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(12) United States Patent (10) Patent No.: US 9,714,897 B2 Kim Et Al

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(12) United States Patent (10) Patent No.: US 9,714,897 B2 Kim Et Al USOO9714897B2 (12) United States Patent (10) Patent No.: US 9,714,897 B2 Kim et al. (45) Date of Patent: Jul. 25, 2017 (54) HYDROGEL PARTICLES WITH TUNABLE (58) Field of Classification Search OPTICAL PROPERTIES AND METHODS None FOR USING THE SAME See application file for complete search history. (71) Applicant: SLINGSHOT BIOSCIENCES, INC., Emeryville, CA (US) (56) References Cited U.S. PATENT DOCUMENTS (72) Inventors: Jeffrey Kim, Berkeley, CA (US); Oliver Liu, San Francisco, CA (US); 4,704,891 A 11/1987 Recktenwald et al. Jeremy Agresti, El Cerrito, CA (US); 4,774,189 A 9, 1988 Schwartz Anh Tuan Nguyen, San Jose, CA (US) (Continued) (73) Assignee: Slingshot Biosciences, Inc., Emeryville, FOREIGN PATENT DOCUMENTS CA (US) WO 89.10566 11, 1989 (*) Notice: Subject to any disclaimer, the term of this WO OOO8212 2, 2000 patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. OTHER PUBLICATIONS (21) Appl. No.: 15/018,769 Ugelstad, J. and Mork, P.C., “Swelling of Oligomer-Polymer Par (22) Filed: Feb. 8, 2016 ticles. New Methods of Preparation of Emulsions and Polymer Dispersions.” Advances in Colloid and Interface Sciences, 13 (65) Prior Publication Data (1980), pp. 101-140. US 2016/O25885.6 A1 Sep. 8, 2016 (Continued) Related U.S. Application Data Primary Examiner — Robert Xu (60) Provisional application No. 62/114,004, filed on Feb. (74) Attorney, Agent, or Firm — Cooley LLP. Nathan W. 9, 2015, provisional application No. 62/184,192, filed Poulsen on Jun. 24, 2015. (57) ABSTRACT (51) Int. C. Hydrogel particles and their use in cytometic applications GOIN 3L/00 (2006.01) are described. The hydrogel particles described herein are GOIN 15/10 (2006.01) selectively tunable to have at least one optical property (Continued) Substantially similar to the at least one optical property of a (52) U.S. C. target cell. In this regard, the hydrogel particles provided CPC ........... G0IN 15/1012 (2013.01): CI2O I/04 herein in one aspect, are used as a calibration reagent for the (2013.01); G0IN I/28 (2013.01); G0IN detection of a target cell in a sample. 15/1434 (2013.01); (Continued) 26 Claims, 13 Drawing Sheets A) CE). NE C-3 *CE) flexible ibrary of parameters US 9,714,897 B2 Page 2 (51) Int. Cl. FOREIGN PATENT DOCUMENTS CI2O I/04 (2006.01) WO O 132829 5, 2001 GOIN I/28 (2006.01) WO 03000014 A2 1/2003 GOIN 15/14 (2006.01) WO 2008115653 A2 9, 2008 GOIN 1.5/OO (2006.01) WO 2010O25988 A1 3f2010 (52) U.S. Cl. WO 20110984O7 A1 8, 2011 CPC. G0IN 15/1459 (2013.01); G0IN 2001/2893 WO 2012033811 A1 3f2012 (2013.01); G0IN 2015/0065 (2013.01); G0IN 2015/1006 (2013.01); G0IN 2015/1018 OTHER PUBLICATIONS (2013.01); G0IN 2015/149 (2013.01) Lee, Ki-Chang and Lee, Sang-Yun, “Preparation of Highly Cross Linked, Monodisperse Poly(methyl methacrylate) Microspheres by (56) References Cited Dispersion Polymerization; Part II Semi-continuation Processes.” U.S. PATENT DOCUMENTS Macromolecular Research, vol. 16, No. 4, (2008) pp. 293-302. Jin-Woong Kim, Andrew S. Utada, Alberto Fernandez-Nieves, 5,093,234 A 3, 1992 Schwartz Zhibing Hu, and David A.Weitz, "Fabrication of Monodisperse Gel 5,283,079 A 2, 1994 Wang et al. Shells and Functional Microgels in Microfluidic Devices.” Angew. 5,395,688 A 3, 1995 Wang et al. Chem. Int. Ed. (2007) 46, pp. 1819-1822. 5,820,879 A 10, 1998 Fernandez et al. International Search Report and Written Opinion for International 6,586, 176 B1 T/2003 Trnovsky et al. Patent Application No. PCT/US2016/017029, mailed May 19, 6,806,058 B2 10, 2004 Jesperson et al. 2016. RE39,542 E 4, 2007 Jain et al. Patanarut, Alexis, et al. “Synthesis and characterization of hydrogel 7,314,584 B2 1, 2008 Tsutsui et al. particles containing Cibacron Blue F3G-A.” Colloids and Surfaces 8,030,095 B2 10, 2011 Harriman A: Physicochemical and Engineering Aspects 362. 1 (2010): 8-19. 8, 187,885 B2 5, 2012 Purvis, Jr. Luchini, Alessandra, et al. “Smart hydrogel particles: biomarker 8,415,173 B2 4, 2013 Harriman harvesting: one-step affinity purification, size exclusion, and pro 8,704,158 B2 4, 2014 Haberstroh et al. tection against degradation.” Nano letters 8.1 (2008): 350-361. 2003/O132538 A1 T/2003 Chandler Bele, Marjan, Olavi Siiman, and Egon Matijevic. “Preparation and 2005/0176056 A1 8, 2005 Sammak et al. flow cytometry of uniform silica-fluorescent dye microspheres.” 2006/024.0560 A1 10, 2006 Bakker et al. Journal of colloid and interface science 254.2 (2002): 274-282. 