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(12) United States Patent (10) Patent No.: US 9.222,913 B2 Deschamps Et Al

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(12) United States Patent (10) Patent No.: US 9.222,913 B2 Deschamps Et Al US009222913B2 (12) United States Patent (10) Patent No.: US 9.222,913 B2 Deschamps et al. (45) Date of Patent: Dec. 29, 2015 (54) ANALYSIS AND ASSAY OF GLYCATED FOREIGN PATENT DOCUMENTS HAEMOGLOBINS BY CAPILLARY ELECTROPHORESIS, BUFFER EP 1659 398 A1 5, 2006 COMPOSITIONS AND KITS FOR JP 6-5O2244 3, 1994 CAPLLARY ELECTROPHORESS (Continued) (75) Inventors: Gérald Deschamps, Ury (FR); Frédéric OTHER PUBLICATIONS Robert, Mennecy (FR); Denis Simonin, Evry (FR) Margo P. Cohen, Rex S. Clements, Measuring Glycated Proteins: Clinical and Methodological Aspects, Diabetes Technology & Thera (73) Assignee: SEBIA, Lisses (FR) peutics, vol. 1, No. 1, pp. 57-70 (1996).* (*) Notice: Subject to any disclaimer, the term of this (Continued) patent is extended or adjusted under 35 U.S.C. 154(b) by 199 days. Primary Examiner — J. Christopher Ball (21) Appl. No.: 12/827,795 Assistant Examiner — Maris R. Kessel (74) Attorney, Agent, or Firm — Birch, Stewart, Kolasch & (22) Filed: Jun. 30, 2010 Birch, LLP (65) Prior Publication Data US 2011 FOOOO788A1 Jan. 6, 2011 (57) ABSTRACT The invention relates to a method for analysis by capillary (30) Foreign Application Priority Data electrophoresis of glycated haemoglobins comprising at least Jul. 1, 2009 (FR) ...................................... O9 O322O one globin chain comprising a glucose residue bound to the amino acid in the N-terminal position, contained in a biologi (51) Int. Cl. cal sample, said method comprising using a buffer composi G0IN 27/447 (2006.01) tion comprising at least one compound which is capable of (52) U.S. Cl. specifically complexing glucose residues of one or several CPC ................................ G0IN 2744747 (2013.01) glycated haemoglobin(s) and of providing said glycated hae moglobin(s)with several negative electric charges at an alka (58) Field of Classification Search line pH. By way of example this compound may be 3,4- or CPC ................ G01N 27/26: G01N 27/447; G01N 3,5-dicarboxyphenylboronic acid, preferably 3,5-dicarbox 27/44747; C07F 5/02 yphenylboronic acid. Said method may in particular be used USPC .................................. 204/450 468, 600-616 to separate and assay haemoglobin HbA present in a bio See application file for complete search history. logical sample optionally comprising other haemoglobins, in (56) References Cited particular other minor fractions. The invention also concerns buffer compositions for use in said analysis, as well as kits for U.S. PATENT DOCUMENTS the analysis and for the assay of glycated haemoglobins by capillary electrophoresis. 