SMCC | NSC 344483 | Pyrrolines

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Quality Control of SMCC Purity: 97% SDS Specification

COA

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NMR

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Product Details of SMCC

CAS No. :	64987-85-5
Formula :	C₁₆H₁₈N₂O₆
M.W :	334.32
SMILES Code :	O=C(C1CCC(CN2C(C=CC2=O)=O)CC1)ON3C(CCC3=O)=O
Synonyms :	NSC 344483; Succinimidyl-4-(N-maleimidomethyl cyclohexane)-1-carboxylate; SMCC crosslinker
MDL No. :	MFCD00009634
InChI Key :	JJAHTWIKCUJRDK-UHFFFAOYSA-N
Pubchem ID :	125175

Safety of SMCC

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of SMCC

* 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 [ 64987-85-5 ]

[ 64987-85-5 ] Synthesis Path-Downstream 1~35

1
[ 6066-82-6 ]
[ 64987-85-5 ]

References: [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 711 - 713.

2
[ 64987-85-5 ]
[ 20255-95-2 ]
dimyristoyl-N-<<4-(maleimidomethyl)cyclohexyl>carbonyl>phosphatidylethanolamine [ No CAS ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 7455 - 7459.

3
[ 64987-85-5 ]
[ 124659-35-4 ]
{5,9-Bis-carboxymethyl-3-[4-([4-(2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl)-cyclohexanecarbonyl]-amino}-methyl)-benzyl]-1,5,9-triaza-cyclododec-1-yl}-acetic acid [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1989,p. 794 - 796.

4
[ 64987-85-5 ]
[ 62571-86-2 ]
(S)-1-((S)-3-{1-[4-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-cyclohexylmethyl]-2,5-dioxo-pyrrolidin-3-ylsulfanyl}-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid [ No CAS ]

References: [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 711 - 713.

5
[ 23214-92-8 ]
[ 64987-85-5 ]
[ 400647-59-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5071 - 5075.

6
5-(2-aminoethyl)indole-3-acetic acid [ No CAS ]
[ 64987-85-5 ]
5-{2-[4-(maleimidomethyl)cyclohexane-1-carboxamido]ethyl}indole-3-acetic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3229 - 3240.

7
6-(2-aminoethyl)indole-3-acetic acid [ No CAS ]
[ 64987-85-5 ]
[6-(2-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl)-cyclohexanecarbonyl]-amino}-ethyl)-1H-indol-3-yl]-acetic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3229 - 3240.

8
[ 872854-10-9 ]
[ 64987-85-5 ]
[ 872854-12-1 ]

References: [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 1295 - 1306.

9
[ 872854-06-3 ]
[ 64987-85-5 ]
[ 872854-08-5 ]

References: [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 1295 - 1306.

10
[ 872854-03-0 ]
[ 64987-85-5 ]
[ 872854-01-8 ]

References: [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 1295 - 1306.

11
[ 64987-85-5 ]
[ 77420-96-3 ]
[ 872854-14-3 ]

References: [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 1295 - 1306.

12
[ 912816-65-0 ]
[ 64987-85-5 ]
4-(2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl)-cyclohexanecarboxylic acid (3-{2-methoxy-4-[5-(4-methyl-piperazin-1-yl)-1H,1'H-[2,5']bibenzoimidazolyl-2'-yl]-phenoxy}-propyl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6444 - 6452.

