MedKoo Cat#: 574257 | Name: p-APMSF
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

p-APMSF is an irreversible inhibitor of serine proteases. p-APMSF was shown to inhibit cellular encapsulation of immulectin-coated agarose beads.

Chemical Structure

p-APMSF
p-APMSF
CAS#74938-88-8

Theoretical Analysis

MedKoo Cat#: 574257

Name: p-APMSF

CAS#: 74938-88-8

Chemical Formula: C8H10ClFN2O2S

Exact Mass: 252.0136

Molecular Weight: 252.69

Elemental Analysis: C, 38.03; H, 3.99; Cl, 14.03; F, 7.52; N, 11.09; O, 12.66; S, 12.69

Price and Availability

Size Price Availability Quantity
1mg USD 400.00
5mg USD 600.00
10mg USD 800.00
25mg USD 1,000.00
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Synonym
p-APMSF, para-APMSF, (p-Amidinophenyl)methanesulfonyl Fluoride
IUPAC/Chemical Name
4-(aminoiminomethyl)-benzenemethanesulfonyl fluoride, monohydrochloride
InChi Key
KHLLRHIUKOJXLL-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H9FN2O2S.ClH/c9-14(12,13)5-6-1-3-7(4-2-6)8(10)11;/h1-4H,5H2,(H3,10,11);1H
SMILES Code
FS(CC1=CC=C(C(N)=N)C=C1)(=O)=O.Cl
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
p-APMSF is an irreversible inhibitor of serine proteases.
In vitro activity:
the Ki of p-APMSF for all of the above-mentioned proteases is between 1 and 2 microM. In contrast, p-APMSF in large molar excess does not inactivate chymotrypsin or acetylcholinesterase. The unique reactivity of p-APMSF has been further shown in comparison with the related compound p-nitrophenyl (p-amidinophenyl)methanesulfonate which is an active-site titrant for thrombin but reacts poorly with Factor Xa, C1-r, and C1-s and is not hydrolyzed by bovine trypsin or human plasmin. Studies with bovine trypsin have demonstrated that the inhibitory activity of p-APMSF is the result of its interaction with the diisopropyl fluorophosphate reactive site. Reference: Biochemistry. 1980 Oct 14;19(21):4859-64. https://pubmed.ncbi.nlm.nih.gov/6775696/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 50.0 197.87
Water 25.0 98.94
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 252.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Laura R, Robison DJ, Bing DH. (p-Amidinophenyl)methanesulfonyl fluoride, an irreversible inhibitor of serine proteases. Biochemistry. 1980 Oct 14;19(21):4859-64. doi: 10.1021/bi00562a024. PMID: 6775696.
In vitro protocol:
Laura R, Robison DJ, Bing DH. (p-Amidinophenyl)methanesulfonyl fluoride, an irreversible inhibitor of serine proteases. Biochemistry. 1980 Oct 14;19(21):4859-64. doi: 10.1021/bi00562a024. PMID: 6775696.
In vivo protocol:
TBD
1: Liu W, Hashimoto T, Yamashita T, Hirano K. Coagulation factor XI induces Ca2+ response and accelerates cell migration in vascular smooth muscle cells via proteinase-activated receptor 1. Am J Physiol Cell Physiol. 2019 Mar 1;316(3):C377-C392. doi: 10.1152/ajpcell.00426.2018. Epub 2018 Dec 19. PMID: 30566391. 2: Kim DW, Choi JH, Park SE, Kim S, Sapkota K, Kim SJ. Purification and characterization of a fibrinolytic enzyme from Petasites japonicus. Int J Biol Macromol. 2015 Jan;72:1159-67. doi: 10.1016/j.ijbiomac.2014.09.046. PMID: 25316419. 3: Choi JH, Sapkota K, Kim MK, Kim S, Kim SJ. Undariase, a direct-acting fibrin(ogen)olytic enzyme from Undaria pinnatifida, inhibits thrombosis in vivo and exhibits in vitro thrombolytic properties. Appl Biochem Biotechnol. 2014 Aug;173(8):1985-2004. doi: 10.1007/s12010-014-0981-4. Epub 2014 Jun 18. PMID: 24938821. 4: Mitsui S, Yamaguchi N, Osako Y, Yuri K. Enzymatic properties and localization of motopsin (PRSS12), a protease whose absence causes mental retardation. Brain Res. 2007 Mar 9;1136(1):1-12. doi: 10.1016/j.brainres.2006.11.094. Epub 2007 Jan 16. PMID: 17223089. 