New PEPPSI-Pd-NHC complexes bearing 4-hydroxyphenylethyl group: Synthesis, characterization, molecular docking, and bioactivity properties.
NHC complexes
PEPPSI
enzyme inhibition
molecular docking
α-glucosidase
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
Dec 2022
Dec 2022
Historique:
revised:
28
07
2022
received:
04
06
2022
accepted:
30
07
2022
pubmed:
20
8
2022
medline:
3
12
2022
entrez:
19
8
2022
Statut:
ppublish
Résumé
Five 4-hydroxyphenylethyl substituted pyridine enhanced, precatalyst, preparation, stabilization, and initiation-Pd-N-heterocyclic carbene (PEPPSI-Pd-NHC) complexes are synthesized in a straightforward way. All PEPPSI-Pd-NHC complexes were prepared by mixing 4-hydroxyphenylethyl substituted NHC precursors, palladium chloride, potassium carbonate, and potassium bromide in pyridine. All complexes were screened for human carbonic anhydrase I (hCA I) and hCA II, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase (α-Glu) inhibitory activities. The ChE inhibitory activities of the new PEPPSI-Pd-NHC complexes bearing the 4-hydroxyphenylethyl group (1a-e) against α-Glu, AChE, and BChE were determined by the Tao and Ellman methods. The results indicated that all the synthetic complexes exhibited potent inhibitory activities against all targets as compared to the standard inhibitors, revealed by IC
Identifiants
pubmed: 35986370
doi: 10.1002/ardp.202200276
doi:
Substances chimiques
Butyrylcholinesterase
EC 3.1.1.8
Acetylcholinesterase
EC 3.1.1.7
Carbonic Anhydrase Inhibitors
0
Cholinesterase Inhibitors
0
Carbonic Anhydrase I
EC 4.2.1.-
alpha-Glucosidases
EC 3.2.1.20
Pyridines
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2200276Subventions
Organisme : Bartin Üniversitesi
ID : 2020-FEN-B-005
Informations de copyright
© 2022 Deutsche Pharmazeutische Gesellschaft.
Références
A. J. Arduengo, R. L. Harlow, M. J. Kline, J. Am. Chem. Soc. 1991, 113, 361.
M. R. Sura, N. R. Bijivemula, S. R. Pogula, V. K. R. Motakatla, P. Madhvesh, V. G. R. Peddiahgari, Appl. Organomet. Chem. 2018, 32, e4068.
A. Aktaş, D. Barut Celepci, Y. Gök, M. Aygün, ChemistrySelect 2018, 3, 10932.
A. Aktaş, Chin. J. Struct. Chem. 2019, 38, 1664.
C. M. Crudden, D. P. Allen, Coord. Chem. Rev. 2004, 248, 2247.
H.-W. Wanzlick, H.-J. Schönherr, Angew. Chem. Int. Ed. Engl. 1968, 7, 141.
Y. Gök, A. Aktaş, H. Erdoğan, Y. Sarı, Inorg. Chim. Acta 2018, 471, 735.
Y. Sarı, A. Aktaş, D. Barut Celepci, Y. Gök, M. Aygün, Catal. Lett. 2017, 147(9), 2340.
A. Aktaş, Ü. Keleştemur, Y. Gök, S. Balcıoğlu, B. Ateş, M. Aygün, J. Iran. Chem. Soc. 2018, 15, 131.
A. Aktaş, D. Barut Celepci, Y. Gök, M. Aygün, ChemistrySelect 2018, 3(35), 9974.
F. Erdemir, D. Barut Celepci, A. Aktaş, Y. Gök, ChemistrySelect 2019, 4(19), 5585.
F. Türker, İ. Bereket, D. Barut Celepci, A. Aktaş, Y. Gök, J. Mol. Struct. 2020, 1205, 127608.
I. Slimani, L. Boubakri, N. Özdemir, L. Mansour, I. Özdemir, N. Gürbüz, S. Yaşar, M. Sauthier, N. Hamdi, Inorg. Chim. Acta 2022, 532, 120747.
