Skip to main content
SpringerLink
Log in

Nucleobase-Containing Gelators

  • Chapter
  • First Online:
Low Molecular Mass Gelator

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 256))

Abstract

Nucleobases are nitrogenous heterocyclic compounds and have high ability to form directionally controlled multiple intermolecular interaction, i.e., in-plane multiple hydrogen-bonding interactions and stacking interactions perpendicular to the plane. Here the recent development of nucleobase-containing low molecular mass gelators in aqueous and organic systems is reviewed, and the self-assemblies of nucleobase-containing small molecules and their arrangement within the gel are discussed from the molecular, and mesoscopic to the macroscopic level in regard to becoming a macroscale three-dimensional network. Brief overview of the nucleoside-containing supramolecular materials are also presented.

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

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

A:

adenine

AFM:

atomic force microscopy

C:

cytosine

CD:

circular dichroism

G:

guanine

GMP:

guanosine monophosphate

isoG:

isoguanosine

LC:

liquid crystal

SAXS:

Small-angle X-ray scattering

SEM:

scanning electron microscopy

SUV:

small unilamellar vesicle

TEM:

transmission electron microscopy

T gel :

sol-gel transition temperature

THN:

teterahydronaphthalene

U:

uracil

XRD:

X-ray diffraction

References

  1. Terech P, Weiss RG (1997) Chem Rev 97:3133

    Article  CAS  Google Scholar 

  2. Estroff LA, Hamilton AD (2004) Chem Rev 104:1201

    Article  CAS  Google Scholar 

  3. Saenger W (1984) Principles of Nucleic Acid Structure. Springer-Verlag, Berlin Heidelberg New York

    Book  Google Scholar 

  4. Steiner T, Saenger W (1993) J Am Chem Soc 115:4540

    Article  CAS  Google Scholar 

  5. Braga D, Maini L, Polito M, Grepioni F (2004) In: Michael D, Mingos P (eds) Structure and bonding 111. Springer, Berlin Heidelberg New York, p 1

    Google Scholar 

  6. Asensio A, Kobko N, Dannenberg JJ (2003) J Phys Chem A 107:6441

    Article  CAS  Google Scholar 

  7. Guckian KM, Schweitzer BA, Ren RX-F, Sheils CJ, Tahmassebi DC, Kool ET (2000) J Am Chem Soc 122:2213

    Article  CAS  Google Scholar 

  8. Mutai K, Gruber BA, Leonard NJ (1975) J Am Chem Soc 97:4095

    Article  CAS  Google Scholar 

  9. Ts’o POP (1974) Basic principles in nucleic acid chemistry. Academic Press, New York

    Google Scholar 

  10. Kitano H, Ringsdorf H (1985) Bull Chem Soc Jpn 58:2826

    Article  CAS  Google Scholar 

  11. Ariga K, Kunitake T (1998) Acc Chem Res 31:371

    Article  CAS  Google Scholar 

  12. Kurihara K, Ohto K, Honda Y, Kunitake T (1991) J Am Chem Soc 113:5077

    Article  CAS  Google Scholar 

  13. Ebara Y, Itakura K, Okahata Y (1996) Langmuir 12:5165

    Article  CAS  Google Scholar 

  14. Miao WG, Du XZ, Liang YQ (2003) Langmuir 19:5389

    Article  CAS  Google Scholar 

  15. Berti D, Franchi L, Baglioni P, Luisi PL (1997) Langmuir 13:3438

    Article  CAS  Google Scholar 

  16. Kawahara T, Kurihara K, Kunitake T (1992) Chem Lett 1839

    Google Scholar 

  17. Shimomura M, Nakamura F, Ijiro K, Taketsuna H, Tanaka M, Nakamura H, Hasebe K (1997) J Am Chem Soc 119:2341

    Article  CAS  Google Scholar 

  18. Nowick JS, Chen JS (1992) J Am Chem Soc 114:1107

    Article  CAS  Google Scholar 

  19. Nowick JS, Chen JS, Noronha G (1993) J Am Chem Soc 115:7636

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  21. Berti D, Pini F, Baglioni P, Teixeira J (1999) J Phys Chem B 103:1738