2007/0054119 A1 3, 2007 Garstecki et al. Proff, Guenther, et al. "Potential of label-free detection in high 2007/025.9415 A1 11/2007 Zigova et al. content-screening applications.” Journal of Chromatography A 2009, O14896.1 A1 6, 2009 Luchini et al. 2010/023.4252 A1 9, 2010 Moradi-Araghi et al. 1161.1 (2007): 2-8. 2010/028.5594 A1* 11, 2010 Purvis, Jr. .......... GON 15, 1012 Hasegawa, Urara, et al. “Nanogel-quantum dot hybrid nanoparticles 436/10 for live cell imaging.” Biochemical and biophysical research com 2011/0318820 12/2011 Hinz et al. munication 331.4 (2005): 917-921. 2012/0309651 12, 2012 Pregibon .............. C12O 1/6816 Tomczak, Nikodem, et al. “Designer polymer-quantum dot archi 506/16 tectures. Progress in Polymer Science 34.5 (2009): 393-430. 2013/O177973 A1 T/2013 Kondo 2015 O1771.15 A1 6, 2015 Kim et al. * cited by examiner U.S. Patent Jul. 25, 2017 Sheet 1 of 13 US 9,714.897 B2 A) Side Scatter Detector (cellular Complexity) Excitation Forward Scatter light Detector Source B) Side Scatter Detector (cellular complexity) Excitation ward Scatter light Detector U.S. Patent Jul. 25, 2017 Sheet 2 of 13 US 9,714.897 B2 Z‘61– (-)||OOO@? U.S. Patent Jul. 25, 2017 Sheet 3 of 13 US 9,714.897 B2 U.S. Patent US 9,714.897 B2 C)\/ 3248 U.S. Patent Jul. 25, 2017 Sheet S of 13 US 9,714.897 B2 4. 120 3: 70 in nozzie > 100 m nozzle f 110 S. C 3. OO O 2 3O 40 50 s Particiefce diameter Fig. 5 U.S. Patent Jul. 25, 2017 Sheet 6 of 13 US 9,714.897 B2 :?!!!!!!? Fig. 6 U.S. Patent Jul. 25, 2017 Sheet 8 of 13 US 9,714.897 B2 Fig. 8 U.S. Patent Jul. 25, 2017 Sheet 9 of 13 US 9,714.897 B2 Fig. 9 U.S. Patent Jul. 25, 2017 Sheet 10 of 13 US 9,714.897 B2 unable pist: (co)ronomers, chemically Compatible side groups (e.g., aliyanine), biological materia (DNA/RNA organelies whole ceilis), nanoparticles (general side scatter material) artice fortatio: Microfluidic process as outlined or equivalent (spray dispersion, solid-state precipitation, co-fow, etc.) input tuningf optimization Output lateria: Polymerized particie with optional side groups (see ther of pierce catalog for exampies) to allow for secondary labeing with furophores, proteins, Sugars, etc., and generally any chemically compatible materia. eaStreet: Analytical measurement using flow cytometry, microscopy, Cei imaging, coiter Counting, Fig. 10 U.S. Patent Jul. 25, 2017 Sheet 11 of 13 US 9,714.897 B2 & S: 33 ge is x 8. is t C) arra X ana years O x vm . ver O) - a. ara ? ceyX CC U.S. Patent Jul. 25, 2017 Sheet 12 of 13 US 9,714.897 B2 U.S. Patent Jul. 25, 2017 Sheet 13 of 13 US 9,714.897 B2 A. B. S 595-33 color lymph is E04 15105-1 Gate: No Gating Gate. No Gating & grantocyte & gratocyte xx (, is xx 8.2%. s & ---. s 3 SS <g 3w- notcyte: &<g was& Soocyteocvt 3 c. .% 3 c. 88s & * * *.x. & 's lymphocyte : 6.3% { 2,000,000 4,000,000 5,694,883 2,000,000 48,328 SC-A FSC-A C. : Gate.02 No Gating gratiocyte is 5.7%. ; 3. 2,000,000 4,8,328 SC-A Fig. 13 US 9,714,897 B2 1. 2 HYDROGEL PARTICLES WITH TUNABLE method further comprises measuring the at least one optical OPTICAL PROPERTIES AND METHODS property of the hydrogel particle using the cytometric FOR USING THE SAME device. A sample comprising a plurality of cells is inserted into the cytometric device, and the at least one optical CROSS REFERENCE TO RELATED property of individual cells of the plurality are measured. APPLICATIONS Finally, a determination is made, based on the optical property measurement, whether the target cell or plurality This application claims priority from U.S. Provisional thereof is present in the sample. Application No. 62/114,004, filed Feb. 9, 2015 and U.S. In one embodiment of the methods provided herein, the Provisional Application No. 62/184,192, filed Jun. 24, 2015, 10 hydrogel particle comprises a biodegradable monomer. In a the disclosure of each of which is incorporated by reference further embodiment, the biodegradable monomer is a mono herein in their entireties. saccharide, disaccharide, polysaccharide, peptide, protein, or protein domain. In even a further embodiment, the BACKGROUND OF THE INVENTION biodegradable monomer is functionalized with acrylamide 15 or acrylate. Flow cytometry is a technique that allows for the rapid separation, counting, and characterization of individual cells BRIEF DESCRIPTION OF THE FIGURES and is routinely used in clinical and laboratory settings for a variety of applications. The technology relies on directing FIG. 1 illustrates the optical properties of disclosed a beam of light onto a hydrodynamically-focused stream of hydrogel particles compared to polystyrene beads.
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