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132557-72-3

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132557-72-3 Usage

General Description

The chemical 5-Sulfo-2,3,3-trimethyl indolenine sodium salt is a derivative of the indolenine compound, and it is commonly used as a fluorescent dye in various biochemical and analytical applications. It is a water-soluble compound that emits a bright blue fluorescence, making it useful for labeling and tracing biomolecules in biological research. The sodium salt form of the compound increases its solubility in aqueous solutions, making it easier to work with in biological and chemical experiments. Due to its fluorescence properties and water solubility, 5-Sulfo-2,3,3-trimethyl indolenine sodium salt is widely utilized in various fields, including molecular biology, immunology, and cell biology.

Check Digit Verification of cas no

The CAS Registry Mumber 132557-72-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,2,5,5 and 7 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 132557-72:
(8*1)+(7*3)+(6*2)+(5*5)+(4*5)+(3*7)+(2*7)+(1*2)=123
123 % 10 = 3
So 132557-72-3 is a valid CAS Registry Number.
InChI:InChI=1S/C11H13NO3S/c1-7-11(2,3)9-6-8(16(13,14)15)4-5-10(9)12-7/h4-6H,1-3H3,(H,13,14,15)

132557-72-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Sodium 2,3,3-trimethyl-3H-indole-5-sulfonate

1.2 Other means of identification

Product number -
Other names 5-sulphonato-2,3,3-trimethylindolenine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:132557-72-3 SDS

132557-72-3Synthetic route

3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

4-hydrazino-benzenesulfonic acid
98-71-5

4-hydrazino-benzenesulfonic acid

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

Conditions
ConditionsYield
With acetic acid for 3h; Concentration; Fischer Indole Synthesis; Reflux;97%
With acetic acid for 14h; Reflux;94%
With acetic acid at 120℃; Fischer Indole Synthesis;94%
potassium 2,3,3-trimethylindole-5-sulfonate

potassium 2,3,3-trimethylindole-5-sulfonate

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

Conditions
ConditionsYield
With Dowex, strongly acidic hydrogen ion exchange resin In water
4-hydrazinobenzenesulfonic acid hydrochloride

4-hydrazinobenzenesulfonic acid hydrochloride

3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

Conditions
ConditionsYield
With acetic acid Reflux;
2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

potassium 2,3,3-trimethylindole-5-sulfonate

potassium 2,3,3-trimethylindole-5-sulfonate

Conditions
ConditionsYield
With potassium hydroxide In methanol; isopropyl alcohol100%
With potassium hydroxide In methanol; isopropyl alcohol for 0.25h; Concentration; Reflux;98%
With potassium hydroxide In methanol; isopropyl alcohol Reflux;95%
N,N'-diphenylformamidine
864131-95-3

N,N'-diphenylformamidine

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C18H18N2O3S

C18H18N2O3S

Conditions
ConditionsYield
With sulfuric acid; acetic acid In diethylene glycol dimethyl ether at 140℃; for 2h;95%
1,3-propanesultone
1120-71-4

1,3-propanesultone

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

sodium 1-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate

sodium 1-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate

Conditions
ConditionsYield
In toluene for 20h; Heating;91%
Stage #1: 2,3,3-trimethylindole-5-sulfonic acid With sodium acetate In methanol at 20℃; for 0.0833333h;
Stage #2: 1,3-propanesultone In acetonitrile for 0.25h;
3-bromo-N,N,N-trimethyl-1-propanaminium bromide
3779-42-8

3-bromo-N,N,N-trimethyl-1-propanaminium bromide

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

2,3,3-trimethyl-1-[3-(trimethylammonio)propyl]-3H-indolium-5-sulfonic acid dibromide

2,3,3-trimethyl-1-[3-(trimethylammonio)propyl]-3H-indolium-5-sulfonic acid dibromide

Conditions
ConditionsYield
In toluene for 72h; Inert atmosphere; Reflux;91%
In toluene at 130℃; for 72h; Inert atmosphere;81%
In acetonitrile for 72h; Reflux;
In toluene Inert atmosphere; Reflux;
2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

