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(12) United States Patent (10) Patent No.: US 8,877,454 B2 Nishimura Et Al

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(12) United States Patent (10) Patent No.: US 8,877,454 B2 Nishimura Et Al US008877454B2 (12) United States Patent (10) Patent No.: US 8,877,454 B2 Nishimura et al. (45) Date of Patent: Nov. 4, 2014 (54) APPARATUS FOR AUTO-PRETREATING (56) References Cited SUGAR CHAN FOREIGN PATENT DOCUMENTS (75) Inventors: Shinichiro Nishimura, Hokkaido (JP); Yasuro Shinohara, Hokkaido (JP); JP 200529 1958 10/2005 Yoshiaki Miura, Hokkaido (JP): WO WO-2006.112771 10, 2006 Hiroshi Yamazaki, Tokyo (JP); Michio WO WO2007099856 9, 2007 Horiuchi, Tokyo (JP); Hiroaki Motoki, OTHER PUBLICATIONS Tokyo (JP); Toshiharu Kuroda, Tokyo Uematsu et al. “High throughput quantitative glycomics and (JP); Yoko Kita, Hyogo (JP); Mika glycoform-focused proteomics of murine dermis and epidermis'. Nakano, Hyogo (JP) Molecular & Cellular Proteomics, 2005, 4:1977-1989.* Shimaoka et al "One-pot Solid-phase glycoblotting and probing by (73) Assignees: National University Corporation transoximization for high-throughput glycomics and glycoproteom Hokkaido University, Sapporo-Shi, ics', Chem. Eur, J., 2007, 13:1664-1673.* Schlosser etal "Combination of solid-phase affinity capture on mag Hokkaido (JP); Shionogi & Co., Ltd., netic beads and mass spectrometry to study non-covalent interac Chuo-Ku, Osaka (JP) tions: example of minor groove binding drugs'. Rapid Communica tions in Mass Spectrometry, 2005, 19:3307-3314.* (*) Notice: Subject to any disclaimer, the term of this Powell et al. "Stabilization of sialic acids in N-linked oligosac patent is extended or adjusted under 35 charides and gangliosides for analysis by positive ion matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun, in U.S.C. 154(b) by 926 days. mass spectrometry, 1996, 10:1027-1032.* Kita et al., “Quantitative glycomics of human whole serum (21) Appl. No.: 12/681,573 glycoproteins based on the standardized protocol for liberating N-glycans.” Molecular and Cellular Proteomics, 6(8): 1437-1445 (22) PCT Fled : Oct. 3, 2008 (2007). Miura et al., “Rapid and simple solid-phase esterification of Sialic PCT NO.: PCT/UP2O08/O68111 acid residues for quantitative glycomics by mass spectrometry.” (86) Chemistry A European Journal, 13(17);4797-4804 (2007). S371 (c)(1), Yu et al., "A rapid sample preparation method for mass spectrometric characterization of N-Linked glycans. Rapid Communications in (2), (4) Date: Dec. 3, 2010 Mass Spectrometry, 19(16):2331-2336 (2005). Nishimura et al., “High-throughput protein glycomics: Combined (87) PCT Pub. No.: WO2O09/044900 Use of Chemoselective Glycoblotting and MALDI-TOF/TOF Mass PCT Pub. Date: Apr. 9, 2009 Spectrometry.” Angew. Chem. Int. Ed., 44(1):91-96 (2005). (65) Prior Publication Data * cited by examiner US 2011/011 1443 A1 May 12, 2011 Primary Examiner — Bin Shen (74) Attorney, Agent, or Firm — Ropes & Gray LLP. James (30) Foreign Application Priority Data F. Haley, Jr.; Brian M. Gummow Oct. 5, 2007 (JP) ................................. 2007-26268O (57) ABSTRACT Oct. 5, 2007 (JP) ................................. 2007-262.771 To provide an autoanalyzer for analyzing a Sugar chain con tained in a biological sample, in particular, serum. Namely, it (51) Int. C. is intended to provide a method of analyzing a Sugar chain in (2006.01) a sample, which comprises the following steps: A) the Sugar GOIN33/68 (2006.01) chain-releasing step of releasing the Sugar chain in the GOIN3O/72 (2006.01) sample; B) the detection sample-preparing step of preparing HOIJ 49/00 (2006.01) the released Sugar chain for detection; and, in the case of (52) U.S. C. conducting mass spectrometry using a plate, C) the step of CPC ....... GOIN33/6848 (2013.01); G0IN 30/7233 forming a plate for the mass spectrometry having the captured (2013.01); G0IN 2400/00 (2013.01); HOIJ Sugar chain dotted thereon which comprises the step of pro 49/00 (2013.01) viding the tagged Sugar chain sample solution obtained in the USPC .... step B) on a collection plate; and, if required, the step of - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 435/23: 435/4; 435/22 conducting an operation in a solid phase Support-enclosed (58) Field of Classification Search plate to form the plate for mass spectrometry; and D) the step CPC ....... - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - GO1N3O/7233 of analyzing the Sugar chain to be assayed. USPC .... - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 435/4, 22, 23 See applic ation file for complete search history. 