(4-amidinophenyl)methanesulfonyl fluoride profile

(4-amidinophenyl)methanesulfonyl fluoride, also known as **FMSF** or **4-Amidinophenyl methanesulfonyl fluoride**, is a highly selective, irreversible inhibitor of **protein kinases**.

**Structure and Mechanism of Action:**

FMSF is a small molecule with a sulfonyl fluoride group that reacts with the active site of protein kinases. The sulfonyl fluoride group acts as an electrophile, attacking the nucleophilic hydroxyl group of a serine or threonine residue within the kinase active site. This covalent modification results in the irreversible inactivation of the kinase.

**Importance in Research:**

FMSF plays a crucial role in research by enabling the study of:

* **Kinase Function and Regulation:** FMSF can be used to specifically inhibit individual kinases, allowing researchers to investigate the role of specific kinases in various cellular processes.
* **Kinase-Dependent Signaling Pathways:** By blocking the activity of kinases, FMSF can help researchers understand how kinase-mediated signaling pathways are involved in disease pathogenesis.
* **Drug Discovery and Development:** FMSF can be used as a tool to identify new kinase inhibitors with therapeutic potential.

**Applications in Research:**

FMSF has been employed in various research areas, including:

* **Cancer Biology:** FMSF has been used to study the role of kinases in cancer cell proliferation, survival, and metastasis.
* **Neurobiology:** FMSF has been used to investigate the involvement of kinases in neuronal signaling and neurodegenerative diseases.
* **Immunology:** FMSF has been used to study the regulation of immune responses by kinases.

**Advantages of FMSF:**

* **High Selectivity:** FMSF exhibits high selectivity for protein kinases, minimizing off-target effects.
* **Irreversible Inhibition:** The covalent modification of kinases by FMSF results in irreversible inhibition, providing a sustained effect.
* **Ease of Use:** FMSF is relatively easy to use and can be readily incorporated into various research protocols.

**Limitations of FMSF:**

* **Toxicity:** FMSF can be toxic and requires careful handling.
* **Limited Availability:** FMSF may not be readily available commercially.

**Conclusion:**

(4-amidinophenyl)methanesulfonyl fluoride is a valuable research tool for studying the function and regulation of protein kinases. Its high selectivity, irreversible inhibition, and ease of use make it a valuable asset for understanding kinase-dependent signaling pathways and exploring novel therapeutic strategies.

ID Source	ID
PubMed CID	1719
CHEMBL ID	1199253
SCHEMBL ID	537872
MeSH ID	M0088691

Synonym
(4-amidinophenyl)methanesulfonyl fluoride
NCGC00186021-01
(4-carbamimidoylphenyl)methanesulfonyl fluoride
71933-13-6
benzenemethanesulfonyl fluoride, 4-(aminoiminomethyl)-
(p-amidinophenyl)methanesulfonyl fluoride
4-amidinophenylmethanesulfonyl fluoride
SCHEMBL537872
CHEMBL1199253
DTXSID90222219
PMHUSCHKTSTQEP-UHFFFAOYSA-N
AKOS027378079
AS-67595
SDCCGSBI-0633745.P001
NCGC00186021-02
(4-carbamimidoylphenyl)methanesulfonylfluoride
p-apmsf (hydrochloride)

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
thioredoxin reductase	Rattus norvegicus (Norway rat)	Potency	0.3162	0.1000	20.8793	79.4328	AID588453
arylsulfatase A	Homo sapiens (human)	Potency	2.6855	1.0691	13.9551	37.9330	AID720538
euchromatic histone-lysine N-methyltransferase 2	Homo sapiens (human)	Potency	8.4368	0.0355	20.9770	89.1251	AID504332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (18)