1-methyl-2,3,3-trimethyl-3H-indolium-5-sulfonate
174703-04-9

1-methyl-2,3,3-trimethyl-3H-indolium-5-sulfonate

Conditions
ConditionsYield
In acetone; methyl iodide90%
In acetone; methyl iodide90%
methyl iodide
74-88-4

methyl iodide

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

1,2,3,3-tetramethylindolinium-5-sulfonate potassium iodide salt

1,2,3,3-tetramethylindolinium-5-sulfonate potassium iodide salt

Conditions
ConditionsYield
Stage #1: 2,3,3-trimethylindole-5-sulfonic acid With potassium hydroxide In methanol; isopropyl alcohol
Stage #2: methyl iodide In propan-1-ol for 20h; Reflux;
73%
ethyl iodide
75-03-6

ethyl iodide

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

5-sulfo-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide

5-sulfo-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide

Conditions
ConditionsYield
In acetonitrile for 12h; Reflux;68%
3,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzylbromide
246140-08-9

3,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzylbromide

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

N-(3,5-bis(2-(2-methoxyethoxy)ethoxy)ethoxy)benzyl-2,3,3-trimethyl-5-sulfo-3H-indole

N-(3,5-bis(2-(2-methoxyethoxy)ethoxy)ethoxy)benzyl-2,3,3-trimethyl-5-sulfo-3H-indole

Conditions
ConditionsYield
Stage #1: 2,3,3-trimethylindole-5-sulfonic acid With potassium ethoxide In methanol at 20℃; for 0.5h;
Stage #2: 3,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzylbromide In acetonitrile for 48h; Concentration; Inert atmosphere; Reflux;
67.7%
1,4-butane sultone
1633-83-6

1,4-butane sultone

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

4-(2,3,3-trimethyl-5-sulfo-3H-indol-1-ium-1-yl)butane-1-sulfonate
76588-81-3

4-(2,3,3-trimethyl-5-sulfo-3H-indol-1-ium-1-yl)butane-1-sulfonate

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 110℃; for 12h; Inert atmosphere; Schlenk technique;66%
In 1,2-dichloro-benzene at 110℃; for 12h;
at 110℃; under 0.0750075 Torr; for 12h;
croconic acid
488-86-8

croconic acid

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

2,5-bis[2,3,3-trimethyl-3H-indole-5-sulfonic acid]croconaine

2,5-bis[2,3,3-trimethyl-3H-indole-5-sulfonic acid]croconaine

Conditions
ConditionsYield
With pyridine In toluene; butan-1-ol for 10h; Reflux;65%
6-bromohexanoic acid
4224-70-8

6-bromohexanoic acid

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

1-(ε-carboxypentyl)-2,3,3-trimethyl indolenium-5-sulfonate
749838-12-8

1-(ε-carboxypentyl)-2,3,3-trimethyl indolenium-5-sulfonate

Conditions
ConditionsYield
With 1,2-dichloro-benzene at 110℃; for 24h; Inert atmosphere;62%
1,3-propanesultone
1120-71-4

1,3-propanesultone

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

N-(4-sulfonatopropyl)-2,3,3-trimethyl-5-sulfoindolenine
76578-90-0

N-(4-sulfonatopropyl)-2,3,3-trimethyl-5-sulfoindolenine

Conditions
ConditionsYield
With 1,2-dichloro-benzene at 140℃; for 48h; Inert atmosphere;59.2%
triethylammonium 2-butoxy-3-dicyanomethylidene-4-oxocyclobut-1-en-1-olate
905559-84-4

triethylammonium 2-butoxy-3-dicyanomethylidene-4-oxocyclobut-1-en-1-olate

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

3-dicyanomethylene-2-(3,3-dimethyl-5-sulfo-2,3-dihydro-1H-2-indolylidenmethyl)-4-(3,3-dimethyl-5-sulfo-3H-2-indoliumylmethylene)-1-cyclobuten-1-olate

