Microcontact printing (µCP) is a widely used technique for microscale surface patterning. In this study, we present a polymer-supported µCP method for the patterning of (bioactive) glycosylated surfaces under hydrated conditions. Patterning is achieved by direct contact with a grooved polydimethylsiloxane (PDMS) stamp, whose surface was grafted with a dopamine-containing polymer. The polymer brushes offer an anchor for the boronic acid derivative 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (ABOB), used as an ink for surface functionalization, to introduce patterns to three different surfaces as substrates: (1) monosaccharide-modified hydrogel surfaces possessing aldose (glucose, fucose, galactose) or ketose (fructose, sorbose) functions; (2) glycosylated surfaces of polymeric microspheres; and (3) the membranes of mammalian cells, such as human primary gastric cells and others. During µCP, ABOB patterns transferred to the target surface through the formation of carbohydrate-ABOB complexes at fully hydrated, neutral pH conditions. Fluorescence microscopy confirmed the successful transfer of ABOB patterns to glycosylated surfaces, with clear "tattoo-like" signatures observed on hydrogels, glycosylated particle surfaces and cellular interfaces.

Faculty of Science Department of Physical and Macromolecular Chemistry Charles University Hlavova 8 128 43 Prague 2 Czech Republic

Fraunhofer Cluster of Excellence Immune Mediated Diseases CIMD Frankfurt am Main Germany

Fraunhofer Institute of Applied Polymer Research Geiselbergstr 69 14476 Potsdam Germany

Institute of Chemistry University of Potsdam Karl Liebknecht Str 24 25 14476 Potsdam Germany

Responsive Soft Materials and Interfaces Lab Department of Colloid Chemistry Max Planck Institute of Colloids and Interfaces Am Mühlenberg 1 17746 Potsdam Germany

Zobrazit více v PubMed

Reifarth M., Soft Matter 2025, 10.1039/d5sm00355e. PubMed DOI

Xia Y., Whitesides G. M., Annu. Rev. Mater. Sci. 1998, 28, 153–184.

Geissler M., Kind H., Schmidt‐Winkel P., Michel B., Delamarche E., Langmuir 2003, 19, 6283–6296.

James C. D., Davis R. C., Kam L., Craighead H. G., Isaacson M., Turner J. N., Shain W., Langmuir 1998, 14, 741–744.

Kaufmann T., Ravoo B. J., Polym. Chem. 2010, 1, 371–387.

Quist A. P., Pavlovic E., Oscarsson S., Anal. Bioanal. Chem. 2005, 381, 591–600. PubMed

Béduer A., Seichepine F., Flahaut E., Vieu C., Microelectron. Eng. 2012, 97, 301–305.

Bao W., Liang D., Zhang M., Jiao Y., Wang L., Cai L., Li J., Prog. Nat. Sci. Mater. Int. 2017, 27, 669–673.

Xu H., Huskens J., Chem. Eur. J. 2010, 16, 2342–2348. PubMed

Liu G., Petrosko S. H., Zheng Z., Mirkin C. A., Chem. Rev. 2020, 120, 6009–6047. PubMed

Lohmüller T., Aydin D., Schwieder M., Morhard C., Louban I., Pacholski C., Spatz J. P., Biointerphases. 2011, 6, MR1–MR12. PubMed

Madou M. J., Fundamentals of Microfabrication, Second Edition, Boca Raton, CRC Press, 2018.

Kumar A., Whitesides G. M., Appl. Phys. Lett. 1993, 63, 2002–2004.

Love J. C., Estroff L. A., Kriebel J. K., Nuzzo R. G., Whitesides G. M., Chem. Rev. 2005, 105, 1103–1170. PubMed

Xia Y., Kim E., Mrksich M., Whitesides G. M., Chem. Mater. 1996, 8, 601–603.

Xia Y., Venkateswaran N., Qin D., Tien J., Whitesides G. M., Langmuir 1998, 14, 363–371.

Yan L., Huck W. T. S., Zhao X.‐M., Whitesides G. M., Langmuir 1999, 15, 1208–1214.

Yan L., Zhao X.‐M., Whitesides G. M., J. Am. Chem. Soc. 1998, 120, 6179–6180.

Böhm I., Lampert A., Buck M., Eisert F., Grunze M., Appl. Surf. Sci. 1999, 141, 237–243.

Graham D. J., Price D. D., Ratner B. D., Langmuir 2002, 18, 1518–1527.

Zhai L., Laird D. W., McCullough R. D., Langmuir 2003, 19, 6492–6497.

Bernard A., Renault J. P., Michel B., Bosshard H. R., Delamarche E., Adv. Mater. 2000, 12, 1067–1070.

Lim H.‐J., Lee D. Y., Oh Y.‐J., Sens. Actuators A: Phys. 2006, 125, 405–410.

