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Synthesis 2022; 54(23): 5311-5323
DOI: 10.1055/a-1913-3105
DOI: 10.1055/a-1913-3105
paper
Multi-Component Sequential Synthesis of Dihydroorotic Acid-Based Amphiphilic Molecules
Dedicated to the memory of Tommaso Marcelli
Abstract
An efficient multicomponent sequential process, which occurs in mild condition has been exploited for the synthesis of systematically modified amphiphilic molecules where the cationic head is tethered to a lipophilic tail through a dihydroorotic acid linker. The process is operatively simple, high yielding, and flexible. Such a strategy could impact combinatorial synthesis of wide libraries of amphiphilic molecules to be tested as transfection agents and/or as antimicrobials.
Key words
multicomponent reactions - domino process - amphiphilic molecules - cationic lipids - antibacterialSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1913-3105.
- Supporting Information
Publication History
Received: 27 June 2022
Accepted after revision: 29 July 2022
Accepted Manuscript online:
29 July 2022
Article published online:
25 August 2022
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References
- 1 Santos DK. F, Rufino RD, Luna JM, Santos VA, Sarubbo LA. Int. J. Mol. Sci. 2016; 17: 401
- 2a Felgner PL. G, Gadek TR, Holm M, Roman R, Chan HW, Wenz M, Northrop JP, Ringold MG, Danielsen M. Proc. Natl. Acad. Sci. U. S. A. 1987; 84: 7413
- 2b Behr JP, Demeneix B, Loeffer JP, Perez-Mutul J. Proc. Natl. Acad. Sci. U. S. A. 1989; 86: 6982
- 2c Wu GY, Wu CH. J. Biol. Chem. 1987; 262: 4429
- 3a Zabner J. Adv. Drug Delivery Rev. 1997; 27: 17
- 3b Zhi D, Zhang S, Cui S, Zhao Y, Wang Y, Zhao D. Bioconjugate Chem. 2013; 24: 487
- 3c Zhang S, Zhao B, Jiang H, Wang B, Ma B. J. Control. Release 2007; 123: 1
- 3d Bellucci MC, Volonterio A. Antibiotics 2020; 9: 504
- 3e Zhou M, Zheng M, Cai J. ACS Appl. Mater. Interfaces 2020; 12: 21292
- 3f Zhang N, Ma S. Eur. J. Med. Chem. 2019; 184: 111743
- 4a Shai Y. Biopolymers 2002; 66: 236
- 4b Brogen KA. Nat. Rev. Microbiol. 2005; 3: 238
- 4c Anderson N, Borlak J. FEBS Lett. 2006; 23: 5533
- 5a Miller AD. Angew. Chem. Int. Ed. 1998; 37: 1768
- 5b Molla MR, Chakraborty S, Munoz-Sagredo L, Drechsler M, Orian-Rousseau V, Levkin PA. Bioconjugate Chem. 2020; 31: 852
- 6a Dӧmling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
- 6b Dӧmling A. Chem. Rev. 2006; 106: 17
- 6c Dӧmling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
- 7a Zhang Z, You YZ, Hong CY. Macromol. Rapid Commun. 2018; 39: 1800362
- 7b Llevot A, Boukis AC, Oelmann S, Wetzel K, Meier MA. R. Top. Curr. Chem. 2017; 375: 66
- 7c Rivera DG, Ricardo MG, Vasco AV, Wessjohann LA, Van der Eycken EV. Nat. Protoc. 2021; 16: 561
- 7d Reguera L, Mendez Y, Humpierre AR, Valdes O, Rivera DG. Acc. Chem. Res. 2018; 51: 1475
- 8 Malinakova HC. Rep. Org. Chem. 2015; 5: 75
- 9a Molla MR, Bӧser A, Rana A, Schwarz K, Levkin PA. Bioconjugate Chem. 2018; 29: 992
- 9b Molla MR, Chakraborty S, Munoz-Sagredo L, Drechsler M, Orian-Rousseau V, Levkin PA. Bioconjugate Chem. 2020; 31: 852
- 10a Bellucci MC, Terraneo G, Volonterio A. Org. Biomol. Chem. 2013; 11: 2421
- 10b Bellucci MC, Volonterio A. Eur. J. Org. Chem. 2014; 11: 2386
- 10c Bellucci MC, Sani M, Sganappa A, Volonterio A. ACS Comb. Sci. 2014; 16: 711
- 11 Sganappa A, Bellucci MC, Nizet V, Tor Y, Volonterio A. Synthesis 2016; 48: 4443
- 12 Bellucci MC, Frigerio M, Castellano C, Meneghetti F, Sacchetti A, Volonterio A. Org. Biomol. Chem. 2018; 16: 521
- 13 Bellucci MC, Sacchetti A, Volonterio A. ACS Comb. Sci. 2019; 21: 705
- 14a Majeti BK, Singh RS, Yadav SQ, Bathula SR, Ramakrishna S, Diwan PV, Madhavendra SS, Chaudhuri A. Chem. Biol. 2004; 11: 427
- 14b Chen H, Zhang H, McCallum CM, Szoka FC, Guo X. J. Med. Chem. 2007; 50: 4269
- 14c Jubeli E, Maginty AB, Khalique NA, Raju L, Abdulhai M, Nicholson DG, Larsen H, Pungente MD, Goldring WP. D. Bioorg. Med. Chem. 2015; 23: 6364
- 15 Shyam R, Charbonnel N, Job A, Blavignac C, Forestier C, Taillefumier C, Faure S. ChemMedChem 2018; 13: 1513
- 16 Allam A, Dupont L, Behr J-B, Plantier-Royon R. Eur. J. Org. Chem. 2012; 817
- 17 Prepared by reacting N 2,N 6-diBoc-lysine and 6-azido-1-hexanamine in the presence of coupling reagent BOP.
- 18 Neshchadin D, Palumbo F, Sinicropi MS, Andreu I, Gescheidt G, Miranda MA. Chem. Sci. 2013; 4: 1608
- 19a Pennetta C, Bono N, Ponti F, Bellucci MC, Viani F, Candiani G, Volonterio A. Bioconjugate Chem. 2021; 32: 690
- 19b Wexselblatt E, Esko JD, Tor Y. J. Org. Chem. 2014; 79: 6766
- 20 Sugawara A, Maita N, Gouda H, Yamamoto T, Hirose T, Kimura S, Saito Y, Nakano H, Kasai T, Nakano H, Shiomi K, Hirono S, Watanabe T, Taniguchi H, Omura S, Sunazuka T. J. Med. Chem 2015; 12: 4984