Next Article in Journal
Analytical Methods of Phytochemicals from the Genus Gentiana
Next Article in Special Issue
The Chemistry of Alliums
Previous Article in Journal
trans-Double Bond-Containing Liposomes as Potential Carriers for Drug Delivery
Previous Article in Special Issue
Physicochemical Properties, Biological Activity, Health Benefits, and General Limitations of Aged Black Garlic: A Review
Open AccessFeature PaperArticle

Fluorinated Analogs of Organosulfur Compounds from Garlic (Allium sativum): Synthesis, Chemistry and Anti-Angiogenesis and Antithrombotic Studies

1
Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222, USA
2
The Pharmaceutical Research Institute, Albany College of Pharmacy and Health Sciences, Rensselaer, NY 12144, USA
3
Department of Physiology, Veterinary Medicine Faculty, Uludag University, Bursa 16059, Turkey
*
Authors to whom correspondence should be addressed.
Molecules 2017, 22(12), 2081; https://doi.org/10.3390/molecules22122081
Received: 6 October 2017 / Accepted: 24 November 2017 / Published: 28 November 2017
(This article belongs to the Special Issue The Chemistry of Alliums)
We describe the synthesis, reactivity, and antithrombotic and anti-angiogenesis activity of difluoroallicin (S-(2-fluoroallyl) 2-fluoroprop-2-ene-1-sulfinothioate) and S-2-fluoro-2-propenyl-l-cysteine, both easily prepared from commercially available 3-chloro-2-fluoroprop-1-ene, as well as the synthesis of 1,2-bis(2-fluoroallyl)disulfane, 5-fluoro-3-(1-fluorovinyl)-3,4-dihydro-1,2-dithiin, trifluoroajoene ((E,Z)-1-(2-fluoro-3-((2-fluoroallyl)sulfinyl)prop-1-en-1-yl)-2-(2-fluoroallyl)disulfane), and a bis(2-fluoroallyl)polysulfane mixture. All tested organosulfur compounds demonstrated effective inhibition of either FGF or VEG-mediated angiogenesis (anti-angiogenesis activity) in the chick chorioallantoic membrane (CAM) or the mouse Matrigel® models. No embryo mortality was observed. Difluoroallicin demonstrated greater inhibition (p < 0.01) versus organosulfur compounds tested. Difluoroallicin demonstrated dose-dependent inhibition of angiogenesis in the mouse Matrigel® model, with maximal inhibition at 0.01 mg/implant. Allicin and difluoroallicin showed an effective antiplatelet effect in suppressing platelet aggregation compared to other organosulfur compounds tested. In platelet/fibrin clotting (anti-coagulant activity), difluoroallicin showed concentration-dependent inhibition of clot strength compared to allicin and the other organosulfur compounds tested. View Full-Text
Keywords: garlic; allicin; vinyl dithiins; ajoene; difluoroallicin; trifluoroajoene; angiogenesis; anti-angiogenesis; platelet; coagulation; thrombosis; anti-thrombotic; 2-fluoroallyl sulfur compounds garlic; allicin; vinyl dithiins; ajoene; difluoroallicin; trifluoroajoene; angiogenesis; anti-angiogenesis; platelet; coagulation; thrombosis; anti-thrombotic; 2-fluoroallyl sulfur compounds
Show Figures

Graphical abstract

MDPI and ACS Style

Block, E.; Bechand, B.; Gundala, S.; Vattekkatte, A.; Wang, K.; Mousa, S.S.; Godugu, K.; Yalcin, M.; Mousa, S.A. Fluorinated Analogs of Organosulfur Compounds from Garlic (Allium sativum): Synthesis, Chemistry and Anti-Angiogenesis and Antithrombotic Studies. Molecules 2017, 22, 2081. https://doi.org/10.3390/molecules22122081

AMA Style

Block E, Bechand B, Gundala S, Vattekkatte A, Wang K, Mousa SS, Godugu K, Yalcin M, Mousa SA. Fluorinated Analogs of Organosulfur Compounds from Garlic (Allium sativum): Synthesis, Chemistry and Anti-Angiogenesis and Antithrombotic Studies. Molecules. 2017; 22(12):2081. https://doi.org/10.3390/molecules22122081

Chicago/Turabian Style

Block, Eric; Bechand, Benjamin; Gundala, Sivaji; Vattekkatte, Abith; Wang, Kai; Mousa, Shaymaa S.; Godugu, Kavitha; Yalcin, Murat; Mousa, Shaker A. 2017. "Fluorinated Analogs of Organosulfur Compounds from Garlic (Allium sativum): Synthesis, Chemistry and Anti-Angiogenesis and Antithrombotic Studies" Molecules 22, no. 12: 2081. https://doi.org/10.3390/molecules22122081

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop