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[ CAS No. 75350-46-8 ] {[proInfo.proName]}

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Chemical Structure| 75350-46-8
Chemical Structure| 75350-46-8
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Product Details of [ 75350-46-8 ]

CAS No. :75350-46-8 MDL No. :MFCD00077345
Formula : C24H13NO7 Boiling Point : -
Linear Structure Formula :- InChI Key :AYDAHOIUHVUJHQ-UHFFFAOYSA-N
M.W : 427.36 Pubchem ID :122038
Synonyms :
N-(5-Fluoresceinyl)maleimide;5-Maleimido-fluorescein;5-MF
Chemical Name :1-(3',6'-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)-1H-pyrrole-2,5-dione

Calculated chemistry of [ 75350-46-8 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.04
Num. rotatable bonds : 1
Num. H-bond acceptors : 7.0
Num. H-bond donors : 2.0
Molar Refractivity : 113.31
TPSA : 113.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 2.54
Log Po/w (WLOGP) : 2.61
Log Po/w (MLOGP) : 2.49
Log Po/w (SILICOS-IT) : 2.62
Consensus Log Po/w : 2.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.44
Solubility : 0.0155 mg/ml ; 0.0000363 mol/l
Class : Moderately soluble
Log S (Ali) : -4.57
Solubility : 0.0116 mg/ml ; 0.0000271 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.84
Solubility : 0.000623 mg/ml ; 0.00000146 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.7

Safety of [ 75350-46-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 75350-46-8 ]

* 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.

  • Downstream synthetic route of [ 75350-46-8 ]

[ 75350-46-8 ] Synthesis Path-Downstream   1~52

  • 1
  • N-(5-fluoresceinyl)maleamic acid [ No CAS ]
  • [ 75350-46-8 ]
YieldReaction ConditionsOperation in experiment
87% With 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride In N,N-dimethyl-formamide; benzene for 2.5h; Heating;
  • 2
  • [ 75350-46-8 ]
  • β-lactamase I from Bacillus cereus 569/H, E166C mutant [ No CAS ]
  • β-lactamase I from Bacillus cereus 569/H, E166C mutant, labeled with thiol-specific fluorescein-5-maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide at 20℃; for 2h;
  • 3
  • [ 85-61-0 ]
  • [ 75350-46-8 ]
  • C45H49N8O23P3S [ No CAS ]
  • 4
  • goat-anti mouse IgG-α-NHCH2CH2CH2-ω-SH-terminated poly(ethyleneglycol) [ No CAS ]
  • [ 75350-46-8 ]
  • goat-anti mouse IgG-α-NHCH2CH2CH2-ω-S-(fluorescein-5)-terminated poly(ethyleneglycol) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With RX buffer at 25℃; for 2h;
  • 5
  • C43H78N16O14S [ No CAS ]
  • [ 75350-46-8 ]
  • C67H91N17O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In water at 20℃; for 0.25h; Aqueous buffer; 7 The synthesis of lactam bridged peptide conjugate a*-peptide-E*-spacer-AEM-Suc-Flrc, i.e., D-Ala*-peptide-Glu*-spacer-NH-CH2CH2-S-Suc-Flrc (lactam bridge between N-terminus of a* and the side chain COOH group of E*) comprising cyclic peptide a*-peptide-E* and fluorescein-5-succinimide coupled via a thioether bond and spacer units at the C-terminus of the targeting unit, was carried out in aqueous buffer solution at pH 7. The appropriate sulfhydryl-bearing peptide conjugate (a*-peptide-E*-spacer-EAT from example 3) and threefold excess of fluorescein-5-maleimide (Catalogue No. P4361, Promega Corporation, Madison, Wis., USA) were dissolved in 5 mM NaHCO3, and allowed to stay 15 min at room temperature prior to stopping with 0.142 M 2-mercaptoethanol. The product was isolated on RP-HPLC by water-acetonitrile gradient buffered by 0.05 M ammonium acetate.Particular example of fluorescein-labeled cyclic peptide conjugate:a*LRSGRGE*-Teg-AEM-Suc-Flrc (Compound KP008) comprising functional peptide Leu-Arg-Ser-Gly-Arg-Gly and spacer Teg i.e. NH-(CH2CH2-0)3-CH2-CO. Observed positive ion M+1: 1502.54 Da. Calculated MW: 1502.9 Da.
  • 6
  • [ 3326-34-9 ]
  • [ 75350-46-8 ]
  • 7
  • [ 923-16-0 ]
  • [ 942421-03-6 ]
  • UDP-MurNAc-L-Ala-γ-D-Glu-m-DAP [ No CAS ]
  • uridine diphosphate N-acetylglucosamine [ No CAS ]
  • [ 75350-46-8 ]
  • C64H79N9O29S [ No CAS ]
  • C101H138N16O49S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: D-alanyl-D-alanine; D-cysteine-D-alanine; UDP-MurNAc-L-Ala-γ-D-Glu-m-DAP With recombinant Pseudomonas aeruginosa MurF ligase; ATP Hepes buffer; Enzymatic reaction; Stage #2: Enzymatic reaction; Stage #3: uridine diphosphate N-acetylglucosamine; N-(5-fluoresceinyl)maleimide Further stages;
  • 8
  • reduced human galectin-1 [ No CAS ]
  • [ 75350-46-8 ]
  • human galectin-1 FITC-tagged [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide for 1h; aq. phosphate buffer; Darkness; Inert atmosphere;
  • 9
  • Ac-Aib-Asn-Ile-Ile-Aib-Pro-Leu-Leu-Aib-Pro-Ile-Cys-NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • C85H119N15O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; N,N-dimethyl-formamide General procedure: Furthermore, peptides were reacted with fluorescein 5-maleimide (1.5 equiv) in DMF/methanol (1:2; v/v) for 4-24h, and then subjected to reversed-phase HPLC to afford fluorescein-labeled peptides (yield: 42-59%).
  • 10
  • Ac-Aib-Asn-Ile-Ile-Aib-Pro-Leu-Leu-Ala-Pro-Ile-Cys-NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • C84H117N15O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; N,N-dimethyl-formamide General procedure: Furthermore, peptides were reacted with fluorescein 5-maleimide (1.5 equiv) in DMF/methanol (1:2; v/v) for 4-24h, and then subjected to reversed-phase HPLC to afford fluorescein-labeled peptides (yield: 42-59%).
  • 11
  • Ac-Ala-Asn-Ile-Ile-Aib-Pro-Leu-Leu-Aib-Pro-Ile-Cys-NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • C84H117N15O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; N,N-dimethyl-formamide General procedure: Furthermore, peptides were reacted with fluorescein 5-maleimide (1.5 equiv) in DMF/methanol (1:2; v/v) for 4-24h, and then subjected to reversed-phase HPLC to afford fluorescein-labeled peptides (yield: 42-59%).
  • 12
  • Ac-Aib-Asn-Ile-Ile-Ala-Pro-Leu-Leu-Aib-Pro-Ile-Cys-NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • C84H117N15O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; N,N-dimethyl-formamide General procedure: Furthermore, peptides were reacted with fluorescein 5-maleimide (1.5 equiv) in DMF/methanol (1:2; v/v) for 4-24h, and then subjected to reversed-phase HPLC to afford fluorescein-labeled peptides (yield: 42-59%).
  • 13
  • Ac-Aib-Asn-Ile-Ile-Aib-Aib-Leu-Leu-Aib-Aib-Ile-Cys-NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • C83H119N15O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; N,N-dimethyl-formamide General procedure: Furthermore, peptides were reacted with fluorescein 5-maleimide (1.5 equiv) in DMF/methanol (1:2; v/v) for 4-24h, and then subjected to reversed-phase HPLC to afford fluorescein-labeled peptides (yield: 42-59%).
  • 14
  • Ac-Aib-Asn-Ile-Ile-Aib-Pro-Leu-Leu-Aib-Aib-Ile-Cys-NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • C84H119N15O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; N,N-dimethyl-formamide General procedure: Furthermore, peptides were reacted with fluorescein 5-maleimide (1.5 equiv) in DMF/methanol (1:2; v/v) for 4-24h, and then subjected to reversed-phase HPLC to afford fluorescein-labeled peptides (yield: 42-59%).
  • 15
  • Ac-Aib-Asn-Ile-Ile-Aib-Aib-Leu-Leu-Aib-Pro-Ile-Cys-NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • C84H119N15O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; N,N-dimethyl-formamide General procedure: Furthermore, peptides were reacted with fluorescein 5-maleimide (1.5 equiv) in DMF/methanol (1:2; v/v) for 4-24h, and then subjected to reversed-phase HPLC to afford fluorescein-labeled peptides (yield: 42-59%).
  • 16
  • C18H32N2O4S [ No CAS ]
  • [ 75350-46-8 ]
  • C42H45N3O11S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 20℃; for 24h; 9 Synthesis of Oseltamivir-Fluorescein-5-Maleimide (Scheme 10). A stirred solution of oseltamivir phosphonate 100 mg, in 50 mL DCM was treated with 50 mL aqueous Na2CO3 (50 mg). The white solution was stirred over a period of 45 minutes at room temperature. The combined aqueous and organic layers were extracted with dichloromethane (100 mL) and the organic phase was dried over Na2SO4. The combined organic phases were evaporated in a rotary evaporator to yield the product oseltamivir as a liquid, which was used without further purification in the next step. Oseltamivir was reacted with ethylene sulphide in dichloromethane in a sealed tube and heated at 65 degrees centigrade for 6 hours. The reaction was then cooled to room temperature and evaporated in a rotary evaporator to yield the product, which was purified by silica column chromatography (hexane/dichloro methane 20:80 ratio). Ethylene sulphide derivative of oseltamivir and fluorescein-5-maleimide was added to 5 mL of DMF. The reaction mixture was stirred for 24 hours at room temperature and concentrated under vacuum. The crude product was purified by preparative RP-HPLC using aqueous CH3CN. Acetonitrile was removed under vacuum, and pure fractions were freeze-dried to yield oseltamivir-alkyl-fluorescein-5-maleimide as an orange solid.
  • 17
  • C135H194N26O24S3 [ No CAS ]
  • [ 75350-46-8 ]
  • C159H207N27O31S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide 4 Synthesis of biotinylated PPS 1D1 Synthesis of biotinylated PPS 1D1. This synthesis was carried out on NovaSyn TGR resin (EMD Millipore, MA). Fmoc-Cys(Trt)-OH (HOBt, HBTU,DIPEA) was loaded as first amino acid on to the resin and the rest of the PPS 1D1 synthesis was conducted as described previously. At the end 95% TFA, 2.5% water and 2.5% TIS mixture was used to cleave the compound from resin and to remove the side chain protection. Then the TFA was evaporated and resulting solid compound was dissolved in 1: 1 water: Acetonitrile (ACN) mixture. This solution was subjected to HPLC purification using the solvent conditions starting from 100:0 water: ACN to 50:50 water: ACN. The purified compound was lyophilized to obtain the dry product. Biotin-5-maleimide (Thermofisher, MA) dissolved in DMSO was coupled to this compound (1 M: 1 M ratio) in buffer solution at pH 7. The coupled Biotinylated PPS 1D1 compound was purified with HPLC. Synthesis was confirmed using MALDI-TOF MS (Voyager DePro, AB Systems, MA).
  • 18
  • C66H95N13O12S2 [ No CAS ]
  • [ 75350-46-8 ]
  • C91H108N14O21S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide Synthesis and characterization of FITC-PPS 1 This synthesis was carried out on NovaSyn TGR resin (EMD Millipore, MA). Fmoc-Cys(Trt)-OH (HOBt, HBTU,DIPEA) was loaded as first amino acid on to the resin and the rest of the PPS 1 synthesis was conducted as described previously. At the end 95% TFA, 2.5% water and 2.5% TIS mixture was used to cleave the compound from resin and to remove the side chain protection. Then the TFA was evaporated and resulting solid compound was dissolved in 1: 1 water: Acetonitrile (ACN) mixture. This solution was subjected to HPLC purification using the solvent conditions starting from 100:0 water: ACN to 50:50 water: ACN. The purified compound was lyophilized to obtain the dry product. Fluorescein-5-maleimide (Thermofisher, MA) dissolved in DMSO was coupled to this compound (1M: 1 M ratio) in buffer solution at pH 7. The coupled FITC-PPS IDI compound was purified with HPLC. Synthesis was confirmed using MALDI-TOF MS (Voyager DePro, AB Systems, MA).
  • 19
  • HS-HexPhos8 [ No CAS ]
  • [ 75350-46-8 ]
  • C102H187N25O40P8S*8C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water at 20℃; for 2h; [00184] Delivery of thiol-reactive probes: A wide scope of drug and probe molecules can be installed post-oligomerization using a protected thiol initiator (5) as shown in Figure 2, panel B, Strategy 2. This "clickable" conjugation strategy allows for attachment and delivery of drugs containing reactive functionalities that are not compatible with the organocatalytic polymerization or deprotection conditions. Many fluorescent probes, small-molecule therapeutics, and peptides are available as maleimide or iodoacetamide conjugates, and can thus be attached in situ to a thiol-functionalized oligomer immediately before treatment. To explore this strategy, deprotected thiol-initiated HexPhos 8-mer (7) was mixed with fluorescein (FL) maleimide (10) in PBS at room temperature for 2 hours to effect a Michael addition and uptake of the resulting conjugate was determined by flow cytometry (Figure 4, panel A). Cells treated with the FL-maleimide control 10 showed little FL fluorescence, likely only arising from reaction of nucleophiles present on the cell surface. In line with this reasoning, when the FL-maleimide conjugate was pre-reacted with mercaptoethanol to form control conjugate 11 , fluorescence was further reduced. In striking contrast, the FL-HexPhos conjugate 12 showed a 160-fold increase in fluorescence over the control compounds 10 and 11 in line with significant cellular uptake. Treated cells showed a complete shift in population ( >99% transfection) as shown in the flow cytometry histogram (Figure 4, panel B). This demonstrates the viability of maleimide coupling or other thiol-click reactions for delivery of probes or drugs where release is not a requirement for activity.
  • 20
  • C23H23NO9 [ No CAS ]
  • [ 75350-46-8 ]
  • C47H36N2O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-dimethyl-formamide at 80℃; Sealed tube; Inert atmosphere; 4 Example 4 synthesis of compound b In 10 ml of a sealing bottle will compound (32 mg, 0 . 069mmol) dissolved in 5 ml DMF in water-free, vacuum-nitrogen after three times, weighing fluorescein -5 - maleimide (33 mg, 0 . 072mmol) under the nitrogen atmosphere is added to seal the bottle, stirring to dissolve, will seal the bottle to place 80 °C lower sealing reaction for 8 hours. After cooling to room temperature to stop the reaction, methylene chloride and saturated sodium chloride solution extraction washing, collecting the organic layer using water-free magnesium sulfate drying, after filtration the filtrate is concentrated in vacuo, to obtain compound b, compound b of hydrogen and mass spectrum data are as follows:
  • 21
  • C12H26N8O4S [ No CAS ]
  • [ 75350-46-8 ]
  • C36H39N9O11S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine In N,N-dimethyl-formamide for 1h;
  • 22
  • GCGGPRRPRRPRYPGDDASIEDLAEYWARLWNYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPRYPGDDASIEDLAEYWARLWNYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 23
  • GCGGPRRPRRPRYPGDDASIEDLHEYAARLWNYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPRYPGDDASIEDLHEYAARLWNYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 24
  • GCGGPRRPRRPRYPGDDASIEDLHEYWARLANYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPRYPGDDASIEDLHEYWARLANYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 25
  • GCGGPRRPRRPRYPGDDASIEDLHEYWARLWAYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPRYPGDDASIEDLHEYWARLWAYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 26
  • GCGGPRRPRRPRYPGDDASIEDLHEYWARLWNALYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPRYPGDDASIEDLHEYWARLWNALYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 27
  • GCGGPRRPRYPGDDASIEDLHEYWARLWNYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRYPGDDASIEDLHEYWARLWNYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 28
  • GCGGPRRPRRPRYPGDDASIEDLHEYWARLWNYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPRYPGDDASIEDLHEYWARLWNYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 29
  • GCGGPRRPARPRYPGDDASIEDLHEYWARLWNYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPARPRYPGDDASIEDLHEYWARLWNYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 30
  • GCGGPRRPRRPAYPGDDASIEDLHEYWARLWNYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPAYPGDDASIEDLHEYWARLWNYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 31
  • GCGGPRRPRRPRYPGDAASIEDLHEYWARLWNYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPRYPGDAASIEDLHEYWARLWNYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 32
  • GCGGPRRPRRPRYPGDDASAEDLHEYWARLWNYLYAVA [ No CAS ]
  • [ 75350-46-8 ]
  • GCGGPRRPRRPRYPGDDASAEDLHEYWARLWNYLYAVA conjugate with N-(5-fluoresceinyl)maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h;
  • 33
  • C27H41F3N4O10S3 [ No CAS ]
  • [ 75350-46-8 ]
  • C51H54F3N5O17S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;
  • 34
  • model monoclonal IgG1 antibody [ No CAS ]
  • [ 75350-46-8 ]
  • model monoclonal IgG1 antibody interchain cysteine conjugate with fluorescein-5-maleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: model monoclonal IgG1 antibody With tris-(2-carboxyethyl)-phosphine hydrochloride In aq. phosphate buffer at 37℃; for 2h; Stage #2: N-(5-fluoresceinyl)maleimide In aq. phosphate buffer at 2 - 8℃; for 16h; Inert atmosphere;
  • 35
  • (3-(2-(2-(3-((2-(cyclooclylamino)-3,5,6-trifluoro-4-sulfamoylphenyl)sulfonyl)propanamido)ethoxy)ethoxy)propanoyl)cysteine [ No CAS ]
  • [ 75350-46-8 ]
  • 2-(((1-(3-carboxy-4-(6-hydroxy-3-oxo-3H-xanthen -9-yl)phenyl)-2,5-dioxopyrrolidin-3-yl)thio)methyl)-16-((2-(cyclooctylamino)-3,5,6-trifluoro-4-sulfamoylphenyl)sulfonyl) -4,14-dioxo-7,10-dioxa-3,13-diazahexadecanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; 4 Synthesis of 2 -(((1 -(3-carboxy-4-(6-hydroxy-3 -oxo-3H-xanthen -9-yl)phenyl) -2,5- dioxopyrrolidin-3-yl)thio)methyl)-1 6-((2 -(cyclooclylamino) -3,5, 6-trzfluoro-4- sulfamoylphenyl)sulfonyl) -4, 14-dioxo- 7,10 -dioxa-3 , 1 3-diazahexadecanoic acid, 5. To a solution of Compound 4 (5 mg, 0.0068 mmoles) in DMF (1 mL) was added fluorescein-5-maleimide (3.2 mg, 0.0075 mmoles) and N,N-diisopropylethylamine (0.006 ml, 0.034 mmoles) and stirred for 1 hour at room temperature. The crude reaction mixture was purified reverse-phase HPLC [A =2 mM ammonium acetate buffer (pH 7.0), B = CH3CN, solvent gradient: 0% B to 100% B in 30 mini to yield the product as a yellow powder (6 1%). LRMS-LC/MS (mlz): [M + H] calculated for C51H54F3N5017S3, 1161.26; found, 1162.2.
