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79703-25-6-Sceptrin Sceptrin

Sceptrin

For research use only. Not for therapeutic Use.

  • CAT Number: I036103
  • CAS Number: 79703-25-6
  • Molecular Formula: C22H26Br2Cl2N10O2
  • Molecular Weight: 693.22
  • Purity: 98%
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Related Small Molecules: Chlorpromazine     BIO-32546     Clamikalant sodium    

Sceptrin (Cat.No:I036103) is a marine natural product derived from the sponge Agelas sceptrum. It exhibits various biological activities, including anticancer, anti-inflammatory, and antiviral properties. Sceptrin’s unique chemical structure and diverse pharmacological effects make it an intriguing compound for drug discovery and potential therapeutic applications. Further research is ongoing to explore its medical potential.


Catalog Number I036103
CAS Number 79703-25-6
Synonyms

Sceptrin;

Molecular Formula C22H26Br2Cl2N10O2
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name N,N'-(((1R,2R,3S,4S)-3,4-bis(2-amino-1H-imidazol-5-yl)cyclobutane-1,2-diyl)bis(methylene))bis(4-bromo-1H-pyrrole-2-carboxamide) dihydrochloride
InChI InChI=1S/C22H24Br2N10O2.2ClH/c23-9-1-13(27-3-9)19(35)29-5-11-12(6-30-20(36)14-2-10(24)4-28-14)18(16-8-32-22(26)34-16)17(11)15-7-31-21(25)33-15;;/h1-4,7-8,11-12,17-18,27-28H,5-6H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34);2*1H/t11-,12-,17-,18-;;/m1../s1
InChIKey SFGZCXAQLPJJKC-WUYIMCQSSA-N
SMILES NC1=NC=C([C@@H]2[C@@H](C3=CN=C(N)N3)[C@H](CNC(C4=CC(Br)=CN4)=O)[C@H]2CNC(C5=CC(Br)=CN5)=O)N1.[H]Cl.[H]Cl
Reference

