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US 2011 O142815A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0142815 A1 YU (43) Pub. Date: Jun. 16, 2011 (54) COMPOUNDS, COMPOSITION, METHODS, Publication Classification TARGETS FOR CANCERTHERAPY (51) Int. Cl. A6II 3/4I (2006.01) (76) Inventor: Ming YU, Los Angeles, CA (US) A638/43 (2006.01) A 6LX 3L/7052 (2006.01) CI2N 5/09 (2010.01) (21) Appl. No.: 12/667,687 A6IP35/00 (2006.01) (52) U.S. Cl. ........ 424/94.1: 514/381: 514/44 A: 435/375 (22) Filed: Jan. 4, 2010 (57) ABSTRACT This invention describes methods and pharmaceutical com Related U.S. Application Data positions for combinational cancer treatments that are capable of inducing JNK phosphorylation and induce pro (63) Continuation of application No. PCT/US08/69106, grammed cell death. It also identified genes as target for filed on Jul. 2, 2008. anti-cancer drug development and enhancement of the che motherapeutic drug effect for the treatment of cancer. This invention points to a novel method and principle for a new (60) Provisional application No. 60/929,535, filed on Jul. 2, avenue of developing more efficient and low or non cytotoxic 2007. Cancer treatment. Chemical Structure of 2,4-Dinitrophenol (DNP) and WST-3 NO, DNP HO NO WST-3 Patent Application Publication Jun. 16, 2011 Sheet 1 of 19 US 2011/O142815 A1 Fig 1 A Chemical Structure of 2,4-Dinitrophenol (DNP) and WST-3 NO, DNP HO Patent Application Publication Jun. 16, 2011 Sheet 2 of 19 US 2011/O142815 A1 Fig 2 NF-kB Down Stream Gene Expression Levels A 050 a 3 Untreated Cir opcDNA3-Ctrl a KKa-KAT : a KKa-KA-2 8. KKo-KA x KKa-b-KA KKEffect on CK2 mRNA Expression 3. O O O ----- -------- ----- | Un Treated Ctrl pcDNA3-Ctrl KKai-KA KKa-KA-2 KKo-KA KKa-b-KA Fig 3 Combinational Effect of IKK-KA Transfection and WST-1 Treatment A 1.2 KK-KA Effects on Ce Survival r WS-i-O 1.0 - 8 WST-t-yes O 6 KK2-KA IKK-KAKK2 KA Untransfected pCDNA3 KK-KA KK2-KA KK-KA-KK2-KA Patent Application Publication Jun. 16, 2011 Sheet 3 of 19 US 2011/O142815 A1 Fig. 4 WST-1 promotes HT1080 Human Sarcoma cell death by triple combination Treatment KK1-KA Ctrl/HT1080/24hr was GSOP3-P9 / GSO KK1-KA-P9 -X-GSOP9 - K - GSOP3 - - - - - GSO KK-KA w-e GS 20/200 No DNA - GS 20/2OOP3-P9 GS 20/2OO KK-KA. -3s 2O2OOP9 - K - GS 20/2OOP3 --GS 20/200 KK1-KA 10 20 IKK inhibitor Ill Concentration (uM) GS-WST-1, P9-Puc19, P3-pCDNA3 Fig 5 LiC + Apigenin Synergized SCC-6 Cell Death, WST-1 Further Enhanced This Effect A UM-SCC-6/Apigenin+LiCl UM-SCC-6/Apigenin--LiCl+WST-1 1.4 -o-LiCIO -- LiCl1mM -(-e LiC 0 ... - LiC 1mM 1.4 - - -A- - -93mM. -x - 9 OnM s - A - LiCl3m M mix a LiC 10mM m . LiCl30mM mism.LiC 100mM 1.2-28 - LiCl30mM mea LiC 100m 2 a -- i O. 8 O. 1 10 0.1 O Apigenin Concentration (uM) Apigenin Concentration (M) Patent Application Publication Jun. 16, 2011 Sheet 4 of 19 US 2011/O142815 A1 Fig 5 WST-1 induces ROS Generation Aa Si HT1080 Cell Treatedlabeled with CM-H2-DCFDAWSTGT1 for 4 hours, then C CO t; 8 s Untreated 1-330M |-3 OuM Untreated Control & WST-1 r ed -330M Patent Application Publication Jun. 16, 2011 Sheet 5 Of 19 US 2011/O142815 A1 Fig 6 puC19 DNA transfection synergize chemotherapeutic drug effect --r No SCC6/5-FU SCC6/Cis-Platinum Transfecti Transfectio B8 O |--pCDNA3 + - - - pCDNA3 1. 