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US 20070282422A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0282422 A1 Biggs et al. (43) Pub. Date: Dec. 6, 2007 (54) MEDICAL DEVICES AND METHODS FOR Related U.S. Application Data LOCAL DELIVERY OF ELASTN-STABILIZING COMPOUNDS (60) Provisional application No. 60/799,608, filed on May 10, 2006. (75) Inventors: David Paul Biggs, Bloomington, IN (US); Anthony O. Ragheb, West Publication Classification Lafayette, IN (US); Patrick H. Ruane, Redwood City, CA (US) (51) Int. Cl. A6IF 2/82 (2006.01) Correspondence Address: A6F 2/02 (2006.01) BRINKSHOFER GILSON & (52) U.S. Cl. ........................ 623/1.13; 424/423; 623/1.42 LONEACHICAGO/COOK (57) ABSTRACT PO BOX 10395 This invention relates to medical devices and an elastin CHICAGO, IL 60610 (US) stabilizing compound, Such as a phenolic tannin, the medical (73) Assignees: Cook Incorporated; MED Institute, device being adapted to release the elastin-stabilizing com Inc. pound within a body of a patient. This invention also relates to medical devices and methods of treatment of disease. Such (21) Appl. No.: 11/800,217 as aneurysms and aortic dissection. Medical devices may include coated Stents, grafts, stent grafts, balloons and (22) Filed: May 4, 2007 catheters. 20' t 28 26b 12b O O Patent Application Publication Dec. 6, 2007 Sheet 1 of 7 US 2007/0282422 A1 FIGURE 1 Erythrose-PO+PEP HO COH CO2H -- HO COH HO HO Shikimic acid Quinic acid O Gallic acid Tryptophan Hydrolyzable tannins NH ( ) / COH2 areer-es- N -1 CondensedFlavenoids tannins COH2 N. Isoflavones Phenylalanine Cinnamic acid Coumarins Tvrosiney -> HO N COH -es HO-()- N-OH p-Coumaric acid p-Coumaryl alcohol N HO Caffeic acid HO HO CHO N-co. CHO No. Ferulic acid N Coritery alcohol HO HO N COH CHO 5-(OH)-Ferulic acid CHO CHO HO N-coh HO 3. CHO CHO 3 Syringic acid 3 - alcohol polymerization - > grass lignins Legume and dicottignins Patent Application Publication Dec. 6, 2007 Sheet 2 of 7 US 2007/0282422 A1 10 12 Patent Application Publication Dec. 6, 2007 Sheet 3 of 7 US 2007/0282422 A1 24 29 12c ..., . ."...' . i; s:Dejada-PskiD 26c 29 26d / 130 1 11b 11b, is 114 is is iss e 3. ask - 2 as as Patent Application Publication Dec. 6, 2007 Sheet 4 of 7 US 2007/0282422 A1 -- 157 Patent Application Publication Dec. 6, 2007 Sheet 5 of 7 US 2007/0282422 A1 212 200 230 Patent Application Publication Dec. 6, 2007 Sheet 6 of 7 US 2007/0282422 A1 326 310 326 310 Fig. 5B Fig. 5C 326 310 326 310 YIIlyzz // Fig. 5D Fig. 5E 410 440 420 440 430 408 72 ISXSS&KRS2 O is s S7.3S2 S&S w N AN NA NZ passig Ay, Q) Q) \7-N 2 XX. XX XX XXX.X. Q27 NZ Y 63. X SSC Ézis s^XXXX. SSCS/373.6%5 Patent Application Publication Dec. 6, 2007 Sheet 7 of 7 US 2007/0282422 A1 502 510 520 SeezáEigz:SARGIC) aszz SS SASNY S. 522 12 27%22& 530 550 610 602 604 US 2007/0282422 A1 Dec. 6, 2007 MEDICAL DEVICES AND METHODS FOR LOCAL aortic dissections are constantly being sought. Although the DELIVERY OF ELASTN-STABILIZING following discussion focuses on AAA treatment and preven COMPOUNDS tion, it is equally applicable to endovascular disease in other locations, and aortic dissections. RELATED APPLICATIONS 0007 Various implantable medical devices are advanta 0001. The present patent document claims the benefit of geously inserted within various portions of the body. Mini the filing date under 35 U.S.C. S 119(e) of Provisional U.S. mally invasive techniques and instruments for placement of Patent Application Ser. No. 60/799,608, filed May 10, 2006, intralumenal medical devices have been developed to treat which is hereby incorporated by reference. and repair undesirable conditions within body vessels including treatment of conditions that affect blood flow such TECHNICAL FIELD as abdominal aortic aneurysm. Various percutaneous meth ods of implanting medical devices within the body using 0002 This invention relates generally to human and intralumenal transcatheter delivery systems can be used to veterinary medical devices and, more particularly, to treat a variety of Such conditions. One or more intralumenal implantable medical devices incorporating elastin-stabiliz medical devices, such as tubular stent grafts, can be intro ing compounds. The invention also relates to methods of duced to a point of treatment within a body vessel using a treatment and kits and to treating an aorta wall adjacent to delivery catheter device passed through the vasculature an aortic aneurysm as a preventative measure. communicating between a remote introductory location and the implantation site, and released from the delivery catheter BACKGROUND device at the point of treatment within the body vessel. Intralumenal medical devices can be deployed in a body 0003 Diseases of aorta are common in the general popu vessel at a point of treatment and the delivery device lation and may include endovascular disease, including subsequently withdrawn from the vessel, while the medical aneurysms and aortic dissections. device is retained within the vessel to provide sustained 