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Article

Protopine and Allocryptopine Interactions with Plasma Proteins

by
Aleksandra Marciniak
1,
Aleksandra Kotynia
1,
Edward Krzyżak
1,*,
Żaneta Czyżnikowska
1,
Sylwia Zielińska
2,*,
Weronika Kozłowska
2,
Marcel Białas
3,
Adam Matkowski
4 and
Anna Jezierska-Domaradzka
2
1
Department of Basic Chemical Sciences, Wroclaw Medical University, Borowska 211a, 50-556 Wrocław, Poland
2
Division of Pharmaceutical Biotechnology, Department of Pharmaceutical Biology and Biotechnology, Wroclaw Medical University, Borowska 211, 50-556 Wrocław, Poland
3
Student Scientific Club, Division of Pharmaceutical Biotechnology, Department of Pharmaceutical Biology and Biotechnology, Wroclaw Medical University, Borowska 211, 50-556 Wrocław, Poland
4
Division of Pharmaceutical Biology and Botany, Department of Pharmaceutical Biology and Biotechnology, Wroclaw Medical University, Borowska 211a, 50-556 Wrocław, Poland
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2024, 25(10), 5398; https://doi.org/10.3390/ijms25105398
Submission received: 18 April 2024 / Revised: 10 May 2024 / Accepted: 13 May 2024 / Published: 15 May 2024
(This article belongs to the Special Issue Investigation of Natural Products as Sources of Bioactive Molecules)

Abstract

A comprehensive study of the interactions of human serum albumin (HSA) and α-1-acid glycoprotein (AAG) with two isoquinoline alkaloids, i.e., allocryptopine (ACP) and protopine (PP), was performed. The UV-Vis spectroscopy, molecular docking, competitive binding assays, and circular dichroism (CD) spectroscopy were used for the investigations. The results showed that ACP and PP form spontaneous and stable complexes with HSA and AAG, with ACP displaying a stronger affinity towards both proteins. Molecular docking studies revealed the preferential binding of ACP and PP to specific sites within HSA, with site 2 (IIIA) being identified as the favored location for both alkaloids. This was supported by competitive binding assays using markers specific to HSA’s drug binding sites. Similarly, for AAG, a decrease in fluorescence intensity upon addition of the alkaloids to AAG/quinaldine red (QR) complexes indicated the replacement of the marker by the alkaloids, with ACP showing a greater extent of replacement than PP. CD spectroscopy showed that the proteins’ structures remained largely unchanged, suggesting that the formation of complexes did not significantly perturb the overall spatial configuration of these macromolecules. These findings are crucial for advancing the knowledge on the natural product–protein interactions and the future design of isoquinoline alkaloid-based therapeutics.
Keywords: protopine; allocryptopine; albumin; orosomucoid; spectroscopy protopine; allocryptopine; albumin; orosomucoid; spectroscopy

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MDPI and ACS Style

Marciniak, A.; Kotynia, A.; Krzyżak, E.; Czyżnikowska, Ż.; Zielińska, S.; Kozłowska, W.; Białas, M.; Matkowski, A.; Jezierska-Domaradzka, A. Protopine and Allocryptopine Interactions with Plasma Proteins. Int. J. Mol. Sci. 2024, 25, 5398. https://doi.org/10.3390/ijms25105398

AMA Style

Marciniak A, Kotynia A, Krzyżak E, Czyżnikowska Ż, Zielińska S, Kozłowska W, Białas M, Matkowski A, Jezierska-Domaradzka A. Protopine and Allocryptopine Interactions with Plasma Proteins. International Journal of Molecular Sciences. 2024; 25(10):5398. https://doi.org/10.3390/ijms25105398

Chicago/Turabian Style

Marciniak, Aleksandra, Aleksandra Kotynia, Edward Krzyżak, Żaneta Czyżnikowska, Sylwia Zielińska, Weronika Kozłowska, Marcel Białas, Adam Matkowski, and Anna Jezierska-Domaradzka. 2024. "Protopine and Allocryptopine Interactions with Plasma Proteins" International Journal of Molecular Sciences 25, no. 10: 5398. https://doi.org/10.3390/ijms25105398

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