DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-47 are pending. Applicant’s election without traverse of Group I, claims 1-22 in the reply filed on 5/6/2026, is acknowledged. Claims 23-47 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 9, 11, 13 and 15 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 9, 11, 13 and 15 are indefinite because they directed products whereas the claim from which they depend are directed to methods.
Claims 1-4 and 7-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al., PNAS, vol. 101, no. 24 (2004), 8882-8887, in view of Eichler et al., Handbook of Experimental Pharmacology (1966), Vol. XIX, page 70.
Regarding claim 1, Zhang et al. teaches the selective incorporation of 5- hydroxytryptophan into proteins in mammalian cells. See Title. This reads on "protein, polypeptide or a peptide comprising one or more 5-hydoxyindol groups or 5-aminoinodole groups incorporated into the protein, polypeptide or peptide" (current claims 4, 10-15). Further, Zhang et al. teaches 5-HTPP as a probe for protein structure and function. See page 8866.
Zhang et al. does not teach "wherein the 5-hydroxyindole group or 5-aminoindole group is covalently coupled to a diazonium compound."
Eichler et al. teaches that "[p]henolic compounds, including 4-, 5- and 6- hydroxyindoles, react with diazonium salts (diazo coupling) to give azo dyes with are strongly coloured. These reactions are very sensitive and often allow the detection of hydroxyindoles below the microgram level. In non-hydroxylated, and in such compounds where the phenolic group is blocked by ether or ester formation little colour occurs with simple diazonium salts. However, certain complex diazonium salts give colours with indole acids and indolealkylamines and these salts may be useful for identification". Page 70. This reads on "wherein the 5-hydroxyindole group or 5-aminoindole group is covalently coupled to a diazonium compound." In this regard, it is prima facie obviousness to select a known material based on its suitability for its intended use. See Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945).
In this instance, it would have been prima facie obvious to one of ordinary skill in the art prior to the effective filing date of the invention to utilize a diazonium compound to effect the strong detection of 5-HTPP as a probe for protein structure and function as suggested by Eichler et al.
Claims 5 and 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al., PNAS, vol. 101, no. 24 (2004), 8882-8887, in view of Eichler et al., Handbook of Experimental Pharmacology (1966), Vol. XIX, page 70 as applied to claims 1-4 and 7-16 above, and further in view of Gavrilyuk et al., Bioconjugate chemistry, 23 (12):2321-2328 (2012).
Teachings of Zhang et al. and Eichler et al. are discussed above.
Regarding claim 5, neither reference teaches 'wherein the protein is an antibody, or an antibody fragment." Gavrilyuk et al. teaches "4-formylbenzene diazonium hexalluorophosphate (FBDP) is novel bench-stable crystalline diazonium salt that reacts selectively with tyrosine FBDP- conjugation was used for the facile introduction of small molecule tags, poly(ethylene) glycol chains (PEGylation), and functional small molecules onto model proteins and to label the surface of living cells". Abstract. In particular, Gavrilyuk et al. teaches that "[s]ince antibodies constitute perhaps the most important class of proteins in bioconjugation chemisty, we studied the potential of FBDP labeling of the antibody trastuzumab" (current claims 5). Page 8.
It would have been prima facie obvious to one of ordinary skill in the art prior to the effective filing date of the invention to further modify the combination of Zhang et al. and Eicher et al. with Gavrilyuk et al. such that an antibody is modified by incorporating one or more 5- hydroxyindole groups or 5-aminoindole groups thus allowing it to be useful for identification. The modification would be simply a matter of applying a known technique to a known device ready for improvement to yield predictable results. Here, Zhang et al. teaches the incorporation of one or more 5-hydroxyindole groups or 5-aminoindole groups into a protein. Gavrilyuk et al. teaches antibodies as perhaps the most important class of proteins in bioconjugation chemistry and uses a diazonium compound for labeling, which is taught by Eichler et al. It follows that a skilled artisan would be motivated to modify the most important class of proteins by incorporating one or more 5-hydroxyindole groups or 5-aminoindole groups into the protein, as taught by Zhang et al., and using a diazonium compound as taught by Eichler et al. which would have rendered predictable results to one of ordinary skill in the art.
Claims 18-22 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al., PNAS, vol. 101, no. 24 (2004), 8882-8887, in view of Eichler et al., Handbook of Experimental Pharmacology (1966), Vol. XIX, page 70 as applied to claims 1-4 and 7-16 above, and further in view of Jensen et al., Chembiochem, 2016 December 02; 17(23):2216- 2219.
Teachings of Zhang et al. and Eichler et al. are discussed above.
Regarding claim 18, neither reference teaches wherein the diazonium compound is detectably labeled.
Jensen et al. teaches fluorescently labeled tyrosine (current claim 18-20). See page 2.
Regarding claims 21 and 22, neither reference teaches "wherein the compound is immobilized on a solid matrix, surface or support."
Regarding claim 21, Jensen et al. teaches a triazabutadiene scaffold. See page 1, "Abstract." Jensen et al. teaches that "[a]ryl diazonim ion arc masked in the form of triazabutadienes and appended on to proteins. The aryl diazonium ion are released in a light- dependent manner and go on to react with electron-rich aromatic moieties" (current claims 2, 14 and 18). Page 1, "Graphical Abstract." Jensen et al. teaches that "[a]ryl diazonium ions selectively target electron-rich amino acid side chains, most notably tyrosine." Page 2.
Regarding claim 21 and 22, Jensen et al.'s composition would be expected to be cleavable with a suitable reducing agent because it comprises the same materials and combination as recited by the instant claims. See In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990) ("Products of identical chemical composition cannot have mutually exclusive properties.")
Claim Objections
Claim 17 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT S CABRAL whose telephone number is (571)270-3769. The examiner can normally be reached M-F 8 am - 5 pm.
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/ROBERT S CABRAL/Primary Examiner, Art Unit 1614
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