Akademik Veri Yönetim Sistemi
ULUSLARARASI KATILIMLI VIII. POLİMER BİLİM ve TEKNOLOJİ KONGRESİ, Malatya, Türkiye, 20 - 23 Haziran 2022, sa.218, ss.18
Synthesis
of peptide indole derivatives
Zeynep
Gönül, Şenay Akkar, Hasan Küçükbay
Peptides are protein
fragments that perform biological functions in living things. Among peptides,
short peptides are important structures that have found different applications
in biology, chemistry and medicine.[1]
Synthetic and natural peptides are recognized for
their wide array of therapeutic properties.[2] Because of their
highly selective and relatively safe nature, peptides are of interest in
pharmaceutical research and development. Peptide-active drug conjugates have an
important place in peptide chemistry. Indeed, more than 100 peptide-based drug
candidates are currently in clinical trials.[3]
Indoles, which are
important members of heterocyclic compounds in terms of medicinal chemistry,
have important physiological properties. Serotonin, the
happiness hormone, and tryptophan, an essential amino acid, are compounds
containing an indole skeleton.
Many anticancer compounds such as sumatripan,
melatonin, osimertinib and tegaserod approved by the FDA also contain indole in
their structure.[4]
In this study, examples
for the synthesis of benzotriazole mediated peptide-indole conjugates will be
given to combine two important biological structures in a single molecule.
The
general structures of the new compounds are shown below.
Acknowledgments: This
work was financially supported by the İnönü University Research Fund
(FYL-2021/2673 and FOA-2020-2203).
[1] V. Apostolopoulos,
J. Bojarska, T.T. Chai, S. Elnagdy, K. Kaczmarek, J. Matsoukas, R. New, K.
Parang, O.P. Lopez, H. Parhiz, C.O. Perera, M. Pickholz, M. Remko, M. Saviano,
M. Skwarczynski, Y. Tang, W.M. Wolf, T. Yoshiya, J. Zabrocki, P. Zielenkiewicz,
M. Alkhazindar, V. Barriga, K. Kelaidonis, E.M. Sarasia, I. Toth, A global
review on short peptides: Frontiers and perspectives, Molecules. 26 (2021).
https://doi.org/10.3390/molecules26020430.
[2] H.
Küçükbay, N. Buğday, F.Z. Küçükbay, E. Berrino, G. Bartolucci, S. Del, C.
Capasso, C.T. Supuran, Synthesis and carbonic anhydrase inhibitory properties
of novel 4- ( 2- aminoethyl ) benzenesulfonamide-dipeptide conjugates, Bioorg.
Chem. 83 (2019) 414–423. https://doi.org/10.1016/j.bioorg.2018.11.003.
[3] S. Dadashpour, S. Emami, Indole in the
target-based design of anticancer agents: A versatile scaffold with diverse
mechanisms, Eur. J. Med. Chem. 150 (2018) 9–29.
https://doi.org/10.1016/j.ejmech.2018.02.065.
[4] B. Rai, R.D. Shukla, A. Kumar, Zinc
oxide-NP catalyzed direct indolation of in situ generated bioactive
tryptanthrin, Green Chem. 20 (2018) 822–826.
https://doi.org/10.1039/C7GC03479B.
Synthesis
of peptide indole derivatives
Zeynep
Gönül, Şenay Akkar, Hasan Küçükbay
Peptides are protein
fragments that perform biological functions in living things. Among peptides,
short peptides are important structures that have found different applications
in biology, chemistry and medicine.[1]
Synthetic and natural peptides are recognized for
their wide array of therapeutic properties.[2] Because of their
highly selective and relatively safe nature, peptides are of interest in
pharmaceutical research and development. Peptide-active drug conjugates have an
important place in peptide chemistry. Indeed, more than 100 peptide-based drug
candidates are currently in clinical trials.[3]
Indoles, which are
important members of heterocyclic compounds in terms of medicinal chemistry,
have important physiological properties. Serotonin, the
happiness hormone, and tryptophan, an essential amino acid, are compounds
containing an indole skeleton.
Many anticancer compounds such as sumatripan,
melatonin, osimertinib and tegaserod approved by the FDA also contain indole in
their structure.[4]
In this study, examples
for the synthesis of benzotriazole mediated peptide-indole conjugates will be
given to combine two important biological structures in a single molecule.
The
general structures of the new compounds are shown below.
Acknowledgments: This
work was financially supported by the İnönü University Research Fund
(FYL-2021/2673 and FOA-2020-2203).
[1] V. Apostolopoulos,
J. Bojarska, T.T. Chai, S. Elnagdy, K. Kaczmarek, J. Matsoukas, R. New, K.
Parang, O.P. Lopez, H. Parhiz, C.O. Perera, M. Pickholz, M. Remko, M. Saviano,
M. Skwarczynski, Y. Tang, W.M. Wolf, T. Yoshiya, J. Zabrocki, P. Zielenkiewicz,
M. Alkhazindar, V. Barriga, K. Kelaidonis, E.M. Sarasia, I. Toth, A global
review on short peptides: Frontiers and perspectives, Molecules. 26 (2021).
https://doi.org/10.3390/molecules26020430.
[2] H.
Küçükbay, N. Buğday, F.Z. Küçükbay, E. Berrino, G. Bartolucci, S. Del, C.
Capasso, C.T. Supuran, Synthesis and carbonic anhydrase inhibitory properties
of novel 4- ( 2- aminoethyl ) benzenesulfonamide-dipeptide conjugates, Bioorg.
Chem. 83 (2019) 414–423. https://doi.org/10.1016/j.bioorg.2018.11.003.
[3] S. Dadashpour, S. Emami, Indole in the
target-based design of anticancer agents: A versatile scaffold with diverse
mechanisms, Eur. J. Med. Chem. 150 (2018) 9–29.
https://doi.org/10.1016/j.ejmech.2018.02.065.
[4] B. Rai, R.D. Shukla, A. Kumar, Zinc
oxide-NP catalyzed direct indolation of in situ generated bioactive
tryptanthrin, Green Chem. 20 (2018) 822–826.
https://doi.org/10.1039/C7GC03479B.