Useful  Nanotechnologies  Based  on Molecular  Information  Handling
Robot:   A  machine  or  device  that  operates  automatically  or  by  remote  control Computer:   A  device  that ...  p...
Ion-Switchable  Fluorescence Spacer M + Fluorophore Receptor Constant  Fluorescence Fluorophore Spacer Fluorophore Recepto...
Luminescent  molecular  switchable  systems  can gather  and  process  information  Optical  response Chemical  stimulus  ...
The  Miniature James  Bond Luminescent  Sensing
Org.  Biomol.  Chem.  2008,  6 ,  2468 OFF   state Spacer h  PET Fluorophore Receptor ON   state h  PET h  M + Spacer F...
 
Imperiali, Marcus, Cary Stoddart,  Selinger Shinkai, Kubo, Hamachi Fabbrizzi, Quici, Rettig, Resch, Wolfbeis, Daub,  Verho...
Anslyn, Demas Kotschy, Kele Bojinov, Grabchev Lu Sung Suzuki, Holdt, Plenio, Sauer Nielsen, Kilsa Yunus, Hofkens Hall, Wat...
J.  Mater.  Chem .  2005,  15 ,  2640 ‘ Off-On’  sensors  selective  for  Na +   and  K +   Jim  Tusa, Marc  Leiner Hua-Ru...
hydrophilic polymer O O O N H N O O N O N O N O O O O hydrophilic polymer N O O O O O N H N O O O Sodium Potassium recepto...
Disposable Cassette and  OPTI Critical Care Analyzer (CCA) Na +   K +   Ca ++  or Cl - CO 2 O 2   pH tHb 60M  USD  Cassett...
J.  Chem.  Soc.,  Chem.  Commun .  1985, 1669 N Et 2 N Et 2 O N N N H N Et 2 Fluorescent  PET  pH  Sensors LysoSensor TM  ...
Cancer  cells  respond  to  radiation  by  developing  acidic  vesicular  organelles.  Sensor:  Lysosensor  Blue  Paglin  ...
Robots  for  Mapping  Small  Nanospaces Seiichi  Uchiyama  (University  of  Tokyo) Kaoru  Iwai  (Nara  Women’s  University...
A  Popular  Robot
A  Useful  Robot Mars  Rover ‘ Opportunity’ January 2005 ‘ Phoenix’ May 2008
fluorophore spacer receptor ICT fluorophore spacer receptor H H + fine  positioner gross  positioner N S O O N O N N H N O...
. S 1 thexi S 1 thexi S 0 FC S 0 FC non polar solvent polar solvent +   +  E . Solvent  Polarity  Effect  on  ICT  Fluores...
450 500 550 600 650 700 750 800 0 pH Wavelength (nm) I F
20 30 40 70 50 60 0 – 0.4 – 0.8 – 1.6 – 1.2 20 30 40 80 0 – 0.4 – 0.8 – 1.2 p p 10 0 – 0.4 – – – 10 20 40 50 60 70 – – – 1...
generalization integration numeracy games reconfiguring object  identification improved  sensing Molecular Logic  Gates Na...
Kim, Yoon, Jang, Choi, Zhang Rurack, Desouter-Lecomte, Lehn Bouas-Laurent, Desvergne, Bassani, McClenaghan Balzani, Credi,...
Combining  Several  Diagnostic  Tests and  Data  Processing in  a  “ Lab-on-a-Molecule”  David  Magri,  Gareth  McClean, G...
Full Blood Count Date : 20.08.2005 Description  Result  Units  Reference  Ranges  Remarks Haemoglobin 8.70*  g/dl 12.00   ...
Spacer Receptor Receptor Spacer Spacer Fluorophore Receptor O O O O O N N C O 2 C O 2 - - H H + Na + Zn 2+
Wavelength / nm 400 440 480 520 +  Na + , H + , Zn 2+ Na + , H +  Na + , Zn 2+ Na +  H + , Zn 2+  Zn 2+  H No inputs 0 I F
 
1 (high, 0.020) 1 (high) 1 (high) 1 (high) 0 (low, 0.006) 1 (high) 0 (low) 1 (high) 0 (low, 0.007) 0 (low) 1 (high) 1 (hig...
Molecular  Computational  Identification  (MCID) of  Small  Objects   in   Populations Sheenagh  Weir ,   Bernie  McKinney...
Radiofrequency  Identification  (RFID):  The  semiconductor  technology  approach  to  identifying  each  object  (Goods, ...
EXCITATION  WAVELENGTH:   368 nm 500 Wavelength (nm) Fluorescence Intensity 385 100 Increasing pH 422 401 446 Prefabricate...
