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52411-34-4

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52411-34-4 Usage

Chemical Properties

Off-White Crystalline Solid

Check Digit Verification of cas no

The CAS Registry Mumber 52411-34-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,4,1 and 1 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 52411-34:
(7*5)+(6*2)+(5*4)+(4*1)+(3*1)+(2*3)+(1*4)=84
84 % 10 = 4
So 52411-34-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H16N2O2/c15-11-5-1-3-7-13(11)17-9-10-18-14-8-4-2-6-12(14)16/h1-8H,9-10,15-16H2

52411-34-4Synthetic route

1,2-bis(2-nitrophenoxy)ethane
51661-19-9

1,2-bis(2-nitrophenoxy)ethane

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In N,N-dimethyl-formamide at 70 - 80℃; for 20h;95.6%
With hydrazine hydrate; palladium on activated charcoal In ethanol for 2h; Heating;94%
With hydrazine hydrate; palladium on activated charcoal In ethanol for 2h; Heating;91%
1,2-bis-(2-acetylamino-phenoxy)-ethane
67499-49-4

1,2-bis-(2-acetylamino-phenoxy)-ethane

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
bei der Destillation;
ethylene glycol-bis-<2-nitro-phenyl ether >

ethylene glycol-bis-<2-nitro-phenyl ether >

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
With hydrogenchloride; tin
sodium o-nitrophenate
824-39-5

sodium o-nitrophenate

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide
2: H2 / Pd/C / ethanol
View Scheme
Multi-step reaction with 2 steps
1: dimethylformamide / 2 h / Heating
2: 10percent Pd/C / ethanol
View Scheme
Multi-step reaction with 2 steps
1: ethylene glycol / 150 °C
2: Raney nickel; ethanol / Hydrogenation
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide
2: hydrogen; palladium on activated charcoal / methanol
View Scheme
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

dichloropentamethylenetetramine

dichloropentamethylenetetramine

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaOH / ethanol
2: dimethylformamide / 2 h / Heating
3: 10percent Pd/C / ethanol
View Scheme
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / K2CO3 (calcined) / dimethylsulfoxide / 6 h / 130 °C
2: 91 percent / 85percent NH2NH2*H2O / 5percent Pd/C / ethanol / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: K2CO3
2: SnCl2*2H2O, aq. HCl
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 130 °C / Inert atmosphere
2: hydrogen / 5%-palladium/activated carbon / dichloromethane; ethanol / 25 °C
View Scheme
1-(2-chloroethoxy)-2-nitrobenzene
102236-25-9

1-(2-chloroethoxy)-2-nitrobenzene

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 - 140 °C
2: iron; hydrogenchloride / ethanol / 4 h / Reflux
View Scheme
1,2-bis[2-(N-acetoacetamide)phenoxy]ethane

1,2-bis[2-(N-acetoacetamide)phenoxy]ethane

benzaldehyde
100-52-7

benzaldehyde

urea
57-13-6

urea

A

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

B

5-Ethoxy-6-methyl-4-(phenyl)-3,4-dihydropyrimidin-2(1H)-one

5-Ethoxy-6-methyl-4-(phenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol Reflux;
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

1,2-bis[2-(1H-tetrazol-1-yl)phenoxy]ethane

1,2-bis[2-(1H-tetrazol-1-yl)phenoxy]ethane

Conditions
ConditionsYield
With sodium azide; acetic acid at 90℃;99%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

5-(acetoacetamido)-2-benzimidazolinone
26576-46-5

5-(acetoacetamido)-2-benzimidazolinone

C.I. pigment yellow 180

C.I. pigment yellow 180

Conditions
ConditionsYield
Stage #1: 1,2-Bis(2-aminophenoxy)ethane With hydrogenchloride; sodium nitrite In water at 5℃; Large scale;
Stage #2: 5-Acetoacetyl-amino-benzimidazol-2-one With acetic acid; sodium hydroxide In water at 5℃; pH=7; Large scale;
Stage #3: With sodium hydrogencarbonate In water for 3h; pH=7; Reagent/catalyst; Solvent; Large scale;
95.8%
1,1'-bis(isothiocyanatocarbonyl)ferrocene
188853-64-7