1: Ma Z, Wang X, Wang X, Rodriguez RA, Moore CE, Gao S, Tan X, Ma Y, Rheingold AL, Baran PS, Chen C. Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence. Science. 2014 Oct 10;346(6206):219-24. doi: 10.1126/science.1255677. PubMed PMID: 25301624; PubMed Central PMCID: PMC4205478.
2: Ma Z, Wang X, Wang X, Rodriguez RA, Moore CE, Gao S, Tan X, Ma Y, Rheingold AL, Baran PS, Chen C. ORGANIC SYNTHESIS. Response to Comment on “Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence”. Science. 2015 Jul 10;349(6244):149. doi: 10.1126/science.aaa9626. Epub 2015 Jul 9. PubMed PMID: 26160939; PubMed Central PMCID: PMC4536548.
3: Sherman DH, Tsukamoto S, Williams RM. ORGANIC SYNTHESIS. Comment on “Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence”. Science. 2015 Jul 10;349(6244):149. doi: 10.1126/science.aaa9349. Epub 2015 Jul 9. PubMed PMID: 26160938; PubMed Central PMCID: PMC4499860.
4: Cipres A, O’Malley DP, Li K, Finlay D, Baran PS, Vuori K. Sceptrin, a marine natural compound, inhibits cell motility in a variety of cancer cell lines. ACS Chem Biol. 2010 Feb 19;5(2):195-202. doi: 10.1021/cb900240k. PubMed PMID: 20030414; PubMed Central PMCID: PMC2825093.
5: Rodríguez AD, Lear MJ, La Clair JJ. Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol. J Am Chem Soc. 2008 Jun 11;130(23):7256-8. doi: 10.1021/ja7114019. Epub 2008 May 14. PubMed PMID: 18479102.
6: Birman VB, Jiang XT. Synthesis of sceptrin alkaloids. Org Lett. 2004 Jul 8;6(14):2369-71. PubMed PMID: 15228281.
7: Bernan VS, Roll DM, Ireland CM, Greenstein M, Maiese WM, Steinberg DA. A study on the mechanism of action of sceptrin, an antimicrobial agent isolated from the South Pacific sponge Agelas mauritiana. J Antimicrob Chemother. 1993 Oct;32(4):539-50. PubMed PMID: 8288495.
8: Wang X, Chen C. An approach for the synthesis of nakamuric acid. Tetrahedron. 2015 Jun 3;71(22):3690-3693. PubMed PMID: 25983349; PubMed Central PMCID: PMC4430124.
9: Muñoz J, Köck M. Hybrid Pyrrole-Imidazole Alkaloids from the Sponge Agelas sceptrum. J Nat Prod. 2016 Feb 26;79(2):434-7. doi: 10.1021/acs.jnatprod.5b00265. Epub 2016 Feb 12. PubMed PMID: 26872204.
10: Baran PS, Zografos AL, O’Malley DP. Short total synthesis of (+/-)-sceptrin. J Am Chem Soc. 2004 Mar 31;126(12):3726-7. PubMed PMID: 15038721.
11: Wang X, Gao Y, Ma Z, Rodriguez RA, Yu ZX, Chen C. Syntheses of Sceptrins and Nakamuric Acid and Insights into the Biosyntheses of Pyrrole-Imidazole Dimers. Org Chem Front. 2015 Aug 1;2(8):978-984. PubMed PMID: 26328059; PubMed Central PMCID: PMC4551504.
12: Baran PS, O’Malley DP, Zografos AL. Sceptrin as a potential biosynthetic precursor to complex pyrrole-imidazole alkaloids: the total synthesis of ageliferin. Angew Chem Int Ed Engl. 2004 May 10;43(20):2674-7. PubMed PMID: 18629987.
13: O’Malley DP, Li K, Maue M, Zografos AL, Baran PS. Total synthesis of dimeric pyrrole-imidazole alkaloids: sceptrin, ageliferin, nagelamide e, oxysceptrin, nakamuric acid, and the axinellamine carbon skeleton. J Am Chem Soc. 2007 Apr 18;129(15):4762-75. Epub 2007 Mar 22. Erratum in: J Am Chem Soc. 2007 Jun 20;129(24):7702. PubMed PMID: 17375928.
14: Beniddir MA, Evanno L, Joseph D, Skiredj A, Poupon E. Emergence of diversity and stereochemical outcomes in the biosynthetic pathways of cyclobutane-centered marine alkaloid dimers. Nat Prod Rep. 2016 Jul 28;33(7):820-42. doi: 10.1039/c5np00159e. Epub 2016 May 25. Review. PubMed PMID: 27220412.
15: Northrop BH, O’Malley DP, Zografos AL, Baran PS, Houk KN. Mechanism of the vinylcyclobutane rearrangement of sceptrin to ageliferin and nagelamide E. Angew Chem Int Ed Engl. 2006 Jun 19;45(25):4126-30. PubMed PMID: 16703636.
16: Baran PS, Li K, O’Malley DP, Mitsos C. Short, enantioselective total synthesis of sceptrin and ageliferin by programmed oxaquadricyclane fragmentation. Angew Chem Int Ed Engl. 2005 Dec 23;45(2):249-52. PubMed PMID: 16317782.
17: Wang B, Waters AL, Sims JW, Fullmer A, Ellison S, Hamann MT. Complex marine natural products as potential epigenetic and production regulators of antibiotics from a marine Pseudomonas aeruginosa. Microb Ecol. 2013 May;65(4):1068-75. doi: 10.1007/s00248-013-0213-4. Epub 2013 Apr 9. PubMed PMID: 23563743; PubMed Central PMCID: PMC3650628.
18: Rosa R, Silva W, Escalona de Motta G, Rodríguez AD, Morales JJ, Ortiz M. Anti-muscarinic activity of a family of C11N5 compounds isolated from Agelas sponges. Experientia. 1992 Sep 15;48(9):885-7. PubMed PMID: 1397186.
19: Bickmeyer U, Drechsler C, Köck M, Assmann M. Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation. Toxicon. 2004 Jul;44(1):45-51. PubMed PMID: 15225561.
20: Eder C, Proksch P, Wray V, van Soest RW, Ferdinandus E, Pattisina LA, Sudarsono S. New bromopyrrole alkaloids from the Indopacific sponge Agelas nakamurai. J Nat Prod. 1999 Sep;62(9):1295-7. PubMed PMID: 10514317.

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