Mechanism of intracellular detection of glucose through nonenzymatic and boronic acid functionalized carbon dots

Journal of Biomedical Materials Research - Part A

Volumn 103, Issue 9, 2015, Pages 2888-2897

  Kiran, S ^a   Misra, R D K ^a  

^a 500 W University Avenue   (United States)

Author keywords

boronic acid; carbon dots; fluorescence; glucose; nanochemosensors

Indexed keywords

DYNAMIC RESPONSE; DYNAMICS; FLUORESCENCE; GLUCOSE; MOLECULAR BIOLOGY; QUENCHING;

BORONIC ACID; CARBON DOTS; FLUORESCENCE QUENCHING; FUNCTIONALIZATIONS; FUNDAMENTAL MECHANISMS; HIGH SELECTIVITY; NANOCHEMOSENSORS; SELECTIVE ASSEMBLY;

CARBON;

BORONIC ACID DERIVATIVE; CARBON; CARBON DOTS; FLUORESCENT DYE; GLUCOSE; QUANTUM DOT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CARBON BASED NANOCHEMOSENSOR; CELL FUNCTION; CELL VIABILITY; CONJUGATION; ENZYMIC BIOSENSOR; FEMALE; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; HUMAN; HUMAN CELL; INFRARED RADIATION; INTRACELLULAR DETECTION; MICROWAVE RADIATION; MOUSE; NONHUMAN; PHOTOLUMINESCENCE; QUANTUM YIELD; TRANSMISSION ELECTRON MICROSCOPY; ANIMAL; CELL LINE; CELL SURVIVAL; CHEMISTRY; GENETIC PROCEDURES; HELA CELL LINE; INTRACELLULAR FLUID; PROCEDURES; ULTRASTRUCTURE;

ANIMALS; BIOSENSING TECHNIQUES; BORONIC ACIDS; CARBON; CELL LINE; CELL SURVIVAL; FLUORESCENCE; GLUCOSE; HELA CELLS; HUMANS; INTRACELLULAR FLUID; MICE; MICROSCOPY, ELECTRON, TRANSMISSION; QUANTUM DOTS;

EID: 84938211826     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.35421     Document Type: Article

References (58)

