US2004180393A1PendingUtilityA1
Chromogenic substrates of sialidase of bacterial, viral, protozoa and vertebrate origin and methods of making and using the same
Priority: Oct 27, 1997Filed: Oct 6, 2003Published: Sep 16, 2004
Est. expiryOct 27, 2017(expired)· nominal 20-yr term from priority
C07H 15/203C07H 7/027C07H 15/24C12Q 1/34C07H 17/02C07H 15/26C07H 17/075
51
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Claims
Abstract
The current invention relates to the design, synthesis, and biochemical evaluation of chromogenic substrate compounds for sialidases of bacterial, viral, protozoa, and vertebrate (including human) origin. In particular, this invention provides a novel class of effective compounds as chromogenic substrates of these sialidases which yield chromogenic products after reactions catalyzed by sialidase take place. Also provided are methods of making these substrate compounds, methods of diagnosis and prognosis of sialidase related diseases using these substrate compounds.
Claims
exact text as granted — not AI-modified1 . A chromogenic sialidase substrate compound, having a formula selected from the group consisting of General Structure I; General Structure II, General Structure IIIa; General Structure IIIb, General Structure IVa; General Structure IVb; and analogues, salts, and derivatives of the General Structures, wherein the General Structures are defined as follows:
wherein, for General Structure I, R 1 , R 2 , R 4 , and R 5 can each, independently, be selected from the group consisting of H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , and CN, where j is an integer from 0 to 3; wherein R 3 ═NO 2 , CHO, (CR 12 ═CR 12 ) k CN or (CR 12 ═CR 12 ) k NO 2 , where k is an integer from 1 to 3, or
wherein, R 6 , R 7 , R 8 , and R 9 can each, independently, be selected from the group consisting of H, N 3 , R 11 , NO 2 , NHC(═NH)N(R 10 ) 2 , NHC(O)R 11 , C(O)R 11 , Cl, Br, I, F, SR 10 , and (CH 2 ) x C(═NH)N(R 10 ) 2 where x is an integer from 0 to 3; wherein R 10 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 11 =R 10 , OR 10 , or N(R 10 ) 2 ; wherein, R 12 ═H or (CH 2 ) n ; where n is an integer from 0 to 3;
or, also for General Structure I, wherein, R 1 , R 3 , and R 5 can each, independently, be selected from the group consisting of H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , or CN, where j is an integer from 0 to 3; wherein R 2 or R 4 ═H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , CN, where j is an integer from 0 to 3, (CR 12 ═CR 12 ) k CN, and (CR 12 ═CR 12 ) k NO 2 , where k is an integer from 1 to 3 or
wherein, R 6 , R 7 , R 8 , and R 9 can each, independently, be selected from the group consisting of H, N 3 , R 11 , NO 2 , NHC(═NH)N(R 10 ) 2 , NHC(O)R 11 , C(O)R 11 , Cl, Br, I, F, SR 10 , and (CH 2 ) x C(═NH)N(R 10 ) 2 where x is an integer from 0 to 3; wherein R 10 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 11 =R 10 , OR 10 , or N(R 10 ) 2 ; wherein, R 12 ═H or (CH 2 ) n ; where n is an integer from 0 to 3;
or, also for General Structure I, wherein, R 1 or R 5 ═H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , CN, where j is an integer from 0 to 3, (CR 12 ═CR 12 ) k CN and (CR 12 ═CR 12 ) k NO 2 , where k is an integer from 1 to 3; wherein, R 2 , R 3 , and R 4 can each, independently, be selected from the group consisting of H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , and CN, where j is an integer from 0 to 3; wherein, R 6 , R 7 , R 8 , and R 9 are each, independently, selected from the group consisting of H, N 3 , R 11 , NO 2 , NHC(═NH)N(R 10 ) 2 , NHC(O)R 11 , C(O)R 11 , Cl, Br, I, F, SR 10 , (CH 2 ) x C(═NH)N(R 10 ) 2 , where x is an integer from 0 to 3; wherein R 10 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 11 =R 10 , OR 10 , or N(R 10 ) 2 ; wherein R 12 ═H or (CH 2 ) n ; where n is an integer from 0 to 3;
