publication . Article . Other literature type . 2017

Adamantane in Drug Delivery Systems and Surface Recognition

Štimac, Adela; Šekutor, Marina; Mlinarić-Majerski, Kata; Frkanec, Leo; Frkanec, Ruža;
  • Published: 01 Feb 2017
  • Publisher: MDPI AG
  • Country: Croatia
Abstract
The adamantane moiety is widely applied in design and synthesis of new drug delivery systems and in surface recognition studies. This review focuses on liposomes, cyclodextrins, and dendrimers based on or incorporating adamantane derivatives. Our recent concept of adamantane as an anchor in the lipid bilayer of liposomes has promising applications in the field of targeted drug delivery and surface recognition. The results reported here encourage the development of novel adamantane-based structures and self-assembled supramolecular systems for basic chemical investigations as well as for biomedical application.
Subjects
free text keywords: Organic chemistry, Supramolecular chemistry, Liposome, Chemistry, Targeted drug delivery, Combinatorial chemistry, Drug carrier, Drug delivery, Moiety, Adamantane, chemistry.chemical_compound, Dendrimer, liposomes, surface recognition, cyclodextrins, dendrimers, QD241-441, Review
86 references, page 1 of 6

1. Fort, R.C. Adamantane: The Chemistry of Diamond Molecules; Marcel Dekker: New York, NY, USA, 1976.

2. Schwertfeger, H.; Fokin, A.A.; Schreiner, P.R. Diamonds are a chemist's best friend. Diamondoid chemistry beyond adamantane. Angew. Chem. Int. Ed. 2008, 47, 1022-1036. [CrossRef] [PubMed] [OpenAIRE]

3. Gunawan, M.A.; Hierso, J.-C.; Poinsot, D.; Fokin, A.A.; Fokina, N.A.; Tkachenko, B.A.; Schreiner, P.R. Diamondoids: Functionalization and subsequent applications of perfectly defined molecular cage hydrocarbons. New J. Chem. 2014, 38, 28-41. [CrossRef]

4. Landa, S.; Machácˇek, V. Sur l'adamantane, nouvel hydrocarbure extrait du naphte. Collect. Czechoslov. Chem. Commun. 1933, 5, 1-5. [CrossRef] [OpenAIRE]

5. Prelog, V.; Seiwerth, R. Über die Synthese des Adamantans. Ber. Dtsch. Chem. Ges. 1941, 74, 1644-1648. [CrossRef] [OpenAIRE]

6. Schleyer, P.v.R. A Simple Preparation of Adamantane. J. Am. Chem. Soc. 1957, 79, 3292. [CrossRef]

7. Schleyer, P.v.R.; Donaldson, M.M.; Nicholas, R.D.; Cupas, C. Adamantane. Org. Synth. 1962, 42, 8.

8. Fort, R.C.; Schleyer, P.v.R. Adamantane: Consequences of the Diamondoid Structure. Chem. Rev. 1964, 64, 277-300. [CrossRef] [OpenAIRE]

9. Moiseev, I.K.; Makarova, N.V.; Zemtsova, M.N. Reactions of adamantanes in electrophilic media. Russ. Chem. Rev. 1999, 68, 1001-1020. [CrossRef] [OpenAIRE]

10. Davies, W.L.; Grunert, R.R.; Haff, R.F.; McGahen, J.W.; Neumayer, E.M.; Paulshock, M.; Watts, J.C.; Wood, T.R.; Hermann, E.C.; Hoffmann, C.E. Antiviral Activity of 1-Adamantanamine (Amantadine). Science 1964, 144, 862-863. [CrossRef] [PubMed] [OpenAIRE]

11. Dolin, R.; Reichman, R.C.; Madore, H.P.; Maynard, R.; Linton, P.N.; Webber-Jones, J. A controlled trial of amantadine and rimantadine in the prophylaxis of influenza A infection. N. Engl. J. Med. 1982, 307, 580-584. [CrossRef] [PubMed] [OpenAIRE]

12. Liu, J.; Obando, D.; Liao, V.; Lifa, T.; Codd, R. The many faces of the adamantyl group in drug design. Eur. J. Med. Chem. 2011, 46, 1949-1963. [CrossRef] [PubMed] [OpenAIRE]

13. Wanka, L.; Iqbal, K.; Schreiner, P.R. The Lipophilic Bullet Hits the Targets: Medicinal Chemistry of Adamantane Derivatives. Chem. Rev. 2013, 113, 3516-3604. [CrossRef] [PubMed] [OpenAIRE]

14. Horvat, Š.; Mlinaric´-Majerski, K.; Glavaš-Obrovac, L.; Jakas, A.; Veljkovic´, J.; Marczi, S.; Kragol, G.; Rošcˇic´, M.; Matkovic´, M.; Milostic´-Srb, A. Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis, and in Vitro Antitumor Activity. J. Med. Chem. 2006, 49, 3136-3142. [CrossRef] [PubMed] [OpenAIRE]

15. Rošcˇic´, M.; Sabljic´, V.; Mlinaric´-Majerski, K.; Horvat, Š. In Vitro Enzymatic Stabilities of Methionine-enkephalin Analogues Containing an Adamantane-type Amino Acid. Croat. Chem. Acta 2008, 81, 637-640. [OpenAIRE]

