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CAS No. : | 3301-79-9 | MDL No. : | MFCD00036873 |
Formula : | C21H12O7 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BZTDTCNHAFUJOG-UHFFFAOYSA-N |
M.W : | 376.32 | Pubchem ID : | 76806 |
Synonyms : |
6-Carboxyfluorescein
|
Chemical Name : | 3',6'-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-6-carboxylic acid |
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.05 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 95.7 |
TPSA : | 113.29 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.5 cm/s |
Log Po/w (iLOGP) : | 1.58 |
Log Po/w (XLOGP3) : | 2.95 |
Log Po/w (WLOGP) : | 3.26 |
Log Po/w (MLOGP) : | 1.83 |
Log Po/w (SILICOS-IT) : | 2.8 |
Consensus Log Po/w : | 2.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.44 |
Solubility : | 0.0136 mg/ml ; 0.0000362 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.99 |
Solubility : | 0.00384 mg/ml ; 0.0000102 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.5 |
Solubility : | 0.00119 mg/ml ; 0.00000317 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 4.08 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; for 2h; | The resin was incubated for 1 h with 264 mg (0.45 mmol) Fmoc-Cys(Trt)-OH, 144 mg (0.45 mmol) TBTU and 157 mul DIEA (0.9 mmol) in 3 ml DMF and washed 5 times with DMF. After fmoc-removal, Fmoc-Ado-OH was coupled by incubation of 156 mg (0.45 mmol) Fmoc-Ado-OH 173 mg (0.45 mmol) TBTU and 157 mul DIEA (0.9 mmol) in 3 ml DMF according to the procedure above. Fmoc was removed and the resin was reacted with 338 mg (0.9 mmol) 5,<strong>[3301-79-9]6-carboxyfluorescein</strong> (isomeric mixture), 140 mg (0.9 mmol) HOBt and 141 mul (0.9 mmol) DIC in 3 ml DMF for 2 h. Finally the resin was incubated in 2/2/96 (v/v/v) piperidine/DBU/DMF for 10 min, washed 10 times in DCM and dried under vacuum. 12 was cleaved from the resin with 50/5/45 (v/v/v) TFA/TES/DCM for 30 min and purified by RP-HPLC. MS: [MH]+=625 g/mol (MW calculated=624 g/mol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 10 The procedure of Example 8 was followed, but 15 of ganglyoside was used place of 30 mg of ganglyoside, to yield a liposome composition entrapping 6-CF and CDDP at respective entrapment ratios of 17.6percent and 18.0percent and having a 42.5° C. phase transition temperature. | ||
EXAMPLE 12 The procedure of Example 8 was followed, but 45 mg of ganglyoside was used in place of 30 mg of ganglyoside, to yield a liposome composition entrapping 6-CF and CDDP at respective entrapment ratios of 18.8percent and 17.6percent and having a 42.1° C. phase transition temperature. | ||
EXAMPLE 14 The procedure of Example 8 was followed, but 210 mg of DPPC and 90 DSPC were used in place of 270 mg of DPPC and 30 mg of DSPC, to yield a liposome composition entrapping 6-CF and CDDP at respective entrapment ratios of 20.7percent and 21.2percent and having a 44.7° C. phase transition temperature. |
Example 14 30 mg of sodium palmitoyltaurine (PT) was used in place of 30 mg of SMT in Example 1 and treated similarly as in Example 1, to give a liposome composition of the 6-CF entrapment ratio of 22.4percent. | ||
Example 18 40 mg of PMT was used in place of 40 mg of SMT in Example 15 and treated similarly as in Example 15, to give a liposome composition of the 6-CF entrapment ratio of 6.8percent. | ||
Example 19 40 mg of ODS was used in place of 40 mg of SMT in Example 15 and treated similarly as in Example 15, to give a liposome composition of the 6-CF entrapment ratio of 6.5percent. | ||
Example 2 15 mg of SMT was used in place of 30 mg of SMT in Example 1 and treated similarly as in Example 1, to give a liposome composition of the 6-CF entrapment ratio of 34.9percent. | ||
Example 3 45 mg of SMT was used in place of 30 mg of SMT in Example 1 and treated similarly as in Example 1, to give a liposome composition of the 6-CF entrapment ratio of 39.4percent. | ||
Example 4 60 mg of SMT was used in place of 30 mg of SMT in Example 1 and treated similarly as in Example 1, to give a liposome composition of the 6-CF entrapment ratio of 46.3percent. | ||
Example 5 30 mg of sodium palmitoylmethyltaurine (PMT) was used in place of 30 mg of SMT in Example 1 and treated similarly as in Example 1, to give a liposome composition of the 6-CF entrapment ratio of 32.3percent | ||
