Stephacidin B | CAS#360765-75-9 | Cytotoxic fungal metabolite

MedKoo Cat#: 464411 | Name: Stephacidin B

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Description:

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

Stephacidin B is a fungal metabolite that has been found in A. ochraceus. Dimeric stephacidin B is rapidly converted to a monomer, avrainvillamide, in vitro. Stephacidin B is cytotoxic to a variety of cancer cells, including testosterone-independent PC3 and -sensitive LNCaP prostate cancer cells and estradiol-independent SK-BR-3 and -sensitive MCF-7 breast cancer cells. It induces apoptosis in HepG2 and Huh7 hepatocellular carcinoma cells when used at a concentration of 4 µM.

Chemical Structure

Stephacidin B

CAS#360765-75-9

Theoretical Analysis

MedKoo Cat#: 464411

Name: Stephacidin B

CAS#: 360765-75-9

Chemical Formula: C52H54N6O8

Exact Mass: 890.4003

Molecular Weight: 891.04

Elemental Analysis: C, 70.09; H, 6.11; N, 9.43; O, 14.36

Price and Availability

Size	Price	Availability	Quantity
2.5mg	USD 900.00	2 Weeks

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Synonym

Stephacidin B; Stephacidin-B; (–) Stephacidin B; (–)-Stephacidin B;

IUPAC/Chemical Name

N/A

InChi Key

ZKJYVORSURCOMD-GSYUCZBGSA-N

InChi Code

InChI=1S/C52H54N6O8/c1-44(2)19-15-25-29(65-44)13-11-27-33-36-50-28-12-14-30-26(16-20-45(3,4)66-30)35(28)58(64)38(50)47(7,8)31-23-48-17-9-21-54(48)42(61)51(31,53-40(48)59)39(50)56-41(60)49-18-10-22-55(49)43(62)52(36,56)32(24-49)46(5,6)37(33)57(63)34(25)27/h11-16,19-20,31-32,36,39,63H,9-10,17-18,21-24H2,1-8H3,(H,53,59)/t31-,32-,36-,39+,48?,49-,50?,51+,52+/m0/s1

SMILES Code

CC1(C)C=CC2=C(C3=CC=C2O1)N(=C4C35[C@](N(C6=O)[C@]78[C@](C[C@]6(CCC9)N9C8=O)([H])C(C)(C)C%10=C(C%11=CC=C(OC(C)(C)C=C%12)C%12=C%11N%10O)[C@]75[H])([H])[C@@]%13(C(N(CCC%14)C%14(C(N%13)=O)C%15)=O)[C@]%15([H])C4(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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Product Data

Instruction

View handling instruction

Biological target:

Stephacidin B is cytotoxic to a variety of cancer cells, including testosterone-independent PC3 and -sensitive LNCaP prostate cancer cells (IC50s = 0.37 and 0.06 µM, respectively) and estradiol-independent SK-BR-3 and -sensitive MCF-7 breast cancer cells (IC50s = 0.32 and 0.27 µM, respectively).

In vitro activity:

Both stephacidin A and B exhibited in vitro cytotoxicity against several human tumor cell lines. However, stephacidin B demonstrated more potent and selective antitumor activities, especially against prostate testeosterone-dependent LNCaP cells (IC50 = 60 nM). With 15 rings and 9 chiral centers, stephacidin B is one of the most structurally complex alkaloids occurring in nature. Reference: J Am Chem Soc. 2002 Dec 11;124(49):14556-7. https://pubmed.ncbi.nlm.nih.gov/12465964/

In vivo activity:

To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 891.04 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

Formulation protocol:

1. Wulff JE, Herzon SB, Siegrist R, Myers AG. Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture. J Am Chem Soc. 2007 Apr 25;129(16):4898-9. doi: 10.1021/ja0690971. Epub 2007 Mar 31. PMID: 17397160; PMCID: PMC3175819. 2. Qian-Cutrone J, Huang S, Shu YZ, Vyas D, Fairchild C, Menendez A, Krampitz K, Dalterio R, Klohr SE, Gao Q. Stephacidin A and B: two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells. J Am Chem Soc. 2002 Dec 11;124(49):14556-7. doi: 10.1021/ja028538n. PMID: 12465964.