    Article  CAS  Google Scholar 

  22. Berti D, Barbaro P, Bucci I, Baglioni P (1999) J Phys Chem B 103:4916

    Article  CAS  Google Scholar 

  23. Zandomeneghi G, Luisi PL, Mannina L, Segre A (2001) Helv Chim Acta 84:3710

    Article  CAS  Google Scholar 

  24. Berti D, Baglioni P, Bonaccio S, Barsacchi-Bo G, Luisi PL (1998) J Phys Chem B 102:303

    Article  CAS  Google Scholar 

  25. Berti D, Luisi PL, Baglioni P (2000) Colloids Surf A 167:95

    Article  CAS  Google Scholar 

  26. Pincet F, Lebeau L, Cribier S (2001) Eur Biophys J 30:91

    Article  CAS  Google Scholar 

  27. Guschlbauer W, Chantot JF, Thiele D (1990) J Biomol Struct Dyn 8:491

    CAS  Google Scholar 

  28. Gellert M, Lipsett MN, Davies DR (1962) Proc Natl Acad Sci USA 48:2013

    Article  CAS  Google Scholar 

  29. Sasisekharan V, Zimmerman S, Davies DR (1975) J Mol Biol 92:171

    Article  CAS  Google Scholar 

  30. Davis JT (2004) Angew Chem Int Ed 43:668

    Article  CAS  Google Scholar 

  31. Gottarelli G, Spada GP, Garbesi A (1996) In: Sauvage JP, Hosseini MW (eds) Comprehensive supramolecular chemistry, vol. 9. Elsevier, Oxford, p 483 and references therein

    Google Scholar 

  32. Yanagawa H, Ogawa Y, Furuta H, Tsuno K (1988) Chem Lett 269

    Google Scholar 

  33. Yanagawa H, Ogawa Y, Furuta H, Tsuno K (1989) J Am Chem Soc 111:4567

    Article  CAS  Google Scholar 

  34. Itojima Y, Ogawa Y, Tusno K, Handa N, Yangawa H (1992) Biochem 31:4757

    Article  CAS  Google Scholar 

  35. Bombelli FB, Berti D, Keiderling U, Baglioni P (2002) J Phys Chem B 106:11613

    Article  CAS  Google Scholar 

  36. Moreau L, Barthélémy P, Maataoui MEI, Grinstaff MW (2004) J Am Chem Soc 126:7533

    Article  CAS  Google Scholar 

  37. Shimizu T (2002) Macromol Rapid Commun 23:311

    Article  CAS  Google Scholar 

  38. Shimizu T, Iwaura R, Masuda M, Hanada T, Yase K (2001) J Am Chem Soc 123:5947

    Article  CAS  Google Scholar 

  39. Iwaura R, Yoshida K, Masuda M, Yase K, Shimizu T (2002) Chem Mater 14:3047

    Article  CAS  Google Scholar 

  40. Iwaura R, Yoshida K, Masuda M, Ohnishi-Kameyama M, Yoshida M, Shimizu T (2003) Angew Chem Int Ed 42:1009

    Article  CAS  Google Scholar 

  41. Iwaura R, Ohnishi-Kameyama M, Yoshida M, Shimizu T (2002) Chem Commun 2658

    Google Scholar 

  42. Park SM, Lee YS, Kim BH (2003) Chem Commun 2912

    Google Scholar 

  43. Spada GP, Gottarelli G (2004) Synlett 4:596

    Google Scholar 

  44. Gottarelli G, Masiero S, Mezzina E, Spada GP, Mariani P, Recanatini M (1998) Helv Chim Acta 81:2078

    Article  CAS  Google Scholar 

  45. Gottarelli G, Masiero S, Mezzina E, Pieraccini S, Spada GP, Mariani P (1999) Liq Cryst 26:965

    Article  CAS  Google Scholar 

  46. Giorgi T, Grepioni F, Manet I, Mariani P, Masiero S, Mezzina E, Pieraccini S, Saturni L, Spada GP, Gottarelli G (2002) Chem Eur J 8:2143

    Article  CAS  Google Scholar 

  47. Sato T, Seko M, Takasawa R, Yoshikawa I, Araki K (2001) J Mater Chem 11:3018

    Article  CAS  Google Scholar 

  48. Yun YJ, Park SM, Kim BH (2003) Chem Commun 254

    Google Scholar 

  49. Sugiyasu K, Numata M, Fujita N, Park SM, Yun YJ, Kim BH, Shinkai S (2004) Chem Commun 1996

    Google Scholar 

  50. Shinkai S, Murata K (1998) J Mater Chem 8:485

    Article  CAS  Google Scholar 

  51. Murata K, Aoki M, Suzuki T, Harada T, Kawabata H, Komori T, Ohseto F, Ueda K, Shinkai S (1994) J Am Chem Soc 116:6664