  • 36
  • (2R,5S,8S)-8-amino-5-(carboxymethyl)-29-((2-(cyclooctylamino)-3,5,6-trifluoro-4-sulfamoylphenyl)sulfonyl)-2-(mercaptomethyl)-4,7,11,27-tetraoxo-14,17,20,23-tetraoxa-3,6,10,26-tetraazanonacosanoic acid [ No CAS ]
  • [ 75350-46-8 ]
  • 5-(3-(((2R,5S,8S)-8-amino-2-carboxy-5-(carboxymethyl)-29-((2-(cyclooctylamino)-3,5,6-trifluoro-4-sulfamoylphenyl)sulfonyl)-4,7,11,27-tetraoxo-14,17,20,23-tetraoxa-3,6,10,26-tetraazanonacosyl)thio)-2,5-dioxopyrrolidin-1-yl)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; 5 Synthesis of 5-(3-(((2R, 5S,8S) -8-amino-2 -carboxy-5- (carboxymethyl)-29-((2 -(cyclooclylamino) - 3,5, 6-trzfluoro-4-sulfamoylphenyl)sulfonyl)-4, 7,11,2 7-tetraoxo-14,1 7,20, 23-tet raoxa-3, 6,10,26- tetraazanonacosyl)thio)-2, 5-dioxopyrrolidin-] -yl)-2 -(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid, 7. To a solution of Compound 6 (2 mg, 0.002 mmoles) in DMF (1 mL) was added fluorescein-5-maleimide (0.85 mg, 0.002 mmoles) and N,N-diisopropylethylamine (0.002 ml, 0.01 mmoles) and stirred for 1 hour at room temperature. The crude reaction mixture was purified reverse-phase HPLC [A =2 mM ammonium acetate buffer (pH 7.0), B = CH3CN, solvent gradient: 0% B to 100% B in 30 mini to yield the Conjugate 7 as a yellow powder (76%). LRMS-LC/MS (mlz): [M + H]+ calculated for C62H73F3N8023S3, 1450.39; found, 1451.3.
  • 37
  • tert-butyl (2-(3-((2-(cyclooctylamino)-3,5,6-trifluoro-4-sulfamoylphenyl)sulfonyl)propanamido)ethyl)carbamate [ No CAS ]
  • [ 75350-46-8 ]
  • 5-(3-(2-(3-((2-(cyclooctylamino)-3,5,6-trifluoro-4-sulfamoylphenyl)sulfonyl)propanamido)ethyl)thioureido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: tert-butyl (2-(3-((2-(cyclooctylamino)-3,5,6-trifluoro-4-sulfamoylphenyl)sulfonyl)propanamido)ethyl)carbamate With trifluoroacetic acid In dichloromethane for 0.5h; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.0833333h; Stage #3: N-(5-fluoresceinyl)maleimide In N,N-dimethyl-formamide for 1h; 7 Synthesis of5-(3-(2-(3-((2-(cyclooctylamino)-3,5,6-trifluoro-4-sulfamoylphenyl)sulfonyl)propanamido)ethyl)thioureido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid, 9 The tert-butyloxycarbonyl protecting group of Compound 8 (10 mg, 0.008 mmoles) was removed with a mixture of TFA/DCM (20%, 2 ml) for 30 minutes. The TFA/DCM mixture was removed under vacuum and the product brought forward without purification. To the vial containing the deprotected Compound 5, was added DMF (1 ml) and N,Ndiisopropylethylamine (0.007 ml, 0.04 mmoles) and allowed to stir for five minutes before fluorescein-5-maleimide (3.8 mg, 0.0088 mmoles) was added and allowed to stir for an additional hour. The crude mixture was purified without workup by purified reverse-phase HPLC [A = 2 mM ammonium acetate buffer (pH 7.0), B = CH3CN, solvent gradient: 0% B to 100% B in 30 mini to yield the product as a yellow powder (76%). LRMS-LC/MS (mlz): [M + H] calculated for C40H40F3N5010S3, 903.19; found, 904.2.
  • 38
  • N-succinimidyl-D-valine [ No CAS ]
  • [ 75350-46-8 ]
  • C42H35N3O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38.8% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 12h; 4.1.3. Succinimydyl D-Val 5-maleimide-Fluorescein diester 3 5-Maleimide-fluorescein (25 mg, 0.0585 mmol) was dissolved in DMF/DCM (5 ml 1:4,v/v), Suc- D-Valine (29.10 mg, 0.146 mmol), EDC (28.04 mg, 0.146 mmol) and DMAP (0.1equ) were added. The reaction mixture was stirred for 12 h at r.t.. To the reaction mixture was added with 30 ml of CH2Cl2, washed with 0.1M aqueous KHSO4 and water(2×20 ml), dried over Na2SO4, and concentrated in vacuo. The residue was purified with silica gel TCL (1:1, ethyl acetate/hexane) to afford the title diester 17.91 mg as white powder, yield 38.8%. 1H NMR(300 MHz, CD3CN) δ 0.91 (d, J=6.6 Hz, 6H) 1.13 (d, J=6.6, 6H),2.57 (m, 2H), 2.79 (s, 8H), 4.70 (d, J=7.5 Hz, 2H), 6.75-7.15 (m, 8H),7.39 (d, J=8.4 Hz, 1H), 7.80 (d, J=7.8 Hz, 1H), 8.02 (s, 1H); HR ESIMS(m/z), calculated for C42H36O13N3(M+H+) 790.2248, found790.2256.
