Substituted phosphonate fluorescent sensors and use thereof

Details Substituted phosphonate fluorescent sensors and use thereof Substituted phosphonate fluorescent sensors and use thereof

2004-05-14

2009-12-08

Shiao, Rei-tsang (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C548S439000, C548S509000, C548S146000, C546S339000, C549S218000

Reexamination Certificate

active

07629379

ABSTRACT:
The invention relates to new compounds of formula (1) wherein R is hydrogen or a linear or branched C1-40alkyl; where X is O, S, or NR1where R1is a hydrogen, a linear or branched C1-40alkyl, C2-40alkenyl or C2-40alkynyl group, an aryl, a heteroaryl or C1-40alkylaryl or alkylheteroaryl group and where one or both of C and D is OR2, SR2, NR3R4where R2, R3and R4are each independently hydrogen, a linear or branched C1-40alkyl, C2-40alkenyl or C2-40alkynyl group, an aryl or C1-40alkylaryl group or a linear or branched C1-40alkyl NR5R6chain where R5and R6are each independently hydrogen, a linear or branched C1-40alkyl; or an optionally complex metal ion Mn+
wherein n is an integer from 1 to 8; or where one or both of C and D are amino acids or nucleic acids attached via either N, O or S; and wherein m is an integer from 1 to 8; and wherein either: I) A is a known aryl or heteroaryl fluorescent group and B is hydrogen, a linear or branched C1-40alkyl, C2-40alkenyl or C2- 40alkynyl group, an aryl, a heteroaryl or C1-40alkylaryl or alkylheteroaryl group or phosphonate P(O)(OR2)2; II) B is a known aryl or heteroaryl fluorescent group and A is hydrogen, a linear or branched C1-40alkyl, C2-40alkenyl or C2-40alkynyl group, an aryl, a heteroaryl or C1-40alkylaryl or alkylheteroaryl group or a linear or branched C1-40alkyl NR5R6chain, or a linear or branched C1-40 alkylmono or di ester C1-40alkylphosphonate or a linear or branched C1-40alkylphosphonic acid; III) Both A and B are known aryl or heteroaryl fluorescent groups. The compounds are useful as fluorescent sensors for metal cations and have the advantages of excellent water solubility, selectivity and sensitivity to a variety of metal cations even in the presence of high concentrations of Ca+2Na+and K+, good cell permeability, flexible and simple syntheses, ease of attachment to polymers and bio-polymers to aid the identification of both chemical and biological processes as well as for assaying physiological samples and for the attachment to surfaces such as glasses, ceramics and apatites.

REFERENCES:
patent: 5453517 (1995-09-01), Kuhn et al.
patent: WO 99/58521 (1999-11-01), None
patent: WO 01/51497 (2001-07-01), None
patent: WO 02/38190 (2002-05-01), None
Tanaka et al., 1990, CAS: 112:108695.
Arimilli et al., 2003, CAS: 139:381609.
Erion et al., 2000, CAS: 133:84284.
Dang et al., 2000, CAS: 132:222529.
Van Poelje et al., 2002, CAS: 136:123595.
Erion et al., 2001, CAS: 135:348869.
Kasibhatla et al., 1998, CAS: 129: 245147.
He et al. , 1993, CAS: 119:203497.
Bartsch et al., “Selective transport of alkali metal cations in solvent extraction by proton-ionizable dibenzocrown ethers,” Database Caplus, Chemical Abstracts Service, XP002310237 (1p.).
He et al., “Study on organophosphorus compounds with biological activity. Part III. Synthesis properties and biological activity of .alpha.-(benzothiazol-2-yl-oxy)alkanephosphonates,” Database Caplus, Chemical Abstracts Service, XP002310235 (1p).
Jurecka et al., “Synthesis, characterization and extraction behaviour of calyx′4!arene-based phosphonic acids,”J of the Chemical Society(2002) pp. 1370-1377.
Komlev et al., “Phosphorylation of some organic luminophors,” Database Caplus, Chemical Abstracts Service, XP002310236 (1p).
Kunsagi-Mate et al., “Complex formation between 1-chloro-4-(trifluoromethyl)benzene (guest) and 4-tert-butylcalix[4]arenes (host) distally substituted with phosphoric acid or phosphonic ester groups at the lower rim,”Tetrahedron(2002) 58(25):5119-5124.
Pugia et al., “Effect of sidearm length upon competitive alkali metal solvent extraction into chloroform by lipophilic crown phosphonic acid monoalkyl esters,”Analytical Chemistry(1986) 58(13):2723-2726.
Sorori et al., “Lithographic printing plate master for CTP (computer-to-plate) platemaking,” Database Caplus, Chemical Abstracts Service, XP002310234 (1p).

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