Prefabricated  logic  gates  fixed  to  polymer  beads YES O N H PASS 1 N O N H NOT 0 3 5 7 9 11 pH 100 I F 1 YES PASS 1 NOT
Multi-valued  logic  is  available  for  molecular  computational  identification   c.f. binary  logic  needed  in  semico...
acid alkali A A B B C C D D E E F F G G I I J J A ; PASS 1  B ; NOT  C ; PASS 1  D ; PASS 1 + YES (1:1)  E ; YES  F ; NOT ...
J.  Am.  Chem.  Soc .  2007,  129 ,  3050 Parallel  Processing  of  Analog Sensory  Information   Sisira  de  Silva,  Nali...
 I F pH Parallel  processing  to  produce  greatly  increased  dynamic  range RECEPTOR 1 SPACER FLUOROPHORE RECEPTOR 4 SP...
N R 1 R 2 N R 1 R 2 a ; R 1 = R 2 = CH 2 CH 3 b ; R 1 = R 2 = CH 2 CH 2 OH c ; R 1 = H, R 2 = CH 2 CH 2 N(CH 2 CH 3 ) 2 d ...
0 4 2 8 6 10 0 20 60 40 100 80  I F pH 390 500 0 Wavelength (nm)  I F 100
“ Plug-and-Play”  Logic  via  Self-Assembly  Vinny  Vance,  Catherine  Dobbin,  Boontana  Wannalerse Chem.  Commun .  2009...
R L S R L Self-Assembled  YES  Logic: Covalently  bound  YES  Logic: Assembler:  Non-ionic  Detergent  Micelle N N 2 N N n...
O - pK a  = 9.9
R 1 L R 2 S S R 1 L R 2 Self-Assembled  AND  Logic: Covalently  bound  AND  Logic: O - N C O 2 C O 2 O n - C 8 H 1 7 - - p...
11;  10 -8   M  H +   and  0.2  M  Ca 2+   01;  10 -12  M  H +  and  0.2  M  Ca 2+   10;  10 -8   M  H +   only  00;  10 -...
R L S R L Self-Assembled  OR  Logic: Covalently  bound  OR  Logic: Non-selective  Receptor N C O 2 C O 2 O n - C 8 H 1 7 -...
11;  10 -4   M  H +   and  0.2  M  Ca 2+   10;  10 -4  M  H +   only 01;  10 -8   M  H +   and  0.2  M  Ca 2+   00;  10 -8...
Providence Luck Serendipity EPSRC DENI EUROPEAN  COMMISSION JAPAN  SOCIETY  FOR  THE  PROMOTION  OF  SCIENCE
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A Pde Silva Slintec

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Useful Nanotechnologies Based on Molecular Information Handling

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A Pde Silva Slintec

  1. 1. Useful Nanotechnologies Based on Molecular Information Handling
  2. 2. Robot: A machine or device that operates automatically or by remote control Computer: A device that ... processes information
  3. 3. Ion-Switchable Fluorescence Spacer M + Fluorophore Receptor Constant Fluorescence Fluorophore Spacer Fluorophore Receptor < 1 nm > 1 nm
  4. 4. Luminescent molecular switchable systems can gather and process information Optical response Chemical stimulus level Analog region Digital 1 Digital 0
  5. 5. The Miniature James Bond Luminescent Sensing
  6. 6. Org. Biomol. Chem. 2008, 6 , 2468 OFF state Spacer h  PET Fluorophore Receptor ON state h  PET h  M + Spacer Fluorophore Receptor The PET design generalized in Colombo/Belfast Chem. Rev . 1997, 97 , 1515
  7. 8. Imperiali, Marcus, Cary Stoddart, Selinger Shinkai, Kubo, Hamachi Fabbrizzi, Quici, Rettig, Resch, Wolfbeis, Daub, Verhoeven Bouas-Laurent, Desvergne, Lapouyade, Fages, McClenaghan Balzani, Prodi, Barigelletti, Campagna, Soumillion Bharadwaj, Khan Zinic Samanta Grigg, Moore, Brown, James, Davidson, Beer, Stoddart, Parker, Williams, Ward, Sutherland Kuhn, Yang Czarnik, Pearson Morawetz, Pardo Masilamani Turro, Garcia- Espana, Costero, Miranda, Escriche, Luis, Perez- Inestrosa D’Souza Inoue Brown Gawley, Leblanc Lakowicz, Pu Roche, Fahrni Wang, Lindsey Roche Wang, Ma, Moller, Rurack, Schuster, Greiner Reymond Ji Kumar Rajasekharan, Ajayaghosh, Ramaiah, Varma