6 puc19 + puC19 woo. KK1-KA + - - - - - KK1-KA - 1.4 puc19 puc19 3. 2 - - - - KK2-KA + -Xe KK2-KA + <(d 1. puc19 puc19 g --IKK1-KA + to a KK1-KA + KK2-KA - Yew puC 19 pUC19 cus --OCDNA3 -O - pCDNA3 sce O.8 f a puC19 --puc19 5 0.6 . O6 O ar. A c. KK1-KA - Kx - KK1-KA 0.4 - - - - KK2-KA A or KK2-KA O2 - 0.2 - max) as KK1-KA + KK2KA --K - KK-KA . O ...i.d.s.l..l.).jur...i.l. iiii -i-...-kill...!! O | it l-C-DMSO O.O1 O. 1 O.O1 1 OO O vario. DMSO 5-FU Concentration (LM) MMWWMMMM Cis-Platinum Concentration (ug/ml) HT 108 Of Taxe on Co. Untransfec -- Untransfected ted D HTO8Of Cis-Platinum O.9 - ---- P3-P9 -- P3-P9 0.8 - - A - KK-KA ---- KK1-KA-p9 p9 - x - KK2-KA -a - KK2-KA-p9 2.5 - p9 C co - -, - KK1-KA aro KK1-KA ed c 2 KK2-KA es IKK2-KA-p9 V C S 04 --P9 15 - w x O3 - -ga. P3 O.2 - a - KK1-KA-p3 O.5 - is x - KK-KA p3 O. O -- KK2-KA-p3 on + as KK2-KA O 20 40 60 80 OO p3 O 2 3 Taxel Concentration (nM) - - KK1-KA KKKA. Cis-Platinum Concentration (- IKK2-KA-p3 Patent Application Publication Jun. 16, 2011 Sheet 6 of 19 US 2011/O142815 A1 Fig7. Reactive Oxygen Species Generation from Combination Treatment A UM-SCC6Cel/CCK8-KK inhibitor II B UM-SCC6 Cell/WST-1r-IKK inhibitor || - - - 0- - - CCK8 O 3 O ..........., ... wca. CCK8 130 " ' " WST-1r 0 13 O - B - WST-fr 13 O - - - WST. 1r 3 . CCK833 O - A - CCK810 3 O or/ WST-1r 1030 -ko. WST-r O 35 on 8 - WST. 1r - A - CCK80 35 - - - - - CCK81 35 --A - CCK8335 - - - - CCK810 35 -A- WST-1r 3 |35 -O-WST-1r 10 |35 -t, - WST-1r O - A - CCK8 O 310 - 3 - CCK81 310 -- WST-1r 13 10 on-a- WST-1r 33 10 -- WST-1r 1C -- CCK833 10 -- CCK810 13 10 10000 8 O O O O 60 120 180 240 O "time Of Ten (min)" 240 Time of Treatment (min) C SCC6/CCK8/Ap/ROS D SCC6/GS/Ap/ROS - O - CCK80 Ap O CCK81 Ap 0 o wst-1ro Apo ---- wsT-1r 1 Apo - - - CCK83 Ap O CCK810 Ap 0-- - WST-1r 3 Apo - ... WST-1r 10 Apo -a- CCK80 Ap 10 -a - CCK81 Ap 10 – A – WST-1r O Ap 10 -a, - WST-1r 1 Ap 10 --- CCK83 Ap 10 * - CCK810 Ap 1 (- - WST-13 Ap 10 -a- WST-1r 10 Ap 10 -O - CCK80 Ap 30 -- CCK8 1 Ap 30 --O-WST-1r O Ap 30 -a- WST-1r 1 Ap 30 -- CCK83 Ap 30 - CCK810 Ap 3( WST-1r 3 Ap 30 -- WST-1r 10 Ap 3 - CCK80 Ap 100 -o- CCK8 1 Ap 1 Oc -- WST-1r O Ap 100 -e-WST-1r 1 Ap 10 e CCK83 Ap 100 -- CCK810 Ap 1. uu UU -o-WST-1r 3 Ap 100 -- WST-1r 10 Ap 10( 10000 MN 8000 2000 % O 60 120 18O 240 O 60 120 18O 240 Time of Treatment (min) Time of Treatment (min) Ap=Apigenin (3=lKK inhibitor || Patent Application Publication Jun. 16, 2011 Sheet 7 of 19 US 2011/O142815 A1 Fig 8. Combination Treatment with Apigenin and WST-1r Induces Cancer Cell Death 40. a Untreated Ctrl WS-r A Apigenin WST-1 r+Apigenin 120 100 i 8 O USCC6 MD-MB-A23 A431 O80 Ca27 B6-5 294 Ce Lines B 120 - MDA-MB-23 ---Cell - Apigenin MMO C 12O A431 Cell ... -- Apigenin 10 -0- Apigenin () 39 100 -O-ApigenA Age. in 39100 S 100 - ...a Ani?teninESER38 100 80 - 8 80 S& as 60 & 60 2 g s 40 40 o O 3c 20 - 8o 20 O O O 2 4. 