1,1'-bis(isothiocyanatocarbonyl)ferrocene

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

C28H24FeN4O4S2

C28H24FeN4O4S2

Conditions
ConditionsYield
In water; acetone at 20℃; for 5h;89.2%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

1,2-bis(2-phenylthioureidophenoxy)ethane

1,2-bis(2-phenylthioureidophenoxy)ethane

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Addition;88.2%
diglycolyl chloride
21062-20-4

diglycolyl chloride

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

17,18-dihydro-5H,9H-dibenzo[e,n]1,4,10,7,13trioxadiazacyclopentadecine-6,10-(7H,11H)-dione
96656-69-8

17,18-dihydro-5H,9H-dibenzo[e,n]1,4,10,7,13trioxadiazacyclopentadecine-6,10-(7H,11H)-dione

Conditions
ConditionsYield
With pyridine In benzene at 75℃; for 3h;87%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid tetrakis acetoxymethyl ester

1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid tetrakis acetoxymethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 24h; Reflux;87%
3,5-di-tert-butyl-2-hydroxybenzaldehyde
37942-07-7

3,5-di-tert-butyl-2-hydroxybenzaldehyde

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

N,N’-bis(3,5-di-tert-butylsalicylidene)-2,2’-(ethylenedioxy)dianiline

N,N’-bis(3,5-di-tert-butylsalicylidene)-2,2’-(ethylenedioxy)dianiline

Conditions
ConditionsYield
With acetic acid In ethanol for 12h; Reflux; Inert atmosphere; Schlenk technique; Glovebox;86%
With acetic acid In ethanol for 3h; Heating;78%
2-Picolinic acid
98-98-6

2-Picolinic acid

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

1,4-bis[o-(pyridine-2-carboxamidophenyl)]-1,4-dioxabutane
1340527-35-6

1,4-bis[o-(pyridine-2-carboxamidophenyl)]-1,4-dioxabutane

Conditions
ConditionsYield
Stage #1: 2-Picolinic acid; 1,2-Bis(2-aminophenoxy)ethane In pyridine at 20 - 110℃;
Stage #2: With triphenyl phosphite In pyridine Reflux;
86%
2,6-Diacetylpyridine
1129-30-2

2,6-Diacetylpyridine

gadolinium(III) perchlorate hydrate

gadolinium(III) perchlorate hydrate

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Gd(3+)*C23H21N3O2*3ClO4(1-)*5H2O = [Gd(C23H21N3O2)](ClO4)3*5H2O

Gd(3+)*C23H21N3O2*3ClO4(1-)*5H2O = [Gd(C23H21N3O2)](ClO4)3*5H2O

Conditions
ConditionsYield
In ethanol addn. of the hydrated lanthanide perchlorate in EtOH to a warm soln. of 2,6-diacetylpyridine in EtOH, addn. of the diamine in EtOH with stirringand heating, reflux (4 h); filtration, washing (EtOH), drying (vac.); elem. anal.;85.2%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

malononitrile
109-77-3

malononitrile

C20H14N8O2
1401622-89-6

C20H14N8O2

Conditions
ConditionsYield
Stage #1: 1,2-Bis(2-aminophenoxy)ethane With hydrogenchloride; sodium nitrite In water at 5℃; for 0.5h; Cooling with ice;
Stage #2: malononitrile With sodium acetate In ethanol; water
85%
5-ferrocenyl isophthalic acid chloride
1229970-98-2

5-ferrocenyl isophthalic acid chloride

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

A

C32H26FeN2O4

C32H26FeN2O4

B

C64H52Fe2N4O8

C64H52Fe2N4O8

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 12h;A 82%
B 8%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

2,2′-(ethane-1,2-diildiamine)bisbenzaldehyde
33419-93-1

2,2′-(ethane-1,2-diildiamine)bisbenzaldehyde

C30H28N4O2

C30H28N4O2

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol Heating;80%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

