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angelmarin

 
National Institutes of Health

Papers overview

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Review
2020
Review
2020
The coumarins are heterocyclic compounds belonging to the class of benzopyrone enriched in various plants like tonka beans… Expand
2016
2016
A series of functionalized coumarins were synthesized and evaluated for their capacity to inhibit the resistance to starvation of… Expand
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2016
2016
.................................................................................................................................. 4 INTRODUCTION.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5 1. PANCREATIC CANCER. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5 Statistics and Treatments for Pancreatic Cancer. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5 Pancreatic Cancer Cell. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6 2. NATURAL PRODUCTS IN MEDICINE AND ANGELMARIN. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7 Natural Products as Anticancer Agents. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7 Discovery of Angelmarin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9 3. SAR STUDIES OF COUMARIN DERIVATIVES. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10 SAR Study of Hydroxycoumarin Derivatives. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10 SAR Study of Isoprenylated Coumarins. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12 4. PREFERENTIAL CYTOTOXICITY OF COMPOUND 21. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14 Against Other Pancreatic Cancer Cell Lines. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14 Medium Component Study of Compound 21. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15 5. INTRODUCTION TO INVESTIGATION. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18 RESULTS AND DISCUSSION.................................................................................................. 24 1. PREPARATION OF COMPOUND 21. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24 2. TIME DEPENDENT STUDY. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26 3. MEDIUM COMPONENT STUDY ON BxPC-3 AND COMPARISON. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28 New Reference Validation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28 Medium Component Study on BxPC-3. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30 Comparison Among Three Pancreatic Cancer Cell Lines. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32 4. CYTO-ID KIT STUDY OF AUTOPHAGY IN PANC-1. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34 Fluorescence Microscopy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34 Fluorescence Microplate. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37 5. WESTERN BLOTTING ANALYSIS OF AUTOPHAGY IN PANC-1. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 Effect of 21 and Autophagy Inhibitors on Conversion of LC3-I to II . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 Conversion of LC3-I to II Dependent on Time of Incubation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44 CONCLUSION........................................................................................................................... 46 METHODS AND MATERIALS................................................................................................ 47 1. PREPARATION OF COMPOUND 21. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47 2. TUMOR CELL CULTURE AND MEDIA PREPARATION. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48 3. CYTOTOXCITY ASSAYS. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49 4. CYTO-ID AUTOPHAGY DETECTION KIT . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51 5. WESTERN BLOTTING ANALYSIS OF AUTOPHAGY. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 52 REFERENCES ........................................................................................................................... 55 INDEX OF APPENDICES......................................................................................................... 57 
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2015
2015
................................................................................................................................................ 5 INTRODUCTION ....................................................................................................................................... 6 NATURAL PRODUCTS IN MEDICINAL CHEMISTRY .................................................................................... 6 PANCREATIC CANCER ............................................................................................................................... 7 DISCOVERY AND SYNTHETIC HISTORY OF THE SPIROXINS ...................................................................... 9 MEDICINAL SIGNIFICANCE OF SPIROXIN A ............................................................................................ 12 SYNTHESIS OF THE CORE STRUCTURE OF SPIROXIN A ........................................................................... 13 STRUCTURE-ACTIVITY RELATIONSHIP (SAR) STUDY ........................................................................... 15 DISCOVERY OF ANGELMARIN ................................................................................................................. 16 NOVEL ISOPRENYLATED COUMARINS AND THEIR ANTITUMOR ACTIVITY ............................................ 16 INTRODUCTION TO INVESTIGATION ........................................................................................................ 19 1. Validation of Initial Lead Structure ............................................................................................... 19 2. SAR Study based on (S)-34 ............................................................................................................. 20 3. Effect of Medium Components on Cytotoxicity of 50 ..................................................................... 25 RESULTS AND DISCUSSION ............................................................................................................... 27 VALIDATION OF INITIAL LEAD STRUCTURE ........................................................................................... 27 SAR STUDY BASED ON (S)-34 ................................................................................................................ 28 1. Preparation of the SAR Library ..................................................................................................... 29 2. Biological Evaluations of SAR Analogs ......................................................................................... 39 EFFECT OF MEDIUM COMPONENTS ON CYTOTOXICITY OF 50 ............................................................... 44 FUTURE DIRECTIONS .............................................................................................................................. 48 CONCLUSION .......................................................................................................................................... 52 EXPERIMENTAL .................................................................................................................................... 53 GENERAL PROTOCOL .............................................................................................................................. 53 SYNTHESIS OF (R)-1,2-DIHYDRONAPHTHALEN-1-OL ((R)-33) ................................................................ 54 SYNTHESIS OF (R)-TERT-BUTYL((1,2-DIHYDRONAPHTHALEN-1-YL)OXY)DIPHENYLSILANE ((R)-34) ... 56 PREPARATION OF TERT-BUTYL((1,2-DIHYDRONAPHTHALEN-1-YL)OXY)DIPHENYLSILANE (34) ........... 57 SYNTHESIS OF TERT-BUTYLDIPHENYLSILANOL (55) ............................................................................... 58 SYNTHESIS OF (S)-1-(TRITYLOXY)-1,2-DIHYDRONAPHTHALENE ((S)-60) .............................................. 59 SYNTHESIS OF TERT-BUTYLDIMETHYLSILANOL (75) .............................................................................. 61 PREPARATION OF COMPLETE DULBECCO MODIFIED EAGLE’S MEDIUM (DMEM) ................................ 61 PREPARATION OF NUTRIENT-DEPRIVED MEDIUM, NUTRIENT-RICH MEDIUM AND MEDIA 1-6 ........... 62 TUMOR CELL CULTURE PROCEDURES .................................................................................................... 62 GENERAL PROCEDURES OF CYTOTOXICITY ASSAYS ............................................................................. 62 Cytotoxicity Assays of Spiroxin A Derivatives against PANC-1 ........................................................ 63 Cytotoxicity Assays of 50 against PANC-1 ........................................................................................ 63 Cytotoxicity Assays of 50 against BxPc-3 and Capan-2 .................................................................... 64 REFERENCES AND NOTES .................................................................................................................. 65 INDEX OF APPENDICES ....................................................................................................................... 68 
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2012
2012
Inspired by nature: Angelmarin is an anticancer natural product with potent antiausterity activity, that is, selective… Expand
2009
2009
Angelmarin (1), a novel anti-cancer agent, was efficiently synthesized through a highly enantioselective epoxidation and a copper… Expand
Highly Cited
2006
Highly Cited
2006
The CH(2)Cl(2)-soluble extract of Angelica pubescens was found to kill PANC-1 cancer cells preferentially under nutrition… Expand