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US 2004/0166515 A1Published application
Luminescent compounds
AssigneeEwald A. Terpetschnig
InventorsEwald A. Terpetschnig, Leonid D. Patsenker, Anatoliy Tatarets
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Abstract
The invention provides reporter compounds based on squaric, croconic, and/or rhodizonic acid, among others, reactive intermediates used to synthesize the reporter compounds, and methods of synthesizing and using the reporter compounds, among others. The reporter compounds relate generally to the following structure: 1 Here, Z is a four, five, or six-member aromatic ring, and A, B, C, D, E, and F are substituents of Z, where F is absent when Z is a five-member ring, and where E and F are absent when Z is a four-member ring. A, B, C, D, E, and F are selected from a variety of elements and groups, including but not necessarily limited to O, S, Se, Te, C(Ra)(Rb), N—Rc, N(Rd)(Re), W1, and W2. 2
Claims51
A composition of matter comprising a reporter compound, the reporter compound having a four-, five-, or six-member aromatic ring Z, with substituents A, B, C, D, E, and F, according to the formula:
- 48
- wherein F is absent when Z is a five-member ring, and wherein E and F are absent when Z is a four-member ring;
- wherein A, B, C, D, E, and F may be present in any order, provided that B and C are adjacent, in which case each of A, D, E, and F is neutral, or provided that B and C are separated by one of A, D, E, or F, in which case one of A, D, E, and F is negatively charged;
- when the A substituent is neutral, A is selected from the group consisting of ═N—Rc, wherein Rc is selected from the group consisting of aliphatic, heteroatom-substituted aliphatic, polyether, aromatic, reactive aliphatic, and reactive aromatic groups;
- when the A substituent is negatively charged, A is —(N—Rc)−;
- each B and C substituent is selected from the group consisting of W1 and W2, wherein W1 and W2 have the respective formulae
- 49
- where each B and C substituent is W1 if B and C are adjacent on Z, and one of B and C is W1 and the other of B and C is W2 if B and C are separated by one of A, D, E, and F on ring Z;
- each D, E, and F substituent, when present and neutral, is independently selected from the group consisting of ═O, ═S, ═Se, ═Te, ═N—Rc, and ═C(Rf)(Rg), wherein Rc is selected from the group consisting of aliphatic, heteroatom-substituted aliphatic, polyether, aromatic, reactive aliphatic, and reactive aromatic groups, Rf and Rg being selected from the group consisting of carboxylic acid, cyano, carboxamide, carboxylic ester, and aliphatic amine groups;
- D, E, and F, when present and negatively charged, are independently selected from the group consisting of —O−, —S−, —Se−, —Te−, —(N—Rc)−, and —(C(Rf)(Rg))−;
- m and n are independently selected from the group consisting of 0, 1, and 2;
- Y is independently selected for each of B and C from the group consisting of O, S, Se, Te, N—Rh, and C(Ri)(Rj), wherein Rh is selected from the group consisting of H, aliphatic groups, alicyclic groups, aromatic groups, and reactive aliphatic groups, and wherein each of Ri and Rj is selected from the group consisting of aliphatic and reactive aliphatic groups;
- each R1 is independently selected for each of B and C from the group consisting of H, aliphatic groups, alicyclic groups, aromatic groups, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, and ionic substituents capable of increasing the hydrophilicity of the entire compound;
- each of X1, X2, X3, and X4 is independently selected for each of B and C from the group consisting of N, O, S, and C—Rk, wherein Rk is selected from the group consisting of H, F, Cl, Br, I, aliphatic groups, alicyclic groups, aromatic groups, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, ionic Substituents capable of increasing the hydrophilicity of the entire compound, parts of a condensed aromatic or heterocyclic ring, and parts of a substituted condensed aromatic or heterocyclic ring;
- and
- each H may be independently replaced by a fluorine.
13 more elements
A reporter compound having the formula
- 51
- wherein D is selected from the group consisting of O−, S−, Se−, Te−, N—(Rc)−, and C(Rf)(Rg)−, where each Rc is selected from the group consisting of aliphatics, heteroatom-substituted aliphatics, polyethers, aromatics, reactive aliphatics, reactive aromatics, and linked carriers;
- Rf and Rg being selected from the group consisting of carboxylic acids, cyano, carboxamides, carboxylic esters, and aliphatic amines;
- m and n are independently selected from the group consisting of 0, 1, and 2;
- each Y is independently selected from the group consisting of O, S, Se, Te, N—Rh, and C(Ri)(Rj), where Rh is selected from the group consisting of hydrogen, aliphatics, alicyclics, aromatics, and reactive aliphatics;
- and where each of Ri and Rj are H, aliphatic groups, alicyclic groups, aromatic groups, polyethers, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, ionic substituents and spacers containing one or more ionic substituents, capable of increasing the hydrophilicity of the entire compound;
- or Ri and Rj taken in combination for a ring-system that is optionally further substituted by one or more reactive or ionic substituents;
- each R1 is independently selected for each of B and C from the group consisting of hydrogen, aliphatics, alicyclics, aromatics, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, and ionic substituents capable of increasing the hydrophilicity of the entire compound;
- each of X1, X2, X3, and X4 is independently selected from the group consisting of H, N, O, S, and C—Rk, wherein Rk is selected from the group consisting of H, F, Cl, Br, I, aliphatics, alicyclics, aromatics, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, ionic substituents capable of increasing the hydrophilicity of the entire compound, parts of a condensed aromatic or heterocyclic ring, and parts of a substituted condensed aromatic or heterocyclic ring;
- and
- each hydrogen may be independently replaced by a fluorine.
