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(12) Patent Application Publication (10) Pub. No.: US 2016/0122416 A1 Gee Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2016/0122416 A1 Gee Et Al US 2016O122416A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0122416 A1 Gee et al. (43) Pub. Date: May 5, 2016 (54) ANTIBODY COMPOSITION AND BUFFER Publication Classification SYSTEM THEREFOR (51) Int. Cl. (71) Applicant: INNOVA BIOSCIENCES LTD, C07K 16/00 (2006.01) Babraham, Cambridge (GB) C07K L/4 (2006.01) C07K L/3 (2006.01) (72) Inventors: Nicolas Steven Gee, Cambridge (GB); (52) U.S. Cl. Nicolas Steven Gee, Cambridge (GB) CPC. C07K 16/00 (2013.01); C07K 1/13 (2013.01); (21) Appl. No.: 14/894,828 C07K I/14 (2013.01) (22) PCT Filed: May 30, 2014 (57) ABSTRACT A method for conjugating an isolated antibody to a label or (86). PCT No.: PCT/EP2014/061281 derivatisation reagent, which method comprises contacting S371 (c)(1), the antibody with an activated label or activated derivatisation (2) Date: Nov.30, 2015 reagent, or contacting the antibody with the label or derivati sation reagent in the presence of an antibody conjugation (30) Foreign Application Priority Data reagent, in a buffer system which comprises a monocarboxy lic acid buffer compound other than glycine, bearing an amine May 31, 2013 (GB) ................................... 1309759.7 Substituent at the alpha or beta position. Patent Application Publication May 5, 2016 Sheet 1 of 6 US 2016/O122416 A1 Figure 1 5OOOO 4OOOO 23 OO OO OO OO OOOO 1OO 1000 Conjugate dilution factor Patent Application Publication May 5, 2016 Sheet 2 of 6 US 2016/O122416 A1 Figure 2 50000 A.OOOO 3OOOO 2OOOO 10000 100 OOO Conjugate dilution Patent Application Publication May 5, 2016 Sheet 3 of 6 US 2016/O122416 A1 Figure 3 Patent Application Publication May 5, 2016 Sheet 4 of 6 US 2016/O122416 A1 Figure 4 Patent Application Publication May 5, 2016 Sheet 5 of 6 US 2016/O122416 A1 Figure 5 Minutes Patent Application Publication May 5, 2016 Sheet 6 of 6 US 2016/O122416 A1 Figure 6 1 O O 50 100 150 200 u of CHES buffer added US 2016/01 22416 A1 May 5, 2016 ANTIBODY COMPOSITION AND BUFFER labelled, as buffers used to elute affinity columns often cause SYSTEM THEREFOR severe interference in labelling reactions. 0008 Labels of all types are most commonly attached to FIELD OF THE INVENTION lysine residues on antibody molecules. For example, NHS esters of organic fluorescent dyes and the popular isothiocy 0001. The present invention relates to an antibody compo anate derivative of fluorescein (FITC) react with lysine resi sition for use in a conjugation reaction, an antibody isolation dues. While other conjugation chemistries (e.g. thiol-male kit, a method for conjugating an isolated antibody to a label imide) may not obviously involve lysine residues, they are and a buffer system for use in Such a composition, kit or nonetheless nearly always dependent on lysine modification method. at an earlier step in the conjugation process. For example, lysine-directed heterobifunctional NHS ester derivatisation BACKGROUND OF THE INVENTION reagents are commonly used to introduce maleimides and a variety of other functional groups (e.g. protected thiols, 0002 All antibodies are made initially in a crude form azides, iodoacetyl groups) into protein molecules. Carbodi (e.g. immune serum, ascites fluid, hybridoma tissue culture imides, which are used to conjugate antibodies to carboxy Supernatant). Before use in many basic research and diagnos lated microparticles or nanoparticles, involve the reaction of tic applications, antibodies must be purified to remove many Surface carboxyl groups with lysine residues in antibodies (or all) of the contaminating non-antibody proteins and Small resulting in the formation of amide bonds. molecules (e.g. amino acids). 0009. It is well-known that derivatisation or conjugation 0003 Purification is particularly important if the antibody reactions that involve lysine residues cannot be carried out in is to be covalently attached either to a label (e.g. an enzyme, the presence of primary amine-containing Substances, such as organic dye, fluorescent protein or coloured particle) to create free amino acids. This is because Such Substances will com a hybrid reagent, usually referred to as a labelled antibody or pete with the lysine residues in the protein. In the case of antibody conjugate or to a derivatisation reagent for the carbodiimide-mediated reactions (which involves carboxyl to purpose of introducing new functional groups. The antibody amine coupling) the prior art strongly teaches against the use component of a conjugate confers specificity for a particular of additives with either carboxyl or primary amine function antigen (e.g. a protein, drug, peptide or biomarker) and the ality because of problems of competition. label confers measurability so that the conjugate can be used 0010 Thus, popular antibody elution buffers are contrain to detect and quantify the antigen in, for example, western dicated in nearly all types of antibody labelling methods. blots, tissue slices, cultured