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(12) Patent Application Publication (10) Pub. No.: US 2010/0316643 A1 Eckert Et Al US 20100316643A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0316643 A1 Eckert et al. (43) Pub. Date: Dec. 16, 2010 (54) TARGETED ANTIMICROBIAL MOIETIES Related U.S. Application Data (60) Provisional application No. 61/224,825, filed on Jul. (75) Inventors: Randal H. Eckert, Redondo Beach, 10, 2009, provisional application No. 61/150,287, CA (US); Daniel Yarbrough, Los filed on Feb. 5, 2009. Angeles, CA (US); Wenyuan Shi, O O Los Angeles, CA (US); Maxwell Publication Classification Anderson, Sequim, WA (US); Jian (51) Int. Cl. He, Los Angeles, CA (US); Chris A 6LX 39/395 (2006.01) Kaplan, Los Angeles, CA (US); C07K 7/08 (2006.01) Jee-Hyun Sim, Garden Grove, CA C07K I4/00 (2006.01) (US) C07K 9/00 (2006.01) A638/16 (2006.01) Correspondence Address: Y. ity 30.8 TOWNSEND AND TOWNSEND AND CREW, A6IP3L/04 (2006.015 LLP TWO EMBARCADERO CENTER, EIGHTH A6IP3 L/10 (2006.01) FLOOR A6IP33/02 (2006.01) SAN FRANCISCO, CA 94111-3834 US A6IP3L/2 (2006.01) 9 (US) (52) U.S. Cl. ...................... 424/134.1; 530/326; 530/324; (73) Assignee: The Regents of the University of 530/387.3; 514/21.3; 514/21.4; 435/34;977/774 California, Oakland, CA (US) (57) ABSTRACT This invention provides novel targeted antimicrobial compo (21) Appl. No.: 12/701,443 sitions. In various embodiments chimeric moieties are pro vided comprising an antimicrobial peptide attached to a pep (22) Filed: Feb. 5, 2010 tide targeting moiety that binds a bacterial Strain or species. Patent Application Publication Dec. 16, 2010 Sheet 1 of 19 US 2010/0316643 A1 Formula I (91) R= -CH-CH (92) R = W (93) R = Et P = CHCHCOR, (94) R = -H R = H, alkyl, alkoxyl, alkenyl or alkynyl, (95) R = -COCH all from C to C, but preferably H (96), R = -CHO Me = methyl (97) pH R = -CH-CHOH (98) R = -CH=CHCOH (99), R = PR FIG. 1 Patent Application Publication Dec. 16, 2010 Sheet 3 of 19 US 2010/0316643 A1 N NN N X compound M x Y 19 2 SC), 121 HOSiOSCH, CH, N(CH). H 123 125 Z CH, N, 2 126 Z: SON (CHOHOFi) 126 A. SOH FIG. 3 Patent Application Publication Dec. 16, 2010 Sheet 4 of 19 US 2010/0316643 A1 2. N. s 2. N. ? | - N. - N N N Cu H - --- N MonastIal Fast Blue E Monast Ial Fast Blue phthalocyanine) (CI PigittentBlue 15) FIG. 4 Patent Application Publication Dec. 16, 2010 Sheet 5 of 19 US 2010/0316643 A1 X R’ 2-1 S+ R Y R R R R X Y Methylene blue (CH3)2N N(CH3)2 H N S Toluidine blue O (CH)N NH CH N S Neutral red (CH)N NH CH N NH Proflavine HN NH H CH NH Acridine orange (CH),N N(CH) H CH NH Aminacrine H H H C-NH NH Ethacridine HN H OCH5 C-NH. NH Merocyanine-type NaOS Dicarbocyanine-type X R X S21a2N2nal I X R X R Merocyanines Dicarbocyanines - O (MC540) S Et S Se H Se O (DHOCI) FIG. 6 Patent Application Publication Dec. 16, 2010 Sheet 6 of 19 US 2010/0316643 A1 4' 5 4. / N N 3 5 2 W X Y 2 1. Psoraiens Angelicins W X Y Z O CH O O psoralen S CH O O thienocountarin O N O O 8-azacoumarin O CH O S 2-thiofuranOCoumarin O CH () Se 2-Selenofuranocoumarin