  • 39
  • [ 84624-17-9 ]
  • [ 75350-46-8 ]
  • C64H51N3O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
42.2% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 8h; 5-Maleimide-fluorescein (25 mg, 0.0585 mmol) was dissolved in DMF/DCM (5 ml 1:4,v/v), Fmoc D-Valine (43.68 mg, 0.129 mmol), EDC (28.04 mg, 0.146 mmol) and DMAP (0.1 eq.) were added. The reaction mixture was stirred for 8 h at r.t.. To the reaction mixture was added with 30 ml of CH2Cl2, and was washed with 0.1M aqueous KHSO4 and water (2×20 ml), dried over Na2SO4, then concentrated in vacuo. The residue was purified with silica gel TCL (1:1, ethyl acetate/hexane) toafford the title diester 26.4 mg as white powder, yield 42.2%. 1H NMR(300 MHz, CD3COCD3) delta 1.11(d, J=6.6 Hz, 12H), 2.38(m, 2H), 4.26(t,J=6.6 Hz, 2H), 4.34-4.47(m, 6H), 6.99-7.15(m, 6H), 7.23(s, 2H),7.31(m, 4H), 7.40(t, J=6.6 Hz, 4H), 7.56 (m, 1H), 7.72 (t, J=6.6 Hz,4H); 7.84-7.96(m, 5H), 8.09 (m, 1H). HR ESI MS(m/z), calculated forC64H52O13N3(M+H+) 1070.3500, found 1070.3501.
  • 40
  • [ 35661-39-3 ]
  • [ 75350-46-8 ]
  • C60H43N3O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.1% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 8h; 4.1.4. Fmoc Ala 5-maleimide-Fluorescein diester 4 5-Maleimide-fluorescein (25 mg, 0.0585 mmol) was dissolved in DMF/DCM (5 ml 1:4,v/v), Fmoc Ala (55 mg, 0.176 mmol), EDC (28.04 mg, 0.146 mmol) and DMAP (0.1equ) were added. The reaction mixture was stirred for 8 h at r.t.. To the reaction mixture was added with 30 ml of CH2Cl2, and it was washed with 0.1M KHSO4 and water (2×20 ml), dried over Na2SO4, and concentrated in vacuo. The residue was purified with silica gel TCL (1:1, ethyl acetate/hexane) to afford the title diester 30.9 mg as white powder, yield 52.1%. 1H NMR (300 MHz,CD3COCD3) δ 1.59(d, J=7.5 Hz, 6H), 4.25(t, J=7.2 Hz, 2H),4.33-4.46(m, 4H), 4.53(q, J=7.2 Hz, 2H), 6.98-7.42(m, 16H), 7.54(d,J=8.1 Hz, 1H), 7.71(d, 7.5 Hz, 4H), 7.85(d, J=7.8 Hz, 4H),7.87-7.90 (m, 1H), 8.07 (d, J=1.8 Hz, 1H);HR ESI MS(m/z), calculatedfor C60H44O13N3(M+H+) 1014.2874, found 1014.2880.
  • 41
  • [ 75350-46-8 ]
  • [ 676362-60-0 ]
  • C90H138N40O19S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol at 20℃; Inert atmosphere; 4.1.6. General method for synthesis of conjugates of Arg9 peptide andfluorescein diester probes 5-8 General procedure: Arg9 peptide was dissolved in 0.5 ml deoxygenated MeOH and Fmoc amino acid diesters of 5-maleimide fluorescein, N-Succinimidyl-D-Valine diester of 5-maleimide fluorescein (4equi.) or 5-maleimide fluorescein dissolved in 50 μl acetonitrile or MeOH was added, the mixture was shaken under N2 for 2-4 h at r.t. Ethyl ether (10 fold) was used to precipitate the crude products. Purification was carried out with semi-preparative RP-HPLC under gradient program: B (acetonitrilecontaining 0.1%TFA) 0-40% in A (water containing 0.1%TFA) within30 min. The flow rate is 1.0 ml/min and detected under 270 nm. The products were characterized with MALDI-TOF MS (Table.1).
