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MedKoo Cat#: 584182 | Name: Siccanin
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Description:

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

Siccanin, also known as BH-34 and SI 23548, is an antifungal antibiotic with antidermatophytic properties. Siccanin inhibits mitochondrial complex III in the low-micromolar range.

Chemical Structure

Siccanin
Siccanin
CAS#22733-60-4

Theoretical Analysis

MedKoo Cat#: 584182

Name: Siccanin

CAS#: 22733-60-4

Chemical Formula: C22H30O3

Exact Mass: 342.2195

Molecular Weight: 342.48

Elemental Analysis: C, 77.16; H, 8.83; O, 14.01

Price and Availability

Size Price Availability Quantity
1mg USD 650.00 2 weeks
5mg USD 1,600.00 2 Weeks
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Related CAS #
22733-60-4 69353-22-6
Synonym
NSC 135048; NSC135048; NSC-135048; Siccanin.
IUPAC/Chemical Name
(4aS,6aS,11bR,13aS,13bS)-2,3,4,4a,5,6,6a,13b-octahydro-4,4,6a,9-tetramethyl-1H,11bH,13H-benzo[a]furo[2,3,4-mn]xanthen-11-ol
InChi Key
UGGAILYEBCSZIV-ITJSPEIASA-N
InChi Code
InChI=1S/C22H30O3/c1-13-10-14(23)17-15(11-13)25-21(4)9-6-16-20(2,3)7-5-8-22(16)12-24-18(17)19(21)22/h10-11,16,18-19,23H,5-9,12H2,1-4H3/t16-,18-,19-,21-,22-/m0/s1
SMILES Code
OC1=CC(C)=CC2=C1[C@@](OC3)([H])[C@]4([H])[C@]35[C@@](C(C)(C)CCC5)([H])CC[C@]4(C)O2
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
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Siccanin is an inhibitor of mitochondrial complex II (succinate dehydrogenase; IC50s = 0.87 and 9.3 μM for P. aeruginosa and rat mitochondria, respectively). It inhibits the growth of T. mentagrophytes (IC50 = 0.3 μg/ml) via inhibition of succinate oxidation in the mitochondria. It also inhibits the growth of C. albicans strains with IC50 values ranging from 5-40 and 80-90 μg/ml for aerobic and anaerobic conditions, respectively.
In vitro activity:
Siccanin is a potential lead compound for new chemotherapeutics because its species-selective inhibition is unique among succinate dehydrogenase inhibitors. Siccanin was effective against enzymes from P. aeruginosa, P. putida, rat and mouse mitochondria but ineffective or less effective against Escherichia coli, Corynebacterium glutamicum, and porcine mitochondria enzyme. Reference: J Biochem. 2009 Sep;146(3):383-7. https://pubmed.ncbi.nlm.nih.gov/19505951/
In vivo activity:
To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 342.48 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
Formulation protocol:
1. Komatsuya K, Sakura T, Shiomi K, Ōmura S, Hikosaka K, Nozaki T, Kita K, Inaoka DK. Siccanin Is a Dual-Target Inhibitor of Plasmodium falciparum Mitochondrial Complex II and Complex III. Pharmaceuticals (Basel). 2022 Jul 21;15(7):903. doi: 10.3390/ph15070903. PMID: 35890202; PMCID: PMC9319939. 2. Mogi T, Kawakami T, Arai H, Igarashi Y, Matsushita K, Mori M, Shiomi K, Omura S, Harada S, Kita K. Siccanin rediscovered as a species-selective succinate dehydrogenase inhibitor. J Biochem. 2009 Sep;146(3):383-7. doi: 10.1093/jb/mvp085. Epub 2009 Jun 8. PMID: 19505951.
In vitro protocol:
1. Komatsuya K, Sakura T, Shiomi K, Ōmura S, Hikosaka K, Nozaki T, Kita K, Inaoka DK. Siccanin Is a Dual-Target Inhibitor of Plasmodium falciparum Mitochondrial Complex II and Complex III. Pharmaceuticals (Basel). 2022 Jul 21;15(7):903. doi: 10.3390/ph15070903. PMID: 35890202; PMCID: PMC9319939. 2. Mogi T, Kawakami T, Arai H, Igarashi Y, Matsushita K, Mori M, Shiomi K, Omura S, Harada S, Kita K. Siccanin rediscovered as a species-selective succinate dehydrogenase inhibitor. J Biochem. 2009 Sep;146(3):383-7. doi: 10.1093/jb/mvp085. Epub 2009 Jun 8. PMID: 19505951.
In vivo protocol:
To be determined
