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MedKoo Cat#: 562978 | Name: Arcyriaflavin A
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Description:

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

Arcyriaflavin a, a cytotoxic indolocarbazole alkaloid isolated by combined-culture of mycolic acid-containing bacteria and Streptomyces cinnamoneus NBRC 13823, is a cyclin D1-cyclin-dependent kinase4 inhibitor that induces apoptosis and inhibits proliferation of human endometriotic stromal cells.

Chemical Structure

Arcyriaflavin A
CAS#118458-54-1

Theoretical Analysis

MedKoo Cat#: 562978

Name: Arcyriaflavin A

CAS#: 118458-54-1

Chemical Formula: C20H11N3O2

Exact Mass: 325.0851

Molecular Weight: 325.32

Elemental Analysis: C, 73.84; H, 3.41; N, 12.92; O, 9.84

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Arcyriaflavin A; Arcyriaflavin-A;
IUPAC/Chemical Name
12,13-Dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
InChi Key
KAJXOWFGKYKMMZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H11N3O2/c24-19-15-13-9-5-1-3-7-11(9)21-17(13)18-14(16(15)20(25)23-19)10-6-2-4-8-12(10)22-18/h1-8,21-22H,(H,23,24,25)
SMILES Code
O=C1NC(C2=C1C3=C(C4=C2C5=C(N4)C=CC=C5)NC6=C3C=CC=C6)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 325.32 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
1: Fernandes JA, Almeida Paz FA, Marques J, Marques MP, Braga SS. Arcyriaflavin A monohydrate. Acta Crystallogr C. 2011 Feb;67(Pt 2):o57-9. doi: 10.1107/S0108270110052741. Epub 2011 Jan 7. PMID: 21285502. 2: Han JM, Jung HJ. Synergistic Anticancer Effect of a Combination of Berbamine and Arcyriaflavin A against Glioblastoma Stem-like Cells. Molecules. 2022 Nov 17;27(22):7968. doi: 10.3390/molecules27227968. PMID: 36432068; PMCID: PMC9699626. 3: Hirakawa T, Nasu K, Aoyagi Y, Takebayashi K, Narahara H. Arcyriaflavin a, a cyclin D1-cyclin-dependent kinase4 inhibitor, induces apoptosis and inhibits proliferation of human endometriotic stromal cells: a potential therapeutic agent in endometriosis. Reprod Biol Endocrinol. 2017 Jul 18;15(1):53. doi: 10.1186/s12958-017-0272-3. PMID: 28720098; PMCID: PMC5516342. 4: De SK. Novel Arcyriaflavin-A Derivatives as PIM Kinase Inhibitors for Treating Cancer. Anticancer Agents Med Chem. 2023 May 8. doi: 10.2174/1871520623666230508101745. Epub ahead of print. PMID: 37157195. 5: Lee S, Kim KH, Cheon CH. Total Syntheses of Arcyriaflavin A and Calothrixin B Using 2,2'-Bisindole-3-acetic Acid Derivative as a Common Intermediate. Org Lett. 2017 Jun 2;19(11):2785-2788. doi: 10.1021/acs.orglett.7b00687. Epub 2017 May 18. PMID: 28520441. 6: Hoshino S, Zhang L, Awakawa T, Wakimoto T, Onaka H, Abe I. Arcyriaflavin E, a new cytotoxic indolocarbazole alkaloid isolated by combined-culture of mycolic acid-containing bacteria and Streptomyces cinnamoneus NBRC 13823. J Antibiot (Tokyo). 2015 May;68(5):342-4. doi: 10.1038/ja.2014.147. Epub 2014 Oct 22. PMID: 25335694. 7: Adeva M, Sahagún H, Caballero E, Peláez-Lamamié De Clairac R, Medarde M, Tomé F. Open analogues of arcyriaflavin A. Synthesis through Diels-Alder reaction between maleimides and 1-aryl-3-tert-butyldimethylsiloxy-1, 3-butadienes. J Org Chem. 2000 Jun 2;65(11):3387-94. doi: 10.1021/jo991815x. PMID: 10843621. 8: Robey RW, Shukla S, Steadman K, Obrzut T, Finley EM, Ambudkar SV, Bates SE. Inhibition of ABCG2-mediated transport by protein kinase inhibitors with a bisindolylmaleimide or indolocarbazole structure. Mol Cancer Ther. 2007 Jun;6(6):1877-85. doi: 10.1158/1535-7163.MCT-06-0811. PMID: 17575116. 