FIG. 7 HO O OH HO 21 Me HO Me HO O OH O H Hypericin Perylenequinonoids R R R R R/R -CHC(OH)MeCH(COMe)- OMe OMe hypocrellin A RJR -CI ICMe=C(COMe)- OMe OMe hypocrellin B -CHCHMeCOPh -CHCHMeOCO-p-CHOH OMe OMe. Calphostin C FIG. 8 Patent Application Publication Dec. 16, 2010 Sheet 7 of 19 US 2010/0316643 A1 FIG. 9 Patent Application Publication Dec. 16, 2010 Sheet 8 of 19 US 2010/0316643 A1 Ns s s sS s - f s Y. 8 &. R sSS ^ Y & SS. SS's S. SS S S.s S S S 'SS s s & s & & s R Y. s s s Patent Application Publication Dec. 16, 2010 Sheet 9 of 19 US 2010/0316643 A1 E1 Sarassssssssssssssssssssssssssssssssssars 'Kwrxxxxx xxxxxxxxxxxxx xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx xxxxxxxxx xxxxxxxxxxxxx xxxxxx S*::::::::::::::::: swy sS. S. S. S. xxxxxaxxxxxxxaxaraxxxxxaxxxxxxxxxxaxxxxxxx xxx xxxx xxxxx xxxx xxxxx xxxx xxxxx xxxx xxxxx xxxx xxxxx xxxxx xxxx SYYYYYYYYYYss SSSSSWSSSSSSSSWSSSSSSSSS E. 8 : SS-as-as----------------- S. SYYYYYYYYYYYYYYYYYYYYYYY 3 s S K X X S S srcrxxxxx xxxxxs sty vsS &S s s S ac *Xxxxxxxxxxxxxxxxxxxxxxxxxxx www.wixxxxxxxxxxxxxxxx xxxxxxxxx' Syrissyrsssssssssssssssssssssy sees S-axxx-xx-xx-xx-aa-S S Sa.S xxxxxxxxxxxYxxxxx FIG. 12 Patent Application Publication Dec. 16, 2010 Sheet 10 of 19 US 2010/0316643 A1 TFFRFLNRG GG-k^\f RKFLKKWLL KKHRKHRKHRKHGGG MH(KH)-20 (mw 4884.91) DAANEAGGG-k^M FIRKFLKKWLL KKHRKHRKHRKHGGG BL(KH)-20 (mw 4373.4) TFFRFLNRGGG-k^M FIRKFLKKWLL DAAN EAGGG M8(BL)-20 (mw 3798.01) FIG. 13 Patent Application Publication Dec. 16, 2010 Sheet 11 of 19 US 2010/0316643 A1 8) CO mAU -0 () () S.() (). S() ().() Retention volume (mL) FIG. 14A Patent Application Publication Dec. 16, 2010 Sheet 12 of 19 US 2010/0316643 A1 is&'s sk sess is Mass (m/z) FIG. 14B Patent Application Publication Dec. 16, 2010 Sheet 13 of 19 US 2010/0316643 A1 - BLOKH)-20 - -I-M8(KH-20 iron M8(BL)-20 | -- BD2.20 s “No Peptide FIG. 15A . -e-BLKH)-20 . --M80KH)-20 were B. 2 3. s 5 f Time (h) FIG. 15B Patent Application Publication Dec. 16, 2010 Sheet 14 of 19 US 2010/0316643 A1 r(- BL(KH)-20 --M8(KH-20 -A-M8(BL-20 ^ - B).() & -- Ne Peptide 1 - s 5 6 Time (i) FIG. 15C -e- BL(KH-20 f --M8(KH-20 -& s - 1.4 rth- AE8(BL)-20 - -e- BD2.20 a. 2 s S 6 Time (h FIG. 15D Patent Application Publication Dec. 16, 2010 Sheet 15 of 19 US 2010/0316643 A1 ... " -e-BL(KH)-20 ... " -- M8(KH-20 -A-M8(BL-20 . who B). 1 -i- No Peptide .9 2. S { Tinae (h) FIG. 15E 1E04 ; 1E03 1E02 iu. researrarae us stasksvaawaak rural SI8(K-20 vis(BL-20 BLKEI-20 3). titrates FIG. 16 Patent Application Publication Dec. 16, 2010 Sheet 16 of 19 US 2010/0316643 A1 ZL‘61-I Patent Application Publication Dec. 16, 2010 Sheet 18 of 19 US 2010/0316643 A1 s : S. s rs w se s s C. cs S S S to r *t ri test83 series assaarea Patent Application Publication Dec. 16, 2010 Sheet 19 of 19 US 2010/0316643 A1 O4 O.35 - O.3 - 0.25 - FIG. 20 US 2010/0316643 A1 Dec. 16, 2010 TARGETED ANTIMICROBAL MOIETIES more effector disclosed herein. Any targeting moiety dis closed herein can be attached to any one or more antimicro CROSS-REFERENCE TO RELATED bial peptide disclosed