Cyclophostin | CAS#144773-26-2 | AChE inhibitor

MedKoo Cat#: 561832 | Name: Cyclophostin

Description:

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

Cyclophostin is an irreversible inhibitor of acetylcholinesterase (AChE).

Chemical Structure

Cyclophostin

CAS#144773-26-2

Theoretical Analysis

MedKoo Cat#: 561832

Name: Cyclophostin

CAS#: 144773-26-2

Chemical Formula: C8H11O6P

Exact Mass: 234.0293

Molecular Weight: 234.14

Elemental Analysis: C, 41.04; H, 4.74; O, 41.00; P, 13.23

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Cyclophostin;

IUPAC/Chemical Name

(3R,8aR)-3-Methoxy-5-methyl-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one

InChi Key

OMPQJMDGDAAXPE-NPMWZIQKSA-N

InChi Code

InChI=1S/C8H11O6P/c1-5-7-6(3-12-8(7)9)4-13-15(10,11-2)14-5/h6H,3-4H2,1-2H3/t6-,15-/m1/s1

SMILES Code

O=C1OC[C@]2([H])CO[P@](OC(C)=C21)(OC)=O

Appearance

Solid powder

Purity

>98% (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

>2 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 234.14 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.

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

1: Viljoen A, Richard M, Nguyen PC, Fourquet P, Camoin L, Paudal RR, Gnawali GR, Spilling CD, Cavalier JF, Canaan S, Blaise M, Kremer L. Cyclipostins and Cyclophostin analogs inhibit the antigen 85C from Mycobacterium tuberculosis both in vitro and in vivo. J Biol Chem. 2018 Jan 4. pii: jbc.RA117.000760. doi: 10.1074/jbc.RA117.000760. [Epub ahead of print] PubMed PMID: 29301937. 2: Nguyen PC, Madani A, Santucci P, Martin BP, Paudel RR, Delattre S, Herrmann JL, Spilling CD, Kremer L, Canaan S, Cavalier JF. Cyclophostin and cyclipostins analogs, new promising molecules to treat mycobacterial-related diseases. Int J Antimicrob Agents. 2017 Dec 11. pii: S0924-8579(17)30435-1. doi: 10.1016/j.ijantimicag.2017.12.001. [Epub ahead of print] PubMed PMID: 29241819. 3: Nguyen PC, Delorme V, Bénarouche A, Martin BP, Paudel R, Gnawali GR, Madani A, Puppo R, Landry V, Kremer L, Brodin P, Spilling CD, Cavalier JF, Canaan S. Cyclipostins and Cyclophostin analogs as promising compounds in the fight against tuberculosis. Sci Rep. 2017 Sep 18;7(1):11751. doi: 10.1038/s41598-017-11843-4. PubMed PMID: 28924204; PubMed Central PMCID: PMC5603573. 4: Martin BP, Vasilieva E, Dupureur CM, Spilling CD. Synthesis and comparison of the biological activity of monocyclic phosphonate, difluorophosphonate and phosphate analogs of the natural AChE inhibitor cyclophostin. Bioorg Med Chem. 2015 Dec 15;23(24):7529-34. doi: 10.1016/j.bmc.2015.10.044. Epub 2015 Oct 30. PubMed PMID: 26585276. 5: Vasilieva E, Dutta S, Malla RK, Martin BP, Spilling CD, Dupureur CM. Rat hormone sensitive lipase inhibition by cyclipostins and their analogs. Bioorg Med Chem. 2015 Mar 1;23(5):944-52. doi: 10.1016/j.bmc.2015.01.028. Epub 2015 Jan 22. PubMed PMID: 25678014; PubMed Central PMCID: PMC4340684. 6: Point V, Malla RK, Carrière F, Canaan S, Spilling CD, Cavalier JF. Enantioselective inhibition of microbial lipolytic enzymes by nonracemic monocyclic enolphosphonate analogues of cyclophostin. J Med Chem. 2013 Jun 13;56(11):4393-401. doi: 10.1021/jm4000787. Epub 2013 May 16. PubMed PMID: 23651298. 7: Point V, Malla RK, Diomande S, Martin BP, Delorme V, Carriere F, Canaan S, Rath NP, Spilling CD, Cavalier JF. Synthesis and kinetic evaluation of cyclophostin and cyclipostins phosphonate analogs as selective and potent inhibitors of microbial lipases. J Med Chem. 2012 Nov 26;55(22):10204-19. doi: 10.1021/jm301216x. Epub 2012 Nov 7. PubMed PMID: 23095026; PubMed Central PMCID: PMC3518039. 8: Malla RK, Bandyopadhyay S, Spilling CD, Dutta S, Dupureur CM. The first total synthesis of (±)-cyclophostin and (±)-cyclipostin P: inhibitors of the serine hydrolases acetyl cholinesterase and hormone sensitive lipase. Org Lett. 2011 Jun 17;13(12):3094-7. doi: 10.1021/ol200991x. Epub 2011 May 17. PubMed PMID: 21591624; PubMed Central PMCID: PMC3129627. 9: Dutta S, Malla RK, Bandyopadhyay S, Spilling CD, Dupureur CM. Synthesis and kinetic analysis of some phosphonate analogs of cyclophostin as inhibitors of human acetylcholinesterase. Bioorg Med Chem. 2010 Mar 15;18(6):2265-74. doi: 10.1016/j.bmc.2010.01.063. Epub 2010 Feb 4. PubMed PMID: 20189400; PubMed Central PMCID: PMC2841358. 10: Bandyopadhyay S, Dutta S, Spilling CD, Dupureur CM, Rath NP. Synthesis and biological evaluation of a phosphonate analog of the natural acetyl cholinesterase inhibitor cyclophostin. J Org Chem. 2008 Nov 7;73(21):8386-91. doi: 10.1021/jo801453v. Epub 2008 Sep 27. PubMed PMID: 18821801; PubMed Central PMCID: PMC2726048. 11: Iwata Y, de Kort M, Challiss RA, van der Marel GA, van Boom JH, Miyamoto S. Conformational analysis of cyclophostin and designed analogs in comparison with the potent IP3 receptor agonist adenophostin A. Drug Des Discov. 2001;17(3):253-63. PubMed PMID: 11469755. 12: Kurokawa T, Suzuki K, Hayaoka T, Nakagawa T, Izawa T, Kobayashi M, Harada N. Cyclophostin, acetylcholinesterase inhibitor from Streptomyces lavendulae. J Antibiot (Tokyo). 1993 Aug;46(8):1315-8. PubMed PMID: 8407597.