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Open AccessArticle

Asymmetric Synthesis and Evaluation of Danshensu-Cysteine Conjugates as Novel Potential Anti-Apoptotic Drug Candidates

1
Shanghai Key Laboratory of Bioactive Small Molecules, Department of Pharmacology, School of Pharmacy, Fudan University, Shanghai 201203, China
2
Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Wei-Zhu Zhong
Int. J. Mol. Sci. 2015, 16(1), 628-644; https://doi.org/10.3390/ijms16010628
Received: 1 October 2014 / Accepted: 24 December 2014 / Published: 29 December 2014
(This article belongs to the Section Biochemistry)
We have previously reported that the danshensu-cysteine conjugate N-((R)-3-benzylthio-1-methoxy-1-oxo-2-propanyl)-2-acetoxy-3-(3,4-diacetoxyphenyl) propanamide (DSC) is a potent anti-oxidative and anti-apoptotic agent. Herein, we further design and asymmetrically synthesize two diastereoisomers of DSC and explore their potential bioactivities. Our results show that DSC and its two diastereoisomers exert similar protective effects in hydrogen peroxide (H2O2)-induced cellular injury in SH-SY5Y cells, as evidenced by the increase of cell viability, superoxide dismutase (SOD), and reduced glutathione (GSH) activity, and glutathione peroxidase (GPx) expression, and the decrease of cellular morphological changes and nuclear condensation, lactate dehydrogenase (LDH) release, and malondialdehyde (MDA) production. In H2O2-stimulated human umbilical vein endothelial cells (HUVEC), DSC concentration-dependently attenuates H2O2-induced cell death, LDH release, mitochondrial membrane potential collapse, and modulates the expression of apoptosis-related proteins (Bcl-2, Bax, caspase-3, and caspase-9). Our results provide strong evidence that DSC and its two diastereoisomers have similar anti-oxidative activity and that DSC exerts significant vascular-protective effects, at least in part, through inhibition of apoptosis and modulation of endogenous antioxidant enzymes. View Full-Text
Keywords: Danshensu derivative; apoptosis; asymmetric synthesis; endothelial cells Danshensu derivative; apoptosis; asymmetric synthesis; endothelial cells
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MDPI and ACS Style

Pan, L.-L.; Wang, J.; Jia, Y.-L.; Zheng, H.-M.; Wang, Y.; Zhu, Y.-Z. Asymmetric Synthesis and Evaluation of Danshensu-Cysteine Conjugates as Novel Potential Anti-Apoptotic Drug Candidates. Int. J. Mol. Sci. 2015, 16, 628-644. https://doi.org/10.3390/ijms16010628

AMA Style

Pan L-L, Wang J, Jia Y-L, Zheng H-M, Wang Y, Zhu Y-Z. Asymmetric Synthesis and Evaluation of Danshensu-Cysteine Conjugates as Novel Potential Anti-Apoptotic Drug Candidates. International Journal of Molecular Sciences. 2015; 16(1):628-644. https://doi.org/10.3390/ijms16010628

Chicago/Turabian Style

Pan, Li-Long; Wang, Jie; Jia, Yao-Ling; Zheng, Hong-Ming; Wang, Yang; Zhu, Yi-Zhun. 2015. "Asymmetric Synthesis and Evaluation of Danshensu-Cysteine Conjugates as Novel Potential Anti-Apoptotic Drug Candidates" Int. J. Mol. Sci. 16, no. 1: 628-644. https://doi.org/10.3390/ijms16010628

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