C21H22N2O3

C21H22N2O3

C56H54N8O8

C56H54N8O8

Conditions
ConditionsYield
Stage #1: 1,2-Bis(2-aminophenoxy)ethane With hydrogenchloride In water at 20℃; for 2h;
Stage #2: With sodium nitrite In water at 0 - 5℃; for 1.83333h;
Stage #3: C21H22N2O3 Further stages;
78.3%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

3-Pyridyl isocyanate
15268-31-2

3-Pyridyl isocyanate

C26H24N6O4

C26H24N6O4

Conditions
ConditionsYield
In toluene; acetonitrile at 60℃; for 3h;75%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

chloroacetyl chloride
79-04-9

chloroacetyl chloride

1,2-bis(o-chloroacetamidophenoxy)ethane
773896-18-7

1,2-bis(o-chloroacetamidophenoxy)ethane

Conditions
ConditionsYield
With sodium carbonate In dichloromethane; water for 1h;74%
(E,E)-monochloroglyoxime
4732-58-5, 17019-15-7, 17019-20-4

(E,E)-monochloroglyoxime

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

N,N'-[2,2'-{ethane-1,2-di-yl-bis(oxy)bis(2,1-phenylene)}bis(N'-hydroxy)-2-(hydroxyimino)acetamidamide]
1246657-96-4

N,N'-[2,2'-{ethane-1,2-di-yl-bis(oxy)bis(2,1-phenylene)}bis(N'-hydroxy)-2-(hydroxyimino)acetamidamide]

Conditions
ConditionsYield
With sodium carbonate In ethanol at 60℃; for 12h;73.55%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

1,2-bis<2-<1-(ethoxycarbonyl)ethyl>aminophenoxy>ethane

1,2-bis<2-<1-(ethoxycarbonyl)ethyl>aminophenoxy>ethane

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 140℃; for 4h;71%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

benzil
134-81-6

benzil

2,3-diphenyl-1,4-diaza-7,10-dioxo-5,6:11,12-dibenzo[e,k]-cyclododeca-1,3-diene[N2O2]ane

2,3-diphenyl-1,4-diaza-7,10-dioxo-5,6:11,12-dibenzo[e,k]-cyclododeca-1,3-diene[N2O2]ane

Conditions
ConditionsYield
With hydrogenchloride In ethanol Heating;71%
quinolin-2-ylmethylbromide
5632-15-5

quinolin-2-ylmethylbromide

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

N,N,N',N'-tetrakis(2-quinolylmethyl)-1,2-bis(2-aminophenoxy)ethane

N,N,N',N'-tetrakis(2-quinolylmethyl)-1,2-bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 36h; Reflux;71%
2,6-Pyridinedicarboxaldehyde
5431-44-7

2,6-Pyridinedicarboxaldehyde

neodymium(III) perchlorate hydrate

neodymium(III) perchlorate hydrate

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Nd(3+)*C21H17N3O2*3ClO4(1-)*4H2O = [Nd(C21H17N3O2)](ClO4)3*4H2O

Nd(3+)*C21H17N3O2*3ClO4(1-)*4H2O = [Nd(C21H17N3O2)](ClO4)3*4H2O

Conditions
ConditionsYield
In ethanol addn. of the hydrated lanthanide perchlorate in EtOH to a warm soln. of 2,6-diformylpyridine in EtOH, addn. of the diamine in EtOH with stirringand heating, reflux; filtration, concn., pptn. on addn. of Et2O; elem. anal.;70.5%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

1,2-Bis(4-t-butyl-2-chlorosulfonylphenoxy)ethane
113487-24-4

1,2-Bis(4-t-butyl-2-chlorosulfonylphenoxy)ethane

4',5''''-Di-t-butyl-5,6,9,10,15,16,19,20-tetrabenzo-8,17-diaza-1,4,11,14-tetraoxa-7,18-dithiacycloicosane-7,7,18,18-tetraoxide
113487-18-6

4',5''''-Di-t-butyl-5,6,9,10,15,16,19,20-tetrabenzo-8,17-diaza-1,4,11,14-tetraoxa-7,18-dithiacycloicosane-7,7,18,18-tetraoxide