13
[ 64987-85-5 ]
[ 60-32-2 ]
[ 172100-40-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 420℃; for 4h;	DIEA (78 pL, 0.50 mmol) and 6-aminohexanoic acid (44 mg, 0.33 mmol) were added to a solution of succinimidyl-4-(N-maleimidomethyl)cyclohexane-1 -carboxylate (0.30 mmol) in DMF (5 mL) in a 40 mL vial, and the reaction mixture was stirred at rt for 4 h. Thereaction mixture was then purified by HPLC and lyophilized to give 76-(4-((2,5-dioxo-2,5- dihydro-1 H-pyrrol-1 -yl)methyl)cyclohexanecarboxam ido)hexanoic acid (i-2). MS (M+1) =351, 1H-NMR (MeOD, 400 MHz) O 7.79 (bs, 1H), 6.76 (s, 2H), 3.29 (d, 2H, J=4.4 Hz), 3.10 (m, 2H), 2.24 (t, 2H, J=7.2 Hz), 2.07 (m, 4H), 1.56(m, 3H) 1.43 (m, 3H), 1.33 (m, 3H), 0.97 (m, 2 H).
	In water; N,N-dimethyl-formamide; at 20℃; for 4.08333h;	A solution of succinimidyl 4-[N-maleimidomethyl]cyclohexane-l-carboxylate (PIERCE Ref: 22360) (25 mmol) in DMF (10OmL) was stirred for 5 min, and was added at room temperature to a solution of 6-aminohexanoic acid (50 mmol) (SIGMA Ref: A2504) in H2O(50 mL). The mixture was stirred for 4h at room temperature. Dichloromethane was added(100 mL) and the organic layer was washed with water (3x150 mL) and then with 5percent aqueous citric acid (3x150 mL) to remove 6-aminohexanoic acid excess. The organic layer was dried under vacuum and the resulting white powder was stored at -200C.

References: [1]Patent: WO2016/71856,2016,A1 .Location in patent: Page/Page column 113.
[2]Patent: WO2007/113687,2007,A2 .Location in patent: Page/Page column 44.

14
tranexamic acid [ No CAS ]
[ 64987-85-5 ]
4-[((N-maleimidomethyl)cyclohexanecarboxamido)methyl]cyclohexanecarboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; N,N-dimethyl-formamide; at 20℃; for 4.08333h;	A solution of succinimidyl 4-[N-maleimidomethyl]cyclohexane-l-carboxylate (PIERCE Ref: 22360) (25 mmol) in DMF (100 mL) was stirred for 5 min, and was added at room temperature to a solution of tralphapiji-4-(aminomethyl)cyclohexanecarboxylic acid (50 mmol) (SIGMA ref: 08455) in H2O (50 mL). The mixture was stirred for 4h at room temperature. Dichloromethane was added (100 mL) and the organic layer was washed with water (3x150 mL) and then with 5percent aqueous citric acid (3x150 mL) to remove trans-4- <n="46"/>(aminomethyl)cyclohexanecarboxylic acid excess. The organic layer was dried under vacuum and the resulting white powder was stored at -20°C.

References: [1]Patent: WO2007/113687,2007,A2 .Location in patent: Page/Page column 44-45.

15
C₅₆H₉₆N₆O₁₃ [ No CAS ]
[ 64987-85-5 ]
C₆₈H₁₀₉N₇O₁₆ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4759 - 4765.

16
[ 64987-85-5 ]
C₄₁H₄₆N₂O₁₆S*C₈H₁₉N [ No CAS ]

References: [1]Synthetic Communications,2004,vol. 34,p. 2407 - 2414.

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide;Aqueous phosphate buffer;Conversion of starting material;	A 20 mM solution of SMCC (6.69 mg/mL) was prepared in dimethylsulfoxide (DMSO). The solution was diluted 1/40 in Assay Buffer and the absorbance of the samples measured at 302 nm. The concentration of the stock solution was calculated using an extinction coefficient of 602 M-1cm-1.
	In dimethyl sulfoxide;Aqueous phosphate buffer;Conversion of starting material;	A 20 mM solution of SMCC (6.69 mg/mL) was prepared in DMSO. The solution was diluted 1/40 in Assay Buffer and the absorbance of the samples was measured at 302 nm. The concentration of the stock solution was calculated using a molar extinction coefficient of 602 M-1 cm-1.

