Compounds > bis(2-(succinimidooxycarbonyloxy)ethyl)sulfone
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bis(2-(succinimidooxycarbonyloxy)ethyl)sulfone

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Description

Bis(2-(succinimidooxycarbonyloxy)ethyl)sulfone (BSES) is a cross-linking reagent used in various applications. It is a bifunctional reagent containing two N-hydroxysuccinimide (NHS) esters linked by a sulfone group. This structure allows BSES to react with primary amines in proteins, peptides, and other molecules, forming stable amide bonds.

BSES has been utilized for various purposes, including:

- Cross-linking proteins: BSES can be used to cross-link proteins, resulting in the formation of stable protein complexes. This can be useful for studying protein-protein interactions, immobilizing enzymes, and creating protein-based biomaterials.
- Modification of antibodies: BSES can be used to modify antibodies, allowing them to be conjugated with various molecules, such as enzymes, fluorescent dyes, or drugs. This enhances the functionality of antibodies and enables their application in diverse fields like diagnostics and therapy.
- Synthesis of bioconjugates: BSES is employed in the synthesis of bioconjugates by linking therapeutic agents or diagnostic probes to proteins or other biomolecules. This approach enables the development of targeted drug delivery systems and advanced diagnostic tools.

BSES is studied due to its unique properties as a cross-linking reagent. Its stability, high reactivity, and water-solubility make it suitable for various applications in biochemistry, biotechnology, and pharmaceuticals.

The synthesis of BSES typically involves reacting succinic anhydride with N-hydroxysuccinimide to form NHS ester. Subsequently, the NHS ester reacts with 2-hydroxyethyl sulfone to yield BSES.

Overall, BSES is a versatile reagent employed in numerous applications related to protein modification, antibody engineering, and bioconjugate synthesis. Its importance lies in its ability to form stable covalent bonds with proteins, enabling the development of novel therapeutic, diagnostic, and research tools.'
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bis(2-(succinimidooxycarbonyloxy)ethyl)sulfone: bifunctional reagent for intramolecular crosslinking of insulin; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID93771
SCHEMBL ID43777
MeSH IDM0058189

Synonyms (29)

Synonym
nsc338309
57683-72-4
nsc-338309
bsocoes
bis[2-(n-succinimidyl-oxycarbonyloxy)ethyl] sulfone, >=97.0% (chn)
bis(2-(succinimidooxycarbonyloxy)ethyl)sulfone
(2,5-dioxopyrrolidin-1-yl) 2-[2-(2,5-dioxopyrrolidin-1-yl)oxycarbonyloxyethylsulfonyl]ethyl carbonate
bis[2-(succinimidooxycarbonyloxy)ethyl]sulfone
nsc 338309
einecs 260-904-8
disuccinimido sulphonylbis(ethylenecarbonate)
1,1'-[sulfonylbis(2,1-ethanediyloxycarbonyloxy)]bis-2,5-pyrrolidinedione
bis[2-(n-succinimidyl-oxycarbonyloxy)ethyl] sulfone
bis[2-(succinimidooxycarbonyloxy)ethyl] sulfone
FT-0623114
AKOS015915672
SCHEMBL43777
bis-2-(succinimidoxycarbonyloxy)ethyl sulfone
DTXSID20206385
bis[2-(succinimidooxycarbonyloxy)-ethyl]sulfone
bis(2,5-dioxopyrrolidin-1-yl) (sulfonylbis(ethane-2,1-diyl)) bis(carbonate)
CS-0181242
bis[2-(n-succinimidyl-oxycarbonyloxy)ethyl] sulfon
mfcd00047123
bis(2,5-dioxopyrrolidin-1-yl) 2,2'-sulfonylbis(ethane-2,1-diyl) dicarbonate
H28VHA5U7J
2,5-pyrrolidinedione, 1,1'-[sulfonylbis(2,1-ethanediyloxycarbonyloxy)]bis-
bis[2-(n-succinimidyloxycarbonyloxy)ethyl]sulfone
carbonic acid, c,c'-(sulfonyldi-2,1-ethanediyl) c,c'-bis(2,5-dioxo-1-pyrrolidinyl) ester
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (61.54)18.7374
1990's4 (30.77)18.2507
2000's1 (7.69)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.74