  • 42
  • C43H61N13O14S2 [ No CAS ]
  • [ 75350-46-8 ]
  • C67H74N14O21S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h; Darkness;
  • 43
  • C81H116N22O21S3 [ No CAS ]
  • [ 75350-46-8 ]
  • C105H129N23O28S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 0.5h; Darkness;
  • 44
  • all-L-(TGRAKRRMQYNRR-β-Ala-Lys(N<SUB>3</SUB>)-Cys)NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • all-L-(TGRAKRRMQYNRR-β-Ala-Lys(N<SUB>3</SUB>)-Cys(3-succinimidyl-N-5-fluorescein)) [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% In dimethyl sulfoxide at 20℃; for 4h;
  • 45
  • all-D-(TGRAKRRMQYNRR-β-Ala-Lys(N<SUB>3</SUB>)-Cys)NH<SUB>2</SUB> [ No CAS ]
  • [ 75350-46-8 ]
  • all-D-(TGRAKRRMQYNRR-β-Ala-Lys(N<SUB>3</SUB>)-Cys(3-succinimidyl-N-5-fluorescein)) [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% In dimethyl sulfoxide at 20℃; for 4h;
  • 46
  • C72H83F4N21O21S [ No CAS ]
  • [ 75350-46-8 ]
  • C96H96F4N22O28S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer; N,N-dimethyl-formamide for 3h; 11 Synthesis of Conjugate 47 Bi-ESV6-Peptide (Pll, 1 mg, 0.59 pmol, 1.0 eq) is dissolved in PBS pH 7.4 (840 pL). Maleimido- Fluorescein (0.76 mg, 1.77 pmol, 3.0 eq) is added as dry DMF solution (160 pF). The reaction is stirred for 3 h. The crude material is purified by reversed-phase HPFC (Water 0.1% TF A/Acetonitrile 0.1%TFA 9.5:0.5 to 2:8 in 20 min) and lyophilized, to obtain a yellow solid. MS(ES+) m/z 2114.7 (M+H)
  • 47
  • C66H82F2IN17O21S [ No CAS ]
  • [ 75350-46-8 ]
  • C90H95F2IN18O28S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer; N,N-dimethyl-formamide for 3h; 11 Synthesis of Conjugate 52 AlbuTag-ESV6-Peptide (P12, 1 mg, 0.61 mihoI. 1.0 eq) is dissolved in PBS pH 7.4 (840 pL). Maleimido- Fluorescein (0.78 mg, 1.82 pmol, 3.0 eq) is added as dry DMF solution (160 pF). The reaction is stirred for 3 h. (0510) The crude material is purified by reversed-phase HPFC (Water 0.1% TF A/Acetonitrile 0.1%TFA 9.5:0.5 to 2:8 in 20 min) and lyophilized, to obtain a yellow solid. MS(ES+) m/z 2073.6 (M+H)
  • 48
  • (2R,5S,8S,11S)-8-(4-aminobutyl)-5,11-bis(carboxymethyl)-16-(4-(3-((4-((2-((S)-2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)carbamoyl)quinolin-6-yl)oxy)propyl)piperazin-1-yl)-2-(mercaptomethyl)-4,7,10,13,16-pentaoxo-3,6,9,12-tetraazahexadecanoic acid [ No CAS ]
  • [ 75350-46-8 ]
  • C69H72F2N12O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
39.3% In aq. phosphate buffer; dimethyl sulfoxide for 3h; 7.1 Synthesis of Conjugate 25 SH-Cys-Asp-Lys-Asp-HK (1 mg, 0.954 pmol, 1.0 eq) was dissolved in PBS pH 7.4 (800 pL). Fluorescein-5 -maleimide (817 pg, 1.909 pmol, 2.0 eq) was added as dry DMSO solution (200 pL). The reaction was stirred for 3 h. The crude material was purified by reversed-phase HPLC (Water 0.1% TF A/Acetonitrile 0.1%TFA 9.5:0.5 to 2:8 in 20 min) and lyophilized, to obtain a yellow solid (373 nmol, 39.1%). MS(ES+) m/z 1476.47 (M+1H)1+
  • 49
  • (2R,5S,8S,11S)-8-(4-aminobutyl)-5,11-bis(carboxymethyl)-16-((4-((2-((S)-2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)carbamoyl)quinolin-8-yl)amino)-2-(mercaptomethyl)-4,7,10,13,16-pentaoxo-3,6,9,12-tetraazahexadecanoic acid [ No CAS ]
  • [ 75350-46-8 ]
  • (2R,5S,8S,11S)-8-(4-aminobutyl)-5,11-bis(carboxymethyl)-16-((4-((2-((S)-2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)carbamoyl)quinolin-8-yl)amino)-2-(((1-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)-2,5-dioxopyrrolidin-3-yl)thio)methyl)-4,7,10,13,16-pentaoxo-3,6,9,12-tetraazahexadecanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
19.3% In aq. phosphate buffer; dimethyl sulfoxide for 3h; 7.1 Synthesis of Conjugate 15 SH-Cys-Asp-Lys-Asp-ESV6 (2 mg, 2.171 pmol, 1.0 eq) was dissolved in PBS pH 7.4 (800 pL). Fluorescein-5 -maleimide (1.8 mg, 4.343 pmol, 2.0 eq) was added as dry DMSO solution (200 pL). The reaction was stirred for 3 h. The crude material was purified by reversed-phase HPLC (Water 0.1% TF A/Acetonitrile 0.1%TFA 9.5:0.5 to 2:8 in 20 min) and lyophilized, to obtain a yellow solid (420 nmol, 19.3%). MS(ES+) m/z 1348.36 (M+1H)1+ Figure 25 shows structure, chromatographic profile and LC/MS analysis of conjugate 15. MS(ES+) m/z 1348.36 (M+1H)+.