Conditions
ConditionsYield
In dichloromethane for 192h; Heating;70%
allyloxyacetyl chloride
56680-79-6

allyloxyacetyl chloride

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

1,2-bis(o-allyloxyacetamidophenoxy)ethane

1,2-bis(o-allyloxyacetamidophenoxy)ethane

Conditions
ConditionsYield
With TEA In dichloromethane at 20℃;70%
2,6-Pyridinedicarboxaldehyde
5431-44-7

2,6-Pyridinedicarboxaldehyde

manganese(II) nitrate

manganese(II) nitrate

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

{Mn(C5H3N(CHNC6H4OCH2)2)(NO3)2}
54586-12-8

{Mn(C5H3N(CHNC6H4OCH2)2)(NO3)2}

Conditions
ConditionsYield
In acetonitrile mixing of CH3CN solns. of the pyridine dialdehyde, the required dianiline, and the metal salt (slight excess); room temp. for 24 h;; slow evapn. under N2; elem. anal.;;70%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

2,2'-(ethane-1,2-diylbis(oxy))bis(N-(pyridine-2-ylmethyl)aniline)
1260103-17-0

2,2'-(ethane-1,2-diylbis(oxy))bis(N-(pyridine-2-ylmethyl)aniline)

Conditions
ConditionsYield
Stage #1: pyridine-2-carbaldehyde; 1,2-Bis(2-aminophenoxy)ethane In methanol for 12h; Reflux;
Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 6h;
70%
Stage #1: pyridine-2-carbaldehyde; 1,2-Bis(2-aminophenoxy)ethane In methanol for 4h; Reflux;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃;
60%
2-Hydroxy-4-methoxybenzaldehyde
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

6,6'-((1Z,1'Z)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(3-methoxyphenol)

6,6'-((1Z,1'Z)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(3-methoxyphenol)

Conditions
ConditionsYield
In methanol for 2h; Reflux;70%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

4-pyridyl isocyanate
70067-45-7

4-pyridyl isocyanate

C26H24N6O4

C26H24N6O4

Conditions
ConditionsYield
In toluene; acetonitrile at 60℃; for 3h;70%
2,6-Pyridinedicarboxaldehyde
5431-44-7

2,6-Pyridinedicarboxaldehyde

manganese(II) perchlorate

manganese(II) perchlorate

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

{Mn(C5H3N(CHNC6H4OCH2)2)(ClO4)2}*H2O

{Mn(C5H3N(CHNC6H4OCH2)2)(ClO4)2}*H2O

Conditions
ConditionsYield
With H2O In acetonitrile mixing of CH3CN solns. of the pyridine dialdehyde, the required dianiline, and the metal salt (slight excess); room temp. for 24 h;; slow evapn. under N2; elem. anal.;;67%
2,6-Pyridinedicarboxaldehyde
5431-44-7

2,6-Pyridinedicarboxaldehyde

gadolinium(III) perchlorate hydrate

gadolinium(III) perchlorate hydrate

1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Gd(3+)*C21H17N3O2*3ClO4(1-)*8H2O*C2H5OH = [Gd(C21H17N3O2)](ClO4)3*8H2O*C2H5OH

Gd(3+)*C21H17N3O2*3ClO4(1-)*8H2O*C2H5OH = [Gd(C21H17N3O2)](ClO4)3*8H2O*C2H5OH

Conditions
ConditionsYield
In ethanol addn. of the hydrated lanthanide perchlorate in EtOH to a warm soln. of 2,6-diformylpyridine in EtOH, addn. of the diamine in EtOH with stirringand heating, reflux; filtration, concn., pptn. on addn. of Et2O; elem. anal.;65.5%
1,2-Bis(2-aminophenoxy)ethane
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

mercury(II) iodide

mercury(II) iodide

Hg2I4(2,2'-(ethane-1,2-diylbis(oxy))dibenzenamine)

Hg2I4(2,2'-(ethane-1,2-diylbis(oxy))dibenzenamine)

Conditions
ConditionsYield
In methanol; chloroform CHCl3-soln. of N-compd. was layered onto MeOH soln. of HgI2; crystn. for 30 days, elem. anal.;65%

