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SDA maleimide

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Physical properties
Molecular weight250.26
SolventDMSO
Storage, safety and handling
H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22
StorageFreeze (< -15 °C); Minimize light exposure
Alternative formats
SDA azide
SDA alkyne

OverviewpdfSDSpdfProtocol


Molecular weight
250.26
SDA maleimide is an excellent heterobifunctional crosslinker that effectively combines two established chemical modalities, thiol-selective maleimide chemistry and diazirine-based photoaffinity labeling. Its maleimide group forms covalent thioether bond with thiol groups on one protein, while the diazirine moiety exhibit efficient photoreactivity towards amino acid side chains or peptide backbones on another protein within the prescribed spacer arm distance, once activated by long-wave UV light (330-370 nm). SDA's two-step chemical crosslinking process can be easily activated using conventional laboratory UV lamps, streamlining experimental protocols. Furthermore, SDA crosslinkers demonstrate excellent photostability even under standard laboratory lighting conditions, eliminating the need for a light-restricted environment. Given that diazirine maleimide is membrane-permeable, it might be suited for in vivo intracellular and intramembrane conjugations and investigating protein-protein interactions.

Calculators


Common stock solution preparation

Table 1. Volume of DMSO needed to reconstitute specific mass of SDA maleimide to given concentration. Note that volume is only for preparing stock solution. Refer to sample experimental protocol for appropriate experimental/physiological buffers.

0.1 mg0.5 mg1 mg5 mg10 mg
1 mM399.584 µL1.998 mL3.996 mL19.979 mL39.958 mL
5 mM79.917 µL399.584 µL799.169 µL3.996 mL7.992 mL
10 mM39.958 µL199.792 µL399.584 µL1.998 mL3.996 mL

Molarity calculator

Enter any two values (mass, volume, concentration) to calculate the third.

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References


View all 28 references: Citation Explorer
Rearrangements of Nitrile Imines: Ring Expansion of Benzonitrile Imines to Cycloheptatetraenes and Ring Closure to 3-Phenyl-3 H-diazirines.
Authors: Bégué, Didier and Dargelos, Alain and Wentrup, Curt
Journal: The Journal of organic chemistry (2019): 8668-8673
Thioether-Polyglycidol as Multivalent and Multifunctional Coating System for Gold Nanoparticles.
Authors: Feineis, Susanne and Lutz, Johanna and Heffele, Lora and Endl, Elmar and Albrecht, Krystyna and Groll, Jürgen
Journal: Advanced materials (Deerfield Beach, Fla.) (2018)
Rapid Mapping of Protein Interactions Using Tag-Transfer Photocrosslinkers.
Authors: Horne, Jim E and Walko, Martin and Calabrese, Antonio N and Levenstein, Mark A and Brockwell, David J and Kapur, Nikil and Wilson, Andrew J and Radford, Sheena E
Journal: Angewandte Chemie (International ed. in English) (2018): 16688-16692
Problems and Solutions in Click Chemistry Applied to Drug Probes.
Authors: Zhong, Weilong and Sun, Bo and Lu, Cheng and Yu, Hengheng and Wang, Changhua and He, Lingfei and Gu, Ju and Chen, Shuang and Liu, Yanrong and Jing, Xiangyan and Bi, Zhun and Yang, Guang and Zhou, Honggang and Sun, Tao and Yang, Cheng
Journal: Scientific reports (2016): 35579
Modulation of endogenous Cysteine Protease Inhibitor (ICP) 1 expression in Entamoeba histolytica affects amoebic adhesion to Extracellular Matrix proteins.
Authors: Lee, Young Ah and Saito-Nakano, Yumiko and Kim, Kyeong Ah and Min, Arim and Nozaki, Tomoyoshi and Shin, Myeong Heon
Journal: Experimental parasitology (2015): 7-15
Active site labeling of cysteine cathepsins by a straightforward diazomethylketone probe derived from the N-terminus of human cystatin C.
Authors: Garenne, Thibaut and Saidi, Ahlame and Gilmore, Brendan F and Niemiec, Elżbieta and Roy, Vincent and Agrofoglio, Luigi A and Kasabova, Mariana and Lecaille, Fabien and Lalmanach, Gilles
Journal: Biochemical and biophysical research communications (2015): 250-4
Protein-polymer conjugation via ligand affinity and photoactivation of glutathione S-transferase.
Authors: Lin, En-Wei and Boehnke, Natalie and Maynard, Heather D
Journal: Bioconjugate chemistry (2014): 1902-9
Generic methods for micrometer- and nanometer-scale surface derivatization based on photochemical coupling of primary amines to monolayers of aryl azides on gold and aluminum oxide surfaces.
Authors: El Zubir, Osama and Barlow, Iain and Ul-Haq, Ehtsham and Tajuddin, Hairul A and Williams, Nicholas H and Leggett, Graham J
Journal: Langmuir : the ACS journal of surfaces and colloids (2013): 1083-92
Surface cathepsin B protects cytotoxic lymphocytes from self-destruction after degranulation.
Authors: Balaji, Kithiganahalli N and Schaschke, Norbert and Machleidt, Werner and Catalfamo, Marta and Henkart, Pierre A
Journal: The Journal of experimental medicine (2002): 493-503
Cross-linking of the fingers subdomain of human immunodeficiency virus type 1 reverse transcriptase to template-primer.
Authors: Peletskaya, E N and Boyer, P L and Kogon, A A and Clark, P and Kroth, H and Sayer, J M and Jerina, D M and Hughes, S H
Journal: Journal of virology (2001): 9435-45