6 8 1 O O 2 4 6 8 1 O WST-1r Concenrtration (%) WST-1r Concenrtration (%) D 120 MDAMB-231 Ce E 120 A431 Cell 1 O O 8 O 60 40 20 . O 2O 40 SO 8O Apigenin Concentration (M) 40 Apigenin Concentration (uM) Patent Application Publication Jun. 16, 2011 Sheet 8 of 19 US 2011/O142815 A1 Fig 9. Comparison of Cancer cells and non cancer cells' response to WST-1r and Apigenin Apigenin () 60 Apigenin 30 Apigenin 100 140 120 100 80 60 40 20 O WST-1 r () 1() () () O () HEKa UM-SCC6 Ca27 Cell Line and Treatment Patent Application Publication Jun. 16, 2011 Sheet 9 of 19 US 2011/O142815 A1 Fig 10 Time course and Dose Response of WST-1r and Dose Response of Apigenin (Ap) involved in the Combination Treatment of WST-1r with Apigenin A 16O Ca27 Ap (uM) O Ap (uM) 3 Ap (uM) 10 14.0 - E. Ap (uM) 30 g Ap (uM) 100 120 - OO - 80 - 6O – 40 a. Treatment B 2 O O HT1080 Eg Ap (uM) 0 O Ap (uM) 3 EAp (uM) 10 Ed Ap (uM) 30 Ap (uM) 100 5 O Treatment SCC6 o 20 a Ap (UM) 30 Ap (UM) 100 C C was 8 > S g te dis O O Treatment Patent Application Publication Jun. 16, 2011 Sheet 10 of 19 US 2011/O142815 A1 Fig 11. Effect Of KK inhibitOr -WST-1r COmbination Treatment A 120 -- SK-Mel-5 Cells WST-1r 0% B120 T294 BMS345541 (uM) 0 EWSEE 3: BMS345541 (uM) 3 100 -------------- OO + BMs:4554 (um to 5 80 380 . 5 (5 60 & 60 5 a SSO 40 S 40 g 2O 2O O O | O 3 10 O 1 BMS345541 Concentration (M) WST-1r Concentration (%) C | O Ctrl BMS-345541 WST-1r BMS-345541+WST-1r 5 120 S 100 CD 80 s' 60 > E 40 e S. 20 HEKa T294 SK-Me-5 Fig 12.
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    US 2009031 1494A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0311494 A1 YAMASHTA et al. (43) Pub. Date: Dec. 17, 2009 (54) RELIEF PRINTING PLATE PRECURSOR FOR (30) Foreign Application Priority Data LASER ENGRAVING, RELIEF PRINTING PLATE, AND PROCESS FOR PRODUCING Jun. 17, 2008 (JP) ................................. 2008-157907 RELEF PRINTING PLATE Feb. 10, 2009 (JP) ................................. 2009-028816 (75) Inventors: Masako YAMASHITA, Publication Classification Shizuoka-ken (JP); Atsushi (51) Int. Cl. SUGASAKI, Shizuoka-ken (JP) B32B 3/00 (2006.01) Correspondence Address: GO3F 7/20 (2006.01) Moss & Burke, PLLC GO3F 7/004 (2006.01) 401 Holland Lane, Suite 407 Alexandria, VA 22314 (US) (52) U.S. Cl. .................... 428/195.1: 430/306: 430/286.1 (73) Assignee: FUJIFILM CORPORATION, (57) ABSTRACT Tokyo (JP) A relief printing plate precursor for laser engraving, including (21) Appl. No.: 12/476,260 a relief forming layer containing (A) a polymerizable com pound having an ethylenic unsaturated bond. (B) a binder (22) Filed: Jun. 2, 2009 polymer, and (C) a compound having deodorizing ability. 11 50 FA - 42 SUB SCANNING DIRECTION -10 - 228 7.s 55 21B EEE m w 24B 24A 27B 27A N Patent Application Publication Dec. 17, 2009 US 2009/0311494 A1 F.G. 1 FA SCANNING DIRECTION 7OA a. CSy ra & 5A - 27WSNS AD 23Ar S3EEASEE21 E-25sagaa EEEEEEEEEEEEEEEEEEEEEEEEE-22s awslighlights fskillsw. 21B 2 TTT "TT". US 2009/031 1494 A1 Dec. 17, 2009 RELEF PRINTING PLATE PRECURSORFOR mask to develop and remove an uncured area, and there is LASER ENGRAVING, RELIEF PRINTING room for improvement since development treatment is nec PLATE, AND PROCESS FOR PRODUCING essary.
