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US 2015/0346170 A1 Huang Et Al US 2015 0346170A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0346170 A1 Huang et al. (43) Pub. Date: Dec. 3, 2015 (54) EXTRACTION, DERIVATIZATION, AND Publication Classification QUANTIFICATION OF ANALYTES (51) Int. C. (71) Applicant: QUANTALYTICAL LABS INC., GOIN30/72 (2006.01) Camarillo, CA (US) HOIJ 49/00 (2006.01) GOIN3/84 (2006.01) (72) Inventors: Qi Huang, Camarillo, CA (US); Philip (52) U.S. C. A. Dimson, San Pedro, CA (US); CPC ............ G0IN30/7233 (2013.01); G0IN30/84 Karsten R. Liegmann, Altadena, CA (2013.01); H01J 49/0031 (2013.01); G0IN (US) 2030/8435 (2013.01); G0IN 2030/027 (73) Assignee: QUANTALYTICAL LABS INC., (2013.01) Camarillo, CA (US) (21) Appl. No.: 14/726,530 (57) ABSTRACT (22) Filed: May 30, 2015 The present specification discloses methods for determining Related U.S. Application Data the presence one or more analytes in a test sample, materials (60) Provisional application No. 62/005,676, filed on May useful to perform the disclosed methods, and kits comprising 30, 2014. reagents useful to practice the disclosed methods. Patent Application Publication Dec. 3, 2015 Sheet 2 of 19 US 2015/0346170 A1 sco'AsLaju scipasual GTI‘61-I sdoAsueu sdoAsueu sd'Asusu Patent Application Publication Dec. 3, 2015 Sheet 3 of 19 US 2015/0346170 A1 §§§ dae, og sdaksusu sdakisuelu sdo'Asusu GOD? g?; N sdoAsusu sd'Asusu Patent Application Publication Dec. 3, 2015 Sheet 4 of 19 US 2015/0346170 A1 taedae 0009 tidae taeg tidae tae). sdo'suau sdo'ssueu 3dok.sueu sda Asusu N sck'kisueru Patent Application Publication Dec. 3, 2015 Sheet 5 of 19 US 2015/0346170 A1 sd'aigueui sd'Asieu fedssue Patent Application Publication Dec. 3, 2015 Sheet 6 of 19 US 2015/0346170 A1 Patent Application Publication Dec. 3, 2015 Sheet 7 of 19 US 2015/0346170 A1 Patent Application Publication Dec. 3, 2015 Sheet 8 of 19 US 2015/0346170 A1 scious sdo issueu sdalueu sdisus NN sdaisuou NN Patent Application Publication Dec. 3, 2015 Sheet 9 of 19 US 2015/0346170 A1 stokugusgu §§ ÇÖZ sdoisiayu LGROEG, sdais.usgu scs'Asuru Patent Application Publication Dec. 3, 2015 Sheet 10 of 19 US 2015/0346170 A1 sdoi183 808 issu scoksusu N N sd:Asusu Patent Application Publication Dec. 3, 2015 Sheet 11 of 19 US 2015/0346170 A1 Patent Application Publication Dec. 3, 2015 Sheet 12 of 19 US 2015/0346170 A1 skisuelu sco'Agsugu sda'ssusu sdisusu sda Asueu s issueu Patent Application Publication Dec. 3, 2015 Sheet 13 of 19 US 2015/0346170 A1 N N Patent Application Publication Dec. 3, 2015 Sheet 14 of 19 US 2015/0346170 A1 : es s s s C w N cy cesw V So Sg. 2 SSN ? es e C ss E s | is8 Ss's 2.SS -------------------------------------------------------------------------- as s ,: ,; S., ,. ., ,. ,. ,. ,. , ,. ,. ,. ,. , ,. ,. as, a, , a, tr;, , , , S2, is, 5, s, is, is, 5, s, is, a , , , co co to r on to co (N () ( ( a c e o O ( - - - - - - - - - - sco'ssueu Patent Application Publication Dec. 3, 2015 Sheet 15 of 19 Patent Application Publication Dec. 3, 2015 Sheet 16 of 19 US 2015/0346170 A1 s : s S s s ci S S Le is N s v-c2 | SSg 8 L wa s v y st SSs S e ce is S5. is SS g X s HN is5. Trrrrrrrrrrrrrr rrn rrn rrrrrrrrrrr, rurrrrrr, r a Patent Application Publication Dec. 3, 2015 Sheet 17 of 19 US 2015/0346170 A1 :eeuwSu?uegze:1>sdo'000ýze:?ôleHSjunoo9000z? v o cro Sodo'AISueu Patent Application Publication Dec. 3, 2015 Sheet 18 of 19 US 2015/0346170 A1 S Patent Application Publication Dec. 3, 2015 Sheet 19 of 19 US 2015/0346170 A1 sjunoo|90049233/VS°°°u?ugg'e¿lºsdovoorø69:9außeH US 2015/03461 70 A1 Dec. 3, 2015 EXTRACTION, DERIVATIZATION, AND estradiol, estriol), cannabinoids Such as A-9-tetrahydrocan QUANTIFICATION OF ANALYTES nabinol (THC), serotonin, amino acids, BPA, and many other primary and secondary amine containing, or phenol contain 0001. This application claims priority under 35 U.S.C. ing molecules in a biological sample. The desired analyte can S119(e) to U.S. Provisional Application 62/005,676 filed be selectively and sensitively detected and measured by mass May 30, 2014, the entire contents of which are hereby spectrometry, including tandem mass spectrometry technolo expressly incorporated by reference. gies. The entire quantification process includes a sample 0002. There is a need to obtain fast, streamlined, and auto preparation process that employs a Solid phase extraction to mated methods for detection of particular analytes. In the capture the analyte, followed by a chemical derivatization of medical context, such methods would facilitate the detection the analyte, then quantification via LC-MS/MS technologies, of analytes. Such as drugs, hormones, signaling agents, and as described herein. amino acids. In the agricultural and public health context, the 0007. It was discovered during this work that the combi detection of residual