIDE; G PROTEIN COUPLED RECEPTOR; MCOTI-I PROTEIN, MOMORDICA COCHINCHINENSIS; ONCOPROTEIN; PEPTIDE FRAGMENT; PLANT PROTEIN; PROTO-ONCOGENE PROTEINS C-MAS-1;

ANIMAL; CELL SURVIVAL; CHEMISTRY; CHO CELL LINE; CRICETULUS; DRUG EFFECTS; HUMAN; METABOLISM; MYOCARDIAL INFARCTION; NEOPLASMS; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN STABILITY; SYNTHESIS;

ANGIOTENSIN I; ANIMALS; CELL SURVIVAL; CHO CELLS; CRICETULUS; CYCLOTIDES; HUMANS; MYOCARDIAL INFARCTION; NEOPLASMS; PEPTIDE FRAGMENTS; PLANT PROTEINS; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN STABILITY; PROTO-ONCOGENE PROTEINS; RECEPTORS, G-PROTEIN-COUPLED;

EID: 84963668266     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21020152     Document Type: Article

References (35)

1. Gallagher, P.E.; Cook, K.; Soto-Pantoja, D.; Menon, J.; Tallant, E.A. Angiotensin peptides and lung cancer. Curr. Cancer Drug Targets 2011, 11, 394-404. [CrossRef] [PubMed]
2. Menon, J.; Soto-Pantoja, D.R.; Callahan, M.F.; Cline, J.M.; Ferrario, C.M.; Tallant, E.A.; Gallagher, P.E. Angiotensin-(1-7) inhibits growth of human lung adenocarcinoma xenografts in nude mice through a reduction in Cyclooxygenase-2. Cancer Res. 2007, 67, 2809-2815. [CrossRef] [PubMed]
3. Gallagher, P.E.; Tallant, E.A. Inhibition of human lung cancer cell growth by Angiotensin-(1-7). Carcinogenesis 2004, 25, 2045-2052. [CrossRef] [PubMed]
4. Tallant, E.A.; Clark, M.A. Molecular mechanisms of inhibition of vascular growth by Angiotensin-(1-7). Hypertension 2003, 42, 574-579. [CrossRef] [PubMed]
5. Tallant, E.A.; Diz, D.I.; Ferrario, C.M. State-of-the-art lecture. Antiproliferative actions of Angiotensin-(1-7) in vascular smooth muscle. Hypertension 1999, 34, 950-957. [CrossRef] [PubMed]
6. Craik, D.J.; Daly, N.L.; Bond, T.; Waine, C. Plant cyclotides: A unique family of cyclic and knotted proteins that defines the cyclic cystine knot structural motif. J. Mol. Biol. 1999, 294, 1327-1336. [CrossRef] [PubMed]
7. Daly, N.L.; Rosengren, K.J.; Craik, D.J. Discovery, structure and biological activities of cyclotides. Adv. Drug Deliv. Rev. 2009, 61, 918-930. [CrossRef] [PubMed]
8. Gould, A.; Ji, Y.; Aboye, T.L.; Camarero, J.A. Cyclotides, a novel ultrastable polypeptide scaffold for drug discovery. Curr. Pharm. Des. 2011, 17, 4294-4307. [CrossRef] [PubMed]
9. Puttamadappa, S.S.; Jagadish, K.; Shekhtman, A.; Camarero, J.A. Backbone dynamics of cyclotide Mcoti-I free and complexed with trypsin. Angew. Chem. Int. Ed. Engl. 2010, 49, 7030-7034. [CrossRef] [PubMed]
10. Puttamadappa, S.S.; Jagadish, K.; Shekhtman, A.; Camarero, J.A. Erratum in: Backbone dynamics of cyclotide mcoti-i free and complexed with trypsin. Angew. Chem. Int. Ed. Engl. 2011, 50, 6948-6949. [CrossRef]
11. Austin, J.; Kimura, R.H.; Woo, Y.H.; Camarero, J.A. In vivo biosynthesis of an ala-scan library based on the cyclic peptide Sfti-1. Amino Acids 2010, 38, 1313-1322. [CrossRef] [PubMed]