1. Rabinovitch B, March WF, Adams RL,. Noninvasive glucose monitoring of the aqueous humor of the eye: Part L measurement of very small optical rotations. Diabetes Care 1982; 5: 254-258.
2. Hatoum IJ, Hu FB, Nelson JJ, Rimm EB,. Lipoprotein-associated phospholipase A2Activity and incident coronary heart disease among men and women with type 2. Diabetes 2010; 59: 1239-1243.
3. Elasy TA,. Blood pressure control in diabetes: Where is the ownership? Clin Diabet 2010; 28: 97-98.
4. Robinson MR, Eaton RP, Haaland DM, Koepp GW, Thomas EV, Stallard BR, Robinson PL,. Noninvasive glucose monitoring in diabetic patients: A preliminary evaluation. Clin Chem 1992; 38: 1618-1622.
5. Sander EP, Odell SS, Hood KK,. Diabetes-specific family conflict and blood glucose monitoring in adolescents with type 1 diabetes: Mediational role of diabetes self-efficacy. Diabet Spectrum 2010; 23: 89-94.
6. Stephenson-Brown A, Wang HC, Iqbal P, Preece JA, Long Y, Fossey JS, James TD, Mendes PM,. Glucose selective surface plasmon resonance-based bis-boronic acid sensor. Analyst 2013; 138: 7140-7145.
7. Yang W, Gao X, Wang B,. Boronic acid compounds as potential pharmaceutical agents. Med Res Rev 2003; 23: 346-368.
8. Wang W, Gao X, Wang B., Boronic acid-based sensors for carbohydrates. Curr Org Chem 2002; 6: 1285-1317.
9. Lavigne JJ, Anslyn EV,. Teaching old indicators new tricks: A colorimetric chemosensing ensemble for tartrate/malate in beverages. Angew Chem Int Ed 1999; 38: 3666-3669.
10. Eggert H, Frederiksen J, Morin C, Norrild JC,. A new glucose-selective fluorescent bisboronic acid. First report of strong α-furanose complexation in aqueous solution at physiological pH. J Org Chem 1999; 64: 3846-3852.
11. Wang W, Gao S, Wang B,. Building fluorescent sensors by template polymerization: The preparation of a fluorescent sensor for D-fructose. Org Lett 1999; 1: 1209-1212.
12. Arimori S, Bosch LI, Ward CJ, James TD,. Fluorescent internal charge transfer (ICT) saccharide sensor. Tetrahedron Lett 2001; 42: 4553-4555.
13. Karnati VV, Gao X, Gao S, Yang W, Ni W, Sankar S, Wang B,. A glucose-selective fluorescence sensor based on boronicacid-diol recognition. Bioorg Med Chem Lett 2002; 12: 3373-3377.
14. James TD, Sandanayake KRAS, Shinkai S,. Chiral discrimination of monosachrides using a fluorescent molecular sensor. Nature (London) 1995; 374: 345-347.
15. Cao H, Diaz DI, DiCesare D, Lakowicz JR, Heagy MD,. Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose. Org Lett 2002; 4: 1503-1505.
16. Trupp S, Schweitzer A, Mohr GJ,. A fluorescent water-soluble naphthalimide-based receptor for saccharides with highest sensitivity in the physiological pH range. Org Biomol Chem 2006; 4: 2965-2968.
17. Westmark PR, Gardiner SJ, Smith B,. Selective monosaccharide transport through lipid bilayers using boronic acid carriers. J Am Chem Soc 1996; 118: 11093-11100.
18. Riggs JA, Hossler KA, Smith BD, Karpa MJ, Griffin G, Duggan PJ,. Nucleotide carrier mixture with transport selectivity for ribonucleoside-5'-phosphates. Tetrahedron Lett 1996; 37: 6303-6306.
19. Draffin SP, Duggan PJ, Duggan SAM,. Highly fructose selective transport promoted by boronic acids based on a pentaerythritol core. Org Lett 2001; 3: 917-920.
20. Liu X, Hubbard J, Scouten W,. Synthesis and structural investigation of two potential boronate affinity chromatography ligands. J Organometallic Chem 1995; 493: 91-94.
21. Psotova J, Janiczek O,. Boronate affinity-chromatography and the applications. Chem Listy 1995; 89: 641-648.
22. Singhal RP, Ramamurthy B, Govindraj N, Sarwar Y,. New ligands for boronate affinity-chromatography-Synthesis and properties. J Chromatogr A 1991; 543: 17-38.
23. Fang H, Kaur G, Wang B,. Progress in boronic acidbased fluorescent glucose sensors. J Fluoresc 2004; 14: 481-489.
24. Di Cesare N, Pinto MR, Schanze KS, Lakowicz JR,. Saccharide detection based on the amplified fluorescence quenching of a water-soluble poly(phenylene ethynylene) by a boronic acid functionalized benzyl viologen derivative. Langmuir 2002; 18: 7785-7787.
25. Di Cesare N, Lakowicz JR,. Spectral properties of fluorophores combining the boronic acid group with electron donor or withdrawing groups. Implication in the development of fluorescence probes for saccharides. J Phys Chem A 2001; 105: 6834-6840.
26. Shoji E, Freund MS,. Potentiometric saccharide detection based on the pKa changes of poly(aniline boronic acid). J Am Chem Soc 2002; 124: 12486-12493.
27. Takahashi S, Anzai J,. Phenylboronic acid monolayer-modified electrodes sensitive to sugars. Langmuir 2005; 21: 5102-5107.
28. Yoon J, Czarnik AW,. Fluorescent chemosensors of carbohydrates. A means of chemically communicating the binding of polyols in water based on chelation-enhanced quenching. J Am Chem Soc 1992; 114: 5874-5875.
29. James TD, Sandanayake, KRAS. Chiral discrimination of monosaccharides using a fluorescent molecular sensor. Nature (London) 1995; 374: 345-347.
30. James TD, Sandanayake KRAS, Shinkai S,. Novel photoinduced electron transfer sensor for saccharides based on a boronic acid and an amine. Chem Commun 1994; 477-478.