Lawrence, Adams, Qian Das Lincoln Walt, Miller, Lippard Smith Jin Qian, Tian, Chen Bianchi, Pallavicini Lippolis Akkaya, Valkan Koide Chattopadyay Hsu, Chiu Whitten Leigh, Callan Plater, Gunnlaugsson, O’Shea, Kruger Bruckner Shizuka, Teramae, Chatterjee, Kimura, Osa, Sakamoto, Iwai, Nakatsuji, Fukuzumi, Tanaka, Nagano, Imai, Nagamura, Akasaka Gee Chang Tsien, Barbas, Rebek Kulatilleke de Silva, McCoy Pina, Pischel, Lodeiro Shanzer, Eichen, Willner Wu, Li, Chen, Chang, Kim Yoon, Bhattacharya, Maitra Guo, Lin Tang de Silva Diaz-Fernandez Valeur, Lehn, Weiss, Leray Jiang de Silva, Kruger Pfeffer Yagi Levine,
  8. 9. Anslyn, Demas Kotschy, Kele Bojinov, Grabchev Lu Sung Suzuki, Holdt, Plenio, Sauer Nielsen, Kilsa Yunus, Hofkens Hall, Watkinson Meallet, Mallet, Vicens Ghosh Zhu, Wang, Kim, Hong, Zuo, Guo, Huang, Liu, Yao, Fu De Costa Wainwright Yoshida, Ooyama, Sasamoto Todd Nakamura Saleh Seeberger Mashraqui Hancock Ramamurthy He, Ji You Houston Heagy Cho Burdette Lin Magri Rudkevich Sango Toyooka
  9. 10. J. Mater. Chem . 2005, 15 , 2640 ‘ Off-On’ sensors selective for Na + and K + Jim Tusa, Marc Leiner Hua-Rui He, Mark Mortellaro (Roche)
  10. 11. hydrophilic polymer O O O N H N O O N O N O N O O O O hydrophilic polymer N O O O O O N H N O O O Sodium Potassium receptor hydrophilic polymer hydrophilic polymer spacer fluorophore linker
  11. 12. Disposable Cassette and OPTI Critical Care Analyzer (CCA) Na + K + Ca ++ or Cl - CO 2 O 2 pH tHb 60M USD Cassette sales ambulances, hospitals, GP and vet surgeries
  12. 13. J. Chem. Soc., Chem. Commun . 1985, 1669 N Et 2 N Et 2 O N N N H N Et 2 Fluorescent PET pH Sensors LysoSensor TM Blue and Green (Molecular Probes) DAYA RUPASINGHE NIMAL GUNARATNE
  13. 14. Cancer cells respond to radiation by developing acidic vesicular organelles. Sensor: Lysosensor Blue Paglin et al (Sloan-Kettering Center, NY) Cancer Res . 2001, 61 , 439 18  m
  14. 15. Robots for Mapping Small Nanospaces Seiichi Uchiyama (University of Tokyo) Kaoru Iwai (Nara Women’s University) Angew. Chem. Int. Ed . 2008, 47 , 4667
  15. 16. A Popular Robot
  16. 17. A Useful Robot Mars Rover ‘ Opportunity’ January 2005 ‘ Phoenix’ May 2008
  17. 18. fluorophore spacer receptor ICT fluorophore spacer receptor H H + fine positioner gross positioner N S O O N O N N H N O O H 10
  18. 19. . S 1 thexi S 1 thexi S 0 FC S 0 FC non polar solvent polar solvent + + E . Solvent Polarity Effect on ICT Fluorescence hexane CH 2 Cl 2 CH 3 OH I f 
  19. 20. 450 500 550 600 650 700 750 800 0 pH Wavelength (nm) I F
  20. 21. 20 30 40 70 50 60 0 – 0.4 – 0.8 – 1.6 – 1.2 20 30 40 80 0 – 0.4 – 0.8 – 1.2 p p 10 0 – 0.4 – – – 10 20 40 50 60 70 – – – 1.2 p Δ p K a Δ K a 80 O O H 10 O O H O H O H O O H Polarity ( ε ) Polarity ( ε )
  21. 22. generalization integration numeracy games reconfiguring object identification improved sensing Molecular Logic Gates Nature 1993, 364 , 42 Nature Nanotechnol . 2007, 2 , 399 George Boole 1849-64, Cork
