ATP-binding peptide-hydrogel composite
synthesized by molecular imprinting on beads

• Authors: Ayana Takata , Kenji Usui , Jun Matsui
• Languages of publication: EN

Abstracts

EN

Molecular imprinting has been recognized as a
useful technique to produce synthetic mimics of functional
proteins, such as antibodies and enzymes. However, only
a few studies have examined peptides as starting materials
for synthesizing molecularly imprinted polymers in
spite of the expectation that peptides would be suitable
materials for realizing water-compatibility and proteinlike
functions. In this study, molecular imprinting was
performed using a vinyl-end-capped on-beads-peptide
as functional monomer to produce an on-beads-peptide
hydrogel composite selective for ATP; the on-beadspeptide
peptide, of which sequence was designed to
possess both an adenine-recognition site and phosphate
recognition site, was co-polymerized with NIPAM and BIS
in the presence of ATP as a template species. The resultant
ATP-imprinted composite showed 14-times higher affinity
and an enhanced selectivity towards ATP, suggesting that
the peptide conformation, i.e. a mutual orientation of the
two binding sites, was pre-organized and immobilized in
a manner where the ATP binding is more favored.

Keywords

EN

peptide; hydrogel; ATP

• Publisher: De Gruyter Open
• Journal: Molecular Imprinting
• Year: 2014
• Volume: 2
• Issue: 1

Dates

online

23 - 2 - 2016

accepted

28 - 12 - 2015

received

3 - 8 - 2015

Contributors

author

Ayana Takata

• Department of Nanobiochemistry, FIRST,
  Konan University, 7-1-20 Minatojima-minami-machi, Chuo-ku, Kobe
  650-0047, Japan

author

Kenji Usui

• Department of Nanobiochemistry, FIRST,
  Konan University, 7-1-20 Minatojima-minami-machi, Chuo-ku, Kobe
  650-0047, Japan

author

Jun Matsui

• Department of Nanobiochemistry, FIRST,
  Konan University, 7-1-20 Minatojima-minami-machi, Chuo-ku, Kobe
  650-0047, Japan

References

• [1] Chen L., Xuab S., Lia J., Recent advances in molecularimprinting technology: current status, challenges andhighlighted applications, Chem. Soc. Rev., 2011,40, 2922-2942.[WoS]
• [2] Martín-Esteban A., Molecularly-imprinted polymers as aversatile, highly selective tool in sample preparation, TrACTrends in Analytical Chemistry, 2013, 45, 169-181.
• [3] Sharma P.S., Iskierko Z., Pietrzyk-Le A., D’Souza F., KutnerW., Bioinspired intelligent molecularly imprinted polymersfor chemosensing: A mini review, Electrochemistry Communications,2015, 50, 81-87.[WoS]
• [4] Tiwari M.P., Prasad A., Molecularly imprinted polymer basedenantioselective sensing devices: A review, Anal. Chim. Acta,2015, 853, 1–18.
• [5] Wulff G., Liu J., Design of biomimetic catalysts by molecularimprinting in synthetic polymers: the role of transition statestabilization, Acc Chem Res., 2012, 45, 239-247.[WoS]
• [6] Yoshimatsu K., Koide H., Hoshino Y., Shea K.J., Preparation ofAbiotic Polymer Nanoparticles for Sequestration and Neutralizationof a Target Peptide Toxin, Nature Prot., 2015, 10,595–604.
• [7] Sellergren B., Molecularly imprinted polymers: man-mademimics of antibodies and their application in analyticalchemistry, Elsevier, 2000.
• [8] Matsui J., Nagano J., Miyoshi D., Tamaki K., Sugimoto N., Anapproach to peptide-based ATP receptors by a combination ofrandom selection, rational design, and molecular imprinting,Biosens Bioelectron., 2009, 25, 563-567.[WoS]
• [9] Matsui J., Kamitakahara Y., Nagano J., Ono Y., Komai S., MiyoshiD., Tamaki K., Sugimoto N., Molecular imprinting within asingle peptide molecule for synthesizing a water-soluble ATPreceptor, In: Ishida H., Peptide science 2006. Proceedings ofthe 43rd Japanese peptide symposium, Yokohama, November5-8, 2006, Japanese Peptide Society, 2006.
• [10] Matsuurua, K., Rational design of self-assembled proteins andpeptides for nano- and micro-sized architectures, RSC Adv.,2014, 4, 2942-2953.
• [11] Stachelhaus T., Schneider A., Marahiel M.A., Rational designof peptide antibiotics by targeted replacement of bacterial andfungal domains, Science, 1995, 269, 69-72.
• [12] Shin D.S., Kim D.H., Chung W.J., Lee Y.S., Combinatorial solidphase peptide synthesis and bioassays, J. Biochem. Mol. Biol.2005, 38, 517-525.
• [13] Matsui J., Akamatsu K., Nishiguchi S., Miyoshi D., NawafuneH., Tamaki K., Sugimoto N., Composite of Au nanoparticles andmolecularly imprinted polymer as a sensing material, Anal.Chem., 2004, 76, 1310.
• [14] Chan W.C., White P.D. (Eds), Fmoc solid phase peptidesynthesis: a practical approach (the practical approach series),Oxford University Press, 2000.
• [15] Connors K.A., Binding constants: the measurement ofmolecular complex stability, Wiley-Interscience, 1987.
• [16] Nakano S., Fukuda M., Tamura T., Sakaguchi R., Nakata E.,Morii T., Simultaneous Detection of ATP and GTP by CovalentlyLinked Fluorescent Ribonucleopeptide Sensors, J. Am. Chem.Soc., 2013, 135, 3465–3473.[WoS]
• [17] Xu Z., Singh N.J., Lim J., Pan J., Kim H.N., Park S., Kim K.S., YoonJ., Unique sandwich stacking of pyrene-adenine-pyrene forselective and ratiometric fluorescent sensing of ATP at physiologicalpH, J. Am. Chem. Soc., 2009, 131, 15528–15533.
• [18] Guo Y., Sun X., Yang G., liu J., Ultrasensitive detection of ATPbased on ATP regeneration amplification and its application incell homogenate and human serum, Chem. Commun., 2014,50,7659-7662.[WoS]
• [19] Moro A.J., Cywinski P.J., Körsten S., Mohr G.J., An ATPfluorescent chemosensor based on a Zn(II)-complexed dipicolylaminereceptor coupled with a naphthalimide chromophore,Chem. Commun., 2010, 46, 1085-1087.
• [20] Thoden J.B., Blanchard C.Z., Holden H.M., Waldrop G.L.,Movement of the biotin carboxylase B-domain as a result of ATPbinding, J. Biol. Chem., 2000, 275, 16183-16190.
• [21] Scheiner, S., Hydrogen bonding: a theoretical perspective,Oxford University Press, 1997.
• [22] Israelachvili J.N., Intermolecular and surface forces, 3rd Ed,Academic Press, 2011.
• [23] Hoshino Y., Ohashi R.C., Miura Y., Rational Design of SyntheticNanoparticles with a Large Reversible Shift of Acid DissociationConstants: Proton Imprinting in Stimuli Responsive NanogelParticles, Adv. Mater., 2014, 26. 3718-3723.[WoS]
• [24] Brahme N.M., Smith, Jr. W.T., Some Intramolecular MichaelAdditions of Adenine Derivatives, J. Heterocyclic Chem., 1985,22, 109-112. [Crossref]

Identifiers

DOI

10.1515/molim-2015-0008