Scalaradial | CAS#53527-28-9 | marine sesterterpenoid

MedKoo Cat#: 461898 | Name: Scalaradial

Description:

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

Scalaradial is a marine sesterterpenoid isolated from the sponge Cacospongia mollior with anti-inflammatory effects.

Chemical Structure

Scalaradial

CAS#53527-28-9

Theoretical Analysis

MedKoo Cat#: 461898

Name: Scalaradial

CAS#: 53527-28-9

Chemical Formula: C27H40O4

Exact Mass: 428.2927

Molecular Weight: 428.61

Elemental Analysis: C, 75.66; H, 9.41; O, 14.93

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.

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Related CAS #

No Data

Synonym

Scalaradial;

IUPAC/Chemical Name

(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-1,2,3,4,4a,4b,5,6,6a,7,10,10a,10b,11,12,12a-hexadecahydrochrysen-6-yl acetate

InChi Key

ADWFEADZGIHPDE-QGERINELSA-N

InChi Code

InChI=1S/C27H40O4/c1-17(30)31-23-14-22-25(4)12-7-11-24(2,3)20(25)10-13-26(22,5)21-9-8-18(15-28)19(16-29)27(21,23)6/h8,15-16,19-23H,7,9-14H2,1-6H3/t19-,20-,21-,22+,23-,25-,26-,27+/m0/s1

SMILES Code

CC(O[C@H]1C[C@@H]2[C@]3(CCCC(C)([C@@H]3CC[C@]2([C@@H]4CC=C([C@@H]([C@@]14C)C=O)C=O)C)C)C)=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