3-dicyanomethylene-2-(3,3-dimethyl-5-sulfo-2,3-dihydro-1H-2-indolylidenmethyl)-4-(3,3-dimethyl-5-sulfo-3H-2-indoliumylmethylene)-1-cyclobuten-1-olate

Conditions
ConditionsYield
In toluene; butan-1-ol for 13h; Reflux;56%
bromoacetic acid
79-08-3

bromoacetic acid

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C13H16NO5S(1+)*Br(1-)

C13H16NO5S(1+)*Br(1-)

Conditions
ConditionsYield
In toluene at 100℃; for 72h; Inert atmosphere;44%
squaric acid
2892-51-5

squaric acid

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

2-(3,3-dimethyl-5-sulfo-2,3-dihydro-1H-2-indolylidenmethyl)-4-(3,3-dimethyl-5-sulfo-3H-2-indoliumylmethylene)-3-oxo-1-cyclobuten-1-olate

2-(3,3-dimethyl-5-sulfo-2,3-dihydro-1H-2-indolylidenmethyl)-4-(3,3-dimethyl-5-sulfo-3H-2-indoliumylmethylene)-3-oxo-1-cyclobuten-1-olate

Conditions
ConditionsYield
In toluene; butan-1-ol for 12h; Reflux;43%
sodium hydroxide
1310-73-2

sodium hydroxide

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

sodium 2,3,3-trimethyl-3H-indole-5-sulfonate
287188-58-3

sodium 2,3,3-trimethyl-3H-indole-5-sulfonate

Conditions
ConditionsYield
In ethanol; water; isopropyl alcohol at 20℃; for 4h;39%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

trans-2-(3,4,5-trimethoxystyryl)-3,3-dimethyl-3H-indoleninium-5-sulfonate
1229662-40-1

trans-2-(3,4,5-trimethoxystyryl)-3,3-dimethyl-3H-indoleninium-5-sulfonate

Conditions
ConditionsYield
With potassium carbonate at 100℃; for 4h; neat (no solvent); stereoselective reaction;38%
1-(ε-carboxypentyl)-2,3,3-trimethyl indolenium-5-sulfonate
749838-12-8

1-(ε-carboxypentyl)-2,3,3-trimethyl indolenium-5-sulfonate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C29H35N2O8S2(1+)

C29H35N2O8S2(1+)

Conditions
ConditionsYield
Stage #1: 2,3,3-trimethylindole-5-sulfonic acid With sulfuric acid; acetic acid
Stage #2: N,N-dimethyl-formamide In diethylene glycol dimethyl ether at 140℃;
Stage #3: 1-(ε-carboxypentyl)-2,3,3-trimethyl indolenium-5-sulfonate With pyridine; acetic anhydride at 90℃;
38%
3-bromo-N,N,N-trimethyl-1-propanaminium bromide
3779-42-8

3-bromo-N,N,N-trimethyl-1-propanaminium bromide

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

2,3,3-trimethyl-1-[3-(trimethylammonium)propyl]-3H-indolinium-5-sulfonate bromide

2,3,3-trimethyl-1-[3-(trimethylammonium)propyl]-3H-indolinium-5-sulfonate bromide

Conditions
ConditionsYield
In toluene at 70℃; for 48h; Inert atmosphere;36%
In 1,2-dichloro-benzene at 130℃; for 72h; Inert atmosphere;
2-Chloroethanesulfonyl chloride
1622-32-8