52411-34-4Relevant articles and documents

Diaryl-substituted polyethers with acetoacet-anilide fragment in the synthesis of dihydro-pyrimidine-containing podands

Radionova,Titova, Yu. A.,Isenov,Fedorova,Rusinov,Charushin

, p. 998 - 1004 (2014)

The interaction of ortho-aminoaryl polyethers, derivatives of mono-, di-, and triethylene glycol, with acetyl ketene, generated from 2,2,6-trimethyl-4H-1,3-dioxin-4-one produced acetoacetanilide- containing podands. 2,2,6-Trimethyl-4H-1,3-dioxin-4-one reacted with aminoaryl-substituted podands containing a short polyether chain (1-2 atoms) in toluene medium without catalyst. Acetoacetanilide- containing podands with longer polyether chains could be obtained by using triethylamine or acetic acid as catalyst. Acetoacetanilide-containing podands were used in the Biginelli reaction as CH-active components.

A Comprehensive Study of the Ca2+ Ion Binding of Fluorescently Labelled BAPTA Analogues

Csomos, Attila,Kontra, Bence,Jancsó, Attila,Galbács, Gábor,Deme, Ruth,Kele, Zoltán,Rózsa, Balázs József,Kovács, Ervin,Mucsi, Zoltán

, p. 5248 - 5261 (2021/10/19)

Since its development, the ionophore BAPTA (1,2-bis(2-aminophenoxy)-ethane-N,N,N’,N’-tetraacetic acid) has been used unchanged in calcium sensing applications. In this work we present a comprehensive experimental and theoretical study of novel alterations in the structure of BAPTA, with a focus on the systematic modification of the chain connecting the two aromatic rings of the molecule (denoted as “linker”). A bis-(diethylamino)xantene fluorophore was also attached to the structures in a fixed position and the structure-fluorescence response relationship of these molecules was investigated in addition. The effect of the linker's length, the number of oxygen atoms in this chain and even the removal of one of the rings was tested; these all proved to significantly alter the characteristics of the compounds. For example, it was found that the second aromatic ring of BAPTA is not essential for the turn-on of the fluorescence. We also demonstrated that successful sensing can be realized even by replacing the chain with a single oxygen atom, which suggests the availability of a new calcium binding mode of the chelator. The reliable turn-on characteristic, the steep Ca2+ fluorescence titration curve and the intense fluorescence emission combine to make this compound a prospective candidate as a calcium sensing molecular probe in diagnostic neurobiological applications.

A Copper Nanocluster-Based Fluorescent Probe for Real-Time Imaging and Ratiometric Biosensing of Calcium Ions in Neurons

Liu, Zhichao,Jing, Xia,Zhang, Sanjun,Tian, Yang

, p. 2488 - 2497 (2019/02/12)

Fluorescent calcium ion (Ca2+) sensing and imaging have become an essential technique for investigation of signaling pathways of Ca2+ and understanding the role of Ca2+ in neurodegenerative disease. Herein a copper nanocluster (CuNC)-based ratiometric fluorescent probe was developed for real-time sensing and imaging of Ca2+ in neurons, in which a specific Ca2+ ligand with two formaldehyde groups was synthesized and further conjugated with polyethylenimine (PEI) to form a new ligand molecule for the synthesis of CuNCs. Meanwhile, water-soluble Alex Fluor 660 NHS ester was immobilized onto CuNCs as a reference element. The developed ratiometric fluorescence nanoprobe demonstrated a good linearity with Ca2+ concentration in the range of 2-350 μM, and a detection limit down to 220 ± 11 nM was achieved. In addition, the response time of the present probe for Ca2+ was found to be less than 2 s with good stability and high selectivity. Taking advantage of the low cytotoxicity and good biocompatibility of the developed nanoprobe, it was discovered that the histamine-induced cytoplasmic Ca2+ increase in various parts of neurons was different. Moreover, it was found O2--induced cytoplasmic Ca2+ burst and O2--induced neuronal death possibly resulted from Ca2+ overload in the neurons.

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