F. İmik, S. Yaşar, İ. Özdemir, J. Organomet. Chem. 2019, 896, 162.
F. İmik, S. Yaşar, İ. Özdemir, Inorg. Chim. Acta 2019, 495, 118969.
P. Nun, J. Martinez, F. Lamaty, Synlett 2009, 2009, 1761.
I. Al Nasr, N. Touj, W. Koko, T. Khan, I. Özdemir, S. Yaşar, N. Hamdi, Catalysts 2020, 10, 1190.
S. Y. Hussaini, R. A. Haque, M. R. Razali, J. Organomet. Chem. 2019, 882, 96.
W. Liu, R. Gust, Chem. Soc. Rev. 2013, 42(2), 755.
S. Akkoç, V. Kayser, İ. Ö. İlhan, D. E. Hibbs, Y. Gök, P. A. Williams, B. Hawkins, F. Lai, J. Organomet. Chem. 2017, 839, 98.
S. Akkoç, İ. Özer İlhan, Y. Gök, P. J. Upadhyay, V. Kayser, Inorg. Chim. Acta 2016, 449, 75.
T. Scattolin, E. Bortolamiol, S. Palazzolo, I. Caligiuri, T. Perin, V. Canzonieri, N. Demitri, F. Rizzolio, L. Cavallo, B. Dereli, M. V. Mane, S. P. Nolan, F. Visentin, ChemComm 2020, 56(81), 12238.
G. Dahm, C. Bailly, L. Karmazin, S. Bellemin-Laponnaz, Organomet. Chem. 2015, 794, 115.
F. Türker, C. Gürses, D. Barut Celepci, A. Aktaş, B. Ateş, Y. Gök, Arch. Pharm. 2019, 352(12), 1900187.
F. Erdemir, D. Barut Celepci, A. Aktaş, Y. Gök, R. Kaya, P. Taslimi, Y. Demir, İ. Gulçin, Bioorg. Chem. 2019, 91, 103134.
F. Türker, S. Abbas, A. Noma, A. Aktaş, K. Al- Khafaji, T. Taşkın Tok, B. Ateş, Y. Gök, Monatsh. Chem. 2020, 151, 1557.
1228 S. Daşgın, Y. Gök, D. Barut Celepci, P. Taslimi, M. İzmirli, A. Aktaş, İ. Gulcin, J. Mol. Struct. 2020, 1228, 129442.
S. Bal, Ö. Demirci, B. Şen, P. Taslimi, A. Aktaş, Y. Gök, M. Aygün, I. Gülçin, Polyhedron 2021, 198, 115060.
S. Hashmi, S. Khan, Z. Shafiq, P. Taslimi, M. Ishaq, N. Sadeghian, H. S. Karaman, N. Akhtar, M. Islam, A. Asari, H. Mohamad, İ. Gulçin, Bioorg. Chem. 2021, 107, 104554.
H. U. Celebioglu, Y. Erden, F. Hamurcu, P. Taslimi, O. S. Şentürk, Ü. Özdemir Özmen, B. Tuzun, İ. Gulçin, J. Biomol. Struct. 2021, 39(15), 5539.
S. Bal, R. Kaya, Y. Gök, P. Taslimi, A. Aktaş, M. Karaman, İ. Gülçin, Bioorg. Chem. 2020, 94, 103468.
C. Caglayan, P. Taslimi, C. Türk, İ. Gulcin, F. M. Kandemir, Y. Demir, Ş. Beydemir, Environ. Sci. Pollut. Res. 2020, 27, 10607.
İ. Gülçin, B. Trofimov, R. Kaya, P. Taslimi, y Sobenina, E. Schmidt, O. Petrova, S. Malysheva, N. Gusarova, V. Farzaliyev, A. Sujayev, S. Alwasel, C. T. Supuran, Bioorg. Chem. 2020, 103, 104171.
E. Guzel, U. M. Kocyigit, P. Taslimi, I. Gulcin, S. Erkan, M. Nebioglu, B. S. Arslan, I. Sisman, J. Biomol. Struct. 2022, 40(2), 733.
İ. Gülçin, Z. Bingöl, P. Taslimi, A. C. Gören, S. H. Alwasel, A. Z. Tel, Chem. Biodivers. 2022, 19, e202100775.
M. Huseynova, V. Farzaliyev, A. Medjidov, M. Aliyeva, M. Özdemir, P. Taslimi, Y. Zorlu, B. Yalçın, O. Şahin, J. Mol. Struct. 2020, 1248, 131470.
M. Yiğit, D. Barut Celepci, P. Taslimi, B. Yiğit, E. Çetinkaya, İ. Özdemir, M. Aygün, İ. Gülçin, Bioorg. Chem. 2022, 120, 105566.
S. Akocak, P. Taslimi, N. Lolak, M. Işık, M. Durgun, Y. Budak, C. Türkeş, İ. Gülçin, Ş. Beydemir, Chem. Biodivers. 2021, 18, e2000958.