2-Chloroethanesulfonyl chloride

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

1-(2-sulfonatoethyl)-2,3,3-trimethyl-3H-indolenine-5-sulfonic acid
262283-53-4

1-(2-sulfonatoethyl)-2,3,3-trimethyl-3H-indolenine-5-sulfonic acid

Conditions
ConditionsYield
With triethylamine In acetonitrile for 6h; Heating / reflux;35%
With triethylamine In acetonitrile for 6h; Heating / reflux;35%
Stage #1: 2-Chloroethanesulfonyl chloride; 2,3,3-trimethylindole-5-sulfonic acid In ISOPROPYLAMIDE at 20℃; for 5h;
Stage #2: With methanol; sodium hydroxide In ISOPROPYLAMIDE; water at 20℃; for 2.5h;
Stage #1: 2-Chloroethanesulfonyl chloride; 2,3,3-trimethylindole-5-sulfonic acid In ISOPROPYLAMIDE at 20℃; for 5h;
Stage #2: With sodium hydroxide In methanol; water at 20℃;
1-(6-Carboxypentyl)-2,3,3-trimethylindoleninium 5-sulfonamide
366451-26-5

1-(6-Carboxypentyl)-2,3,3-trimethylindoleninium 5-sulfonamide

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C29H36N3O7S2(1+)

C29H36N3O7S2(1+)

Conditions
ConditionsYield
Stage #1: 2,3,3-trimethylindole-5-sulfonic acid With sulfuric acid; acetic acid
Stage #2: N,N-dimethyl-formamide In diethylene glycol dimethyl ether at 140℃;
Stage #3: 1-(6-Carboxypentyl)-2,3,3-trimethylindoleninium 5-sulfonamide With pyridine; acetic anhydride at 90℃;
35%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C23H23N2O6S2(1-)*H(1+)

C23H23N2O6S2(1-)*H(1+)

Conditions
ConditionsYield
With acetic acid for 2h; Heating / reflux;25%
Stage #1: orthoformic acid triethyl ester; 2,3,3-trimethylindole-5-sulfonic acid With pyridine for 0.166667h; Heating / reflux;
Stage #2:
5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,2,3,3-tetramethyl-3H-indolium
312961-81-2

5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,2,3,3-tetramethyl-3H-indolium

malonaldehyde bis(phenylimine) monohydrochloride
51143-32-9, 123071-42-1, 137692-98-9

malonaldehyde bis(phenylimine) monohydrochloride

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

[(1E,3E)-5-(3,3-dimethyl-5-sulfo-1,3-dihydro-2H-indol-2-ylidene)-1,3-pentadienyl]-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3,3-trimethyl-3H-indolium
312961-82-3

[(1E,3E)-5-(3,3-dimethyl-5-sulfo-1,3-dihydro-2H-indol-2-ylidene)-1,3-pentadienyl]-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3,3-trimethyl-3H-indolium

Conditions
ConditionsYield
With benzoic acid anhydride; benzoic acid In DMF (N,N-dimethyl-formamide) at 90℃; for 3h;23%
1-(ε-carboxypentyl)-2,3,3-trimethyl indolenium-5-sulfonate
749838-12-8

1-(ε-carboxypentyl)-2,3,3-trimethyl indolenium-5-sulfonate

N,N'-diphenylformamidine
864131-95-3

N,N'-diphenylformamidine

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C29H34N2O8S2

C29H34N2O8S2

Conditions
ConditionsYield
Stage #1: N,N'-diphenylformamidine; 2,3,3-trimethylindole-5-sulfonic acid With sulfuric acid; acetic acid at 140 - 160℃; for 3.5h;
Stage #2: 1-(ε-carboxypentyl)-2,3,3-trimethyl indolenium-5-sulfonate With pyridine; acetic anhydride at 90℃; for 1h;
17%
2-chloromalonaldehyde
36437-19-1

2-chloromalonaldehyde

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C25H25ClN2O6S2

C25H25ClN2O6S2

Conditions
ConditionsYield
In methanol at 60 - 70℃; for 6h;13.7%
2-Bromo-malonaldehyde
2065-75-0

2-Bromo-malonaldehyde

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C25H25BrN2O6S2

C25H25BrN2O6S2

Conditions
ConditionsYield
In methanol at 60 - 70℃; for 6h;13.1%
triethylammonium 5-(2-hydroxy-3,4-dioxocyclobut-1-en-1-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate

triethylammonium 5-(2-hydroxy-3,4-dioxocyclobut-1-en-1-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

