Skip to main content
SpringerLink
Log in

Molecular Recognition and Hydrogen-Bonded Amphiphiles

  • Chapter
  • First Online:
Book cover Colloid Chemistry II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 227))

Abstract

Amphiphiles bearing polar heads capable of forming hydrogen bond(s) exhibit unique organizational and aggregational properties. Thus they are hierarchically organized in supramolecular assemblies, which in turn interact through hydrogen bonding with other complementary counterparts affording larger and more elaborated aggregates. For liposomes, which are primarily investigated in this review, a number of examples have demonstrated their interaction mode and the associated phenomena as related with the structural features of the supramolecular aggregates obtained. A limited number of molecular recognition experiments is discussed for micellar systems due to their dynamic character and non-clearly defined shape and interface. The recognition between cells, following incorporation of recognizable amphiphiles in their membranes, demonstrate the approximate resemblance of liposomes with cells as well as the similarities of liposomal interactions with those of the cells.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. a) Lichtenthaler FW (1994) Angew Chem Int Ed Engl 33:2364; b) Koshland DE Jr (1994) Angew Chem Int Ed Engl 33:2375; c) Rebek J Jr (1996) Acta Chem Scand 50:707

    Article  Google Scholar 

  2. Fischer E (1894) Ber Dtsch Chem Ges 27:2985

    Article  CAS  Google Scholar 

  3. a) Whitesides GM, Simanek EE, Mathias JP, Seto CT, Chin DN, Mammen D, Gordon DM (1995) Acc Chem Res 28:37; b) MacDonald C, Whitesides GM (1994) Chem Rev 94:2383; c) Fyte MC, Stoddart JF (1997) Acc Chem Res 30:401; d) Prins LJ, Reinhoudt D, Timmerman P (2001) Angew Chem Int Ed Engl 40:2382

    Article  CAS  Google Scholar 

  4. a) Hamilton AA (1990) J Chem Educ 67:821; b) Schneider H-J (1991) Angew Chem Int Ed Engl 30:1417; c) Smithrud DB, Sanford EM, Chao I, Ferguson SB, Carcanague DR, Evanseck JD, Houk KN, Diederich F (1990) Pure Appl Chem 62:2227; d) Rebek J Jr (1996) Chem Soc Rev 255; e) Mecozzi S, Rebek J Jr (1998) Chem Eur J 4:1016

    Article  CAS  Google Scholar 

  5. a) Fan E, Vicent C, Geib SJ, Hamilton AD (1994) Chem Mater 6:1113; b) Etter MC, Reutzel SM (1991) J Am Chem Soc 113:2586; c) Desiraju GR (1995) Angew Chem Int Ed Engl 34:2311; d) Lehn J-M (1996) Supramolecular chemistry.VCH Weinheim New York; e) Etter MC (1990) Acc Chem Res 23:120; f) Lawrence DS, Jiang T, Levett AM (1995) Chem Rev 95:2229; g) Philp D, Stoddart JF (1995) Angew Chem Int Ed Engl 35:2311; h) Hosseini MW, De Cian A (1998) Chem Commun 727; i) Niemeyer CM (2001) Angew Chem Int Ed Engl 40:4128

    Article  CAS  Google Scholar 

  6. a) Paleos CM, Tsiourvas D (1995) Angew Chem Int Ed Engl 34:1696; b) Kato T (1998) Hydrogen-bonded systems. In: Demus D, Goodby J, Gray GW, Spiess HW, Vill V (eds) Handbook of liquid crystals. Wiley-VCH, Weiheim, p 969; c) Blunk D, Praefcke K, Vill V (1998) Amphotropic liquid crystals. In: Demus D, Goodby J, Gray GW, Spiess HW, Vill V (eds) Handbook of liquid crystals. Wiley-VCH, Weiheim, p 305; d) Paleos CM, Tsiourvas D (2001) Liq Cryst 28:1127

    Article  CAS  Google Scholar 

  7. Kawasaki T, Tokuhiro M, Kimizuka N, Kunitake T (2001) J Am Chem Soc 123:6792

    Article  CAS  Google Scholar 

  8. Mammen M, Choi S-K, Whitesides GM (1998) Angew Chem Int Ed Engl 37:2754

    Article  Google Scholar 

  9. Onda M, Yoshihara K, Koyano H, Ariga K, Kunitake T (1996) J Am Chem Soc 118:8524

    Article  CAS  Google Scholar 

  10. a) Cooper GM (1997) The cell. A molecular approach. ASM Press, Washington DC, p 467; b) Paleos CM, Sideratou Z, Tsiourvas D (2001) Chem Bio Chem 2:305–310

    Google Scholar 

  11. a) Käs J, Sackmann E (1991) Biophys J 60:825; b) Decher G, Ringsdorf H, Venzmer J, Bitter-Suermann D, Weisberger C (1990) Biochim Biophys Acta 1023:357; c) Menger FM, Lee SJ (1995) Langmuir 11:3685; d) Bradley J-C, Guedeau-Boudeville M-A, Jandeau G, Lehn J-M (1997) Langmuir 13:2457

    Google Scholar 

  12. a) Paleos CM, Tsiourvas D (1997) Adv Mater 9:695 and references cited therein; b) Ariga K, Kunitake T (1998) Acc Chem Res 31:371 and references cited therein