12. Huang, Y.H.; Colgrave, M.L.; Clark, R.J.; Kotze, A.C.; Craik, D.J. Lysine-scanning mutagenesis reveals an amendable face of the cyclotide kalata B1 for the optimization of nematocidal activity. J. Biol. Chem. 2010, 285, 10797-10805. [CrossRef] [PubMed]
13. Simonsen, S.M.; Sando, L.; Rosengren, K.J.; Wang, C.K.; Colgrave, M.L.; Daly, N.L.; Craik, D.J. Alanine scanning mutagenesis of the prototypic cyclotide reveals a cluster of residues essential for bioactivity. J. Biol. Chem. 2008, 283, 9805-9813. [CrossRef] [PubMed]
14. Felizmenio-Quimio, M.E.; Daly, N.L.; Craik, D.J. Circular proteins in plants: Solution structure of a novel macrocyclic trypsin inhibitor from momordica cochinchinensis. J. Biol. Chem. 2001, 276, 22875-22882. [CrossRef] [PubMed]
15. Garcia, A.E.; Camarero, J.A. Biological activities of natural and engineered cyclotides, a novel molecular scaffold for peptide-based therapeutics. Curr. Mol. Pharmacol. 2010, 3, 153-163. [CrossRef] [PubMed]
16. Contreras, J.; Elnagar, A.Y.; Hamm-Alvarez, S.F.; Camarero, J.A. Cellular uptake of cyclotide Mcoti-I follows multiple endocytic pathways. J. Control. Release 2011, 155, 134-143. [CrossRef] [PubMed]
17. Cascales, L.; Henriques, S.T.; Kerr, M.C.; Huang, Y.H.; Sweet, M.J.; Daly, N.L.; Craik, D.J. Identification and characterization of a new family of cell-penetrating peptides: Cyclic cell-penetrating peptides. J. Biol. Chem. 2011, 286, 36932-36943. [CrossRef] [PubMed]
18. Ji, Y.; Majumder, S.; Millard, M.; Borra, R.; Bi, T.; Elnagar, A.Y.; Neamati, N.; Shekhtman, A.; Camarero, J.A. In vivo activation of the P53 tumor suppressor pathway by an engineered cyclotide. J. Am. Chem. Soc. 2013, 135, 11623-11633. [CrossRef] [PubMed]
19. Henriques, S.T.; Craik, D.J. Cyclotides as templates in drug design. Drug Discov. Today 2010, 15, 57-64. [CrossRef] [PubMed]
20. Aboye, T.L.; Ha, H.; Majumder, S.; Christ, F.; Debyser, Z.; Shekhtman, A.; Neamati, N.; Camarero, J.A. Design of a novel cyclotide-based Cxcr4 antagonist with anti-human immunodeficiency virus (HIV)-1 activity. J. Med. Chem. 2012, 55, 10729-10734. [CrossRef] [PubMed]
21. Chan, L.Y.; Gunasekera, S.; Henriques, S.T.; Worth, N.F.; Le, S.J.; Clark, R.J.; Campbell, J.H.; Craik, D.J.; Daly, N.L. Engineering pro-angiogenic peptides using stable, disulfide-rich cyclic scaffolds. Blood 2011, 118, 6709-6717. [CrossRef] [PubMed]
22. Sommerhoff, C.P.; Avrutina, O.; Schmoldt, H.U.; Gabrijelcic-Geiger, D.; Diederichsen, U.; Kolmar, H. Engineered cystine knot miniproteins as potent inhibitors of human mast cell tryptase beta. J. Mol. Biol. 2010, 395, 167-175. [CrossRef] [PubMed]
23. Wang, Y.; Qian, C.; Roks, A.J.; Westermann, D.; Schumacher, S.M.; Escher, F.; Schoemaker, R.G.; Reudelhuber, T.L.; van Gilst, W.H.; Schultheiss, H.P.; et al. Circulating rather than cardiac Angiotensin-(1-7) stimulates cardioprotection after myocardial infarction. Circ. Heart Fail 2010, 3, 286-293. [CrossRef] [PubMed]