8 more elements
A composition of matter comprising a photoluminescent compound, the photoluminescent compound having a four-, five-, or six-member aromatic ring Z, with substituents A, B, C, D, E, and F, according to the formula:
- 52
- wherein F is absent when Z is a five-member ring, and wherein E and F are absent when Z is a four-member ring;
- wherein A, B, C, D, E, and F may be present in any order, provided that B and C are adjacent, in which case each of A, D, E, and F is neutral, or provided that B and C are separated by one of A, D, E, or F, in which case one of A, D, E, and F is negatively charged;
- when the A substituent is neutral, A is ═O;
- when the A substituent is negatively charged, A is —O−;
- where each D, E, and F substituent, when present and neutral, is independently selected from the group consisting of ═O, ═S, ═Se, ═Te, ═N—Rc, and ═C(Rf)(Rg), wherein each of Rc is selected from the group consisting of aliphatic, heteroatom-substituted aliphatic, polyether, aromatic, reactive aliphatic, and reactive aromatic groups, hydrogen, CN, OH, SO3H, and COO—Rm, where Rm is selected from a group consisting of hydrogen, aliphatic substituents, aromatic substituents, reactive aliphatic substituents, reactive aromatic substituents, and linked carriers, and Rf and Rg are selected from the group consisting of carboxylic acid, cyano, carboxamide, carboxylic ester, and aliphatic amine groups;
- D, E, and F, when present and negatively charged, are independently selected from the group consisting of —O−, —S−, —Se−, —Te−, —(N—Rc)−, and —(C(Rf)(Rg))−;
- each B and C substituent is selected from the group consisting of W1 and W2, wherein W1 and W2 have the respective formulae
- 53
- where each B and C substituent is W1 if B and C are adjacent on Z, and one of B and C is W1 and the other of B and C is W2 if B and C are separated by one of A, D, E, and F on ring Z;
- m and n are independently selected from the group consisting of 0, 1, and 2;
- each Y is independently selected for each of B and C from the group consisting of O, S, N—Rh, and C(Ri)(Rj), wherein Rh is selected from the group consisting of H, aliphatic groups, alicyclic groups, aromatic groups, spacers bound to ionic and reactive groups, and Ri and Rj are selected from the group consisting of H, aliphatic groups, alicyclic groups, aromatic groups, polyether groups, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, ionic substituents and spacers containing one or more ionic substituents capable of increasing the hydrophilicity of the entire compound;
- or Ri and Rj taken in combination form a ring-system that is optionally further substituted by one or more reactive or ionic substituents;
- provided that at least one Y is C(Ri)(Rj ), and at least one of Ri or Rj includes a reactive group, a linked carrier, or an ionic substituent capable of increasing the hydrophilicity of the entire compound;.
- each R1 is independently selected for each of B and C from the group consisting of H, aliphatic groups, alicyclic groups, aromatic groups, polyether groups, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, and ionic substituents capable of increasing the hydrophilicity of the entire compound;
- each of X1, X2, X3, and X4 is independently selected for each of B and C from the group consisting of N, O, S, and C—Rk, wherein Rk is selected from the group consisting of H, F, Cl, Br, I, aliphatic groups, alicyclic groups, aromatic groups, polyether groups, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, ionic substituents capable of increasing the hydrophilicity of the entire compound, parts of a condensed aromatic or heterocyclic ring, and parts of a substituted condensed aromatic or heterocyclic ring;
- and
- each H may be independently replaced by a fluorine.
15 more elements
A compound having the formula
- 55
- wherein D is selected from the group consisting of O−, S−, Se−, Te−, N—(Rc)−, and C(Rf)(Rg)−, wherein Rc is selected from the group consisting of aliphatic, heteroatom-substituted aliphatic, polyether, aromatic, reactive aliphatic, and reactive aromatic groups, Rf and Rg are selected from the group consisting of carboxylic acid, cyano, carboxamide, carboxylic ester, and aliphatic amine groups;
- m and n are independently selected from the group consisting of 0, 1, and 2;
- Y is selected from the group consisting of O, S, Se, Te, N—Rh, and C (Ri)(Rj), wherein Rh is selected from the group consisting of H, aliphatic groups, alicyclic groups, aromatic groups, and reactive aliphatic groups, and wherein each of Ri and Rj are H, aliphatic groups, alicyclic groups, aromatic groups, polyethers, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, ionic substituents and spacers containing one or more ionic substituents, capable of increasing the hydrophilicity of the entire compound;
- or Ri and Rj taken in combination form a ring-system that is optionally substituted by one or more reactive or ionic substituents;
- (CX) is an alkyl chain with 1-22 carbon atoms, a polyether chain, any other polycarbon chair, or part of a ring system;
- K is selected from the group consisting of COOH, N-hydroxy succinimide, iodoacetamide, maleimide, sulfonychloride, phosphoramidite, and SO3−, PO3−, OH, or NH2;
- each R1 is independently selected for each of B and C from the group consisting of H, aliphatic groups, alicyclic groups, aromatic groups, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, and ionic substituents capable of increasing the hydrophilicity of the entire compound;
- each of X1, X2, X3, and X4 is independently selected from the group consisting of H, N, O, S, and C—Rk, wherein Rk is selected from the group consisting of H, F, Cl, Br, I, aliphatic groups, alicyclic groups, aromatic groups, linked carriers, reactive groups capable of covalent attachment to a carrier, spacers bound to one or more reactive groups capable of covalent attachment to a carrier, ionic substituents capable of increasing the hydrophilicity of the entire compound, parts of a condensed aromatic or heterocyclic ring, and parts of a substituted condensed aromatic or heterocyclic ring;
- and
- each H may be independently replaced by a fluorine.
8 more elements
A compound having the formula
- 56
Dependencies are inferred from the claim text.