levels of antibiotics, pesticides or other nation of Solid phase extraction with a chemical derivatiza contaminants is integral to the safety of the food we eat and tion with Fmoc chloride and LC-MS/MS provides analyte water we drink. Furthermore, recent changes in the standards specific, sensitive, accurate, stable and robust measurements for food labeling, such as “hormone free” or “organic” have of levels of catecholamines at 10 pg/ml or lower in blood created a need for streamlined testing in the agricultural plasma/serum sample. Quantification methods for metaneph realm. rines and thyroid hormones were also developed with similar 0003 Catecholamines are essential hormones or neu sensitivity and accuracy. rotransmitters that are important in maintaining a body’s 0008 Sensitive and accurate measurements of these ana healthy conditions. Neurological disorders such as Parkin lytes at levels relevant to the clinical setting is useful, particu son's disease, or Alzheimer's disease often may alter the larly at low pico-gram per milliliter range, at Small sample levels of these substances in the blood. Elevated levels of size (100 uL or less of blood plasma/serum sample), with a metanephrines (derivatives of catecholamines) may be simple process which can be easily configured to be auto indicative of onset of certain cancers such as pheochromocy mated, with an analyte specific results, without any analyte toma. Similarly, metanephrines (metanephrine and normeta crossovers that are often seen under other analytical tech nephrine), thyroid hormones (thyroxine T4,3,5,5'-triiodothy niques such as radioimmunoassay (RIA). ronine T3, and 3,3',5-triiodothyronine rT3), estrogen hormones (estrone, esterol, estradiol, and estriol), delta-9- BRIEF DESCRIPTION OF THE DRAWINGS tetrahydrocannabinol (THC) its derivatives and metabolites, etc., are among many other biologically interesting molecular 0009 FIGS. 1A and 1B present example data showing the markers that are important for clinicians to determine the chromatograms for the internal standard equivalent 100 pg status of a patient. (FIG. 1A) and for the catecholamine spiked plasma (FIG. 0004 Traditionally, clinical quantification of catechola 1B). mines were carried out via radio immunoassays (RIA). In (0010 FIGS. 2A and 2B represent data obtained at 10 and recent years, due to the technology advancement in Mass 100 pg/ml of each catecholamine. Spectroscopy, there is a gradual shift in testing platform from 0011 FIG. 3 provides the chromatograms for the meta RIA to liquid chromatography mass spectrometry (LCMS). nephrines: top being metanephrine (659.210/268.400), Often times, the LCMS based assays provide a fast, sensitive, middle being normetanephrine (645. 100/166.100) and lower and analyte specific readout, which an RIA assay may lack. being metanephrine (659.210/268.400). However, catecholamines are difficult to detect as they are (0012 FIGS. 4A, 4B, 4C, and 4D provide the spectra for prone to be oxidized and degraded. Further, the current art in the various shifts in metanephrine and normetanephrine. catecholamines/metanephrine quantification often involves (0013 FIGS.5A,5B,5C, and 5D provide the various peaks complex and cumbersome extraction procedures with at each shift for the Thyroid hormones: plasma with 5 ng/ml unstable extraction recovery, thus giving rise to results which equivalent (FIG. 5A), plasma blank (FIG. 5B), plasma 1 are often unreliable, and with high lower limits of quantifica ng/ml (FIG.5C), and 200 uL BSA with 1 ng/ml (FIG. 5D). tion (LLOQ); for example an LLOQ in >10 ng/mL range. (0014 FIGS. 6A, 6B, and 6C provide data for each of the Also, the existing extraction process is unable to provide a thyroid hormones T3 at 31.3 pg/ml (FIG. 6A), rT3 at 31.3 reliable sample for derivatization. pg/mL (FIG. 6B), and T4 at 31.3 pg/ml (FIG. 6C). 0005 Drugs include both illegal and legal drugs and (0015 FIGS. 7A, 7B, and 7C provide the linearity data for metabolites or derivatives thereof. The detection of these the quantification of 11-nor-9-carboxy-delta-9-tetrahydro compounds for forensic or prescription compliance are very cannabinol in Urine; 1,000 pg/ml (FIG. 7A), 100 pg/ml (FIG. important. Again, these drugs may not be stable in bodily 7B), and 10 pg/ml (FIG.7C). fluids and therefore, detection may be difficult. In any event, (0016 FIGS. 8A and 8B provide recovery data from the there is a great need for a fully automated and simplified quantification of 11-nor-9-carboxy-delta-9-tetrahydrocan detection/quantification procedure which minimizes the nabinol in Urine: Recovery-1,000 pg/rxn of Standard (FIG. room for human involvement or error. 8A)and Recovery of 1,000 pg/rxn Extracted Spike (FIG.8B). SUMMARY DETAILED DESCRIPTION 0006. This invention document provides materials and 0017.
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