>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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 428.61 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: Cassiano C, Margarucci L, Esposito R, Riccio R, Tosco A, Casapullo A, Monti MC. In cell scalaradial interactome profiling using a bio-orthogonal clickable probe. Chem Commun (Camb). 2014 Jun 7;50(45):6043-5. doi: 10.1039/c4cc00989d. Epub 2014 Apr 28. PubMed PMID: 24769547. 2: De Stefano D, Tommonaro G, Malik SA, Iodice C, De Rosa S, Maiuri MC, Carnuccio R. Cacospongionolide and scalaradial, two marine sesterterpenoids as potent apoptosis-inducing factors in human carcinoma cell lines. PLoS One. 2012;7(4):e33031. doi: 10.1371/journal.pone.0033031. Epub 2012 Apr 3. PubMed PMID: 22509253; PubMed Central PMCID: PMC3317917. 3: Margarucci L, Monti MC, Chini MG, Tosco A, Riccio R, Bifulco G, Casapullo A. The inactivation mechanism of human group IIA phospholipase A(2) by Scalaradial. Chembiochem. 2012 Oct 15;13(15):2259-64. doi: 10.1002/cbic.201200453. Epub 2012 Sep 24. PubMed PMID: 23008213. 4: Torregrosa G, Pérez-Asensio FJ, Burguete MC, Castelló-Ruiz M, Salom JB, Alborch E. Chronic intracerebroventricular delivery of the secretory phospholipase A2 inhibitor, 12-epi-scalaradial, does not improve outcome after focal cerebral ischemia-reperfusion in rats. Exp Brain Res. 2007 Jan;176(2):248-59. PubMed PMID: 16874515. 5: Monti MC, Casapullo A, Cavasotto CN, Napolitano A, Riccio R. Scalaradial, a dialdehyde-containing marine metabolite that causes an unexpected noncovalent PLA2 Inactivation. Chembiochem. 2007 Sep 3;8(13):1585-91. PubMed PMID: 17691073. 6: de Carvalho MS, Jacobs RS. Two-step inactivation of bee venom phospholipase A2 by scalaradial. Biochem Pharmacol. 1991 Sep 27;42(8):1621-6. PubMed PMID: 1930288. 7: Marshall LA, Winkler JD, Griswold DE, Bolognese B, Roshak A, Sung CM, Webb EF, Jacobs R. Effects of scalaradial, a type II phospholipase A2 inhibitor, on human neutrophil arachidonic acid mobilization and lipid mediator formation. J Pharmacol Exp Ther. 1994 Feb;268(2):709-17. PubMed PMID: 8113982. 8: Barnette MS, Rush J, Marshall LA, Foley JJ, Schmidt DB, Sarau HM. Effects of scalaradial, a novel inhibitor of 14 kDa phospholipase A2, on human neutrophil function. Biochem Pharmacol. 1994 Apr 29;47(9):1661-7. PubMed PMID: 8185681. 9: Monti MC, Casapullo A, Riccio R, Gomez-Paloma L. The inactivation of phospholipase A2 by scalaradial: a biomimetic study by electrospray mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(3):303-8. PubMed PMID: 15645482. 10: Xie Y, Yu Z, Liu L, Guo Y, Lou L. Biphasic regulation of extracellular signal-regulated kinases by scalaradial, a secretory phospholipase A(2) inhibitor. Cancer Biol Ther. 2006 Aug;5(8):988-92. Epub 2006 Aug 3. PubMed PMID: 16760675. 11: Glaser KB, Lock YW. Regulation of prostaglandin H synthase 2 expression in human monocytes by the marine natural products manoalide and scalaradial. Novel effects independent of inhibition of lipid mediator production. Biochem Pharmacol. 1995 Sep 28;50(7):913-22. PubMed PMID: 7575673. 12: Xie Y, Liu L, Huang X, Guo Y, Lou L. Scalaradial inhibition of epidermal growth factor receptor-mediated Akt phosphorylation is independent of secretory phospholipase A2. J Pharmacol Exp Ther. 2005 Sep;314(3):1210-7. Epub 2005 May 27. PubMed PMID: 15923342. 13: Glaser KB, Sung ML, Hartman DA, Lock YW, Bauer J, Walter T, Carlson RP. Cellular and topical in vivo inflammatory murine models in the evaluation of inhibitors of phospholipase A2. Skin Pharmacol. 1995;8(6):300-8. PubMed PMID: 8688196. 14: Payá M, Terencio MC, Ferrándiz ML, Alcaraz MJ. Involvement of secretory phospholipase A2 activity in the zymosan rat air pouch model of inflammation. Br J Pharmacol. 1996 Apr;117(8):1773-9. PubMed PMID: 8732290; PubMed Central PMCID: PMC1909548. 15: Elhady SS, El-Halawany AM, Alahdal AM, Hassanean HA, Ahmed SA. A New Bioactive Metabolite Isolated from the Red Sea Marine Sponge Hyrtios erectus. Molecules. 2016 Jan 15;21(1):82. doi: 10.3390/molecules21010082. PubMed PMID: 26784155. 16: Starkus JG, Poerzgen P, Layugan K, Kawabata KG, Goto JI, Suzuki S, Myers G, Kelly M, Penner R, Fleig A, Horgen FD. Scalaradial Is a Potent Inhibitor of Transient Receptor Potential Melastatin 2 (TRPM2) Ion Channels. J Nat Prod. 2017 Oct 27;80(10):2741-2750. doi: 10.1021/acs.jnatprod.7b00515. Epub 2017 Oct 11. PubMed PMID: 29019677. 17: Manzo E, Gavagnin M, Somerville MJ, Mao SC, Ciavatta ML, Mollo E, Schupp PJ, Garson MJ, Guo YW, Cimino G. Chemistry of Glossodoris nudibranchs: specific occurrence of 12-keto scalaranes. J Chem Ecol. 2007 Dec;33(12):2325-36. Epub 2007 Nov 15. PubMed PMID: 18000710. 18: Gavagnin M, Mollo E, Docimo T, Guo YW, Cimino G. Scalarane metabolites of the nudibranch Glossodoris rufomarginata and Its dietary sponge from the South China Sea. J Nat Prod. 2004 Dec;67(12):2104-7. PubMed PMID: 15620263. 19: Ruipérez V, Casas J, Balboa MA, Balsinde J. Group V phospholipase A2-derived lysophosphatidylcholine mediates cyclooxygenase-2 induction in lipopolysaccharide-stimulated macrophages. J Immunol. 2007 Jul 1;179(1):631-8. PubMed PMID: 17579085. 20: Liu Y, Levy R. Phospholipase A2 has a role in proliferation but not in differentiation of HL-60 cells. Biochim Biophys Acta. 1997 Mar 1;1355(3):270-80. PubMed PMID: 9060998.