or, for General Structure II, wherein, R 1 , R 2 , R 3 , and R 4 are each, independently, selected from the group consisting of H, R 11 , OC(O)R 11 , NO 2 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , and CN, where j is an integer from 0 to 3; wherein, R 5 ═H or (CH 2 ) k CH 3 , where k is an integer from 0 to 4; wherein, R 6 , R 7 , R 8 , and R 9 are each, independently, selected from the group consisting of H,N 3 , R 11 , NO 2 , NHC(═NH)N(R 10 ) 2 1 NHC(O)R 11 , C(O)R 11 , Cl, Br, I, F, SR 10 , and (CH 2 ) x C(═NH)N(R 10 ) 2 , where x is an integer from 0 to 3; wherein, R 10 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer form 0 to 3; wherein, R 11 =R 10 , OR 10 , or N(R 10 ) 2 ;
or, for General Structure IIIa, wherein, R 1 ═H, R 8 , OC(O)R 8 , NO 2 , NHC(O)R 8 , Cl, Br, I, F, CHO, C(O)R 8 , C(N—OH)NH 2 , OPO 3 R 7 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 7 , OSO 3 R 7 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 7 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 3 , R 4 , R 5 , and R 6 are each, independently, selected from the group consisting of H, N 3 , R 8 , NO 2 , NHC(═NH)N(R 7 ) 2 , NHC(O)R 8 , C(O)R 8 , Cl, Br, I, F, SR 7 , and (CH 2 ) j C(═NH)N(R 7 ) 2 , where x is an integer from 0 to 3; wherein R 7 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 8 =R 7 , OR 7 , or N(R 7 ) 2 ;
or, for General Structure IIIb, wherein, R 1 ═H, R 8 , OC(O)R 8 , NO 2 , Cl, Br, I, F, CHO, C(O)R 8 , C(N—OH)NH 2 , OPO 3 R 7 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 7 , OSO 3 R 7 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 7 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 3 , R 4 , R 5 , and R 6 are each, independently, selected from the group consisting of H, N 3 , R 8 , NO 2 , NHC(═NH)N(R 7 ) 2 , NHC(O)R 8 , C(O)R 8 , Cl, Br, I, F, SR 7 , and (CH 2 ) x C(═NH)N(R 7 ) 2 , where x is an integer from 0 to 3; wherein R 7 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 8 =R 7 , OR 7 , or N(R 7 ) 2 ;
or, for General Structure IVa, wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are each, independently, selected from the group consisting of H, R 13 , OC(O)R 13 , NO 2 , Cl, Br, I, F, CHO, C(O)R 13 , C(N—OH)NH 2 , OPO 3 R 12 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 2 , OSO 3 R 12 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 12 , and CN, where j is an integer from 0 to 3; wherein, R 8 , R 9 , R 10 , R 11 are each, independently, selected from the group consisting of H, N 3 , R 13 , NO 2 , NHC(═NH)N(R 12 ) 2 , NHC(O)R 13 , C(O)R 13 , Cl, Br, I, F, SR 12 , and (CH 2 ) x C(═NH)N(R 12 ) 2 , where x is an integer from 0 to 3; wherein, R 12 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer form 0 to 3; wherein, R 13 ═R 12 , OR 12 , or N(R 2 ) 2 ;
or, for General Structure IVb, wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are each, independently, selected from the group consisting of H, R 13 , OC(O)R 13 , NO 2 , Cl, Br, I, F, CHO, C(O)R 3 , C(N—OH)NH 2 , OPO 3 R 12 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 12 , OSO 3 R 12 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 12 , and CN, where j is an integer from 0 to 3; wherein, R 1 , R 9 , R 10 , and R 11 are each, independently, selected from the group consisting of H, N 3 , R 13 , NO 2 , NHC(═NH)N(R 12 ) 2 , NHC(O)R 13 , C(O)R 3 , Cl, Br, I, F, SR 12 , and (CH 2 ) x C(═NH)N(R 12 ) 2 , where x is an integer from 0 to 3; wherein, R 12 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer form 0 to 3; wherein, R 13 =R 12 , OR 2 , or N(R 12 ) 2 , and analogs, salts, and derivatives thereof.