Assay ID	Title	Year	Journal	Article
AID1347405	qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection	2020	ACS chemical biology, 07-17, Volume: 15, Issue:7	High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID588349	qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID588378	qHTS for Inhibitors of ATXN expression: Validation
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504836	Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation	2002	The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16	Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347057	CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation	2019	PloS one, , Volume: 14, Issue:7	Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347058	CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation	2019	PloS one, , Volume: 14, Issue:7	Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347050	Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay	2019	Science translational medicine, 07-10, Volume: 11, Issue:500	Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347049	Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen	2019	Science translational medicine, 07-10, Volume: 11, Issue:500	Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347045	Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line	2019	Science translational medicine, 07-10, Volume: 11, Issue:500	Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347410	qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library	2019	Cellular signalling, 08, Volume: 60	A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID1347151	Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347059	CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation	2019	PloS one, , Volume: 14, Issue:7	Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	5 (17.24)	18.7374
1990's	9 (31.03)	18.2507
2000's	6 (20.69)	29.6817
2010's	4 (13.79)	24.3611
2020's	5 (17.24)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	29 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
betaine glycine betaine : The amino acid betaine derived from glycine.	1.98	1	amino-acid betaine; glycine derivative	fundamental metabolite
3-hydroxybenzylhydrazine 3-hydroxybenzylhydrazine: decarboxylase inhibitor; RN given refers to parent cpd; structure	1.99	1	phenols
benzamidine benzamidine: RN given refers to parent cpd. benzamidine : A carboxamidine that is benzene carrying an amidino group.	1.99	1	benzenes; carboxamidine	serine protease inhibitor
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	1.98	1	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2	1	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
phenylmethylsulfonyl fluoride Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.	4.28	19	acyl fluoride	serine proteinase inhibitor
isoflurophate Isoflurophate: A di-isopropyl-fluorophosphate which is an irreversible cholinesterase inhibitor used to investigate the NERVOUS SYSTEM.	1.98	1	dialkyl phosphate
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.37	2	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
galactose galactopyranose : The pyranose form of galactose.	1.99	1	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	1.98	1	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	1.96	1	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	1.98	1	amino sulfonic acid; bile acid taurine conjugate	human metabolite
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	1.99	1	dithiocarbamic acids	chelator; copper chelator
hydrazine diamine : Any polyamine that contains two amino groups.	1.99	1	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
4-toluenesulfonyl fluoride 4-toluenesulfonyl fluoride: inhibitor of peptide hydrolases; structure in second source	1.99	1
glycocholic acid Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	1.98	1	bile acid glycine conjugate	human metabolite
ubenimex ubenimex: growth inhibitor	1.98	1
phleomycins Phleomycins: Water-soluble, copper-containing low molecular weight polypeptides obtained from the culture medium of Streptomyces verticillus. They are specific inhibitors of DNA synthesis in bacteria and have been found to act as antitumor agents. They have also been used against rust fungi of plants.. phleomycin : A mixture of glycopeptide antibiotics originally isolated from the bacterium Streptomyces verticillus whose components all contain a thiazolinylthiazole moiety and can form complexes with redox-active metals such as Co, Cu, and Fe. (Bleomycins are very similar to phleomycins, but have a bithiazole moiety in place of the thiazolinylthiazole moiety).	1.99	1
methyl mannoside, (alpha-d)-isomer methylmannoside: RN given refers to (D)-isomer; see also record for 3-O-methylmannose. methyl alpha-D-mannoside : A methyl mannoside having alpha-configuration at the anomeric centre.	1.99	1	alpha-D-mannoside; methyl mannoside
phenylalanyl-prolyl-arginine-chloromethyl ketone phenylalanyl-prolyl-arginine-chloromethyl ketone: do not confuse with Pro-Phe-Arg-CH2-Cl or with Phe-Phe-Arg-CH2-Cl, both sometimes also referred to as PPACK	1.98	1
isoleucyl-prolyl-arginine-4-nitroanilide isoleucyl-prolyl-arginine-4-nitroanilide: chromogenic substrate for tissue plasminogen activator; RN given refers to D-Ile-L-Pro-L-Arg-isomer	1.98	1
thrombin receptor peptide sfllrnp thrombin receptor peptide SFLLRNP: a synthetic peptide that induces early events of T cell activation and synergizes with TCR cross-linking for CD69 expression & interleukin-2 production; thrombin receptor agonist; do not confuse with TRAP peptide	2	1
polidocanol Polidocanol: An alkyl polyglycol ether of LAURYL ALCOHOL, chemically defined as an alcohol ethoxylate having an average alkyl chain of 12–14 carbon atoms, and an ethylene oxide chain of 9 ethylene oxide units. It is used as a detergent, and medically as a local anesthetic, and as a sclerosing agent for the treatment of ESOPHAGEAL AND GASTRIC VARICES and VARICOSE VEINS.. polidocanol : A hydroxypolyether that is nonaethylene glycol in which one of the terminal hydroxy functions is substituted by a lauryl (dodecyl) group.	1.98	1	hydroxypolyether	hepatotoxic agent; nonionic surfactant; sclerotherapy agent
dermatan sulfate Dermatan Sulfate: A naturally occurring glycosaminoglycan found mostly in the skin and in connective tissue. It differs from CHONDROITIN SULFATE A (see CHONDROITIN SULFATES) by containing IDURONIC ACID in place of glucuronic acid, its epimer, at carbon atom 5. (from Merck, 12th ed). alpha-L-IdopA-(1->3)-beta-D-GalpNAc4S : An oligosaccharide sulfate that is 2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranose in which the hydroxy group at position 3 has been converted to the corresponding alpha-L-idopyranuronoside.. dermatan sulfate : Any of a group of glycosaminoglycans with repeating units consisting of variously sulfated beta1->4-linked L-iduronyl-(alpha1->3)-N-acetyl-D-galactosamine units.	2.02	1	amino disaccharide; glycosylgalactose derivative; iduronic acids; oligosaccharide sulfate
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.	2.39	2	organic sodium salt	detergent; protein denaturant
valyl-leucyl-lysine 4-nitroanilide valyl-leucyl-lysine 4-nitroanilide: chromogenic substrate of plasmin; H-D-Val-Leu-Lys- 4-nitroaniline	1.98	1
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	1.96	1
empigen bb dodecylbetaine: RN given for chloride salt; RN for parent cpd not available 7/93	1.98	1
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	1.98	1	peptide hormone

Condition	Relationship Strength	Studies
Contact Dermatitis [description not available]	2.21	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.63	2
Itching [description not available]	2.21	1
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	2.21	1
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	2.21	1
Congenital Zika Syndrome [description not available]	2.25	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
Onchocerciasis Infection with nematodes of the genus ONCHOCERCA. Characteristics include the presence of firm subcutaneous nodules filled with adult worms, PRURITUS, and ocular lesions.	1.99	1
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	2	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.41	2

(4-amidinophenyl)methanesulfonyl fluoride

Cross-References

Synonyms (17)

Protein Targets (3)

Potency Measurements

Bioassays (18)

Research

Studies (29)

Market Indicators

Research Demand Index: 11.25

Study Types

(4-amidinophenyl)methanesulfonyl fluoride

Cross-References

Synonyms (17)

Protein Targets (3)

Potency Measurements

Bioassays (18)

Research

Studies (29)

Market Indicators

Research Demand Index: 11.25

Study Types

Related Drugs (29)

Related Conditions (10)