Gunawan C. A., Ge M., Zhao C., Nat. Commun. 2014, 5, 3744. PubMed

Stolz Roman L., Inganäs O., Granlund T., Nyberg T., Svensson M., Andersson M. R., Hummelen J. C., Adv. Mater. 2000, 12, 189–195.

Didar T. F., Tabrizian M., Lab Chip 2012, 12, 4363. PubMed

Kane R., Biomaterials 1999, 20, 2363–2376. PubMed

Théry M., Piel M., Micropatterning in Cell Biology, Academic Press, Amsterdam, 2014.

Akarsu P., Grobe R., Nowaczyk J., Hartlieb M., Reinicke S., Böker A., Sperling M., Reifarth M., ACS Appl. Polym. Mater. 2021, 3, 2420–2431. PubMed PMC

Akarsu P., Reinicke S., Lehnen A., Bekir M., Böker A., Hartlieb M., Reifarth M., Small 2023, 2301761. PubMed

Pallab N., Reinicke S., Gurke J., Rihm R., Kogikoski S., Hartlieb M., Reifarth M., Polym. Chem. 2024, 15, 853–867.

Keskin D., Mergel O., Van Der Mei H. C., Busscher H. J., Van Rijn P., Biomacromolecules 2019, 20, 243–253. PubMed PMC

Nolan C. M., Reyes C. D., Debord J. D., García A. J., Lyon L. A., Biomacromolecules 2005, 6, 2032–2039. PubMed

Ancla C., Lapeyre V., Gosse I., Catargi B., Ravaine V., Langmuir 2011, 27, 12693–12701. PubMed

Schmidt S., Zeiser M., Hellweg T., Duschl C., Fery A., Möhwald H., Adv. Funct. Mater. 2010, 20, 3235–3243.

Castaño A. G., Hortigüela V., Lagunas A., Cortina C., Montserrat N., Samitier J., Martínez E., RSC Adv. 2014, 4, 29120.

Zhang H., Hanson Shepherd J. N., Nuzzo R. G., Soft Matter 2010, 6, 2238.

Poellmann M. J., Barton K. L., Mishra S., Johnson A. J. W., Macromol. Biosci. 2011, 11, 1164–1168. PubMed

Peng J., Zhao D., Tang X., Tong F., Guan L., Wang Y., Zhang M., Cao T., Langmuir 2013, 29, 11809–11814. PubMed

Burek M., Wandzik I., Polym. Rev. 2018, 58, 537–586.

Ambury R. F., Merry C. L. R., Ulijn R. V., J. Mater. Chem. 2011, 21, 2901.

Liu X., Lei Z., Liu F., Liu D., Wang Z., Biosens. Bioelectron. 2014, 58, 92–100. PubMed

Sperling M., Reifarth M., Grobe R., Böker A., Chem. Commun. 2019, 55, 10104–10107. PubMed

Du J., Yarema K. J., Adv. Drug Delivery Rev. 2010, 62, 671–682. PubMed PMC

Slomiany B. L., Sarosiek J., Slomiany A., Dig. Dis. 1987, 5, 125–145 PubMed

Kaltner H., Gabius H.‐J., Thromb. Haemost. 2019, 119, 517–533. PubMed

Ghosh P., Chem. Eur. J. 2024, 30, e202401983. PubMed

Jin S., Cheng Y., Reid S., Li M., Wang B., Med. Res. Rev. 2010, 30, 171–257. PubMed PMC

Zhai W., Sun X., James T. D., Fossey J. S., Chem. Asian J. 2015, 10, 1836–1848. PubMed

Worsley G. J., Tourniaire G. A., Medlock K. E., Sartain F. K., Harmer H. E., Thatcher M., Horgan A. M., Pritchard J., J. Diabetes Sci. Technol. 2008, 2, 213–220. PubMed PMC

Melavanki R., Kusanur R., Sadasivuni K. K., Singh D., Patil N. R., Heliyon 2020, 6, e05081. PubMed PMC

Yan J., Springsteen G., Deeter S., Wang B., Tetrahedron 2004, 60, 11205–11209.

Brooks W. L. A., Deng C. C., Sumerlin B. S., ACS Omega 2018, 3, 17863–17870. PubMed PMC

Stephenson‐Brown A., Wang H.‐C., Iqbal P., Preece J. A., Long Y., Fossey J. S., James T. D., Mendes P. M., Analyst 2013, 138, 7140. PubMed

António J. P. M., Russo R., Carvalho C. P., Cal P. M. S. D., Gois P. M. P., Chem. Soc. Rev. 2019, 48, 3513–3536. PubMed

Deshayes S., Cabral H., Ishii T., Miura Y., Kobayashi S., Yamashita T., Matsumoto A., Miyahara Y., Nishiyama N., Kataoka K., J. Am. Chem. Soc. 2013, 135, 15501–15507. PubMed

Ellis G. A., Palte M. J., Raines R. T., J. Am. Chem. Soc. 2012, 134, 3631–3634. PubMed PMC