1: Bellotti MG, Riviera L. Siccanin: a new antifungal antibiotic with antidermatophytic properties. In vitro studies. Chemioterapia. 1985 Dec;4(6):431-3. PubMed PMID: 3830412. 2: Mogi T, Kawakami T, Arai H, Igarashi Y, Matsushita K, Mori M, Shiomi K, Omura S, Harada S, Kita K. Siccanin rediscovered as a species-selective succinate dehydrogenase inhibitor. J Biochem. 2009 Sep;146(3):383-7. doi: 10.1093/jb/mvp085. Epub 2009 Jun 8. PubMed PMID: 19505951. 3: Trost BM, Shen HC, Surivet JP. An enantioselective biomimetic total synthesis of (-)-siccanin. Angew Chem Int Ed Engl. 2003 Aug 25;42(33):3943-7. PubMed PMID: 12949876. 4: Trost BM, Shen HC, Surivet JP. Biomimetic enantioselective total synthesis of (-)-siccanin via the Pd-catalyzed asymmetric allylic alkylation (AAA) and sequential radical cyclizations. J Am Chem Soc. 2004 Oct 6;126(39):12565-79. PubMed PMID: 15453789. 5: Sugawara S. Siccanin, a new antifungal antibiotic. II. In vivo studies. Antimicrob Agents Chemother (Bethesda). 1969;9:253-6. PubMed PMID: 5396496. 6: Hirai K, Okuda S, Nozoe S, Iitaka Y. The crystal and molecular structure of siccanin p-bromobenzenesulphonate. Acta Crystallogr B. 1969 Dec 15;25(12):2630-8. PubMed PMID: 5395581. 7: Nemlioğlu F. The therapeutic action of Siccanin in superficial dermatophyte infections. J Int Med Res. 1979;7(4):332-4. PubMed PMID: 488524. 8: Meyer-Rohn J. [Piadar (Ladar): new antimycotic drug containing the antifungal agent siccanin (author's transl)]. Mykosen. 1979 Jul;22(7):255-8. German. PubMed PMID: 381921. 9: Nose K, Endo A. Mode of action of the antibiotic siccanin on intact cells and mitochondria of Trichophyton mentagrophytes. J Bacteriol. 1971 Jan;105(1):176-84. PubMed PMID: 4250609; PubMed Central PMCID: PMC248339. 10: Naito A. [Tracing the past half century of my microbial transformation studies]. Yakugaku Zasshi. 2000 Oct;120(10):839-48. Review. Japanese. PubMed PMID: 11082697. 11: Sakuda S, Prabowo DF, Takagi K, Shiomi K, Mori M, Ōmura S, Nagasawa H. Inhibitory effects of respiration inhibitors on aflatoxin production. Toxins (Basel). 2014 Mar 26;6(4):1193-200. doi: 10.3390/toxins6041193. PubMed PMID: 24674936; PubMed Central PMCID: PMC4014728. 12: Yamaguchi H, Uchida K, Tanaka T, Yamaguchi T. [Therapeutic efficacy of a topical tolnaftate preparation in guinea pig model of tinea pedis]. Jpn J Antibiot. 2001 Jun;54(6):323-30. Japanese. PubMed PMID: 11521512. 13: Kitaura K, Araki Y, Marumo H. [The therapeutic effect of nanaomycin A against experimental Trichophyton mentagrophytes infection in guinea pigs (author's transl)]. Jpn J Antibiot. 1980 Jul;33(7):728-32. Japanese. PubMed PMID: 7452913. 14: Yamamuro D, Uchida R, Takahashi Y, Masuma R, Tomoda H. Screening for microbial metabolites affecting phenotype of Caenorhabditis elegans. Biol Pharm Bull. 2011;34(10):1619-23. PubMed PMID: 21963505. 15: Matsuki M, Kanatsu H, Watanabe T, Ogasawara A, Mikami T, Matsumoto T. Effects of antifungal drugs on proliferation signals in Candida albicans. Biol Pharm Bull. 2006 May;29(5):919-22. PubMed PMID: 16651719. 16: Trost BM, Shen HC, Dong L, Surivet JP, Sylvain C. Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): scope, mechanism, and applications. J Am Chem Soc. 2004 Sep 29;126(38):11966-83. PubMed PMID: 15382932. 17: Hirai K. [Nostalgic review of one student of Prof. Tsuda about natural product, carbanion, thiazoline and beta-lactam chemistry]. Yakugaku Zasshi. 2000 Oct;120(10):891-8. Review. Japanese. PubMed PMID: 11082701. 18: Crippa D, Albanese GC, Sala GP. [Clinical evaluation of a new antimycotic: siccanine]. G Ital Dermatol Venereol. 1985 Sep-Oct;120(5):LVII-LXI. Italian. PubMed PMID: 4077105. 19: Nozoe S, Suzuki KT. The structure of the triprenyl phenol derivatives biosynthetically related to siccanin. Tetrahedron Lett. 1969 Jun;(29):2457-60. PubMed PMID: 5816532. 20: Arai M, Ishibashi K, Okazaki H. Siccanin, a new antifungal antibiotic. I. In vitro studies. Antimicrob Agents Chemother (Bethesda). 1969;9:247-52. PubMed PMID: 5396495.