publication . Article . Other literature type . 2017

Adamantane in Drug Delivery Systems and Surface Recognition

Leo Frkanec; Marina Šekutor; Kata Mlinarić-Majerski; Ruža Frkanec; Adela Štimac;
Open Access English
  • Published: 16 Feb 2017 Journal: Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry, volume 22, issue 2 (eissn: 1420-3049, Copyright policy)
  • Publisher: MDPI
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: Review, adamantane, targeted drug delivery, liposomes, surface recognition, cyclodextrins, dendrimers, Organic chemistry, QD241-441, Supramolecular chemistry, Dendrimer, Drug delivery, Combinatorial chemistry, Drug carrier, chemistry.chemical_compound, chemistry, Liposome, Moiety
86 references, page 1 of 6

Fort, R.C.. Adamantane: The Chemistry of Diamond Molecules. 1976

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 [OpenAIRE] [PubMed] [DOI]

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 [OpenAIRE] [DOI]

Landa, S., Macháček, V.. Sur l’adamantane, nouvel hydrocarbure extrait du naphte. Collect. Czechoslov. Chem. Commun.. 1933; 5: 1-5 [OpenAIRE] [DOI]

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

Schleyer, P.v.R.. A Simple Preparation of Adamantane. J. Am. Chem. Soc.. 1957; 79: 3292 [OpenAIRE] [DOI]

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

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

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

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 [OpenAIRE] [PubMed] [DOI]

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 [PubMed] [DOI]

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 [OpenAIRE] [PubMed] [DOI]

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

Horvat, Š., Mlinarić-Majerski, K., Glavaš-Obrovac, L., Jakas, A., Veljković, J., Marczi, S., Kragol, G., Roščić, M., Matković, M., Milostić-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 [PubMed] [DOI]

Roščić, M., Sabljić, V., Mlinarić-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: Review, adamantane, targeted drug delivery, liposomes, surface recognition, cyclodextrins, dendrimers, Organic chemistry, QD241-441, Supramolecular chemistry, Dendrimer, Drug delivery, Combinatorial chemistry, Drug carrier, chemistry.chemical_compound, chemistry, Liposome, Moiety
86 references, page 1 of 6

Fort, R.C.. Adamantane: The Chemistry of Diamond Molecules. 1976

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 [OpenAIRE] [PubMed] [DOI]

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 [OpenAIRE] [DOI]

Landa, S., Macháček, V.. Sur l’adamantane, nouvel hydrocarbure extrait du naphte. Collect. Czechoslov. Chem. Commun.. 1933; 5: 1-5 [OpenAIRE] [DOI]

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

Schleyer, P.v.R.. A Simple Preparation of Adamantane. J. Am. Chem. Soc.. 1957; 79: 3292 [OpenAIRE] [DOI]

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

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

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

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 [OpenAIRE] [PubMed] [DOI]

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 [PubMed] [DOI]

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 [OpenAIRE] [PubMed] [DOI]

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

Horvat, Š., Mlinarić-Majerski, K., Glavaš-Obrovac, L., Jakas, A., Veljković, J., Marczi, S., Kragol, G., Roščić, M., Matković, M., Milostić-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 [PubMed] [DOI]

Roščić, M., Sabljić, V., Mlinarić-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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