4,861,728 A * 8/1989 Wagner ......................... 436,501 5,120,413 A * 6/1992 Chen et al. .................... 204,451 (Continued) 15 Claims, 16 Drawing Sheets DAD1 D, Sig=415,8Ref=off (2101101A1C00011.D) DAD1 D, Sig=415,8Ref=off (2101101A1C00003.D) DAD1 D, Sig=415,8Ref=off (2101101A1C00007.D) mAU AO 80 3,4-Dicarboxyphenylboronic Acid A1a, A1b 10 12 14 16 18 min US 9.222,913 B2 Page 2 (56) References Cited Song et al., Sensors and Actuators B: Chemical, "Boronic acid modified thin film interface for specific binding of glycated hemo U.S. PATENT DOCUMENTS globin (HbAlc) and electrochemical biosensing, vol. 140, pp. 233 239, (2009). 5,599.433 A * 2, 1997 Keo et al. ...................... 204,451 5,631,364 A 5/1997 Sundrehagen et al. 2002/0173044 A1 11/2002 Pachl et al. Chen et al., “Practical Method for the Synthesis of Substituted 2010.018711.0 A1 7/2010 Tanaka et al. Phenylboronic Acids”, Journal of Sichuan Normal University (Natu ral Science), vol. 23, No. 5 (2000) pp. 511-512. FOREIGN PATENT DOCUMENTS Hall, D.G., Boronic Acids: Preparation and Applications in Organic WO WO92,08984 5, 1992 Synthesis and Medicine (e.d. D.G. Hall), Wiley-VCHVerlag GmbH WO WO96,22524 A1 T 1996 WO WO98,40750 A1 9, 1998 & Co. KGaA. Weinheim, FRG, doi:10.1002/3527606548.ch1, pp. WO WO 2008/O29685 A1 3, 2008 1-57 and 79-80 only. WO WO 2008/O29885 A1 3, 2008 Menard et al., “Quantitative Determination of Glycosolated Hemo OTHER PUBLICATIONS globin A1 by Agar Gel Electrophoresis”. Clin. Chem, vol. 26, No. 11 (1980) pp. 1598-1602. French Preliminary Search Report mailed on Feb. 9, 2010 for the corresponding Priority French application No. 0903220. * cited by examiner U.S. Patent Dec. 29, 2015 Sheet 1 of 16 US 9.222,913 B2 Current Electropherogram(s) DAD1E,Sig=415,8 Ref-off (111207A1C00001.D) mAU 400 - 300 - 200 - 100 - 20 go 4o so in U.S. Patent Dec. 29, 2015 Sheet 2 of 16 US 9.222,913 B2 Current Electropherogram(s) DAD, E,Sig=415,8 Ref-off (11 1207W1C00007.D) *DAD1 E. Sig=415,8Ref=off (111207W1C00008.D) 150 - 125 - 100 75 25 - 30 325' 35 375 40 42.5 45 min Figure 2 U.S. Patent Dec. 29, 2015 Sheet 3 of 16 US 9.222,913 B2 Current Electropherogram(s) DAD1E,Sig=415,8Ref=off (131207W1C00003.D) *DAD1 E,Sig=415,8 Ref-off (131207W1C00004.D) mAU 175 150 125 100 75 50 25 - U.S. Patent Dec. 29, 2015 Sheet 4 of 16 US 9,222,913 B2 Current Electropherogram(s) DAD, E,Sig=415.8 Ref-off (131207A1C00005.D) *DAL)1 Esig=415,8 Ref-off (131207W1C00006.D) mAU - 175 150 125 100 75 so 25 2 2s so 32 34 36 38 min Figure 4 U.S. Patent Dec. 29, 2015 Sheet 5 of 16 US 9,222,913 B2 Current Electropherogram(s) - - - DAD1 E,Sig=415,8Ref=off (131207W1C00007.D) *DAD1E,Sig=415,8 Ref-off (131207W1C00008.D) mAU 140 120 100 . 