86 references, page 1 of 6
Abstract
The adamantane moiety is widely applied in design and synthesis of new drug delivery systems and in surface recognition studies. This review focuses on liposomes, cyclodextrins, and dendrimers based on or incorporating adamantane derivatives. Our recent concept of adamantane as an anchor in the lipid bilayer of liposomes has promising applications in the field of targeted drug delivery and surface recognition. The results reported here encourage the development of novel adamantane-based structures and self-assembled supramolecular systems for basic chemical investigations as well as for biomedical application.
Subjects
free text keywords: Organic chemistry, Supramolecular chemistry, Liposome, Chemistry, Targeted drug delivery, Combinatorial chemistry, Drug carrier, Drug delivery, Moiety, Adamantane, chemistry.chemical_compound, Dendrimer, liposomes, surface recognition, cyclodextrins, dendrimers, QD241-441, Review
86 references, page 1 of 6

1. Fort, R.C. Adamantane: The Chemistry of Diamond Molecules; Marcel Dekker: New York, NY, USA, 1976.

2. Schwertfeger, H.; Fokin, A.A.; Schreiner, P.R. Diamonds are a chemist's best friend. Diamondoid chemistry beyond adamantane. Angew. Chem. Int. Ed. 2008, 47, 1022-1036. [CrossRef] [PubMed] [OpenAIRE]

3. Gunawan, M.A.; Hierso, J.-C.; Poinsot, D.; Fokin, A.A.; Fokina, N.A.; Tkachenko, B.A.; Schreiner, P.R. Diamondoids: Functionalization and subsequent applications of perfectly defined molecular cage hydrocarbons. New J. Chem. 2014, 38, 28-41. [CrossRef]

4. Landa, S.; Machácˇek, V. Sur l'adamantane, nouvel hydrocarbure extrait du naphte. Collect. Czechoslov. Chem. Commun. 1933, 5, 1-5. [CrossRef] [OpenAIRE]

5. Prelog, V.; Seiwerth, R. Über die Synthese des Adamantans. Ber. Dtsch. Chem. Ges. 1941, 74, 1644-1648. [CrossRef] [OpenAIRE]

6. Schleyer, P.v.R. A Simple Preparation of Adamantane. J. Am. Chem. Soc. 1957, 79, 3292. [CrossRef]

7. Schleyer, P.v.R.; Donaldson, M.M.; Nicholas, R.D.; Cupas, C. Adamantane. Org. Synth. 1962, 42, 8.

8. Fort, R.C.; Schleyer, P.v.R. Adamantane: Consequences of the Diamondoid Structure. Chem. Rev. 1964, 64, 277-300. [CrossRef] [OpenAIRE]

9. Moiseev, I.K.; Makarova, N.V.; Zemtsova, M.N. Reactions of adamantanes in electrophilic media. Russ. Chem. Rev. 1999, 68, 1001-1020. [CrossRef] [OpenAIRE]

10. Davies, W.L.; Grunert, R.R.; Haff, R.F.; McGahen, J.W.; Neumayer, E.M.; Paulshock, M.; Watts, J.C.; Wood, T.R.; Hermann, E.C.; Hoffmann, C.E. Antiviral Activity of 1-Adamantanamine (Amantadine). Science 1964, 144, 862-863. [CrossRef] [PubMed] [OpenAIRE]

11. Dolin, R.; Reichman, R.C.; Madore, H.P.; Maynard, R.; Linton, P.N.; Webber-Jones, J. A controlled trial of amantadine and rimantadine in the prophylaxis of influenza A infection. N. Engl. J. Med. 1982, 307, 580-584. [CrossRef] [PubMed] [OpenAIRE]

12. Liu, J.; Obando, D.; Liao, V.; Lifa, T.; Codd, R. The many faces of the adamantyl group in drug design. Eur. J. Med. Chem. 2011, 46, 1949-1963. [CrossRef] [PubMed] [OpenAIRE]

13. Wanka, L.; Iqbal, K.; Schreiner, P.R. The Lipophilic Bullet Hits the Targets: Medicinal Chemistry of Adamantane Derivatives. Chem. Rev. 2013, 113, 3516-3604. [CrossRef] [PubMed] [OpenAIRE]

14. Horvat, Š.; Mlinaric´-Majerski, K.; Glavaš-Obrovac, L.; Jakas, A.; Veljkovic´, J.; Marczi, S.; Kragol, G.; Rošcˇic´, M.; Matkovic´, M.; Milostic´-Srb, A. Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis, and in Vitro Antitumor Activity. J. Med. Chem. 2006, 49, 3136-3142. [CrossRef] [PubMed] [OpenAIRE]

15. Rošcˇic´, M.; Sabljic´, V.; Mlinaric´-Majerski, K.; Horvat, Š. In Vitro Enzymatic Stabilities of Methionine-enkephalin Analogues Containing an Adamantane-type Amino Acid. Croat. Chem. Acta 2008, 81, 637-640. [OpenAIRE]

86 references, page 1 of 6
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publication . Article . Other literature type . 2017

Adamantane in Drug Delivery Systems and Surface Recognition

Štimac, Adela; Šekutor, Marina; Mlinarić-Majerski, Kata; Frkanec, Leo; Frkanec, Ruža;