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Polymers for Delivering a Substance Into a Cell

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Polymers for Delivering a Substance Into a Cell Missouri University of Science and Technology Scholars' Mine Chemical and Biochemical Engineering Faculty Linda and Bipin Doshi Department of Chemical Research & Creative Works and Biochemical Engineering 02 Aug 2012 Polymers for Delivering a Substance into a Cell Kaushal Rege Ravindra S. Kane Steven M. Cramer Sutapa Barua Missouri University of Science and Technology, [email protected] Follow this and additional works at: https://scholarsmine.mst.edu/che_bioeng_facwork Part of the Chemical Engineering Commons Recommended Citation K. Rege et al., "Polymers for Delivering a Substance into a Cell," U.S. Patents, Aug 2012. This Patent is brought to you for free and open access by Scholars' Mine. It has been accepted for inclusion in Chemical and Biochemical Engineering Faculty Research & Creative Works by an authorized administrator of Scholars' Mine. This work is protected by U. S. Copyright Law. Unauthorized use including reproduction for redistribution requires the permission of the copyright holder. For more information, please contact [email protected]. US 20120196923A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0196923 A1 Rege et al. (43) Pub. Date: Aug. 2, 2012 (54) POLYMERS FOR DELIVERING A Related U.S. Application Data SUBSTANCE INTO A CELL (60) Provisional application No. 61/178,654, filed on May 15, 2009. (76) Inventors: Kaushal Rege, Chandler, AZ (US); O O Ravindra S. Kane, Niskayuna, NY Publication Classification (US); Steven M. Cramer, (51) Int. Cl. Schenectady, NY (US); Sutapa A63L/7088 (2006.01) Barua, Tempe, AZ (US) C07D 303/36 (2006.01) C07C 217/50 (2006.01) (21) Appl. No.: 13/318,384 CI2N 5/071 (2010.01) (52) U.S. Cl. ......... 514/44 R; 435/375; 549/551:564/504 (22) PCT Filed: May 17, 2010 (57) ABSTRACT (86). PCT No.: PCT/US 10/35094 Disclosed herein are polymers that can be made cationic and used to deliver a substance into a cell. Also disclosed are S371 (c)(1), pharmaceutical compositions comprising the polymers and (2), (4) Date: Jan. 13, 2012 methods of using the polymers. Patent Application Publication Aug. 2, 2012 Sheet 1 of 8 US 2012/0196923 A1 R2 HN NH O Q7. Vandlor 2 SR 11 2 Ass-N-N-1H Branched Polymer Figure 1 a Patent Application Publication Aug. 2, 2012 Sheet 2 of 8 US 2012/0196923 A1 o/o-o-éo 1 Q/r ok-o -AO 5 ethyleneglycoldiglycidylether (EDGE) (ii) Poly(ethyleneglycol) diglycidyl ether (PEGDE) |- 2 a-roke- neopentylglycoldiglycidyletherÁ-o-X-o-A. (NPDGE) Poly(propyleneglycol) diglycidyl ether (PPGDE) ouAO 3 O 7 1,4-Butanediolodiglycidylether (14B) (^-ore Auo O?ory (i) 8 1,4-cyclohexanedimethanol diglycidylether (14C) 4 ^erorsHO (ii) glycerol diglycidylether (GDE) Figure 1b Patent Application Publication Aug. 2, 2012 Sheet 3 of 8 US 2012/0196923 A1 cr" aniline HN1)\1\ butylamine C 1-(2-aminoethyl)piperidine HN11o-N-N-101NH. 4,7,10-Trioxa-1, 13-tridecanediamine r N1\1\N H2 H2N-N-N - 1 4-Bis-(3-aminopropyl)piperazine H2N->NH, ethylenediamine H N-n-N-N-NH2 N-(2-aminoethyl)-1,3-propanediamine H2NN-N-N-N-N-NH2 3,3'-diamino-N-methyldipropylamine H HN1)-N1)-NH. diethylenetriamine H H N-N-N-N-N-N-N-N-NH2H H pentaethylenehexaamine Figure 1c Patent Application Publication Aug. 2, 2012 Sheet 4 of 8 US 2012/0196923 A1 z9.InáH 1,4C %. Fluorescence Decreased Patent Application Publication Aug. 2, 2012 Sheet 5 of 8 US 2012/0196923 A1 s SS n S r S (gz-Edo eA3ee) 3. Leo, fuTA r ey s g as 8 S87'-O7' oXP e . S87'-O9dN S9 y'-OS) e'e-ado e 25 Sigv'l-BOOdd- LOOSDB Oulue-NOS) OgAld G-d 8 o s s gz-Edo emeel E upeoud fun Patent Application Publication Aug. 2, 2012 Sheet 6 of 8 US 2012/0196923 A1 l s us . E o cy . g t se an c ga-Ido emiere 3. ugeoid fu IT 't e i S S. Si S97'-07' . S87'-ON e'e-ads Es Sigv'- Ogld Ge-d to alik r 9 sia an (ga-do emiere) S. Leod fluff Patent Application Publication Aug. 2, 2012 Sheet 7 of 8 US 2012/0196923 A1 OpE-25 polymer 1,4C-1,4 Bis polymer pE-25:pGL3 polyplex 14C-1,4 Bis polyplex 1O: 25:1 50:1 Polymer:pg 3 plasmid Ratio Figure 4 Patent Application Publication Aug. 2, 2012 Sheet 8 of 8 US 2012/0196923 A1 Time (h) 8. EGDE 3,3' some 14C1,4 Bis Figure 5a (b) (3S , 2 at=Oh 15 05 SO O besigsse sease AR 5 Wavenumber (cm) Figure 5b US 2012/0196923 A1 Aug. 2, 2012 POLYMERS FOR DELIVERINGA a Substance into a cell using a polymer or pharmaceutical SUBSTANCE INTO A CELL composition. In yet a further aspect, the disclosed subject matter relates to methods for treating a disorder by adminis CROSS-REFERENCE TO RELATED tering to a subject a polymer and a substance to be delivered APPLICATIONS into a cell, or by administering to a subject a pharmaceutical 0001. This application claims the benefit of priority to composition comprising a polymer and a Substance to be U.S. Provisional Application No. 61/178,654, filed on May delivered into a cell. 15, 2009, which is incorporated by reference herein in its 0007 Additional advantages will be set forth in part in the entirety. description that follows, and in part will be obvious from the description, or can be learned by practice of the aspects STATEMENT REGARDING FEDERALLY described below. It is to be understood that both the foregoing SPONSORED RESEARCH ORDEVELOPMENT general description and the following detailed description are exemplary and explanatory only and are not restrictive. 0002. This invention was made with U.S. Government support under grant no. CBET 0829128 awarded by the National Science Foundation. The government has certain BRIEF DESCRIPTION OF THE DRAWINGS rights in the invention. 0008. The accompanying drawings, which are incorpo rated in and constitute a part of this specification, illustrate BACKGROUND several embodiments of the invention and together with the 0003 Delivery vehicles are often used to delivery a sub description, serve to explain the principles of the invention. stance into a cell. Viruses, for example, are effective at deliv 0009 FIG. 1a is a reaction scheme employed for the gen ering DNA into mammaliancells. However, concerns regard eration of the library of eighty cationic polymers. FIG.1b is a ing safety, immunogenicity, repeated dosage, viral list of the diglycidyl ethers used in the combinatorial matrix degradation, and production scale-up have motivated the of the polymer library. FIG. 1c is a list of the amines used in investigation of nonviral approaches for delivering a Sub the combinatorial matrix of the polymer library. stance into a cell. A variety of nonviral delivery vehicles have 0010 FIG. 2 is a three-dimensional bar plot showing been discovered. For the delivery of anionic substances or DNA-binding activity of the diglycidyl ether based cationic Substances that can be made anionic, such as therapeutic polymer library determined using the ethidium bromide dis agents, peptides, polynucleic acids, and the like, cationic placement assay. The percent fluorescence decreased upon polymers are particularly useful. For example, cationic poly polymer binding to calf Thymus DNA intercalated with mers can deliver exogenous DNA to cells and enhance the Ethidium Bromide was used to measure polymer efficacy. efficacy of virus-mediated gene transfer. A few examples of 0011 FIGS. 3a-care plots demonstrating transfection of known cationic polymers used to deliver genes into cells mammalian cells using polymer leads selected from the DNA include poly(L-lysine), poly(ethylene imine), chitosan, binding screen (Example 2). Polymer transfection efficacies polyamidoamine or PAMAM dendrimers and poly(vinyl pyr are reported as relative to that of pEI-25. Relative efficacy rolidone). data are plotted on a logarithmic scale (y-axis) and statistical 0004. Unfortunately, most cationic polymers exhibit high significance using p-values was determined by comparing cytotoxicities. As a result, alternative delivery vehicles have data for a given polymer with pBI-25. (3.a) Polymer-mediated been developed that exhibit lower cytotoxities, such as poly transfection of PC3-PSMA cells in the absence of serum mers based on cyclodextrin and carbohydrate comonomers, using a polymer: pGL3 plasmid ratio of 25:1 (w/w). (3b) as well as genetically engineered protein-based polymers. To Transfection of PC3-PSMA cells in the absence of serum date, however, even the alternative delivery vehicles are not using different polymer: plasmid ratios of the 1,4C-1.4 Bis optimal and are not as effective as viral delivery vehicles in polymer. (3.c) Polymer-mediated transfection of PC3-PSMA vivo. (Glover, D. J.; Lipps, H. J.; Jans, D. A. “Towards safe, cells in the presence of 10% fetal bovine serum using a non-viral therapeutic gene expression in humans.” Nat. Rev. polymer: pGL3 plasmid ratio of 25:1. (3d) Polymer-mediated Genet. 2005, 6 (4), 299-310.) transfection of murine osteoblasts using 1,4C-1.4 Bis and 0005 Thus, both the cytotoxicity and the low efficacy of pEI-25 polymers in the presence of 10% fetal bovine serum nonviral delivery vehicles is a significant limitation in the using a polymer pGL3 plasmid ratio of 25:1. development of safer alternatives to viral delivery vehicles. 0012 FIG. 4 is a plot displaying the percentage of dead Accordingly, there exists a need for improved nonviral mate PC3-PSMA cells following polymer/polyplex treatment (Ex rials for delivering a substance into a cell that are both effec ample 4). tive and safe. These needs and other needs are addressed by 0013 FIG.
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