24. Loot, A.E.; Roks, A.J.; Henning, R.H.; Tio, R.A.; Suurmeijer, A.J.; Boomsma, F.; van Gilst, W.H. Angiotensin-(1-7) attenuates the development of heart failure after myocardial infarction in rats. Circulation 2002, 105, 1548-1550. [CrossRef] [PubMed]
25. Iusuf, D.; Henning, R.H.; van Gilst, W.H.; Roks, A.J. Angiotensin-(1-7): Pharmacological properties and pharmacotherapeutic perspectives. Eur. J. Pharm. 2008, 585, 303-312. [CrossRef] [PubMed]
26. Hernandez, J.F.; Gagnon, J.; Chiche, L.; Nguyen, T.M.; Andrieu, J.P.; Heitz, A.; Trinh Hong, T.; Pham, T.T.; le Nguyen, D. Squash trypsin inhibitors from momordica cochinchinensis exhibit an atypical macrocyclic structure. Biochemistry 2000, 39, 5722-5730. [CrossRef] [PubMed]
27. Jagadish, K.; Gould, A.; Borra, R.; Majumder, S.; Mushtaq, Z.; Shekhtman, A.; Camarero, J.A. Recombinant expression and phenotypic screening of a bioactive cyclotide against alpha-synuclein-induced cytotoxicity in baker's yeast. Angew. Chem. Int. Ed. Engl. 2015, 54, 8390-8394. [CrossRef] [PubMed]
28. Jagadish, K.; Borra, R.; Lacey, V.; Majumder, S.; Shekhtman, A.; Wang, L.; Camarero, J.A. Expression of fluorescent cyclotides using protein trans-splicing for easy monitoring of cyclotide-protein interactions. Angew. Chem. Int. Ed. Engl. 2013, 52, 3126-3131. [CrossRef] [PubMed]
29. Borra, R.; Camarero, J.A. Recombinant expression of backbone-cyclized polypeptides. Biopolymers 2013, 100, 502-509. [CrossRef] [PubMed]
30. Austin, J.; Wang, W.; Puttamadappa, S.; Shekhtman, A.; Camarero, J.A. Biosynthesis and biological screening of a genetically encoded library based on the cyclotide Mcoti-I. Chembiochem 2009, 10, 2663-2670. [CrossRef] [PubMed]
31. Durik, M.; van Veghel, R.; Kuipers, A.; Rink, R.; Haas Jimoh Akanbi, M.; Moll, G.; Danser, A.H.; Roks, A.J. The effect of the thioether-bridged, stabilized Angiotensin-(1-7) analogue cyclic ang-(1-7) on cardiac remodeling and endothelial function in rats with myocardial infarction. Int. J. Hypertens 2012, 2012, 536426. [CrossRef] [PubMed]
32. Kluskens, L.D.; Nelemans, S.A.; Rink, R.; de Vries, L.; Meter-Arkema, A.; Wang, Y.; Walther, T.; Kuipers, A.; Moll, G.N.; Haas, M. Angiotensin-(1-7) with thioether bridge: An angiotensin-converting enzyme-resistant, potent Angiotensin-(1-7) analog. J. Pharmacol. Exp. Ther. 2009, 328, 849-854. [CrossRef] [PubMed]
33. Camarero, J.A.; Mitchell, A.R. Synthesis of proteins by native chemical ligation using fmoc-based chemistry. Protein Pept. Lett. 2005, 12, 723-728. [CrossRef] [PubMed]
34. Cavanagh, J.; Rance, M. Suppression of cross relaxation effects in tocsy spectra via a modified disi-2 mixing sequence. J. Magn. Res. 1992, 96, 670-678.
35. Wuthrich, K. NMR of Proteins and Nucleic Acids; John Wiley & Sons: New York, NY, USA, 1986.