Winblade N. D., Nikolic I. D., Hoffman A. S., Hubbell J. A., Biomacromolecules 2000, 1, 523–533. PubMed

Kwok K. S., Zuo Y., Choi S. J., Pahapale G. J., Gu L., Gracias D. H., Nano Lett. 2023, 23, 7477–7484. PubMed PMC

Asha A. B., Peng Y.‐Y., Cheng Q., Ishihara K., Liu Y., Narain R., ACS Appl. Mater. Interfaces 2022, 14, 9557–9569. PubMed

Scarano W., Lu H., Stenzel M. H., Chem. Commun. 2014, 50, 6390–6393. PubMed

Rowe L., El Khoury G., Lowe C. R., J. Mol. Recognit. 2016, 29, 232–238. PubMed

Su J., Chen F., Cryns V. L., Messersmith P. B., J. Am. Chem. Soc. 2011, 133, 11850–11853. PubMed PMC

Chen Y., Diaz‐Dussan D., Wu D., Wang W., Peng Y.‐Y., Asha A. B., Hall D. G., Ishihara K., Narain R., ACS Macro Lett. 2018, 7, 904–908. PubMed

Cho S., Hwang S. Y., Oh D. X., Park J., J. Mater. Chem. A 2021, 9, 14630–14655.

Chumillas S., Palomäki T., Zhang M., Laurila T., Climent V., Feliu J. M., Electrochim. Acta. 2018, 292, 309–321.

Adamczyk‐Woźniak A., Borys K. M., Sporzyński A., Chem. Rev. 2015, 115, 5224–5247. PubMed

Valenzuela S. A., Howard J. R., Park H. M., Darbha S., Anslyn E. V., J. Org. Chem. 2022, 87, 15071–15076. PubMed

Seera S. D. K., Pester C. W., ACS Polym. Au 2023, 3, 428–436. PubMed PMC

Zheng Z., Ling J., Müller A. H. E., Macromol. Rapid Commun. 2014, 35, 234–241. PubMed

Hemmatpour H., De Luca O., Crestani D., Stuart M. C. A., Lasorsa A., Van Der Wel P. C. A., Loos K., Giousis T., Haddadi‐Asl V., Rudolf P., Nat. Commun. 2023, 14, 664. PubMed PMC

Yang J., Bos I., Pranger W., Stuiver A., Velders A. H., Cohen Stuart M. A., Kamperman M., J. Mater. Chem. A 2016, 4, 6868–6877.

Calosso M., Charpentier D., Vaillancourt M., Bencheqroun M., St‐Pierre G., Wilkes B. C., Guindon Y., ACS Med. Chem. Lett. 2012, 3, 1045–1049. PubMed PMC

De Coen R., Vanparijs N., Risseeuw M. D. P., Lybaert L., Louage B., De Koker S., Kumar V., Grooten J., Taylor L., Ayres N., Van Calenbergh S., Nuhn L., De Geest B. G., Biomacromolecules 2016, 17, 2479–2488. PubMed

Vrbata D., Ďorďovič V., Seitsonen J., Ruokolainen J., Janoušková O., Uchman M., Matějíček P., Chem. Commun. 2019, 55, 2900–2903. PubMed

Zhang X., Liu G., Ning Z., Xing G., Carbohydr. Res. 2017, 452, 129–148. PubMed

Wu X., Li Z., Chen X.‐X., Fossey J. S., James T. D., Jiang Y.‐B., Chem. Soc. Rev. 2013, 42, 8032–8048. PubMed

Nicholls M. P., Paul P. K. C., Org. Biomol. Chem. 2004, 2, 1434–1441. PubMed

Schnaitman C. A., J. Bacteriol. 1971, 108, 545–552. PubMed PMC

Sheldrick G. M., C Struct. Chem. 2015, 71, 3–8. PubMed PMC

Sheldrick G. M., Acta Crystallogr. A. Found. Crystallogr. 2008, 64, 112–122. PubMed

Macrae C. F., Sovago I., Cottrell S. J., Galek P. T. A., McCabe P., Pidcock E., Platings M., Shields G. P., Stevens J. S., Towler M., Wood P. A., J.Appl. Crystallogr. 2020, 53, 226–235. PubMed PMC

Glass P., Chung H., Washburn N. R., Sitti M., Langmuir 2009, 25, 6607–6612. PubMed

Yu S., Liu Y., Shang C., Du Y., Liu J., Tetrahedron. Lett. 2021, 72, 153072.

Maryanoff B. E., McComsey D. F., Costanzo M. J., Hochman C., Smith‐Swintosky V., Shank R. P., J. Med. Chem. 2005, 48, 1941–1947. PubMed

Toyoshima Y., Kawamura A., Takashima Y., Miyata T., J. Mater. Chem. B 2022, 10, 6644–6654. PubMed

López M. G., Gruenwedel D. W., Carbohydr. Res. 1991, 212, 37–45.