US 12,461,106 B2
Ultra bright dimeric or polymeric dyes with spacing linker groups
Tracy Matray, Snohomish, WA (US); and Sharat Singh, Rancho Santa Fe, CA (US)
Assigned to Sony Group Corporation, Tokyo (JP)
Filed by SONY GROUP CORPORATION, Tokyo (JP)
Filed on Feb. 8, 2024, as Appl. No. 18/436,594.
Application 18/436,594 is a continuation of application No. 18/425,634, filed on Jan. 29, 2024.
Application 18/425,634 is a continuation of application No. 17/959,857, filed on Oct. 4, 2022.
Application 17/959,857 is a continuation of application No. 17/121,596, filed on Dec. 14, 2020, granted, now 12,270,812.
Application 17/121,596 is a continuation of application No. 15/801,035, filed on Nov. 1, 2017, granted, now 10,866,244, issued on Dec. 15, 2020.
Application 15/801,035 is a continuation of application No. 15/481,378, filed on Apr. 6, 2017, granted, now 9,851,359, issued on Dec. 26, 2017.
Claims priority of provisional application 62/318,935, filed on Apr. 6, 2016.
Prior Publication US 2024/0255514 A1, Aug. 1, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. G01N 33/58 (2006.01); C07F 9/09 (2006.01); C07F 9/572 (2006.01); C07F 9/6558 (2006.01); C07F 9/6561 (2006.01); C09B 3/14 (2006.01); C09B 11/26 (2006.01); C09B 69/10 (2006.01); G01N 33/52 (2006.01); G01N 33/533 (2006.01); C07F 9/576 (2006.01)
CPC G01N 33/582 (2013.01) [C07F 9/091 (2013.01); C07F 9/572 (2013.01); C07F 9/65583 (2013.01); C07F 9/65586 (2013.01); C07F 9/6561 (2013.01); C09B 3/14 (2013.01); C09B 11/26 (2013.01); C09B 69/101 (2013.01); C09B 69/102 (2013.01); C09B 69/103 (2013.01); C09B 69/109 (2013.01); G01N 33/52 (2013.01); G01N 33/533 (2013.01); C07F 9/09 (2013.01); C07F 9/094 (2013.01); C07F 9/098 (2013.01); C07F 9/5765 (2013.01)] 19 Claims
 
1. A compound having the following structure (IA):

OG Complex Work Unit Chemistry
or a stereoisomer, salt or tautomer thereof, wherein:
M is, at each occurrence, independently a fluorescent dye, wherein at least one occurrence of M has absorbance for use in fluorescence resonance energy transfer (FRET), and at least one occurrence of M has emissions for use in FRET;
L1 is at each occurrence, independently either i) an alkylene linker; ii) a heteroalkylene linker including at least one nitrogen atom; or iii) a linker comprising a triazolyl functional group;
L2 and L3 are, at each occurrence, independently an alkylene or heteroalkylene linker;
R1 is, at each occurrence, H;
R2 is Q, or a protected form thereof, or a linker comprising a covalent bond to Q;
R3 comprises a deoxythymidine (dT) group;
R4 is, at each occurrence, OH, O or ORd;
R5 is, at each occurrence, oxo;
Rd is a counter ion;
Q is a moiety comprising a sulfhydryl, disulfide, activated ester, isothiocyanate, azide, alkyne, alkene, diene, dienophile, acid halide, sulfonyl halide, phosphine, «-haloamide, biotin, amino or maleimide functional group, wherein the activated ester is an N-succinimide ester, imidoester or polyflourophenyl ester, and wherein the azide is an alkyl azide or acyl azide;
m is, at each occurrence, independently an integer of one to 10;
n is an integer of one to 32; and
z is an integer from 2 to 25.