2 . The compound, according to claim 1 , wherein said compound has the following formul
a:
wherein, R 1 , R 2 , R 4 , and R 5 can each, independently, be selected from the group consisting of H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(NOH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , and CN, where j is an integer from 0 to 3; wherein R 3 ═NO 2 , CHO, (CR 12 ═CR 12 ) k CN or (CR 12 ═CR 12 ) k NO 2 , where k is an integer from 1 to 3, or
wherein, R 6 , R 7 , R 8 , and R 9 can each, independently, be selected from the group consisting of H, N 3 , R 11 , NO 2 , NHC(═NH)N(R 10 ) 2 1 NHC(O)R 11 , C(O)R 11 , Cl, Br, I, F, SR 10 , and (CH 2 ) x C(═NH)N(R 10 ) 2 where x is an integer from 0 to 3; wherein R 10 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 11 =R 10 , OR 10 , or N(R 10 ) 2 ; wherein, R 12 ═H or (CH 2 ) n ; where n is an integer from 0 to 3;
or, also for General Structure I, wherein, R 1 , R 3 , and R 5 can each, independently, be selected from the group consisting of H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , or CN, where j is an integer from 0 to 3; wherein R 2 or R 4 ═H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , CN, where j is an integer from 0 to 3, (CR 12 ═CR 12 ) k CN, and (CR 12 ═CR 12 )NO 2 , where k is an integer from 1 to 3 or
wherein, R 6 , R 7 , R 8 , and R 9 can each, independently, be selected from the group consisting of H, N 3 , R 11 , NO 2 , NHC(═NH)N(R 10 ) 2 , NHC(O)R 11 , C(O)R 11 , Cl, Br, I, F, SR 10 , and (CH 2 ) x C(═NH)N(R 10 ) 2 where x is an integer from 0 to 3; wherein R 10 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 11 =R 10 , OR 10 , or N(R 10 ) 2 ; wherein, R 12 ═H or (CH 2 ) n ; where n is an integer from 0 to 3;
or, also for General Structure I, wherein, R 1 or R 5 ═H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , CN, where j is an integer from 0 to 3, (CR 12 ═CR 12 ) k CN and (CR 12 ═CR 12 ) k NO 2 , where k is an integer from 1 to 3; wherein, R 2 , R 3 , and R 4 can each, independently, be selected from the group consisting of H, R 11 , OC(O)R 11 , NO 2 , NHC(O)R 11 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , and CN, where j is an integer from 0 to 3; wherein, R 6 , R 7 , R 8 , and R 9 are each, independently, selected from the group consisting of H, N 3 , R 11 , NO 2 , NHC(═NH)N(R 10 ) 2 , NHC(O)R 11 , C(O)R 11 , Cl, Br, I, F, SR 10 , (CH 2 ) x C(═NH)N(R 10 ) 2 , where x is an integer from 0 to 3; wherein R 10 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 11 =R 10 , OR 10 , or N(R 10 ) 2 ; wherein R 12 ═H or (CH 2 ) n ; where n is an integer from 0 to 3.
3 . The compound, according to claim 1 , wherein said compound has the following formula:
wherein, R 1 , R 2 , R 3 , and R 4 are each, independently, selected from the group consisting of H, R 11 , OC(O)R 11 , NO 2 , Cl, Br, I, F, CHO, C(O)R 11 , C(N—OH)NH 2 , OPO 3 R 10 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 10 , OSO 3 R 10 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 10 , and CN, where j is an integer from 0 to 3; wherein, R 5 ═H or (CH 2 ) k CH 3 , where k is an integer from 0 to 4; wherein, R 6 , R 7 , R 8 , and R 9 are each, independently, selected from the group consisting of H, N 3 , R 11 , NO 2 , NHC(═NH)N(R 10 ) 2 , NHC(O)R 11 , C(O)R 11 , Cl, Br, I, F, SR 10 , and (CH 2 ) x C(═NH)N(R 10 ) 2 , where x is an integer from 0 to 3; wherein, R 10 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer form 0 to 3; wherein, R 11 =R 10 , OR 10 , or N(R 10 ) 2 .
4 . The compound, according to claim 1 , wherein said compound has the following formula:
wherein, R 1 ═H, R 8 , OC(O)R 8 , NO 2 , NHC(O)R 8 , Cl, Br, I, F, CHO, C(O)R 8 , C(NOH)NH 2 , OPO 3 R 7 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 7 , OSO 3 R 7 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 7 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 3 , R 4 , R 5 , and R 6 are each, independently, selected from the group consisting of H, N 3 , R 8 , NO 2 , NHC(═NH)N(R 7 ) 2 , NHC(O)R 8 , C(O)R 8 , Cl, Br, I, F, SR 7 , and (CH 2 ) x C(═NH)N(R 7 ) 2 , where x is an integer from 0 to 3; wherein R 7 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 8 =R 7 , OR 7 , or N(R 7 ) 2 .
