# US 10,865,218 B2 · Fluoride fluorescence probe

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- Number: US 10,865,218 B2
- Document ID: US10865218B2
- Status: Granted
- Kind: B2
- Application number: 16/005,817
- Filed: 2018-06-12
- Published: 2018-12-27
- Granted: 2020-12-15
- Earliest claimed: 2017-06-22
- Assignees: The Procter & Gamble Company
- Applicants: The Procter & Gamble Company
- Inventors: Yunming Shi; Ross Strand; Tao Yi; Peng Wei; FengFeng Xue
- Web page: https://patentgrep.com/patent/US10865218B2

## CPC

- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- G01N 21/643: {non-biological material}
- G01N 31/22: using chemical indicators (G01N31/02 takes precedence)
- G01N 2021/6439: {with indicators, stains, dyes, tags, labels, marks}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

Methylene blue (MB) derivatives selectively detect F− by desilylation reaction to act as a fluorescent probe.

## Claims

### Claim 1

A compound selected from the group consisting of:
(i) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(ii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(iii)4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(iv) 4-((trimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(v) 4-((tri-tert-butylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(vi) 4-((triethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(vii) 3,5-dimethyl-4-((trimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(viii) 4-((triphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(ix) 4-((methyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(x) 4-((diisopropyl(phenyl)silyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(xi) 3-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(xii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xiii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xiv) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xv) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xvi) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xvii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xviii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis (phenylamino)-10H-phenothiazine-10-carboxylate;
(xix) 4-((tert-butyldiphenylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xx) 4-((tert-butyldiphenylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxi) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xxii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxiii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxiv) 4-((triisopropylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxv) 4-((triisopropylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxvi) 4-((triisopropylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxvii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(phenylamino)-10H-phenothiazine-10-carboxylate;
(xxviii) 4-((tert-butyldiisopropylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xxix) 4-((tert-butyldiisopropylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxx) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xxxi) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxxii) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxxiii) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxxiv) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxxv) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxxvi) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxxvii) 4-((tert-butyldimethylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xxxviii) 4-((tert-butyldimethylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxxix) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenoxazine-10-carboxylate;
(xl) 3-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate; and
(xli) 4-((tert-butyldimethylsilyl)oxy)benzyl 2,8-bis(dimethylamino)-10-methylphenazine-5(10H)-carboxylate.

### Claim 2 (depends on 1)

A method of detecting fluorine ion in a composition, the method comprising the steps of:
(a) incubating the composition with a compound according to claim 1;
(b) shining excitation light to the incubated composition; and
(c) detecting light emission from the compound from 620 nm to 760 nm.

### Claim 3 (depends on 1)

A method of quantitating fluorine ion in a biofilm, the method comprising the steps of:
(a) treating a biofilm with an oral care composition;
(b) labeling the treated biofilm with a compound according to claim 1;
and
(c) quantitating the labeled fluorine by measuring fluorescence light emitted from the labeled fluorine.