  • (Piper Nigrum L.) Products Based on LC-MS/MS Analysis

    (Piper Nigrum L.) Products Based on LC-MS/MS Analysis

    molecules Article Nontargeted Metabolomics for Phenolic and Polyhydroxy Compounds Profile of Pepper (Piper nigrum L.) Products Based on LC-MS/MS Analysis Fenglin Gu 1,2,3,*, Guiping Wu 1,2,3, Yiming Fang 1,2,3 and Hongying Zhu 1,2,3,* 1 Spice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences, Wanning 571533, China; [email protected] (G.W.); [email protected] (Y.F.) 2 National Center of Important Tropical Crops Engineering and Technology Research, Wanning 571533, China 3 Key Laboratory of Genetic Resources Utilization of Spice and Beverage Crops, Ministry of Agriculture, Wanning 571533, China * Correspondence: [email protected] (F.G.); [email protected] (H.Z.); Tel.: +86-898-6255-3687 (F.G.); +86-898-6255-6090 (H.Z.); Fax: +86-898-6256-1083 (F.G. & H.Z.) Received: 16 July 2018; Accepted: 7 August 2018; Published: 9 August 2018 Abstract: In the present study, nontargeted metabolomics was used to screen the phenolic and polyhydroxy compounds in pepper products. A total of 186 phenolic and polyhydroxy compounds, including anthocyanins, proanthocyanidins, catechin derivatives, flavanones, flavones, flavonols, isoflavones and 3-O-p-coumaroyl quinic acid O-hexoside, quinic acid (polyhydroxy compounds), etc. For the selected 50 types of phenolic compound, except malvidin 3,5-diglucoside (malvin), 0 L-epicatechin and 4 -hydroxy-5,7-dimethoxyflavanone, other compound contents were present in high contents in freeze-dried pepper berries, and pinocembrin was relatively abundant in two kinds of pepper products. The score plots of principal component analysis indicated that the pepper samples can be classified into four groups on the basis of the type pepper processing.
  • Transcriptomic and Metabolomic Joint Analysis Reveals Distinct Flavonoid Biosynthesis Regulation for Variegated Testa Color Deve

    Transcriptomic and Metabolomic Joint Analysis Reveals Distinct Flavonoid Biosynthesis Regulation for Variegated Testa Color Deve

    Transcriptomic and metabolomic joint analysis reveals distinct flavonoid biosynthesis regulation for variegated testa color development in peanut (Arachis hypogaea L.) Mengdie Hu1,Jiawei Li1, Mingyu Hou1,Xiaoqing Liu1,Shunli Cui1,Xinlei Yang1,Lifeng Liu1,Xiaoxia Jiang2, Guojun Mu1* 1.North China Key Laboratory for Crop Germplasm Resources of Education Ministry, College of Agronomy, Hebei Agricultural University, Baoding, China 071001. 2.Hebei Yiyuan Ecological Agriculture Technology Co, Ltd, Baoding, China 074200 [email protected] (M.H.);[email protected] (J.L.);[email protected] (M.H.);[email protected] (X.L.); [email protected] (S.C.);[email protected] (L.Y.);[email protected] (L.L.);[email protected] (X.J.) * Correspondence:[email protected];Tel:+86-1380-326-0389 Abstract: Peanut (Arachis hypogaea L.) is one of the important oil and economic crops, among which the variegated testa peanut is a unique member. But the molecular mechanisms underlying the pigment synthesis in variegated testa are still unclear. Differentially expressed genes (DEGs) in pigment metabolism pathway in colored area indicated there were 27 DEGs highly related to the synthesis of variegated testa color among 1,050 DEGs,which were 13 up-regulated and 14 down-regulated,consisting of 3 PALs, 1 C4H, 2 CHSs, 1 F3H, 1 F3'H, 2 DFRs, 2 LARs, 2 IAAs, 4 bHLHs and 9 MYBs. GO analysis indicated DEGs were similarly enriched in 3 branches.KEGG analysis suggested flavonoid biosynthesis is the most direct metabolic pathway for the synthesis of testa variegation.The liquid chromatography tandem mass spectrometry (LC-MS/MS) results showed that cyanidin and delphinidin were the main metabolites that caused the color difference between the colored area and the non-colored area.