    Article  CAS  Google Scholar 

  52. Snip E, Shinkai S, Reinhoudt DN (2001) Tetrahedron Lett 42:2153

    Article  CAS  Google Scholar 

  53. Snip E, Koumoto K, Shinkai S (2002) Tetrahedron 58:8863

    Article  CAS  Google Scholar 

  54. Numata M, Shinkai S (2003) Chem Lett 32:308

    Article  CAS  Google Scholar 

  55. Zimmerman SC, Corbin PS (2000) In: Structure and Bonding 96. Springer, Berlin Heidelberg New York, p 63

    Google Scholar 

  56. Kato T (2000) In: Structure and Bonding 96. Springer, Berlin Heidelberg New York, p 95

    Google Scholar 

  57. Rieth LR, Eaton RF, Coates GW (2001) Angew Chem Int Ed 40:2153

    Article  CAS  Google Scholar 

  58. Thibault RJ, Hotchkiss PJ, Gray M, Rotello VM (2003) J Am Chem Soc 125:11249

    Article  CAS  Google Scholar 

  59. Lin DC, Yurke B, Langrana NA (2004) J Biomechanical Eng 126:104

    Article  Google Scholar 

  60. Brunsveld L, Folmer BJB, Meijer EW, Sijbesma RP (2001) Chem Rev 101:4071

    Article  CAS  Google Scholar 

  61. Guan Z, Roland JT, Bai JZ, Ma SX, Mclntire TM, Nguyen M (2004) J Am Chem Soc 126:2058

    Article  CAS  Google Scholar 

  62. Fouquey C, Lehn J-M, Levelut A-M (1990) Adv Mater 2:254

    Article  CAS  Google Scholar 

  63. Sivakova S, Rowan SJ (2003) Chem Commun 2428

    Google Scholar 

  64. Folmer BJB, Sijbesma RP, Meijer EW (2001) J Am Chem Soc 123:2093

    Article  CAS  Google Scholar 

  65. Hirschberg JHKK, Koevoets RA, Sijbesma RP, Meijer EW (2003) Chem Eur J 9:4222

    Article  CAS  Google Scholar 

  66. Marlow AL, Mezzina E, Spada GP, Masiero S, Davis JT, Gottarelli G (1999) J Org Chem 64:5116

    Article  CAS  Google Scholar 

  67. Tirumala S, Davis JT (1997) J Am Chem Soc 119:2769

    Article  CAS  Google Scholar 

  68. Lee SC, Lamb JD, Cai MM, Davis JT (2001) J Inclusion Phenom Macrocyclic Chem 40:51

    Article  CAS  Google Scholar 

  69. Forman SL, Fettinger JC, Pieraccine S, Gottarelli G, Davis JT (2000) J Am Chem Soc 122:4060

    Article  CAS  Google Scholar 

  70. Sidorov V, Kotch FW, El-Kouedi M, Davis JT (2000) Chem Commun 2369

    Google Scholar 

  71. Pieraccini S, Gottarelli G, Mariani P, Masiero S, Saturni L, Spada GP (2001) Chirality 13:7

    Article  CAS  Google Scholar 

  72. Giorgi T, Lena S, Mariani P, Cremonini MA, Masiero S, Pieraccini S, Rabe JP, Samori P, Spada GP, Gottarelli G (2003) J Am Chem Soc 125:14741

    Article  CAS  Google Scholar 

  73. Kanie K, Nishii M, Yasuda T, Taki T, Ujiie S, Kato T (2001) J Mater Chem 11:2875

    Article  CAS  Google Scholar 

  74. Rinaldi R, Branca E, Cingolani R, Masiero S, Spada GP, Gottarelli G (2001) Appl Phys Lett 78:3541

    Article  CAS  Google Scholar 

  75. Maruccio G, Visconti P, Arima V, D’Amico S, Biasco A, D’Amone E, Cingolani R, Rinaldi R, Masiero S, Giorgi T, Gottarelli G (2003) Nanoletters 3:479

    Article  CAS  Google Scholar 

  76. Araki K, Takasawa R, Yoshikawa I (2001) Chem Commun 1826

    Google Scholar 

  77. Yoshikawa I, Li J, Sakata Y, Araki K (2004) Angew Chem Int Ed 43:100

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, 153-8505, Tokyo, Japan

    Koji Araki & Isao Yoshikawa

Authors
  1. Koji Araki
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Isao Yoshikawa
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Koji Araki .

Rights and permissions

Reprints and permissions

Copyright information

© 2005 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Araki, K., Yoshikawa, I. (2005). Nucleobase-Containing Gelators. In: Low Molecular Mass Gelator. Topics in Current Chemistry, vol 256. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b107173

Download citation

Publish with us

Policies and ethics

Search

Navigation