  22. 23. Kim, Yoon, Jang, Choi, Zhang Rurack, Desouter-Lecomte, Lehn Bouas-Laurent, Desvergne, Bassani, McClenaghan Balzani, Credi, Venturi, Gentili Bharadwaj, Khan Samanta Adleman, Ghadiri, de Silva, Pina, Pischel Garcia- Espana, Brown Raymo, Zhu Akkaya Ji Gunnlaugsson, MacDonaill Birge, Stojanovic, Seeman, Avouris, Katz, Sokolov, Privman Langford Stefanovic, Wasielewski, Levine, Speiser, Shanzer, Willner, Shabat, Ashkenasy, Lotan, Van der Boom, Rabani, Shapiro, Eichen Konermann Remacle Reif Diederich, Constable, Schluter de Silva Wettig Perez- Jin Schneider, Uchiyama, Aida, Leigh, Callan James, Stoddart, Parker, Beer, Chin, Jones, Williams, Tucker, Zauner, Fallis, Aldridge, Steed Szacilowski Chiu Gust, Moore Steer, Iwai, Okamoto, Sugimoto, Hirai, Redmond, Miranda Kimura Miyashita, Suzuki Tian, Wang, Jin, Lu Lerner, Barbas, Wang Wu Toma Conrad, Liu Bazan Andreasson, Sun Liu Tanaka, Fujita, Breaker, Das Kumar Lu Zhang, Zhu, Yan, Li, Fu, Huang, Zhang, Mihara, Nojima, Tomizaki, Matsui, Pischel Fujimoto, Akashi Qian, He, Yu Yang Benenson Stoddart, Vasquez- Lopez Yuan, Fang, Voegtle Shi, Tong, Wang Kinbara, Ariga, Magri Yurke Yeow, Hamilton Doorn Hill, Miyashita, Stoddart, Smith, Zink, Heath, Smolke Walt, Pandey Matsui Inestrosa,
  23. 24. Combining Several Diagnostic Tests and Data Processing in a “ Lab-on-a-Molecule” David Magri, Gareth McClean, Gareth Brown J. Am. Chem. Soc . 2006, 128 , 4950
  24. 25. Full Blood Count Date : 20.08.2005 Description Result Units Reference Ranges Remarks Haemoglobin 8.70* g/dl 12.00 17.50 Low RBC 2.34* x 10x6/mm3 3.50 6.00 Low PCV 26.70* % 40.00 54.00 Low MCV 114.10* fl 70.00 96.00 High MCH 37.20 pg 27.00 32.00 High MCHC 32.60 g/dl 30.00 ….35.00 …Normal PLATELETS 140,000.00 mm3 150,000.00 450,000.00 Low WBC 8,200.00 mm3 4,000.00 11,000.00 Normal NEUTROPHILS 48.00 % 40.00 75.00 …normal LYMPHOCYTES48.00 % 10.00 45.00 High EOSINOPHILS 2.0 % 1.00 6.00 Normal MONOCYTES 2.00 % < 10.00 Normal Performed by Sysmex/Hycell Automated Haematology Analyzers Logical combination of ‘high’ and ‘low’ parameters identifies disease
  25. 26. Spacer Receptor Receptor Spacer Spacer Fluorophore Receptor O O O O O N N C O 2 C O 2 - - H H + Na + Zn 2+
  26. 27. Wavelength / nm 400 440 480 520 + Na + , H + , Zn 2+ Na + , H + Na + , Zn 2+ Na + H + , Zn 2+ Zn 2+ H No inputs 0 I F
  27. 29. 1 (high, 0.020) 1 (high) 1 (high) 1 (high) 0 (low, 0.006) 1 (high) 0 (low) 1 (high) 0 (low, 0.007) 0 (low) 1 (high) 1 (high) 0 (low, 0.006) 0 (low) 0 (low) 1 (high) 0 (low, 0.003) 1 (high) 1 (high) 0 (low) 0 (low, 0.002) 1 (high) 0 (low) 0 (low) 0 (low, 0.001) 0 (low) 1 (high) 0 (low) 0 (low, 0.001) 0 (low) 0 (low) 0 (low) 3-Input AND Logic Truth Table Output Fluor n  F Input 3 Zn 2+ Input 2 H + Input 1 Na +
  28. 30. Molecular Computational Identification (MCID) of Small Objects in Populations Sheenagh Weir , Bernie McKinney Dave Pears, Mark James (Avecia) Nature Mater . 2006, 5 , 787
  29. 31. Radiofrequency Identification (RFID): The semiconductor technology approach to identifying each object (Goods, People) in an entire population 1 mm x 1 mm RFID chip (Hitachi)
  30. 32. EXCITATION WAVELENGTH: 368 nm 500 Wavelength (nm) Fluorescence Intensity 385 100 Increasing pH 422 401 446 Prefabricated YES logic gate fixed to polymer bead (0.1 mm) 0
  31. 33. Prefabricated logic gates fixed to polymer beads YES O N H PASS 1 N O N H NOT 0 3 5 7 9 11 pH 100 I F 1 YES PASS 1 NOT
  32. 34. Multi-valued logic is available for molecular computational identification c.f. binary logic needed in semiconductor computing Combinations of: Many (>5) excitation colours Many (>5) emission colours Many (>5) types (YES, NOT, PASS 1 , AND,…) Many (>5) chemical inputs (H + , Na + ,…) Many (>2) thresholds (pH 7, pH 4,…) Many (>5) combinations ( YES + PASS 1 , YES + 2 PASS 1 ,…) Conservatively, millions of  m objects can be encoded!