cells, blood samples, urine, and Neitherglycine nor citric acid can be present in carbodiimide SO. O. mediated reactions between an antibody and a label because 0004. A key step in antibody purification is the binding of the reaction involves the condensation of an amine and a the antibody either to an antigen affinity column or to a carboxyl group. column bearing immobilised protein A, protein G, or protein 0011 For example, in Bioconjugate Techniques, Herman L., which interact with regions of antibodies not directly son GT, 1995, ISBN 0-12-342336-8, p 102 (and p 117 in the involved in antigen binding. Purification of antibody on an updated 2nd edition, 2008 ISBN 9780123705013) the follow antigen affinity column is advantageous in that antibodies of ing advice is is given: "Avoid carboxylate- or amine-contain irrelevant antigen specificity in the crude sample are not ing buffers, such as citrate, acetate, glycine, or Tris'. retained by the column. Such methods of affinity purification 0012 Bangs Labs, tech note 205 with reference to carbo are robust and reliable and are widely used to purify antibod diimide coupling states "Buffers containing free amines, such ies from crude samples such as serum, ascites fluid and hybri as Tris or Glycine, should be avoided. doma tissue culture Supernatant. 0013 Reactions using carboxyl-containing microspheres 0005 Regardless of which approach to purification is are discussed in Immobilization of Enzymes and Cells, used, the column-bound antibody is usually eluted with a 2006, ed. Guisan J M, p 223, ISBN 1-58829-290-8) and the low-pH buffer (typically comprising glycine or citric acid) following cautionary note given: "Buffers containing free and then quickly neutralised, for example, with Tris buffer, amines, such as Tris ofsic glycine should be avoided'. pH 8.0-9.0, to minimise low pH-induced damage of the anti 0014. A carbodiimide-dependent biotinylation kit (EZ body. (e.g. Thermo Scientific Protein Purification Technical Link R. Amine-PEGn-Biotin, product code 26136) from Ther Handbook, ref 160161707/08). Elution with low pH glycine moFisher states: "Avoid buffers containing primary amines or citric acid buffers is popular because of their low cost and (Tris, glycine, etc.) or carboxyls (acetate, citrate, etc.) because they have good buffering capacity at the pH values because they will quench the reaction’. required for disruption of antibody-antigen interactions. 00.15 G Biosciences procedure for its Carboxyl Coupling 0006 Before storage, neutralised purified antibodies are Resin warns: “NOTE: For coupling reactions using EDC usually (but not always) dialysed against PBS or some other avoid the use of buffers containing free amines orphosphates near-neutral-pH buffer. Often other substances (e.g. BSA, as these will interfere with coupling efficiency. Tris, acetate sodium azide, detergents) will be added to the dialysed anti and glycine buffers all readily react with EDC or the coupling body for the purpose of stabilisation or preventing microbial intermediate'. growth. 0016 Finally, a protocol for use with a carboxylated gold 0007. It is extremely rare when purchasing an antibody conjugation kit states: Any other amine or carboxyl contain from commercial sources to be given information about the ing molecules in the protein solution (including protein sta dialysis steps used in the purification process. Thus it may be bilizers) will compete with the conjugation reaction.” unclear whether buffer components from the purification pro (OceanNanotech, product code GCK). cess remain in the final preparation of antibody. Such consid 0017. In the case of lysine-directed modification reactions erations are critically important if the antibody is to be which do not also involve carboxyl modification, citric acid US 2016/01 22416 A1 May 5, 2016 may be tolerated but glycine is always contraindicated e.g. the antibody when bound to the affinity matrix, wherein the DyLight(R) Amine-Reactive Dyes protocol (Thermo Scien buffer comprises a monocarboxylic acid buffer compound tific, No 2032.11) states: Buffers that contain primary other than glycine, bearing an amine Substituent at the alpha amines (e.g., Tris or glycine) will interfere because they react or beta position. with the NHS-ester moiety. 0026. In a further aspect, the present invention provides a 0018 Potentially interfering small molecules such as gly method for conjugating an isolated antibody to a label. The cine and citric acid in an antibody sample may be removed by method comprises contacting the antibody with the activated dialysis or desalting before the antibody is used in conjuga label, or label in the presence of an antibody conjugation tion reactions. The efficiency of removal of such molecules by reagent, in a buffer system which comprises a monocarboxy dialysis is related to the volume of the antibody sample rela lic acid buffer compound other than glycine, bearing an amine tive to that of the dialysis buffer, the number of changes of the Substituent at the alpha or beta position.
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