# US 5,702,952 A · Labelled boronic acid derivatives > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,702,952 A - Document ID: US5702952A - Status: Granted - Kind: A - Application number: 08/804,328 - Filed: 1997-02-21 - Granted: 1997-12-30 - Earliest claimed: 1994-03-31 - Assignees: Axis Biochemicals ASA - Inventors: Erling Sundrehagen; Frank Frantzen - Web page: https://patentgrep.com/patent/US5702952A ## CPC - G01N 33/532: Production of labelled immunochemicals - C07F 5/025: {Boronic and borinic acid compounds} - Y10S 436/815: Test for named compound or class of compounds - Y10S 436/825: Pretreatment for removal of interfering factors from sample - Y10T 436/25125: Digestion or removing interfering materials - Y10T 436/25375: Liberation or purification of sample or separation of material from a sample [e.g., filtering, centrifuging, etc.] - G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q) - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract The invention provides novel labelled boronic acid conjugates of formula ##STR1## (wherein V is a reporter moiety; W.sup.2 is a bond or an organic linker moiety; W.sup.1 is a *SO.sub.2 NR.sup.2, *CONR.sup.2 or *CH.sub.2 N.sup..sym. R.sup.2.sub.2 group bound at the *-marked atom to the phenyl ring; R.sup.1 is hydrogen or an electron withdrawing substituent group; and each R.sup.2 independently is hydrogen or an optionally hydroxylated and optionally C.sub.1-6 -alkoxylated C.sub.1-6 -alkyl group) and salts thereof, e.g. for use in assays for cis-diols such as glycated blood proteins, having enhanced water-solubility and storage stability. ## Claims ### Claim 1 An assay kit comprising a compound of formula III ##STR24## (wherein V is a reporter moiety; W.sup.2 is a bond or an organic linker moiety; W.sup.1 is a *SO.sub.2 NR.sup.2, *CONR.sup.2 or *CH.sub.2 N.sup..sym. R.sup.2.sub.2 group bound at the *-marked atom to the phenyl ring; R.sup.1 is hydrogen or an electron withdrawing substituent group; and each R.sup.2 independently is hydrogen or an optionally hydroxylated and optionally C.sub.1-6 -alkoxylated C.sub.1-6 -alkyl group) or a salt thereof, means for contacting a cis-diol containing fluid sample therewith, means for separating cis-diol:boronic acid conjugates thus formed and, optionally, means for assessing thus separated cis-diol:boronic acid conjugates. ### Claim 2 (depends on 1) A kit as claimed in claim 1 wherein said compound of formula III or salt thereof is present in a zinc salt containing aqueous solution buffered to a pH in the range 6.5 to 8.0. ### Claim 3 (depends on 2) A kit as claimed in claim 2 wherein said means for contacting comprises a mixing vessel and said means for separating comprises a porous web. ### Claim 4 (depends on 1) A kit as claimed in claim 1, wherein, in said compound of formula III or salts thereof, W.sup.1 is a SO.sub.2 NR.sup.2 or CONR.sup.2 group attached to the phenyl ring at the 4-position thereof. ### Claim 5 (depends on 1) A kit as claimed in claim 1, wherein, in said compound of formula III or salts thereof, W.sup.1 is a SO.sub.2 NR.sup.2 or CONR.sup.2 group attached to the phenyl ring at the 2, 3, 5 or 6-position thereof. ### Claim 6 (depends on 1) A kit as claimed in claim 1, wherein, in said compound of formula III or salts thereof, W.sup.1 is a CH.sub.2 N.sup..sym. R.sub.2.sup.2 group attached to the phenyl ring at the 3 or 5 position thereof. ### Claim 7 (depends on 1) A kit as claimed in claim 1, wherein, in said compound of formula III or salts thereof, W.sup.1 is a CH.sub.2 N.sup..sym. R.sub.2 .sup.2 group