0004 Endovascular disease may be characterized by improvement in valve function or to increase vessel patency. weakened vessels due to elastin breakdown, which results in For example, an implanted stent graft can improve vessel dilation of vessels and aneurysm. An aneurysm is a sac function by permitting relatively less turbulent fluid flow formed by localized dilatation of the wall of an artery, a vein, through the stent graft conduit bridging the site of an or the heart. Common areas where aneurysms occur and aneurysm. cause adverse medical conditions include the coronary arter ies, the carotid arteries, various cerebral arteries, and the SUMMARY thoracic and abdominal aorta as well as iliac and femoral 0008. In one embodiment, the invention provides a medi arteries. When a local dilatation of a vessel occurs, irregular cal device and an elastin-stabilizing compound, the medical blood flow patterns result in the lumen of the vessel, device being adapted to release an elastin-stabilizing com Sometimes leading to clot formation. Typically, the wall of pound within a body of a patient. The medical device may the vessel also progressively dilates and weakens, often be implantable. The elastin-stabilizing compound may be a resulting in vessel rupture. Vessel rupture, in turn, often phenolic tannin. The phenolic tannin may be a hydrolyzable causes dramatic negative consequences such as a stroke, tannin or a condensed tannin. The phenolic tannin may be when a cerebral vessel ruptures, or even death, when an selected from gallotannins, ellagitannins, epicatechins, cat abdominal aortic aneurysm (“AAA”) ruptures. Continued echins, proanthocyanidins, derivatives, and mixtures degeneration can result in an increase in aneurysm size due thereof. The phenolic tannin may be selected from the group to thinning of the medial connective tissue of the aorta and of compounds: tannic acid; B-1.2.3.4.6-Pentagalloyl-O-D- loss of elastin. Glucopyranose; B-1.2.2.3,6-Pentagalloyl-O-D-glucose; 1.2, 3.6-tetragalloyl glucose, 1.3.4.6-tetragalloyl glucose: Acer 0005 Aortic dissections occur when the inner layer of the itannin=2,6-di-O-galloyl-1,5-anhydro-D-glucitol; aorta’s artery wall splits open (dissects). The normal aorta Hamamelitannin; Ellagitannin; Eugeniin, Casuarictin; contains collagen, elastin, and Smooth muscle cells that Corilagin; Geraniin, Davidiin, Castalagin; Vescalagin; contribute to the intima, media, and adventitia, which are the Euphorbin: Oenethein B: Epicatechenin: Catechin: Epigal layers of the aorta. Hypertension with aging is believed to locatechin; Gallocatechin: Epiafzelechin: Afzelechin: Epi contribute to degenerative changes that may lead to break catechin (4B->8)-catechin: Epicatechin (4B->8)-epicatechin; down of the collagen, elastin, and Smooth muscle cells and Catechin (4C.->8)-catechin: Catechin (4C.->8)-epicatechin; ultimately dissection of the aorta. Aortic dissection is more Sorghum procyanidin; epicatechin-(4b->8)-epicatechin 15 likely to occur where pressure on the artery wall from blood (4b->8)-catechin: Aurantinidin; Cyanidin; Delphinidin; flow is high, such as the proximal aorta or the ascending Europinidin; Luteolinidin; Pelargonidin; Malvidin; Peoni aorta (the first segment of the aorta). When the aortic wall din; Petunidin; Apigeninidin; Robinetinidin; Fisetinidin; splits, the pulses of blood can penetrate the artery wall and Guibourtinidin; Robinetinidol-(4C->8)-catechin-(6C.->4a)- its inner layer, causing the aorta to tear or split further. This robinetinidol; Profisetinidin; Epicatechin (2B-->7.4?-->8)- tear usually continues distally (away from the heart) down epicatechin; Leucofisetinidin; Leucopelargonidin; Leuco the descending aorta and into its major branches. Less often, cyanidin; Leucodelphinidin; Leucoapigeninidin; the tear may run proximally (back toward the heart). Aortic Leucoluteolinidin, derivatives, and mixtures thereof. The dissection can also start in the descending (distal) segment phenolic tannin may be pentagalloyl glucose (PGG). The of the aorta. medical device may be an implantable medical device. The 0006. In light of these consequences, improved devices implantable medical device may be an endolumenal medical and methods of treating and/or preventing aneurysms and device Such as a stent, the elastin-stabilizing compound US 2007/0282422 A1 Dec. 6, 2007 releasably associated with the stent. The stent may comprise 0015 FIG. 2B is a cross section of a strut of an implant a plurality of interconnected Struts and bends, the elastin able medical device comprising a single-layer coating con stabilizing compound releasably associated with the struts, figuration. bends, or a combination thereof. Alternatively, the stent may comprise a plurality of Z-STENTSR). The implantable medi 0016 FIG. 2C is a cross section of a strut of an implant cal device may be a stent graft comprising a Support frame able medical device comprising a two-layer coating con attached to a flexible tubular covering, the elastin-stabilizing figuration.
