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Molecules 2017, 22(12), 2081; doi:10.3390/molecules22122081

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.
Received: 6 October 2017 / Accepted: 24 November 2017 / Published: 28 November 2017
(This article belongs to the Special Issue The Chemistry of Alliums)
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Abstract

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
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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.

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