18
[ 64987-85-5 ]
trastuzumab [ No CAS ]
Trastuzumab-SMCC [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Aqueous phosphate buffer;	Trastuzumab antibody was obtained from Genentech for conjugation to DM1 using the non-cleavable heterobifunctional cross-linking reagent SMCC. The antibody was buffer-exchanged from 50 mM potassium phosphate/2 mM EDTA, pH 6.0 into 50 mM potassium phosphate/50 mM sodium chloride/2 mM EDTA, pH 6.5 (Buffer A). The antibody was then reacted with 7.5-fold molar excess SMCC linker and purified by Sephadex G25 resin before it was conjugated with DM1. The final conjugate was again purified by Sephadex G25 resin. The resulting conjugate contained 3.1 moles of DM1 per mole of antibody.
	In dimethyl sulfoxide; at 20℃; for 2h;Aqueous phosphate buffer;	The antibody was modified using a 7.5-fold molar excess of SMCC at 20 mg/mL antibody. The reaction was carried out in Buffer A (95percent v/v) with DMSO (5percent v/v) for 2 hours at room temperature with stirring.

References: [1]Patent: US2005/169933,2005,A1 .Location in patent: Page 14.
[2]Patent: US2005/169933,2005,A1 .Location in patent: Page 15.

19
huC₂₄₂ [ No CAS ]
[ 64987-85-5 ]
huC₂₄₂-SMCC [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; at 20℃; for 2h;Aqueous phosphate buffer;	The antibody was split into two samples; one was modified using a 7.5-fold molar excess of SMCC cross-linker, the other with a 8.5-fold molar excess of SMCC cross-linker. Samples were reacted at 8 mg/mL antibody. The reactions were carried out in Buffer A (95percent v/v) with DMSO (5percent v/v) for 2 hours at room temperature with stirring.

References: [1]Patent: US2005/169933,2005,A1 .Location in patent: Page 14.

20
rituximab [ No CAS ]
[ 64987-85-5 ]
Rituximab crosslinked with [succinimidyl 4-(maleimidomethyl) cyclohexane-1-carboxylate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With edetate disodium; In water; dimethyl sulfoxide; at 20℃; for 1h;pH 7.5;	1. Derivatization with SMCC. Five mg of Rituximab at a concentration of 5 mg/mL in 0.05M phosphate buffer containing 3 mM Na2EDTA (PBE; pH 7.5) and 2.5 muL of SMCC (9.3 mg/mL in dimethyl sulfoxide) were incubated with continuous rotation at room temperature for 1 h using a SMCC/Rituximab molar ratio of 4.5. Conjugated protein was purified by chromatography on a PD-10 column in the same PBE buffer. 2. Derivatization with SATA. Five mg of Rituximab at a concentration of 5 mg/mL in PBE buffer was mixed with 2.5 muL of SATA (5.8 mg/mL in dimethyl sulfoxide) and incubated at room temperature for 1h using a SATA/Rituximab molar ratio of 4.0. The excess SATA was then removed by chromatography on a PD-10 column and the purified protein was deacetylated with 5 mg of hydroxylamine-HCl (Sigma) for 5 min at room temperature. Excess hydroxylamine-HCl was removed by chromatography on a PD-10 column. 3. Rituximab Homodimer Formation and Physical Characterization SMCC- and SATA-derived proteins were mixed together and incubated with continuous rotation at room temperature for 1-2 h. The preparation was dialyzed overnight in PBS at 4° C., sterilized by filtration through a 0.22 mum non-pyrogenic filter (Costar, Corning, N.Y.), and further fractionated on a Superose 6 Column (FPLC) using the Pharmacia AKTA described above at flow rate of 0.5 mL/min. In general, the polymer revealed a retention time of approximately 16 min while the dimer revealed a retention time of approximately 29 min by FPLC. The protein fractions from FPLC were further concentrated using a Centricon YM-100 (Millipore, Billerica, Mass.), filter sterilized, and analyzed by SDS/PAGE. The expected molecular weights of the Rituximab dimer was observed for the dimer preparation by non-reducing SDS-PAGE. A 2percent agarose gel was used with murine IgM as a standard (970 kDa) for sizing the polymer. By this method, one band was resolved for the Rituximab polymer which was slightly higher than that of IgM corresponding to the molecular weight of approximately 5 immunoglobulin molecules.