  33. 35. acid alkali A A B B C C D D E E F F G G I I J J A ; PASS 1 B ; NOT C ; PASS 1 D ; PASS 1 + YES (1:1) E ; YES F ; NOT G ; PASS 1 I ; YES J ; PASS 0
  34. 36. J. Am. Chem. Soc . 2007, 129 , 3050 Parallel Processing of Analog Sensory Information Sisira de Silva, Nalin Goonesekera, Suram Patuwathavithana, Sydney Ramyalal (Colombo) Nimal Gunaratne, Mark Lynch, Kemuel Nesbitt
  35. 37.  I F pH Parallel processing to produce greatly increased dynamic range RECEPTOR 1 SPACER FLUOROPHORE RECEPTOR 4 SPACER FLUOROPHORE RECEPTOR 3 SPACER FLUOROPHORE RECEPTOR 2 SPACER FLUOROPHORE
  36. 38. N R 1 R 2 N R 1 R 2 a ; R 1 = R 2 = CH 2 CH 3 b ; R 1 = R 2 = CH 2 CH 2 OH c ; R 1 = H, R 2 = CH 2 CH 2 N(CH 2 CH 3 ) 2 d ; R 1 , R 2 = CH 2 CH 2 N(CH 3 )CH 2 CH 2 1.4 404, 426, 443 (0.56, 0.008) 393(4.01), 372(4.01), 353(3.76) d 4.1 404, 426, 443 (0.55, 0.014) 395(4.03), 374(4.03), 355(3.81) c 6.1 405, 427, 445 (0.56, 0.005) 395(4.10), 374(4.09), 355(3.87) b 8.1 405, 427, 445 (0.59, 0.004) 393(4.03), 372(4.02), 353(3.81) a pK a Emission  (  max ,  min ) Absorption  (log  )
  37. 39. 0 4 2 8 6 10 0 20 60 40 100 80  I F pH 390 500 0 Wavelength (nm)  I F 100
  38. 40. “ Plug-and-Play” Logic via Self-Assembly Vinny Vance, Catherine Dobbin, Boontana Wannalerse Chem. Commun . 2009, 1386
  39. 41. R L S R L Self-Assembled YES Logic: Covalently bound YES Logic: Assembler: Non-ionic Detergent Micelle N N 2 N N n - C 9 H 1 9 n - C 9 H 1 9 Ru II O O H 10 O - Long-lived (100 ns) lumophore
  40. 42. O - pK a = 9.9
  41. 43. R 1 L R 2 S S R 1 L R 2 Self-Assembled AND Logic: Covalently bound AND Logic: O - N C O 2 C O 2 O n - C 8 H 1 7 - - pK a = 9.9 pK a = 5.8 Log  Ca2+ = 1.5
  42. 44. 11; 10 -8 M H + and 0.2 M Ca 2+ 01; 10 -12 M H + and 0.2 M Ca 2+ 10; 10 -8 M H + only 00; 10 -12 M H + only O - N C O 2 C O 2 O n - C 8 H 1 7 - -
  43. 45. R L S R L Self-Assembled OR Logic: Covalently bound OR Logic: Non-selective Receptor N C O 2 C O 2 O n - C 8 H 1 7 - - binds H + or Ca 2+ pK a = 5.8 Log  Ca  = 1.5
  44. 46. 11; 10 -4 M H + and 0.2 M Ca 2+ 10; 10 -4 M H + only 01; 10 -8 M H + and 0.2 M Ca 2+ 00; 10 -8 M H + only N C O 2 C O 2 O n - C 8 H 1 7 - -
  45. 47. Providence Luck Serendipity EPSRC DENI EUROPEAN COMMISSION JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE
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