S. B. Kassa, P. Taslimi, Ş. Özel, B. Gür, İ. Gülçin, Y. Onganer, Colloids Surf. A 2022, 632, 127839.
G. Bitencourt-Ferreira, W. F. de Azevedo, Molegro Virtual Docker for Docking Docking Screens for Drug Discovery, Humana, New York, NY 2019, p. 149.
S. Kusumaningrum, E. Budianto, S. Kosela, W. Sumaryono, F. Juniarti, J. Appl. Sci. 2014, 4, 47.
X. Y. Meng, H. X. Zhang, M. Mezei, M. Cui, Curr. Comput.-Aided Drug Des. 2011, 7, 146.
A. Behçet, T. Çağlılar, D. Barut Celepci, A. Aktas, P. Taslimi, Y. Gök, M. Aygün, R. Kaya, İ. Gülçin, J. Mol. Struct. 2018, 1170, 160.
H. Genc Bilgicli, P. Taslimi, B. Akyuz, B. Tuzun, İ. Gulcin, Arch. Pharm. 2020, 353(1), 1900304.
A. Günsel, A. T. Bilgiçli, B. Barut, P. Taslimi, A. Ozel, I. Gülçin, Z. Biyiklioglu, M. Nilüfer Yarasir, J. Mol. Struct. 2020, 1214, 128210.
U. M. Koçyiğit, Y. Budak, M. B. Gürdere, N. Dürü, P. Taslimi, İ. Gulçin, M. Ceylan, Monatsh. Chem. 2019, 150(4), 721.
A. Cetin, F. Turkan, P. Taslimi, İ. Gulçin, J. Biochem. Mol. Toxicol. 2019, 33(3), e22261.
Q. Tariq, S. Malik, A. Khan, M. Moazzam Naseer, S. Ullah Khan, A. Ashraf, M. Ashraf, M. Rafiq, K. Mahmood, M. Nawaz Tahir, Z. Shafiq, Bioorg. Chem. 2019, 84, 372.
V. G. Klochkov, E. N. Bezsonova, M. Dubar, D. D. Melekhina, V. V. Temnov, E. V. Zaryanova, N. A. Lozinskaya, D. A. Babkov, A. A. Spasov, Bioorg. Med. Chem. Lett. 2022, 55, 128449.
E. A. Johnson, C. E. Tsai, J. Lucci, Y. Harrison-Shahan, A. J. Azzaro, Neuropharmacology 1992, 31, 95.
M. Boztas, Y. Çetinkaya, M. Topal, İ. Gülçin, A. Menzek, E. Şahin, M. Tanc, C. T. Supuran, J. Med. Chem. 2015, 58(2), 640.
H. Goksu, M. Topal, A. Keskin, M. S. Gültekin, M. Çelik, İ. Gülçin, M. Tanc, C. T. Supuran, Arch. Pharm. 2016, 349(6), 466.
P. Taslimi, İ. Gülçin, N. Öztaşkın, Y. Çetinkaya, S. Göksu, S. H. Alwasel, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2016, 31(4), 603.
M. Nar, Y. Çetinkaya, İ. Gülçin, A. Menzek, J. Enzyme Inhib. Med. Chem. 2013, 28(2), 402.
Y. Çetinkaya, H. Göçer, İ. Gülçin, A. Menzek, Arch. Pharm. 2014, 347(5), 354.
S. Göksu, A. Naderi, Y. Akbaba, P. Kalın, A. Akıncıoğlu, İ. Gülcin, S. Durdaği, R. E. Salmas, Bioorg. Chem. 2014, 56, 75.
M. Tuğrak, H. İ. Gül, H. Sakagami, İ. Gülçin, C. T. Supuran, Bioorg. Chem. 2018, 81, 433.
Y. Sari, A. Aktaş, P. Taslimi, Y. Gök, C. Caglayan, İ. Gulçin, J. Biochem. Mol. Toxicol. 2018, 32(1), e22009.
B. Yiğit, M. Yiğit, D. Barut Celepci, Y. Gök, A. Aktaş, M. Aygün, P. Taslimi, İ. Gulçin, ChemistrySelect 2018, 3(27), 7976.
F. Turkan, A. Cetin, P. Taslimi, M. Karaman, İ. Gülçin, Bioorg. Chem. 2019, 86, 420.
K. Küçükoğlu, H.İ. Gül, P. Taslimi, İ. Gülçin, C. T. Supuran, Bioorg. Chem. 2019, 86, 316.
A. Maharramov, R. Kaya, P. Taslimi, M. Kurbanova, A. Sadigova, V. Farzaliyev, A. Sujayev, İ. Gulçin, Arch. Pharm. 2019, 352(2), e1800317.