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    ABSTRACT YUZUAK, SEYIT. Utilizing Metabolomics and Model Systems to Gain Insight into Precursors and Polymerization of Proanthocyanidins in Plants (Under the direction of Dr. De-Yu Xie). Proanthocyanidins (PAs) are oligomers or polymers of flavan-3-ols. In plants, PAs have multiple protective functions against biotic and abiotic stresses. PAs are also important nutraceuticals existing in common beverages and food products to benefit human health. To date, although the biosynthesis of PAs has been intensively studieed and fundamental progress has been made in over the past decades, many questions remain unanswered. For example, its direct precursors of extension units are unknown and their monomer structure diversity are also unclear. These questions about proanthocyanidins result from not having of model systems and effective technologies. Our laboratory has made significant progress in enhancing the understanding of these unknown and unclear points regarding proanthocyanidins. In my dissertation research reported here, I focus on two areas: testing muscadine as a crop system to develop metabolomics for studying precursor diversity and isolating enzymes from a red cell tobacco system to understand the precursors of the extension units of PA. First, I developed a metabolomics protocol to analyze anthocyanidins and anthocyanins in muscadine grape. This study demonstrated that muscadine berries can produce at least six anthocyanidins, revealing the diversity of pathway precursors for PAs. The Journal of Agriculture and Food Chemistry is reviewing this work. Second, I developed a metabolomics protocol of HPLC-qTOF-MS/MS to analyze flavan- 3-ols and dimeric PAs in muscadine grape. This study also demonstrated the high structure diversity of flavan-3-ols, particularly methylated flavan-3-ols.
  • Interactions with Microbial Proteins Driving the Antibacterial Activity of Flavonoids

    Interactions with Microbial Proteins Driving the Antibacterial Activity of Flavonoids

    pharmaceutics Review Interactions with Microbial Proteins Driving the Antibacterial Activity of Flavonoids Giuliana Donadio 1,†, Francesca Mensitieri 2,†, Valentina Santoro 1, Valentina Parisi 1,3, Maria Laura Bellone 1,3, Nunziatina De Tommasi 1, Viviana Izzo 2 and Fabrizio Dal Piaz 2,* 1 Department of Pharmacy, University of Salerno, 84084 Fisciano, Italy; [email protected] (G.D.); [email protected] (V.S.); [email protected] (V.P.); [email protected] (M.L.B.); [email protected] (N.D.T.) 2 Department of Medicine and Surgery, University of Salerno, 84082 Baronissi, Italy; [email protected] (F.M.); [email protected] (V.I.) 3 PhD Program in Drug Discovery and Development, Department of Pharmacy, University of Salerno, 84084 Fisciano, Italy * Correspondence: [email protected] † These authors contributed equally to this work. Abstract: Flavonoids are among the most abundant natural bioactive compounds produced by plants. Many different activities have been reported for these secondary metabolites against numerous cells and systems. One of the most interesting is certainly the antimicrobial, which is stimulated through various molecular mechanisms. In fact, flavonoids are effective both in directly damaging the envelope of Gram-negative and Gram-positive bacteria but also by acting toward specific molecular targets essential for the survival of these microorganisms. The purpose of this paper is to present an overview of the most interesting results obtained in the research focused on the study of the Citation: Donadio, G.; Mensitieri, F.; interactions between flavonoids and bacterial proteins. Despite the great structural heterogeneity Santoro, V.; Parisi, V.; Bellone, M.L.; of these plant metabolites, it is interesting to observe that many flavonoids affect the same cellular De Tommasi, N.; Izzo, V.; Dal Piaz, F.