  • 50
  • C84H106N18O22S2 [ No CAS ]
  • [ 75350-46-8 ]
  • C108H119N19O29S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 20℃; for 2h; Darkness; Synthesis of Ub4_ix-FITC For synthesizing FITC labeled cyclic peptide, a similar strategy as described in Figure 8A was employed. However, Fmoc-Cys(Acm) was coupled as the first amino acid for a late stage modification. After cyclization step, Cys(Acm) was unmasked by adding 10 equiv of PdCh in 6 M Gn.HCl/200 mM phosphate buffer (pH 7.5) to the peptide (2 mM) in the same buffer and incubated at 37 °C for 30 min. In the following step, the peptide with the free thiol was dissolved in argon purged 6 M Gn.HCl/200 mM phosphate buffer (pH 7.5, 2 mM). A solution of fluorescein-5-maleimide (3.0 equiv) in DMF was added to the peptide at room temperature under dark conditions. The progress of the reaction was monitored by HPFC using a C4 analytical column with a gradient of 0-60% B in 30 min. After completion of reaction, 2 h, the crude peptide was filtered and purified by HPFC employing C4 column and gradient 0-60% B in 60 minutes.
In N,N-dimethyl-formamide at 20℃; for 2h; Darkness; Synthesis of Ub4_ix-FITC For synthesizing FITC labeled cyclic peptide, a similar strategy as described in Figure 8A was employed. However, Fmoc-Cys(Acm) was coupled as the first amino acid for a late stage modification. After cyclization step, Cys(Acm) was unmasked by adding 10 equiv of PdCh in 6 M Gn.HCl/200 mM phosphate buffer (pH 7.5) to the peptide (2 mM) in the same buffer and incubated at 37 °C for 30 min. In the following step, the peptide with the free thiol was dissolved in argon purged 6 M Gn.HCl/200 mM phosphate buffer (pH 7.5, 2 mM). A solution of fluorescein-5-maleimide (3.0 equiv) in DMF was added to the peptide at room temperature under dark conditions. The progress of the reaction was monitored by HPFC using a C4 analytical column with a gradient of 0-60% B in 30 min. After completion of reaction, 2 h, the crude peptide was filtered and purified by HPFC employing C4 column and gradient 0-60% B in 60 minutes.
  • 51
  • C93H121N21O25S3 [ No CAS ]
  • [ 75350-46-8 ]
  • C117H134N22O32S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With guanidinium monohydrochloride In aq. phosphate buffer; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Darkness; Synthesis of cyclic peptide 28 Peptide 27 (10.0 mg, 4.93 x 103 mmol, 1.0 equiv) was dissolved in argon purged 6 M Gn.HCl/200 mM phosphate buffer (pH 7.5, 2,695 m, 2 mM). A solution of fluorescein-5-maleimide (6.31 mg, 3.0 equiv) in 50 m of DMF was added to the peptide at room temperature under dark conditions. The progress of the reaction was monitored by HPLC using a C18 analytical column with a gradient of 0-60% B in 30 min. After completion of reaction, 2 h, the crude peptide was filtered and purified using a semi preparative C18 column with a gradient flow of 0-60% B in 60 min give peptide 28 (4.84 mg, 40% yield).
40% With guanidinium monohydrochloride In aq. phosphate buffer; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Darkness; Synthesis of cyclic peptide 28 Peptide 27 (10.0 mg, 4.93 x 103 mmol, 1.0 equiv) was dissolved in argon purged 6 M Gn.HCl/200 mM phosphate buffer (pH 7.5, 2,695 m, 2 mM). A solution of fluorescein-5-maleimide (6.31 mg, 3.0 equiv) in 50 m of DMF was added to the peptide at room temperature under dark conditions. The progress of the reaction was monitored by HPLC using a C18 analytical column with a gradient of 0-60% B in 30 min. After completion of reaction, 2 h, the crude peptide was filtered and purified using a semi preparative C18 column with a gradient flow of 0-60% B in 60 min give peptide 28 (4.84 mg, 40% yield).
  • 52
  • C94H116N18O20S [ No CAS ]
  • [ 75350-46-8 ]
  • C118H129N19O27S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. buffer at 20℃; for 2h; Darkness;
Same Skeleton Products
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