Example 7 15 mg of ODS was used in place of 30 mg of ODS in Example 1 and treated similarly as in Example 1, to give a liposome composition of the 6-CF entrapment ratio of 24.1percent. | ||
Example 8 45 mg of ODS was used in place of 30 mg of ODS in Example 1 and treated similarly as in Example 1, to give a liposome composition of the 6-CF entrapment ratio of 38.3percent. | ||
Example 9 60 mg of ODS was used in place of 30 mg of ODS in Example 1 and treated similarly as in Example 1, to give a liposome composition of the 6-CF entrapment ratio of 40.1percent. | ||
EXAMPLE 2 The procedure of Example 1 was followed, but 15 mg of sulfatide was used in place of 30 mg of sulfatide, to yield a liposome composition entrapping 6-CF at a 23.3percent entrapment ratio and having a 42.4° C. phase transition temperature. | ||
EXAMPLE 13 The procedure of Example 11 was followed, but 15 mg of sulfatide was used in place of 30 mg of sulfatide, to yield a liposome composition entrapping 6-CF and CDDP at respective entrapment ratios of 16.5percent and 16.2percent and having a 42.4° C. phase transition temperature. | ||
EXAMPLE 15 The procedure of Example 11 was followed, but 45 mg of sulfatide was used in place of 30 mg of sulfatide, to yield a liposome composition entrapping 6-CF and CDDP at respective entrapment ratios of 17.6percent and 16.8percent and having a 41.7° C. phase transition temperature. | ||
EXAMPLE 17 The procedure of Example 11 was followed, but 210 mg of DPPC and 90 mg of DSPC were used in place of 270 mg of DPPC and 30 mg of DSPC, to yield a liposome composition entrapping 6-CF and CDDP at respective entrapment ratios of 21.7percent and 18.1percent and having a 44.5° C. phase transition temperature. | ||
EXAMPLE 3 The procedure of Example 1 was followed, but 45 mg of sulfatide was used in place of 30 mg of sulfatide, to yield a liposome composition entrapping 6-CF at a 18.9percent incorporation ratio and having a 42.4° C. phase transition temperature. | ||
EXAMPLE 2 The procedure of Example 1 was followed using a chloroform solution containing 1percent of a 7:3 (w/w) mixture of dipalmitoylphosphatidylcholine and distearoylphosphatidylcholine and a processing temperature of 60° C. to give liposomes with a 6-CF trap ratio of 32.2percent. | ||
Using the thus-obtained MLV dispersion and following the procedure of Example 1, there was obtained liposomes with a 6-CF trap ratio of 21.3percent. | ||
EXAMPLE 3 The procedure of Example 1 was followed using a chloroform solution containing 1percent of distearoylphosphatidylcholine and a processing temperature of 70° C. to give liposomes with a 6-CF trap ratio of 37.7percent. | ||
To a 30-ml portion of MLV as obtained by combining such batches was added 10 ml of ethyl ether and the mixture was processed in the same manner as in Example 4 to give liposomes with an improved 6-CF trap ratio. | ||
EXAMPLE 7 An SUV obtained by comminuting the MLV produced in Example 4 by means of a probe-type ultrasonic shaker was used and processed in the same manner as in Example 4 to give liposomes with an improved 6-CF trap ratio. | ||
The preferred fluorochromes for use in the fluorochrome-protein conjugates are selected from the group consisting of...fluorescein-6-isothiocyanate,5-carboxyfluorescein, succinimidyl ester,6-carboxyfluorescein, succinimidyl ester,5-(and-6)-carboxyfluorescein, succinimidyl ester,... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2 5-(6)-CARBOXYFLUORESCEIN (188 mg, 0.5 MMOL) and dicyclohexylcarbodiimide (113 mg, 0.55 MMOL) are dissolved in DMF (20 ML). The mixture is stirred for 2 hours and cooled to 0C. A solution of hexamethylenediamide (116 mg, 1 MMOL) and DMAP (30 mg) in DMF is added and the mixture is stirred at ambient temperature for 72 hours. The solution is evaporated and the conjugate between CARBOXYFLUORESCEIN and hexamethylene-amine is isolated as monoamide by chromatography (silica, chloroform and methanol) | ||
Step 2 5 (6)-CARBOXYFLUORESCEIN (188 mg, 0.5 MMOL) and dicyclohexylcarbodiimide (113 mg, 0.55 MMOL) are dissolved in DMF (20 ML). The mixture is stirred for 2 hours and cooled to 0C. A solution of hexamethylenediamide (116 MG, 1 MMOL) and DMAP (30 mg) in DMF is added and the mixture is stirred at ambient temperature for 72 hours. The solution is evaporated and the conjugate between CARBOXYFLUORESCEIN and hexamethylene-amine is isolated as monoamide by chromatography (silica, chloroform and methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 73h; | Step 3 5 (6)-Carboxyfluorescein (188 mg, 0.5 MMOL) and dicyclohexylcarbodiimide (113 mg, 0.55 MMOL) are dissolved in DMF (20ML). The mixture is cooled to 0°C and a solution of the monoamide from step 2 above (286 mg, 0.5 MMOL) and DMAP (15 mg) in DMF (5 ml) is added. The mixture is stirred for 1 hour at 0°C and then stirred for 72 hours at ambient temperature. The solution is evaporated and the final conjugate is isolated by chromatography (silica, chloroform and methanol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2. 5 (6)-CARBOXYFLUORESCEIN (0.1 MMOL) and dicyclohexyl carbodiimide (0.11 MMOL) are dissolved in DMF. The mixture is stirred for 3 hours and cooled to 0 °C. A solution of 2,2-bis (HYDROZYMETHYL)-1-AZABICYCLO [2,2, 2] octane-3-one (0.5 MMOL) and DMAP (10 mg) in DMF is added and the mixture is stirred at ambient temperature for 72 hours. The solution is evaporated and the contrast agent is isolate by flash chromatography (silica, ethyl acetate/hexane) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2 5 (6) CARBOXYFLUORESCEIN (1 MMOL) and dicyclohexylcarbodiimide (1 MMOL) are dissolved in DMF (30 ML). The mixture is stirred for 2 hours at ambient temperature. A solution of 7-aminonitrazepam (1 MMOL) and DMAP (20 mg) in DMF (10 mi) is added and the mixture is evaporated and the conjugate between 7-aminonitrazepam and 5 (6) CARBOXYFLUORESCEIN is isolated by chromatography (silica, chloroform/methanol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; at 110℃; for 0.5h; | General procedure: To a solution of <strong>[3301-79-9]5(6)-carboxyfluorescein</strong> (15.0 g, 39.9 mmol) in Ac2O (180 mL) was added pyridine (18 mL, 22.3 mmol) and the reaction was stirred for 30 min at 110 °C. The clear solution was concentrated in vacuo. The crude mixture was dissolved in EtOAc (300 mL) and washed with aqueous KHSO4 (1 M, 2 x 300 mL) and brine (300 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired compound as a light yellow solid (18.1 g, 98percent). HPLC tR 7.5 and 7.6 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.6% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 14.5h;Inert atmosphere; | General procedure: To a stirred solution of 9a (158 mg) and 4-amino-TEMPO (86.2 mg)in dry DMF (2 mL), DCC (104 mg) and HOBt·H2O (68 mg) were addedin an ice-bath under argon atmosphere. The mixture was stirred atroom temperature for 10 h. The reaction mixture was filtered andwashed with CHCl3. After the removal of organic solvents, the residuewas purified by silica-gel column chromatography (CHCl3-MeOH =10:1) to afford 2a (65.2 mg, 47.2percent). By the similar way as 2a, 2b(14.6 mg, Y: 10.6percent) was afforded from 9b (383 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 25℃; for 3h; | A solution of <strong>[3301-79-9]3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-6-carboxylic acid</strong> (752 mg, 2.00 mmol, 1.00 equiv), DIPEA (774 mg, 5.99 mmol, 3.00 equiv), HATU (912 mg, 2.40 mmol, 1.20 equiv), tert-butyl N-(6-aminohexyl)carbamate (475 mg, 2.20 mmol, 1.00 equiv) in DMF (10 mL) was stirred for 3 h at 25 C. The reaction was then quenched by the addition of 50 mL of water. The solids were filtered and the crude product was purified by C18 reverse phase chromatography eluting with H2O/CH3CN to afford 400 mg (35%) of the title compound as a yellow solid. LCMS: [M+H]+ 575.23. |
Tags: 3301-79-9 synthesis path| 3301-79-9 SDS| 3301-79-9 COA| 3301-79-9 purity| 3301-79-9 application| 3301-79-9 NMR| 3301-79-9 COA| 3301-79-9 structure
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H242 | Heating may cause a fire |
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H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
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H316 | Causes mild skin irritation |
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H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
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H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
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H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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