9: Horton PA, Longley RE, McConnell OJ, Ballas LM. Staurosporine aglycone (K252-c) and arcyriaflavin A from the marine ascidian, Eudistoma sp. Experientia. 1994 Sep 15;50(9):843-5. doi: 10.1007/BF01956468. PMID: 7925852. 10: Liu R, Zhu T, Li D, Gu J, Xia W, Fang Y, HongbingLiu, Zhu W, Gu Q. Two indolocarbazole alkaloids with apoptosis activity from a marine-derived actinomycete Z(2)039-2. Arch Pharm Res. 2007 Mar;30(3):270-4. doi: 10.1007/BF02977605. PMID: 17424930. 11: Tian S, Fu L, Zhang J, Xu J, Yuan L, Qin J, Zhang W. Identification of a DNA Methylation-Driven Genes-Based Prognostic Model and Drug Targets in Breast Cancer: In silico Screening of Therapeutic Compounds and in vitro Characterization. Front Immunol. 2021 Oct 20;12:761326. doi: 10.3389/fimmu.2021.761326. PMID: 34745136; PMCID: PMC8567755. 12: Saha S, Banerjee A, Maji MS. Brønsted Acid Catalyzed One-Pot Benzannulation of 2-Alkenylindoles under Aerial Oxidation: A Route to Carbazoles and Indolo[2,3- a]carbazole Alkaloids. Org Lett. 2018 Nov 2;20(21):6920-6924. doi: 10.1021/acs.orglett.8b03063. Epub 2018 Oct 25. PMID: 30358409. 13: Asamizu S, Shiro Y, Igarashi Y, Nagano S, Onaka H. Characterization and functional modification of StaC and RebC, which are involved in the pyrrole oxidation of indolocarbazole biosynthesis. Biosci Biotechnol Biochem. 2011;75(11):2184-93. doi: 10.1271/bbb.110474. Epub 2011 Nov 7. PMID: 22056432. 14: Cartuche L, Sifaoui I, López-Arencibia A, Bethencourt-Estrella CJ, San Nicolás-Hernández D, Lorenzo-Morales J, Piñero JE, Díaz-Marrero AR, Fernández JJ. Antikinetoplastid Activity of Indolocarbazoles from Streptomyces sanyensis. Biomolecules. 2020 Apr 24;10(4):657. doi: 10.3390/biom10040657. PMID: 32344693; PMCID: PMC7226613. 15: Sanchez-Martinez C, Shih C, Faul MM, Zhu G, Paal M, Somoza C, Li T, Kumrich CA, Winneroski LL, Xun Z, Brooks HB, Patel BK, Schultz RM, DeHahn TB, Spencer CD, Watkins SA, Considine E, Dempsey JA, Ogg CA, Campbell RM, Anderson BA, Wagner J. Aryl[a]pyrrolo[3,4-c]carbazoles as selective cyclin D1-CDK4 inhibitors. Bioorg Med Chem Lett. 2003 Nov 3;13(21):3835-9. doi: 10.1016/s0960-894x(03)00791-1. PMID: 14552791. 16: Howard-Jones AR, Walsh CT. Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid. J Am Chem Soc. 2006 Sep 20;128(37):12289-98. doi: 10.1021/ja063898m. PMID: 16967980. 17: Men Y, Hu Z, Dong J, Xu X, Tang B. Formal [1 + 2 + 3] Annulation: Domino Access to Carbazoles and Indolocarbazole Alkaloids. Org Lett. 2018 Sep 7;20(17):5348-5352. doi: 10.1021/acs.orglett.8b02266. Epub 2018 Aug 15. PMID: 30110173. 18: Chilczuk T, Schäberle TF, Vahdati S, Mettal U, El Omari M, Enke H, Wiese M, König GM, Niedermeyer THJ. Halogenation-Guided Chemical Screening Provides Insight into Tjipanazole Biosynthesis by the Cyanobacterium Fischerella ambigua. Chembiochem. 2020 Aug 3;21(15):2170-2177. doi: 10.1002/cbic.202000025. Epub 2020 Apr 16. PMID: 32182403; PMCID: PMC7497240. 19: Kaletaş BK, Mandl C, van der Zwan G, Fanti M, Zerbetto F, De Cola L, König B, Williams RM. Unexpected photophysical properties of symmetric indolylmaleimide derivatives. J Phys Chem A. 2005 Jul 28;109(29):6440-9. doi: 10.1021/jp051035u. PMID: 16833988. 20: Saita K, Nakazono M, Zaitsu K, Nanbu S, Sekiya H. Theoretical study of photophysical properties of bisindolylmaleimide derivatives. J Phys Chem A. 2009 Jul 23;113(29):8213-20. doi: 10.1021/jp9043489. PMID: 19569696.