    Article  CAS  Google Scholar 

  13. New RRC (1990) Liposomes, a practical approach. IRL Press, Oxford

    Google Scholar 

  14. Ahlers M, Mueller W, Reichert A, Ringdorf H, Venzmer J (1990) Angew Chem Int Ed Engl 29:1269

    Article  Google Scholar 

  15. a) Rosano C, Arosio P, Bolognesi M (1999) Biomol Eng 16:5; b) Freitag S, Le Trong I, Klumb LA, Chu V, Chilkoti A, Stayton PS, Stenkamp RE (1999) Biomol Eng 16:13; c) Scief WR, Edwards T, Frey W, Koppenol S, Stayto PS, Vogel V (1999) Biomol Eng 16:29

    Article  CAS  Google Scholar 

  16. Chiruvolou S, Walker S, Israelachvili J, Schmitt FJ, Leckband D, Zasadzinski JA, (1994) Science 264:1753

    Article  Google Scholar 

  17. Noppi-Simpson DA, Needham D (1996) Biophys J 70:1391–1401

    Article  Google Scholar 

  18. Sideratou Z, Foundis J, Tsiourvas D, Nezis IP, Papadimas G, Paleos CM (2002) Langmuir 18:5036

    Article  CAS  Google Scholar 

  19. Walker SA, Kennedy MT, Zasadzinski JA (1997) Nature 387:61

    Article  CAS  Google Scholar 

  20. Paleos CM, Tsiourvas D, Kardassi D (1999) Langmuir 15:282

    Article  CAS  Google Scholar 

  21. Evans DF, Ninham BW (1986) J Phys Chem 90:226

    Article  CAS  Google Scholar 

  22. Cevc G, Richardsen H (1999) Adv Drug Delivery Rev 38:207

    Article  CAS  Google Scholar 

  23. a) Duezguenes N, Wilschut J (1993) Methods Enzymol 230:3; b) Hoekstra D, Duezguenes N (1993) Methods Enzymol 230:15

    Google Scholar 

  24. Menger FM, Keiper JS, Lee SJ (1997) Langmuir 13:4614

    Article  CAS  Google Scholar 

  25. Paleos CM, Sideratou Z, Tsiourvas D (1996) J Phys Chem 100:13, 898

    Article  Google Scholar 

  26. a) Marchi-Artzner V, Jullien L, Gulik-Krzywicki T, Lehn J-M (1997) Chem Commun 117; b) Marchi-Artzner V, Gulik-Krzywicki T, Guedeau-Boudeville M-A, Gosse C, Sanderson JM, Dedieuand L-C, Lehn J-M (2001) Chem Phys Chem 2:367–376

    Google Scholar 

  27. Sideratou Z, Tsiourvas D, Paleos CM, Tsortos A, Nounesis G (2000) Langmuir 16:9186

    Article  CAS  Google Scholar 

  28. a) Ipsen JH, Karlström G, Mouritsen OG, Wennerströem H, Zuckermann MJ (1987) Biochim Biophys Acta 905:162; b) Thewalt LJ, Bloom M (1992) Biophys J 63:1176; c) Vist MR, Davis JH (1990) Biochemistry 29:451; d) Trandum C, Westh P, Jørgensen K, Mouritsen OG (2000) Biophys J 78:2486

    Article  CAS  Google Scholar 

  29. Sideratou Z, Tsiourvas D, Paleos CM, Tsortos A, Pyrpassopoulos S, Nounesis G (2002) Langmuir 18:829

    Article  CAS  Google Scholar 

  30. a) A thorough discussion of the subject in: Faraday Discuss Chem Soc (1986) 77, 209, 340, 341 (81 pages); b) Söderlund T, Jutila A, Kinnunen PKJ (1999) Biophys J 76:896

    Google Scholar 

  31. Pantos A, Sideratou Z, Paleos CM (2002) J Colloid Interface Sci 253:435

    Article  CAS  Google Scholar 

  32. Komatsu H, Okada S (1997) Chem Phys Lipids 85:67

    Article  CAS  Google Scholar 

  33. a) Berti D, Franci L, Baglioni P, Luisi PL (1997) Langmuir 13:3438; b) Berti D, Luisi PL, Baglioni P (2000) Colloids Surf A Physicochem Eng Aspects 167:95

    Article  CAS  Google Scholar 

  34. a) Nowick JS, Chen JS (1992) J Am Chem Soc 114:1107; b) Nowick JS, Chen JS, Noronha G (1993) J Am Chem Soc 115:7636

    Article  CAS  Google Scholar 

  35. Nowick JS, Cao T, Noronha G (1994) J Am Chem Soc 116:3285

    Article  CAS  Google Scholar 

  36. Meier W (2000) Langmuir 16:1457

    Article  CAS  Google Scholar 

  37. Lemieux RU (1996) Acc Chem Res 29:373

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physical Chemistry, NCSR “Demokritos”, 15310 Aghia Paraskevi, Attiki, Greece

    Constantinos M. Paleos & Dimitris Tsiourvas

Authors
  1. Constantinos M. Paleos
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dimitris Tsiourvas
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Max Planck Institute of Colloids and Interfaces, 14424, Potsdam, Germany

    Markus Antonietti

Rights and permissions

Reprints and permissions

Copyright information

© 2003 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Paleos, C.M., Tsiourvas, D. (2003). Molecular Recognition and Hydrogen-Bonded Amphiphiles. In: Antonietti, M. (eds) Colloid Chemistry II. Topics in Current Chemistry, vol 227. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-36412-9_1

Download citation

  • DOI: https://doi.org/10.1007/3-540-36412-9_1

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-00418-9

  • Online ISBN: 978-3-540-36412-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation