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(12) United States Patent (10) Patent No.: US 9.234,015 B2 Sentissi Et Al

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(12) United States Patent (10) Patent No.: US 9.234,015 B2 Sentissi Et Al USOO9234015B2 (12) United States Patent (10) Patent No.: US 9.234,015 B2 Sentissi et al. (45) Date of Patent: Jan. 12, 2016 (54) CHLOROTOXIN POLYPEPTIDES AND 6,028,174 A 2/2000 Ullrich et al. CONUGATES AND USES THEREOF 6,130, 101 A 10/2000 Mao et al. 6,319,891 B1 1 1/2001 Sontheimer et al. 6,429,187 B1 8, 2002 Sontheimer et al. (71) Applicant: MORPHOTEK, INC., Exton, PA (US) 6,514,481 B1 2/2003 Prasadet al. 6,555,652 B1 4/2003 Itoh et al. (72) Inventors: Abdellah Sentissi, Dover, MA (US); 6,667,156 B2 12/2003 Lyons et al. Douglas B. Jacoby, Wellesley, MA (US) 6,767,635 B1 7/2004 Bahr et al. 6,849,714 B1 2/2005 Bridon et al. (73) Assignee: Morphotek, Inc., Exton, PA (US) 6,926,8966,870,029 B2 3/20058, 2005 SontheimerBosslet et al. et al. 6,972,326 B2 12/2005 Haugland et al. (*) Notice: Subject to any disclaimer, the term of this 7,094,868 B2 8, 2006 SNE f al. patent is extended or adjusted under 35 7,252,998 B2 8, 2007 Skerra et al. U.S.C. 154(b) by 0 days. 7.462.446 B2 12/2008 Zhang et al. 7,678,759 B2 3/2010 Sontheimer et al. 8,227,439 B2 7, 2012 O'Neill et al. (21) Appl. No.: 14/450,182 8,470,607 B2 6/2013 Jacoby et al. 8,778,310 B2 7/2014 Zhang et al. (22) Filed: Aug. 1, 2014 2001/0007025 A1 7/2001 Bennett et al. 2001/0055751 A1 12/2001 Reiter et al. (65) Prior Publication Data 2002/0065216 A1 5/2002 Sontheimer et al. 2002/0146749 A1 10/2002 Lyons PH.D. et al. US 2015/OO30537 A1 Jan. 29, 2015 2003/0021810 A1 1/2003 Sontheimer et al. 2003/0201208 A1 10, 2003 Koch et al. 2003/0216322 A1 1 1/2003 Samoylova et al. Related U.S. Application Data 2004/0101822 A1 5, 2004 Wiesner et al. 2004/0102381 A1 5/2004 Ekwuribe et al. (63) Continuation of application No. 13/577,169, filed as 2004/0105.980 A1 6/2004 Sudarshan et al. application No. PCT/US2011/023823 on Feb. 4, 2011, (Continued) now Pat. No. 9,018,347. (60) Provisional application No. 61/301,615, filed on Feb. FOREIGN PATENT DOCUMENTS 4, 2010. CN 1924006. A 3, 2007 CN 1010O3788 A 7/2007 (51) Int. Cl. CN 1O127O158. A 9, 2008 A6 IK38/00 (2006.01) CN 101381405 A 3, 2009 C07K I4/435 (2006.01) CN 101824084 A 9, 2010 A6 IK 47/48 (2006.01) CN 101921769. A 12/2010 C07K 14/00 (2006.01) N ISSA, 35. A6 IK3I/337 (2006.01) EP 1430.131 A2 6, 2004 A6 IK5I/08 (2006.01) EP 2182004 A1 5.2010 (52) U.S. Cl. (Continued) CPC ......... C07K 14/.43522 (2013.01); A61 K3I/337 (2013.01); A61 K47/48215 (2013.01); A61 K OTHER PUBLICATIONS 47/48261 (2013.01); A61 K5I/088 (2013.01); A61 K38/00 (2013.01) Akabani et al., Dosimetry and Radiographic Analysis of 131 I-La (58) Field of Classification Search beled Anti-Tenascin 81C6 Murine Monoclonal Antibody in Newly CPC ............ A61 K38/00; A61K 47/48215: A61 K Diagnosed Patients with Malignant Gliomas: A Phase II Study, Jour 51/088: A61 K31/337; A61K 47/48261; nal of Nuclear Medicine, 46(6):1042-1051 (2005). CO7K 14/43522 (Continued) See application file for complete search history. (56) References Cited Primary Examiner — Julie Ha U.S. PATENT DOCUMENTS Assistant Examiner — Li Ni Komatsu (74) Attorney, Agent, or Firm — Brenda Herschbach Jarrell; 4,444,744 A 4/1984 Goldenberg Choate Hall & Stewart LLP 5,051,364 A 9, 1991 Isacke et al. 5,212.290 A 5/1993 Vogelstein et al. 5,223,253 A 6, 1993 Hall et al. 5,236,844 A 8, 1993 Basset et al. (57) ABSTRACT 5,314,992 A 5/1994 Guyre et al. 5,591,829 A 1/1997 Matsushita Reduced lysine chlorotoxin polypeptides that may be used to 5,626,862 A 5, 1997 Brem et al. generate single species conjugates of chlorotoxin. Conju 5,688,773 A 11/1997 Chiocca et al. gates comprising Such chlorotoxin polypeptides and pharma 5,750,376 A 5, 1998 Weiss et al. 5,756,340 A 5, 1998 Hammocket al. ceutical compositions thereof. Methods of using such com 5,866,570 A 2/1999 Liang et al. positions and/or conjugates. 5,905,027 A 5, 1999 Ullrich et al. 5,935,795 A 8, 1999 Lin et al. 5,985,822 A 11/1999 Edelman et al. 16 Claims, No Drawings US 9.234,015 B2 Page 2 (56) References Cited WO WO-2009052390 A1 4/2009 WO WO-2009052392 A1 4/2009 U.S. PATENT DOCUMENTS WO WO-2009052400 A1 4/2009 WO WO-2009062520 A1 5, 2009 2004/O141981 A1 T/2004 Sontheimer et al. WO WO-2009.140599 6, 2009 2004/0180846 A1 9, 2004 Huang et al. WO WO-2009 108762 A2 9, 2009 2005. O142062 A1 6, 2005 Sontheimer et al. WO WO-2009 117018 A1 9, 2009 2005/0261191 A1 11, 2005 Barasch et al. WO WO-2009 15645.6 A1 12/2009 2006, OO1925.6 A1 1, 2006 Clarke et al. WO WO-2O11057295 A2 5, 2011 2006, OO19347 A1 1, 2006 Cho et al. 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