5: Li BJ, Fan TJ, Yang LL, Cong RS, Li L, Sun WJ, Lu CX, Shi ZP. Purification and characterization of hatching enzyme from shrimp Penaeus chinensis. Arch Biochem Biophys. 2006 Jul 15;451(2):188-93. doi: 10.1016/j.abb.2006.04.008. Epub 2006 May 6. PMID: 16713987. 6: Shi ZP, Fan TJ, Cong RS, Wang XF, Sun WJ, Yang LL. Purification and characterization of hatching enzyme from flounder Paralichthys olivaceus. Fish Physiol Biochem. 2006 Mar;32(1):35-42. doi: 10.1007/s10695-005-5250-6. PMID: 20035476. 7: Ling E, Yu XQ. Cellular encapsulation and melanization are enhanced by immulectins, pattern recognition receptors from the tobacco hornworm Manduca sexta. Dev Comp Immunol. 2006;30(3):289-99. doi: 10.1016/j.dci.2005.05.005. Epub 2005 Jun 17. PMID: 16023723. 8: Saito A, Munakata H. Factor H is a dermatan sulfate-binding protein: identification of a dermatan sulfate-mediated protease that cleaves factor H. J Biochem. 2005 Feb;137(2):225-33. doi: 10.1093/jb/mvi025. PMID: 15749837. 9: von Elert E, Agrawal MK, Gebauer C, Jaensch H, Bauer U, Zitt A. Protease activity in gut of Daphnia magna: evidence for trypsin and chymotrypsin enzymes. Comp Biochem Physiol B Biochem Mol Biol. 2004 Mar;137(3):287-96. doi: 10.1016/j.cbpc.2003.11.008. PMID: 15050516. 10: Oyama E, Takahashi H. Purification and characterization of a thrombin like enzyme, elegaxobin II, with lys-bradykinin releasing activity from the venom of Trimeresurus elegans (Sakishima-Habu). Toxicon. 2003 Apr;41(5):559-68. doi: 10.1016/s0041-0101(02)00363-x. PMID: 12676434. 11: Fontanini D, Jones BL. SEP-1 - a subtilisin-like serine endopeptidase from germinated seeds of Hordeum vulgare L. cv. Morex. Planta. 2002 Oct;215(6):885-93. doi: 10.1007/s00425-002-0823-4. Epub 2002 Jul 13. PMID: 12355148. 12: Komori Y, Tanaka K, Nikai T. Characterization of Habu thrombin-like enzyme (THLE) with a new n-terminal sequence from the venom of Trimeresurus flavoviridis (Habu). J Nat Toxins. 2002 Aug;11(3):205-12. PMID: 12182540. 13: Nikai T, Tateoka M, Komori Y, Tatematsu R. A novel low molecular weight hemorrhagic toxin from Trimeresurus flavoviridis (Vorojima) venom. J Nat Toxins. 2002 Aug;11(3):155-63. PMID: 12182535. 14: Fan TJ, Chiaki K. Purification and Biochemical Characterization of the Hatching Enzyme from Xenopus laevis. Sheng Wu Hua Xue Yu Sheng Wu Wu Li Xue Bao (Shanghai). 1998;30(1):75-80. PMID: 12174302. 15: Pekkarinen AI, Jones BL. Trypsin-like proteinase produced by Fusarium culmorum grown on grain proteins. J Agric Food Chem. 2002 Jun 19;50(13):3849-55. doi: 10.1021/jf020027x. PMID: 12059170. 16: Shintani Y, Hirano K, Nakayama T, Nishimura J, Nakano H, Kanaide H. Mechanism of trypsin-induced contraction in the rat myometrium: the possible involvement of a novel member of protease-activated receptor. Br J Pharmacol. 2001 Aug;133(8):1276-85. doi: 10.1038/sj.bjp.0704206. PMID: 11498513; PMCID: PMC1621164. 17: Komori Y, Tatematsu R, Tanida S, Nikai T. Thrombin-like enzyme, flavovilase, with kinin-releasing activity from Trimeresurus flavoviridis (habu) venom. J Nat Toxins. 2001 Aug;10(3):239-48. PMID: 11491463. 18: Brown JK, Jones CA, Rooney LA, Caughey GH. Mast cell tryptase activates extracellular-regulated kinases (p44/p42) in airway smooth-muscle cells: importance of proteolytic events, time course, and role in mediating mitogenesis. Am J Respir Cell Mol Biol. 2001 Feb;24(2):146-54. doi: 10.1165/ajrcmb.24.2.4165. PMID: 11159048. 19: Shintani Y, Hirano K, Nishimura J, Nakano H, Kanaide H. Enhanced contractile response to thrombin in the pregnant rat myometrium. Br J Pharmacol. 2000 Dec;131(8):1619-28. doi: 10.1038/sj.bjp.0703729. PMID: 11139439; PMCID: PMC1572489. 20: Tatematsu R, Komori Y, Nikai T. A new thrombin-like enzyme, flavoviridiobin from the venom of Trimeresurus flavoviridis (habu). J Nat Toxins. 2000 Nov;9(4):327-39. PMID: 11126511.