herein. APPLICATIONS 0008. In certain embodiments chimeric moieties are pro vided where the chimeric moieties comprise an effector 0001. This application claims priority to U.S. Provisional attached to a peptide targeting moiety comprising or consist Application No. 61/150,287, filed Feb. 5, 2009; and to U.S. ing of the amino acid sequence of a peptide found in Table 2 Provisional Application No. 61/224,825, filed Jul. 10, 2009, and/or Table 15. In certain embodiments the targeting peptide the disclosures of which are incorporated herein by reference comprises or consists of amino acid or retro or inverso or in their entirety for all purposes. retro-inverso sequence or beta sequence of a peptide found in Table 2 and/or Table 15. In certain embodiments the effector STATEMENT OF GOVERNMENTAL SUPPORT comprises a moiety selected from the group consisting of a detectable label, an antimicrobial peptide, an antibiotic, and a 0002. Not Applicable photosensitizer. In certain embodiments the effector com prises an antimicrobial peptide comprising the amino acid FIELD OF THE INVENTION sequence of a peptide found in Table 2, and/or Table 8, and/or Table 9, and/or Table 10. In certain embodiments the effector 0003. The present invention relates to novel targeting pep comprises an antibiotic found in Table 7. In certain embodi tides, novel antimicrobial peptides, chimeric moieties com ments the effector comprises a photosensitizer. In certain prising novel targeting and/or novel antimicrobial peptides embodiments the photosensitizer is selected from the group and uses thereof. consisting of a porphyrinic macrocycle, a porphyrin, a chlo rine, a crown ether, an acridine, an azine, a phthalocyanine, a BACKGROUND OF THE INVENTION cyanine, a psoralen, and a perylenequinonoid. In certain 0004 Antibiotic research at the industrial level was origi embodiments the photosensitizing agent is an agent shown in nally focused on the identification of refined variants of any of FIGS. 1-11. already existing drugs. This resulted example, in the devel 0009. Also provided is a chimeric construct comprising a opment of antibiotics such as newer penicillins, cephalospor targeting moiety attached to an antimicrobial peptide where ins, macrollides, and fluoroquinolones. the antimicrobial peptide comprises or consists of the amino 0005. However, resistance to old and newer antibiotics acid or retro or inverso or retro-inverso sequence of a peptide among bacterial pathogens is evolving rapidly, as exemplified found in Table 2. In certain embodiments the targeting moiety by extended beta-lactamase (ESBL) and quinolone resistant is a peptide that comprises or consists of the amino acid or gram-negatives, multi-resistant gonococci, methicillin resis retro or inverso or retro-inverso or beta sequence of a peptide tant Staphylococcus aureus (MRSA), Vancomycin resistant found in Table 2, and/or Table 3, and/or Table 4, and/or Table enterococci (VRE), penicillin non-susceptible pneumococci 6, and/or Table 15.
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