References: [1]Patent: US2005/214286,2005,A1 .Location in patent: Page/Page column 15.

21
C₅₀H₈₄N₄O₂₆ [ No CAS ]
[ 64987-85-5 ]
C₆₂H₉₇N₅O₂₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%Spectr.	In dimethyl sulfoxide; at 20℃; for 3h;borate-buffered saline;	A solution containing 20 mg (60 mumoles) of N-hydroxysuccinimidyl 4-(N- methylmaleimido)cyclohexane-l-carboxylate (SMCC) in 400 muL of anhydrous DMSO was added to a buffered pH 8.6 solution containing 34 mg (~20 mumoles) of crude YE(ahLac)2 (10) in 10 mM borate-buffered saline. The mixture was stirred at room temperature for 3 h, then purified and desalted by size exclusion gel filtration (G- 10 Sephadex, 0.5 x 33 cm) using 20percent ethanol in H2O. Fractions were collected and those which corresponded to the product by 1H NMR spectroscopy was combined and concentrated under diminished pressure. HPLC analysis and purification of the residue was accomplished on an Rainin reversed phase Ci8 column (4.6 mm x 150 mm). The column was washed with a linear gradient system of 50 mM aqueous sodium phosphate (pH 5.8) containing increasing amounts OfCH3CN (0-20 min at a flow rate of 1.0 mL/min. The eluate was monitored at 277 nm; the product eluted at 9.4 min. The yield was determined by UV spectroscopy (A277 = 0.350/1 mL aliquot; 26 mL solution, 45percent)

References: [1]Patent: WO2006/104530,2006,A1 .Location in patent: Page/Page column 12; 3/5.

22
[ 64987-85-5 ]
[ 153086-78-3 ]
C₂₃H₃₇N₃O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.333333h;	SMCC (0.334 g), monoprotected diamine reagent (0.248 g) and DIEA (0.17 mL) were dissolved in dichloromethane (20 mL), stirred at ambient temperature for 20 min. The product was purified by flash chromatography, and further reacted with TFA (2 mL) and anisole (0.5 mL) for 2 hours, and the final product was isolated after removal of TFA and anisole. The corresponding hydrochloride salt was prepared by dissolving in HCl and evaporating off HCl. Mass spectrum: M+H m/e 368. The process schematically shown in Scheme-6.

References: [1]Patent: US2008/171067,2008,A1 .Location in patent: Page/Page column 17.

23
[ 64987-85-5 ]
[ 909000-59-5 ]
[ 909023-85-4 ]

References: [1]Nucleosides, nucleotides and nucleic acids,2007,vol. 26,p. 1471 - 1477.

24
[ 64987-85-5 ]
acetylcholinesterase [ No CAS ]
acetylcholinesterase and succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate conjugate [ No CAS ]

References: [1]Carbohydrate Research,2008,vol. 343,p. 2101 - 2110.

25
[ 64987-85-5 ]
[ 2450-71-7 ]
[ 1036847-90-1 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 6916 - 6926.

26
LMWH; N-deacetylated [ No CAS ]
[ 64987-85-5 ]
LMWH; maleimide and Alexa Fluor 350 functionalized [ No CAS ]

References: [1]Patent: US2006/240110,2006,A1 .Location in patent: Page/Page column 9.

27
[ 64987-85-5 ]
C₄₈H₄₁N₉O [ No CAS ]
C₆₀H₅₄N₁₀O₄ [ No CAS ]

References: [1]Bioconjugate Chemistry,2010,vol. 21,p. 302 - 312.

28
[ 64987-85-5 ]
C₅₈H₆₁N₉O₈ [ No CAS ]
C₇₀H₇₄N₁₀O₁₁ [ No CAS ]

References: [1]Bioconjugate Chemistry,2010,vol. 21,p. 302 - 312.

29
[ 64987-85-5 ]
[ 1374749-52-6 ]
[ 1374847-68-3 ]