2-(3,3-dimethyl-5-sulfo-2,3-dihydro-1H-2-indolylidenmethyl)-4-(3,3-dimethyl-5-sulfo-3H-2-indoliumylmethylene)-3-(2,4,6-trioxohexahydro-5-pyrimidinyliden)-1-cyclobuten-1-olate

2-(3,3-dimethyl-5-sulfo-2,3-dihydro-1H-2-indolylidenmethyl)-4-(3,3-dimethyl-5-sulfo-3H-2-indoliumylmethylene)-3-(2,4,6-trioxohexahydro-5-pyrimidinyliden)-1-cyclobuten-1-olate

Conditions
ConditionsYield
In pyridine for 18h; Sonication; Reflux;10%
Malondialdehyde, tetrabutylammonium salt
100683-54-3

Malondialdehyde, tetrabutylammonium salt

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

C25H26N2O6S2

C25H26N2O6S2

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 60 - 70℃; for 2h;5.7%
5-carboxymethyl-2,3,3-trimethyl-1-(4-sulfobutyl)-3H-indolium
118672-08-5

5-carboxymethyl-2,3,3-trimethyl-1-(4-sulfobutyl)-3H-indolium

malonaldehyde bis(phenylimine) monohydrochloride
51143-32-9, 123071-42-1, 137692-98-9

malonaldehyde bis(phenylimine) monohydrochloride

2,3,3-trimethylindole-5-sulfonic acid
132557-72-3

2,3,3-trimethylindole-5-sulfonic acid

5-(carboxymethyl)-2-[(1E,3E)-5-(3,3-dimethyl-5-sulfo-1,3-dihydro-2H-indol-2-ylidene)-1,3-pentadienyl]-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium

5-(carboxymethyl)-2-[(1E,3E)-5-(3,3-dimethyl-5-sulfo-1,3-dihydro-2H-indol-2-ylidene)-1,3-pentadienyl]-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium

Conditions
ConditionsYield
With benzoic acid anhydride; benzoic acid In N,N-dimethyl-formamide at 90℃; for 3h;

132557-72-3Relevant articles and documents

Rapid and Selective Labeling of Endogenous Transmembrane Proteins in Living Cells with a Difluorophenyl Ester Affinity-Based Probe

Chan, Hsin-Ju,Lin, Xin-Hui,Fan, Syuan-Yun,Ru Hwu, Jih,Tan, Kui-Thong

, p. 3416 - 3420 (2020)

The long-term stability of affinity-based protein labeling probes is crucial to obtain reproducible protein labeling results. However, highly stable probes generally suffer from low protein labeling efficiency and pose significant challenges when labeling low abundance native proteins in living cells. In this paper, we report that protein labeling probes based on an ortho-difluorophenyl ester reactive module exhibit long-term stability in DMSO stock solution and aqueous buffer, yet they can undergo rapid and selective labeling of native proteins. This novel electrophile can be customized with a wide range of different protein ligands and is particularly well-suited for the labeling and imaging of transmembrane proteins. With this probe design, the identity and relative levels of basal and hypoxia-induced transmembrane carbonic anhydrases were revealed by live cell imaging and in-gel fluorescence analysis. We believe that the extension of this difluorophenyl ester reactive module would allow for the specific labeling of various endogenous membrane proteins, facilitating in-depth studies of their distribution and functions in biological processes.