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.74 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.38 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
fentanyl
Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.		1.9710anilide;
monocarboxylic acid amide;
piperidines		adjuvant;
anaesthesia adjuvant;
anaesthetic;
intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic
dinitrofluorobenzene
Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.		1.9910C-nitro compound;
organofluorine compound		agrochemical;
allergen;
chromatographic reagent;
EC 2.7.3.2 (creatine kinase) inhibitor;
protein-sequencing agent;
spectrophotometric reagent
dithiothreitol
1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.		1.96101,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent
dimethyl adipimidate
Dimethyl Adipimidate: Bifunctional cross-linking agent that links covalently free amino groups of proteins or polypeptides, including those in cell membranes. It is used as reagent or fixative in immunohistochemistry and is a proposed antisickling agent.		1.9910
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		1.9610pseudohalide anionmitochondrial respiratory-chain inhibitor
dimethyl suberimidate
Dimethyl Suberimidate: The methyl imidoester of suberic acid used to produce cross links in proteins. Each end of the imidoester will react with an amino group in the protein molecule to form an amidine.		1.9910
dimethyl pimelimidate
[no description available]		1.9910
1,5-difluoro-2,4-dinitrobenzene
1,5-difluoro-2,4-dinitrobenzene: structure		1.9910
fentanyl isothiocyanate
fentanyl isothiocyanate: specific reagent for irreversible inactivation of delta opiate receptors in rat brain membranes; structure given in first source		1.9710piperidines
dithiobis(succinimidylpropionate)
dithiobis(succinimidylpropionate): used to study interactions of structural proteins; RN given refers to unlabeled cpd		1.9610
n-hydroxysuccinimide suberic acid ester
disuccinimidyl suberate: used as protein cross-linking agent		2.6630
hydroxysuccinimidyl-4-azidobenzoate
N-(4-azidobenzoyloxy)succinimide: structure in first source		1.9610
bis(sulfosuccinimidyl)suberate
bis(sulfosuccinimidyl)suberate: structure given in first source		1.9710
disuccinimidyl tartarate
disuccinimidyl tartarate: RN given refers to (R-(R*,R*)-isomer); structure		1.9910
2-(4-ethoxybenzyl)-1-diethylaminoethyl-5-isothiocyanatobenzimidazole
2-(4-ethoxybenzyl)-1-diethylaminoethyl-5-isothiocyanatobenzimidazole: site directed alkylating agent; selective agonist for mu receptors		1.9710
sodium dodecyl sulfate
Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.		1.9910organic sodium saltdetergent;
protein denaturant
disuccinimidyl glutarate
[no description available]		1.9910
beta-endorphin
beta-Endorphin: A 31-amino acid peptide that is the C-terminal fragment of BETA-LIPOTROPIN. It acts on OPIOID RECEPTORS and is an analgesic. Its first four amino acids at the N-terminal are identical to the tetrapeptide sequence of METHIONINE ENKEPHALIN and LEUCINE ENKEPHALIN.. beta-endorphin : A polypeptide consisting of 31 amino acid residues in the sequence Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu. It is an endogenous opioid peptide neurotransmitter found in the neurons of both the central and peripheral nervous system and results from processing of the precursor protein proopiomelanocortin (POMC).		1.9710
heliodermin
heliodermin: MW 5,900 peptide with secretin-like properties		1.9710
vasoactive intestinal peptide
Vasoactive Intestinal Peptide: A highly basic, 28 amino acid neuropeptide released from intestinal mucosa. It has a wide range of biological actions affecting the cardiovascular, gastrointestinal, and respiratory systems and is neuroprotective. It binds special receptors (RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE).		1.9710
adrenomedullin
Adrenomedullin: A 52-amino acid peptide with multi-functions. It was originally isolated from PHEOCHROMOCYTOMA and ADRENAL MEDULLA but is widely distributed throughout the body including lung and kidney tissues. Besides controlling fluid-electrolyte homeostasis, adrenomedullin is a potent vasodilator and can inhibit pituitary ACTH secretion.		1.9910
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Leukemia
[description not available]		01.9510
Germinoblastoma
[description not available]		01.9710
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		01.9710
Leukemia, Lymphocytic
[description not available]		01.9610
Leukemia, Lymphoid
Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.		01.9610