In vitro protocol:

In vivo protocol:

To be determined

1: Meng Q, Li BX, Xiao X. Toward Developing Chemical Modulators of Hsp60 as Potential Therapeutics. Front Mol Biosci. 2018 Apr 20;5:35. doi: 10.3389/fmolb.2018.00035. PMID: 29732373; PMCID: PMC5920047. 2: Quezada M, Shang Z, Kalansuriya P, Salim AA, Lacey E, Capon RJ. Waspergillamide A, a Nitro depsi-Tetrapeptide Diketopiperazine from an Australian Mud Dauber Wasp-Associated Aspergillus sp. (CMB-W031). J Nat Prod. 2017 Apr 28;80(4):1192-1195. doi: 10.1021/acs.jnatprod.6b01062. Epub 2017 Feb 24. PMID: 28234476. 3: Mikkola R, Andersson MA, Hautaniemi M, Salkinoja-Salonen MS. Toxic indole alkaloids avrainvillamide and stephacidin B produced by a biocide tolerant indoor mold Aspergillus westerdijkiae. Toxicon. 2015 Jun 1;99:58-67. doi: 10.1016/j.toxicon.2015.03.011. Epub 2015 Mar 21. PMID: 25804991. 4: Simpkins N, Pavlakos I, Male L. Rapid access to polycyclic indolines related to the stephacidin alkaloids using a radical cascade. Chem Commun (Camb). 2012 Feb 14;48(14):1958-60. doi: 10.1039/c1cc16510k. Epub 2011 Dec 2. PMID: 22134634. 5: Andersson MA, Mikkola R, Rasimus S, Hoornstra D, Salin P, Rahkila R, Heikkinen M, Mattila S, Peltola J, Kalso S, Salkinoja-Salonen M. Boar spermatozoa as a biosensor for detecting toxic substances in indoor dust and aerosols. Toxicol In Vitro. 2010 Oct;24(7):2041-52. doi: 10.1016/j.tiv.2010.08.011. Epub 2010 Aug 21. PMID: 20732404. 6: Nising CF. Recent synthetic approaches towards the antiproliferative natural products avrainvillamide and stephacidin B. Chem Soc Rev. 2010 Feb;39(2):591-9. doi: 10.1039/b900407f. Epub 2009 Dec 14. PMID: 20111783. 7: Artman GD 3rd, Grubbs AW, Williams RM. Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B. J Am Chem Soc. 2007 May 16;129(19):6336-42. doi: 10.1021/ja070259i. Epub 2007 Apr 25. PMID: 17455936; PMCID: PMC2526546. 8: Wulff JE, Herzon SB, Siegrist R, Myers AG. Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture. J Am Chem Soc. 2007 Apr 25;129(16):4898-9. doi: 10.1021/ja0690971. Epub 2007 Mar 31. PMID: 17397160; PMCID: PMC3175819. 9: Baran PS, Hafensteiner BD, Ambhaikar NB, Guerrero CA, Gallagher JD. Enantioselective total synthesis of avrainvillamide and the stephacidins. J Am Chem Soc. 2006 Jul 5;128(26):8678-93. doi: 10.1021/ja061660s. PMID: 16802835. 10: Escolano C. Stephacidin B, the avrainvillamide dimer: a formidable synthetic challenge. Angew Chem Int Ed Engl. 2005 Dec 2;44(47):7670-3. doi: 10.1002/anie.200502383. PMID: 16252300. 11: Baran PS, Guerrero CA, Hafensteiner BD, Ambhaikar NB. Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B. Angew Chem Int Ed Engl. 2005 Jun 20;44(25):3892-5. doi: 10.1002/anie.200500655. PMID: 15900526. 12: Herzon SB, Myers AG. Enantioselective synthesis of stephacidin B. J Am Chem Soc. 2005 Apr 20;127(15):5342-4. doi: 10.1021/ja0510616. PMID: 15826171. 13: von Nussbaum F. Stephacidin B-A new stage of complexity within prenylated indole alkaloids from fungi. Angew Chem Int Ed Engl. 2003 Jul 14;42(27):3068-71. doi: 10.1002/anie.200301646. PMID: 12866092. 14: Qian-Cutrone J, Huang S, Shu YZ, Vyas D, Fairchild C, Menendez A, Krampitz K, Dalterio R, Klohr SE, Gao Q. Stephacidin A and B: two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells. J Am Chem Soc. 2002 Dec 11;124(49):14556-7. doi: 10.1021/ja028538n. PMID: 12465964.