attached to the phenyl ring at the 2, 4, or 6-position thereof. ### Claim 8 (depends on 1) A kit as claimed in claim 1, wherein, in said compound of formula III or salts thereof, R.sup.1 denotes an SO.sub.2 H, CO.sub.2 H or NO.sub.2 group attached at the 3 or 5 position of the phenyl ring. ### Claim 9 (depends on 1) A kit as claimed in claim 1, wherein, in said compound of formula III or salts thereof, R.sup.1 denotes an SO.sub.2 H, CO.sub.2 H or NO.sub.2 group attached at the 2, 4 or 6-positions of the phenyl ring. ### Claim 10 (depends on 1) A kit as claimed in claim 1, wherein, in said compound of formula III or salts thereof, W.sup.2 is a group of formula IV --X.sup.1 ›(CHR.sup.3).sub.n X.sup.2 !.sub.m --(CHR.sup.3).sub.n --(IV) (wherein each n is independently an integer having a value of 1 to 6, m is 0 or an integer having a value of 1 to 5, X.sup.1 is a bond, an oxygen or sulphur atom, a NR.sup.2 group, or a carboxy or carbonyl group, each X.sup.2 is independently an oxygen or sulphur atom or an NR.sup.2 group, R.sup.2 is as defined in claim 1, and each R.sup.3 independently is hydrogen, hydroxy, formyl, carboxy, or optionally hydroxylated and/or C.sub.1-6 -alkoxylated C.sub.1-6 -alkyl, or a group CHR.sup.3 represents a carbonyl group). ### Claim 11 (depends on 10) A kit as claimed in claim 10, wherein W.sup.2 is selected from the group consisting of: --NH--CH.sub.2 --CHOH--CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 --NH--CH.sub.2 CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 CH.sub.2 CH(COOH)-- --NH--CH.sub.2 CHOH-- --NH--CH.sub.2 CH(COOH)-- --NH--CH.sub.2 --NH--CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- --NH--CH.sub.2 --O--CH.sub.2 -- --NH--CH.sub.2 --O--CH.sub.2 --O--CH.sub.2 -- --NH--CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 -- --NH--CH(COOH)CH.sub.2 CH.sub.2 -- --NH--CH(COOH)CH.sub.2 CH.sub.2 CH.sub.2 -- --NH--CH.sub.2 CH(COOH)CH(COOH)-- groups. --NH--CH.sub.2 CHOHCHOH-- and --NH--CH.sub.2 CH(CHO)CH(CHO)-- ### Claim 12 (depends on 1) A kit as claimed in claim 1, wherein, in said compound of formula III or salts thereof, V is a chromophore or fluorophore. ### Claim 13 (depends on 12) A kit as claimed in claim 12, wherein V has an absorption maximum in the range 600-1000 nm. ### Claim 14 (depends on 12) A kit as claimed in claim 12, wherein V is an azine, triarylmethine, phthalocyanine or cyanine dye. ### Claim 15 (depends on 14) A kit as claimed in claim 14, wherein V is a xylene-cyanole dye. ### Claim 16 (depends on 1, 8) A kit as claimed in claim 1, wherein said compound or salts of formula III are compounds of formula V ##STR25## (where V, W.sup.2 and R.sup.2 are as defined in claim 1, W.sup.2 is a group of formula IV as defined in claim 8, and X.sup.3 is a CO or SO.sub.2 group) and salts thereof. ### Claim 17 (depends on 1) A kit as claimed in claim 1, wherein said compound of formula III or salts thereof are compounds of formula VI ##STR26## (where V, R.sup.1 and W.sup.2 are as defined in claim 1, and W.sup.3 is NHCO or SO.sub.2 NH) and salts thereof. ### Claim 18 (depends on 1) A kit as claimed in claim 1, wherein said compound of formula III or salts thereof are compounds of formula VII ##STR27## (where V, W.sup.2 and R.sup.2 are as defined in claim 1) and salts thereof. ### Claim 19 (depends on 1, 8) A kit as claimed in claim 1, wherein said compound of formula III or salts thereof are compounds of formula VIII ##STR28## (where X.sup.2, R.sup.1, R.sup.3, n, m and W.sup.1 are as defined in claim 8 and X.sup.1* is a reactive functional group) and salts thereof.