80 - 60 40 20 - A1a, A1b 26 28 30 32 34 36 .38 min U.S. Patent Dec. 29, 2015 Sheet 6 of 16 US 9.222,913 B2 Current Electropherogram(s) DAD1 E,Sig=415,8 Ref-off (1312O7\A1C00009.D) *DAD1E,Sig=415,8 Ref-off (131207A1C0001O.D) mAU 140 120 100 80 60 40. 20 A1a, A1b A0 A1C c r s states 26 28 30 32 34 36 38 min Figure 6 U.S. Patent Dec. 29, 2015 Sheet 7 of 16 US 9.222,913 B2 Current Electropherogram(s) DAD1E,Sig=415.8 Ref-off (1911 07W1C00007.D) *DAD1E,Sig=415.8 Ref-off (1911 07W1C00008.D) mAU 175. 150 125 100 75 - 50 - 25 - is 20 22 24, 26 28 min U.S. Patent Dec. 29, 2015 Sheet 8 of 16 US 9.222,913 B2 DAD1 D, Sig=415.8 Ref-off (21 0110\a1C00010.D) DAD1 D, Sig=415,8 Ref-off (21011OW1C00002.D) DAD1 D, Sig-A15,8Ref-off (21011 OW1C00006.D) mAU 80-3,5-Dicarboxyphenylboronic Acid 0 2 4 6 8 10 12 14 16 18 min Figure 8 DAD1 D, Sig=415,8. Ref-off (21011OW1C00011.D) DAD1 D, Sig=415,8Ref=off (2101101A1C00003.D) DAD1 D, Sig=415,8Ref=off (2101101A1C00007.D) mAU AO 80 . 3,4-Dicarboxyphenylboronic Acid U.S. Patent Dec. 29, 2015 Sheet 9 of 16 US 9.222,913 B2 A1c Max O.D.: 0.0291 -T | ? A 2. it.a s= a-&SAs, assesseeast&--- 54O 26O (Seconds) Figure 10 U.S. Patent Dec. 29, 2015 Sheet 10 of 16 US 9.222,913 B2 Max O. D. : 0.1961 300 210 (Seconds) Max O. D. : 0.1961 Hib AC \ Hb A2 sea-arnawk 4s-led-N-a- 54 O' 260" (Seconds) Figure 11 U.S. Patent Dec. 29, 2015 Sheet 11 of 16 US 9.222,913 B2 (3,5-dCPBA) At , t Art Ao At/t at Al-tAo?t Ao (min) 0.16. 0.12. > i 0.08. 0.04 O 20 40 60 80 100 120 140 Concentration of 3,5-dCPBA in buffer (mM) Figure 12 U.S. Patent Dec. 29, 2015 Sheet 12 of 16 US 9.222,913 B2 n Hb E i Hb A1c \\ | Hit A2 3&s. -A- Cl-N-a --V sa-awaasaa-rr 54 O' 260" (Seconds Figure 13 Max O.D. : 0.0561 Hb A A H S Hb.." F N C+A2 f V \ -as -a asHb . -(N-ace. A1c - 2 i. A-Salis A 4|| - 54.0" 260" (Seconds) Figure 14 U.S. Patent Dec. 29, 2015 Sheet 13 of 16 US 9,222,913 B2 - A - A2 540" m 260 it (Seconds) Figure 15 Max O. D. : 0.2301 Hb A 3 - A2 Hbac Sw is A 540". 260 (Seconds) Figure 16 U.S. Patent Dec. 29, 2015 Sheet 14 of 16 US 9.222,913 B2 sample % A.-HPlc T Gross values 4A - Ec s 55 m corrected values: 1 2.W y = 0.9554x + 0.272s 1 O 10 R42 =- 0.9904 af 8 raw values SS 6 2. raw values: a corrected Values 4. y = 1.2532X - 2.8946 R2 = 0.9898 2 O 0 2 4 6 8 10 12 14 % A1C HPLC Figure 17 U.S. Patent Dec. 29, 2015 Sheet 15 of 16 US 9.222,913 B2 HYDRAGEL 15 Hb A1C 1 2 3 4 5 6 7 8 9 Figure 18A Glucose Concentration (g/L) 96 A1c gel % A1c EC O (reference) 4.1 4.2 1 4.5 5 4.6 4.3 10 5.3 4.3 2O 7.8 4.1 30 8.6 4.1 50 14.8 4.1 Figure 18C U.S. Patent Dec. 29, 2015 Sheet 16 of 16 US 9.222,913 B2 Added glucose Ogil Added glucose: 20 gift. SbA. D. O. Max: 0.249 D. Q. Max: 0.274 HbAlc 3, \ ibR2 SibAie 3 \ BibA2 e-A-si-. ...-- o-A-est. ---4----~~ S& Seconds 26 S$8 Secords 2 & 3 riaemoglobin eleciophoresis Haemoglobin eiectrophoresis Added glucose 5 gfi.
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