A highly selective optical probe for sensing of Fe3+ based on a water-soluble croconaine

Ye, Shouchen,Zhang, Chen,Mei, Jinfeng,Li, Zhongyu,Xu, Song,Li, Xiazhang,Yao, Chao

, p. 130 - 137 (2017)

A highly selective water-soluble optical probe, 2,5-bis[2,3,3-trimethyl-3H-indole-5-sulfonic acid]-croconaine (TISC) was successfully synthesized. TISC can efficiently recognize Fe3+ with the existence of competing cations (Na+, Mg2+, Al3+, Cr3+, Zn2+, K+, Ca2+, Ba2+, Pb2+, Ni2+, Co2+, Ag+, Cu2+, Cd2+) in deionized water. The binding constant (Ka) of TISC-Fe3+ was calculated to be about 3.071?×?104?M?1. Correspondingly, the chelating mode of TISC-Fe3+ was confirmed by Job's plot, FT-IR and 1H NMR. Moreover, Fe3+ and EDTA could be employed as inputs and the absorbance which was 745?nm as output so that a molecular logic gate could be realized, and the test strips of TISC showed a high selectivity to Fe3+.

Optimized pH-responsive cyanine fluorochromes for detection of acidic environments

Hilderbrand, Scott A.,Weissleder, Ralph

, p. 2747 - 2749 (2007)

Modulation of pH-responsive cyanine dye pKa values via heteroatom substitution allows for design of fluorescent reporters that are tuned for potential imaging of biologically relevant acidic environments. The Royal Society of Chemistry.

Probing two PESIN-indocyanine-dye-conjugates: Significance of the used fluorophore

Benkert, Vanessa,Cheng, Xia,Hübner, Ralph,Kr?mer, Roland,W?ngler, Bj?rn,W?ngler, Carmen

, p. 1302 - 1309 (2020)

Peptide-dye-conjugates hold a great promise in application for biological and medical imaging of cellular processes and in delineation and characterization of human tumors. In particular, indocyanine dyes are of great interest due to their reported superior properties such as absorption and emission in the near-infrared (NIR) spectral range, favorable Stokes shifts and their well-studied safety profile in humans. In this study, we investigated and describe the influence of indocyanine dyes on different properties of the final peptide-dye-conjugates. As a target peptide, PESIN, a bombesin derivative, was used as a model peptide which addresses GRP receptors overexpressed on different malignancies. Here, we map similarities and differences of the fluorescent conjugates and by this elucidate the influence of the dyes on different properties of the formed conjugates. We performed the dye syntheses, subsequent bioconjugation reactions and in the following investigated the optical properties, water/octanol distribution coefficients and target receptor affinities by in vitro competitive binding studies on PC-3 cells. The obtained results give a handrail to medical and biological researchers planning studies involving indocyanine dye biomolecule conjugates.

A colorimetric squaraine-based probe and test paper for rapid naked eyes detection of copper ion (II)

Liu, Yang,Wang, Liqiu,Guo, Chenxiao,Hou, Yajuan

, p. 3930 - 3933 (2018)

A colorimetric probe N,N’-bis(2-methoxy-ethyl)-2,3,3-trimethyl-3H-squaraine (MOESQ) with H2O solubility was synthesized to detect Cu2+. MOESQ exhibits good selectivity, high sensitivity and fast UV-Vis response toward Cu2+ over other competing ions in CH3CN. The detection limit of MOESQ for Cu2+ in CH3CN can reach 1.88 × 10?7 molL?1. By adsorbing MOESQ on the chromatography paper, a colorimetric test paper for Cu2+ was prepared, which could detect Cu2+ with the color change from blue to faint yellow even in the limit of detection concentration of 10?6 molL?1.

A nitroreductase-activatable near-infrared theranostic photosensitizer for photodynamic therapy under mild hypoxia

Jiao, Long,Liu, Yongzhuo,Peng, Xiaojun,Song, Fengling,Wu, Yingnan,Zheng, Jing

supporting information, p. 5819 - 5822 (2020/06/03)

In this study, a near-infrared (NIR) theranostic photosensitizer was developed based on a heptamethine aminocyanine dye with a long-lived triplet state. This theranostic molecule can be activated by nitroreductase under mild hypoxia to be used in fluorescence imaging and highly efficient photodynamic therapy (PDT) both in 2D and 3D (spheroids) HeLa cell culture models.

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