31. Yan J, Fang H, Wang B,. Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design. Med Res Rev 2005; 25: 490-520.
32. Heller A,. Implanted electrochemical glucose sensors for the management of diabetes. Annu Rev Biomed Eng 1999; 1: 153-175.
33. Li H, Kang Z, Liu Y, Lee ST,. Carbon nanodots: Synthesis, properties and applications. J Mater Chem 2012; 22: 24230-24253.
34. Ding C, Zhu A, Tian Y,. Functional surface engineering of C-dots for fluorescent biosensing and in vivo bioimaging. Acc Chem Res 2014; 47: 20-30.
35. Wei WL, Xu C, Ren JS, Xu BL, Qu. XG,. Sensing metal ions with ion selectivity of a crown ether and fluorescence resonance energy transfer between carbon dots and graphene. Chem Commun 2012; 48: 1284-1286.
36. Bai WJ, Zheng HZ, Long YJ, Mao XJ, Gao M, Zhang LY,. A carbon dots-based fluorescence turn-on method for DNA determination. Anal Sci 2011; 27: 243-246.
37. Lin Z, Xue W, Chen H, Lin JM,. Peroxynitrous-acid-induced chemiluminescence of fluorescent carbon dots for nitrite sensing. Anal Chem 2011; 83: 8245-8251.
38. Zhao HX, Liu LQ, Liu ZD, Wang Y, Zhao XJ, Huang CZ,. Highly selective detection of phosphate in very complicated matrixes with an off-on fluorescent probe of europium-adjusted carbon dots. Chem Commun 2011; 47: 2604-2606.
39. Shi WB, Wang QL, Long YJ, Cheng ZL, Chen SH, Zheng HZ, Huang YM,. Carbon nanodots as peroxidase mimetics and their applications toglucose detection. Chem Commun 2011; 47: 6695-6697.
40. Dai H, Yang CP, Tong YJ, Xu GF, Ma XL, Lin YY, Chen GN,. Label-free electrochemiluminescent immunosensor for α-fetoprotein: Performance of nafion-carbon nanodots nanocomposite films as antibody carriers. Chem Commun 2012; 48: 3055-3057.
41. Xu XY, Ray R, Gu YL, Ploehn HJ, Gearheart L, Raker K, Scrivens WA,. Electrophoretic analysis and purification of fluorescent single-walled carbon nanotube fragments. J Am Chem Soc 2004; 126: 12736-12737.
42. Cao L, Wang X, Meziani MJ, Lu FS, Wang HF, Luo PJG, Lin Y, Harruff BA, Veca LM, Murray D, Xie SY, Sun YP,. Carbon dots for multiphoton bioimaging. J Am Chem Soc 2007; 129: 11318-11319.
43. Hu SL, Niu KY, Sun J, Yang J, Zhao NQ, Du XW,. One-step synthesis of fluorescent carbon nanoparticles by laser irradiation. J Mater Chem 2009; 19: 484-488.
44. Yang ST, Wang X, Wang H, Lu F, Luo PG, Cao L, Meziani MJ, Liu JH, Liu Y, Chen M, Huang Y, Sun YP,. Carbon dots as nontoxic and High-performance fluorescence imaging agents. J Phys Chem C 2009; 113: 18110-18114.
45. Zhao QL, Zhang ZL, Huang BH, Peng J, Zhang M, Pang DW,. Facile preparation of low cytotoxicity fluorescent carbon nanocrystals by electrooxidation of graphite. Chem Commun 2008; 5116-5118.
46. Zheng LY, Chi YW, Dong YQ, Lin JP, Wang BB,. Electrochemiluminescence of water-soluble carbon nanocrystals released electrochemically from graphite. J Am Chem Soc 2009; 131: 4564-4565.
47. Zhou JG, Booker C, Li RY, Zhou XT, Sham TK, Sun XL, Ding ZF,. An electrochemical avenue to blue luminescent nanocrystals from multiwalled carbon nanotubes (MWCNTs). J Am Chem Soc 2007; 129: 744-745.
48. Liu HP, Ye T, Mao CD,. Fluorescent carbon nanoparticles derived from candle soot. Angew Chem Int Ed 2007; 46: 6473-6475.
49. Tian L, Ghosh D, Chen W, Pradhan S, Chang X, Chen S,. Nanosized carbon particles from natural gas soot. Chem Mater 2009; 21: 2803-2809.
50. Dong YQ, Zhou NN, Lin XM, Lin JP, Chi YU, Chen G,. Extraction of electrochemiluminescent oxidized carbon quantum dots from activated carbon. Chem Mater 2010; 22: 5895-5899.
51. Zhai X, Zhang P, Liu C, Bai T, Li W, Dai L, Liu W,. Highly luminescent carbon nanodots by microwave-assisted pyrolysis. Chem Commun 2012; 48: 7955-7957.
52. Zi-An L, Jiang-Nan Z, Fen L, Lan Z, Cai Z, Chen G,. Synthesis of magnetic nanoparticles with immobilized aminophenylboronic acid for selective capture of glycoproteins. J Mater Chem 2011; 21: 518-524.
53. Jaiswal A, Ghosh SS, Chattopadhyay A,. One step synthesis of C-dots by microwave mediated caramelization of poly(ethylene glycol). Chem Commun 2012; 48: 407-409.
54. Shen P, Xia Y,. Synthesis-modification integration: One-step fabrication of boronic acid functionalized carbon dots for fluorescent blood sugar sensing. Anal Chem 2014; 86: 5323-5329.
55. Yang Z, Wang M, Yong AM, Wong SY, Zhang X, Tan H, Chang AY, Li X, Wang J,. Intrinsically fluorescent carbon dots with tunable emission derived from hydrothermal treatment of glucose in the presence of monopotassium phosphate. Chem Commun 2011; 47: 11615-11617.
56. Zhu S, Meng Q, Wang L, Zhang J, Song Y, Jin H, Zhang K, Sun H, Wang H, Yang B,. Highly photoluminescent carbon dots for multicolor patterning, sensors, and bioimaging. Angew Chem Int Ed 2013; 52: 3953-3957.
57. Cordes DB, Gamsey S, Singaram B,. Fluorescent quantum dots with boronic acid substituted viologens to sense glucose in aqueous solution. Angew Chem Int Ed 2006; 45: 3829-3832.
58. Egawa Y, Seki T, Takahashib S, Anzai J,. Electrochemical and optical sugar sensors based on phenylboronic acid and its derivatives. Mater Sci Eng C 2011; 31: 1257-1264.