M. Boztas, P. Taslimi, M. A. Yavari, İ. Gülçin, E. Sahin, A. Menzek, Bioorg. Chem. 2019, 89, 103017.
K. Aksu, H. Akıncıoğlu, İ. Gulçin, L. Kelebekli, Arch. Pharm. 2021, 354(2), e2000254.
A. Behçet, A. Aktaş, Y. Gök, R. Kaya, P. Taslimi, İ. Gulçin, J. Heterocycl. Chem. 2021, 58(2), 603.
N. Bulut, U. M. Koçyiğit, I. H. Gecibesler, T. Dastan, H. Karci, P. Taslimi, S. Durna Dastan, İ. Gulçin, A. Cetin, J. Biochem. Mol. Toxicol. 2018, 32(1), e22006.
B. Kuzu, M. Tan, P. Taslimi, İ. Gülçin, M. Taşpınar, N. Menges, Bioorg. Chem. 2019, 86, 187.
Y. Demir, P. Taslimi, M. S. Özaslan, N. Oztaskin, Y. Çetinkaya, İ. Gulçin, Ş. Beydemir, S. Goksu, Arch. Pharm. 2018, 351, 1800263.
M. Zengin, H. Genc, P. Taslimi, A. Kestane, E. Guclu, A. Ogutlu, O. Karabay, İ. Gulçin, Bioorg. Chem. 2018, 81, 119.
P. Taslimi, M. Işık, F. Türkan, M. Durgun, M. Türkeş, İ. Gulçin, S. Beydemir, J. Biomol. Struct. Dyn. 2021, 39(15), 5449.
D. E. V. Pires, T. L. Blundell, D. B. Ascher, J. Med. Chem. 2015, 58(9), 4066.
J. A. Verpoorte, S. Mehta, J. T. Edsall, J. Biol. Chem. 1967, 242, 4221.
A. Gokhan Aggul, P. Taslimi, M. Kuzu, N. Uzun, S. Bilginer, I. Gulcin, J. Oleo Sci. 2021, 70, 1275.
F. S. Tokalı, P. Taslimi, H. Usanmaz, M. Karaman, K. Şendil, J. Mol. Struct. 2021, 1231, 129666.
G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherston, Biochem. Pharmacol. 1961, 7, 88.
M. Erdoğan, P. Taslimi, B. Tuzun, Arch. Pharm. 2021, 354(6), 2000409.
E. Güzel, Ü. M. Koçyiğit, P. Taslimi, S. Erkan, O. S. Taskin, J. Biochem. Mol. Toxicol. 2021, 35(6), 1.
Y. Tao, Y. Zhang, Y. Cheng, Y. Wang, Biomed. Chromogr. 2013, 27, 148.
S. Rajendrachari, P. Taslimi, A. C. Karaoglanli, O. Uzun, E. Alp, G. Kudur Jayaprakash, Arab. J. Chem. 2021, 14, 103180.
M. K. Erdogan, I. H. Gecibesler, Y. Yapar, R. Gundogdu, M. Kirici, P. Taslimi, Bioorg. Chem. 2021, 113, 105032.
Gaussian 09, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, Gaussian, Inc., Wallingford CT, 2009.
F. Kiefer, K. Arnold, M. Kunzli, L. Bordoli, T. Schwede, The SWISS-MODEL Repository and Associated Resources, Nucleic Acids Res. 2009, 37, D387.
K. Arnold, L. Bordoli, J. Kopp, T. Schwede, Bioinformatics 2006, 22, 195.
L. R. Guerreiro, E. P. Carreiro, L. Fernandes, T. A. F. Cardote, R. Moreira, A. T. Caldeira, R. C. Guedes, A. J. Burke, Bioorg. Med. Chem. 2013, 21, 1911.
W. Lestari, R. Triana Dewi, L. B. Sugeng Kardono, A. Yanuar, Indones. J. Chem. 2017, 17, 144.
K. M. Khan, F. Rahim, A. Wadood, N. Kosar, M. Taha, S. Lalani, A. Khan, M. I. Fakhri, M. Junaid, W. Rehman, M. Khan, S. Perveen, M. Sajid, M. I. Choudhary, Eur. J. Med. Chem. 2014, 81, 245.