5 . The compound, according to claim 1 , wherein said compound has the following formula:
wherein, R 1 ═H, R 8 , OC(O)R 8 , NO 2 , Cl, Br, I, F, CHO, C(O)R 8 , C(N—OH)NH 2 , OPO 3 R 7 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 7 , OSO 3 R 7 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 7 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 3 , R 4 , R 5 , and R 6 are each, independently, selected from the group consisting of H, N 3 , R 8 , NO 2 , NHC(═NH)N(R 7 ) 2 , NHC(O)R 8 , C(O)R 8 , Cl, Br, I, F, SR 7 , and (CH 2 ) x C(═NH)N(R 7 ) 2 , where x is an integer from 0 to 3; wherein R 7 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 8 =R 7 , OR 7 , or N(R 7 ) 2 .
6 . The compound, according to claim 1 , wherein said compound has the following formula:
wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are each, independently, selected from the group consisting of H, R 13 , OC(O)R 13 , NO 2 , Cl, Br, I, F, CHO, C(O)R 13 , C(N—OH)NH 2 , OPO 3 R 12 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 2 , OSO 3 R 12 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 12 , and CN, where j is an integer from 0 to 3; wherein, R 8 , R 9 , R 10 , R 10 are each, independently, selected from the group consisting of H, N 3 , R 13 , NO 2 , NHC(═NH)N(R 2 ) 2 , NHC(O)R 13 , C(O)R 13 , Cl, Br, I, F, SR 12 , and (CH 2 ) x C(═NH)N(R 2 ) 2 , where x is an integer from 0 to 3; wherein, R 12 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer form 0 to 3; wherein, R 13 =R 12 , OR 2 , or N(R 12 ) 2 .
7 . The compound, according to claim 1 , wherein said compound has the following formula:
wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are each, independently, selected from the group consisting of H, R 13 , OC(O)R 13 , NO 2 , Cl, Br, I, F, CHO, C(O)R 13 , C(N—OH)NH 2 , OPO 3 R 12 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 12 , OSO 3 R 12 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 12 , and CN, where j is an integer from 0 to 3; wherein, R 8 , R 9 , R 10 , and R 11 are each, independently, selected from the group consisting of H, N 3 , R 13 , NO 2 , NHC(═NH)N(R 12 ) 2 , NHC(O)R 13 , C(O)R 13 , Cl, Br, I, F, SR 12 , and (CH 2 ) x C(═NH)N(R 12 ) 2 , where x is an integer from 0 to 3; wherein, R 12 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer form 0 to 3; wherein, R 13 =R 12 , OR 12 , or N(R 12 ) 2 .
8 . A composition for measuring sialidase activity level, comprising a carrier and a chromogenic sialidase sustrate compound of claim 1 .
9 . A method of measuring sialidase activity in a sample comprising the step of contacting said sample with a composition comprising a chromogenic sialidase substrate compound of claim 1 .
10 . The method, according to claim 9 , wherein said compound is a compound of claim 2 .
11 . The method, according to claim 9 , wherein said compound is a compound of claim 3 .
12 . The method, according to claim 9 , wherein said compound is a compound of claim 4 .
13 . The method, according to claim 9 , wherein said compound is a compound of claim 5 .
14 . The method, according to claim 9 , wherein said compound is a compound of claim 6 .
15 . The method, according to claim 9 , wherein said compound is a compound of claim 7 .
16 . A method of making a composition for measuring sialidase activity comprising the step of admixing a carrier with a chromogenic sialidase substrate compound of claim 1 .
17 . A method for detecting or monitoring a sialidase-related disease in a human or animal, wherein siad method comprises measuring sialidase activity by contacting a fluid sample from said human or animal with a chromogenic substrate compound of claim 1 .
18 . The method, according to claim 17 , wherein said compound is a compound of claim 2 .
19 . The method, according to claim 17 , wherein said compound is a compound of claim 3 .
20 . The method, according to claim 17 , wherein said compound is a compound of claim 4 .
21 . The method, according to claim 17 , wherein said compound is a compound of claim 5 .
22 . The method, according to claim 17 , wherein said compound is a compound of claim 6 .
23 . The method, according to claim 17 , wherein said compound is a compound of claim 7 .
24 . The method, according to claim 17 , wherein said sialidase is bacterial sialidase in bacterial vaginosis.
25 . The method, according to claim 17 , wherein said sialidase is bacterial sialidase in periodontal diseases.
26 . The method, according to claim 17 , wherein said sialidase is bacterial sialidase in Pseudomonas aeruginosa infection.
27 . The method, according to claim 17 , wherein said sialidase is viral sialidase in influenza virus infection.
28 . The method, according to claim 17 , wherein said sialidase is human sialidase.
29 . The method, according to claim 17 , wherein said sialidase is trans-sialidase in Trypanosoma cruzi infection.Join the waitlist — get patent alerts
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