4 Claims, 42 Drawing Sheets U.S. Patent Nov. 4, 2014 Sheet 1 of 42 US 8,877,454 B2 Fig.1 ~~~~ ---a------------- pr--- U.S. Patent Nov. 4, 2014 Sheet 2 of 42 US 8,877,454 B2 Fig.1A 8 sixt{ysis - Flow chart isiari.XXXXXXXXXXXX errarer aaasaxxxxaass rxxxxx xxxxv, es. a saaSaaS saaaaaaaaaaaaaaaaaaaaaaa - ----------------- U.S. Patent Nov. 4, 2014 Sheet 3 of 42 US 8,877,454 B2 Fig.1B 16 July { g Maxxx swax &M Sa ------------------W------- SSSSSSSS s U.S. Patent Nov. 4, 2014 US 8,877,454 B2 Fig.1C { ~~~~}~~~~ž&~~~~~~~~ 8. * * ****&# | } K. 8 23 S$ ... 8 see:& U.S. Patent Nov. 4, 2014 Sheet 6 of 42 US 8,877,454 B2 U.S. Patent Nov. 4, 2014 Sheet 7 of 42 US 8,877,454 B2 Fig.1F surrors surrors surrors surrors surrors are surrors surrors as U.S. Patent Nov. 4, 2014 Sheet 8 of 42 US 8,877,454 B2 Fig.2 f ten-o- -------ee-er-------- - -- ---- -----" l. 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Yes 16) 300 pil injection of MeOH Suction disposal Third time? Wiping bottom Suction disposal Third time? eS 22) 50 it injection of 50 mMDTT (2) Heat retention 60°C, 5 minutes Q) Heat retention, room temperature, 15 minutes G) or (5) Suction recovery plate for recovery #1 Heat retention 100C, END (5) U.S. Patent Nov. 4, 2014 Sheet 13 of 42 US 8,877,454 B2 Fig.7 Injection from plate for recovery #1 Injection to MALDI plate to MALDPLATE after SPE treatment Plate for mixindi:1 Plate for mixing #2 (6) 2 8) 20 pil injection of free sugar 23) 2 pil injection of free sugar chain-containind filtrate chain-containing filtrate 30) 420 ul injection of the mixed solution to SPE plate 32) 20 t liniection of 10% ACN Suction recovery () olate for recoverV #2 Heat retention 100C, END Injection from plate for recovery #2 to MALDI plate (after SPE treatment) Plate for mixing #2 (6) 23)2 pull injection of free sugar chain-containind filtrate 24) 2 pil injection of MALDI matrix (6) 25) 2 pil injection of MALDI plate (2) U.S. Patent Nov. 4, 2014 Sheet 15 of 42 US 8,877,454 B2 Fig.8A Flow chart for BlotGlycoABC U.S. Patent Sheet 16 of 42 US 8,877,454 B2 Fig.8B s: Arar Maxxar &as s 3. ... wwww.www. s : acas U.S. Patent Nov. 4, 2014 Sheet 17 of 42 US 8,877,454 B2 rararuawa-336 s N. M M M M M second time SWXYYXXxxxx is Third time 530 as s s N &c. Third S U.S. Patent Nov. 4, 2014 Sheet 18 of 42 US 8,877,454 B2 r Third r r r r r time r r r r r r 9 wwwwwwwwwwwwwww. r r r r r r r r r r r r r r r s 3. g 5 sa S. as . Y. s or-i- - 49-35. -----------s 3. Third times 3. (35i S.S. -- -e^^^^^^^^ 3 As xl s w w V r ax. u s warrar xŠssssssssssssssssssssss M\\\\\\\\\\\\\\\\\\\SS------------------------MS&\\\\\\"w Swxxxxxx xxxxxxxxxxxxxxxxxxxxxxxS. Y axaaaaaaaaaaasa O “ time r r r r r r &aaaaaaaaaaaaaaaaaaa ax --. s I'llxy: 362SS ox: r s W r (369 rease s U.S. Patent Nov. 4, 2014 Sheet 19 of 42 US 8,877,454 B2 Fig.8E - S. www.www.www.www. ? ºzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzz$2z r w w w s\ss w w w 'ssicsSS-Xxxx:S U.S. Patent Nov. 4, 2014 Sheet 20 of 42 US 8,877,454 B2 Fig.8F rrrrrrrrr's Szil.........: · Saaaaasaaaaaa. ;&':; ? zzzzzzzzzzzzzzzzzzzzzºzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzz ?zzzzzzzzzzzzzzzzzzzzzzzz... Th ird time :,:?zzzzzzzzzzzzzzºzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzz U.S. Patent Nov. 4, 2014 Sheet 21 of 42 US 8,877,454 B2 Fig.9 <Position and movement> 8 (1) cooling --- Plate for mixing 1 reagent : --------- --'ay (1) Heating/cooling- - - - - 2.I.Y.-----Base suction : 8------Baseisution 92---Reagent position (PCR ------ -> disposal position disposal position traw 1 Lplate) 20-90C (filterplate) (SPE plate) A.
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