MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 585041 | Name: Clerocidin

Description:

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

Clerocidin is a terpenoid antibiotic that inhibits bacterial DNA gyrase.

Chemical Structure

Clerocidin
Clerocidin
CAS#87501-14-2

Theoretical Analysis

MedKoo Cat#: 585041

Name: Clerocidin

CAS#: 87501-14-2

Chemical Formula: C40H56O10

Exact Mass: 696.3873

Molecular Weight: 696.88

Elemental Analysis: C, 68.94; H, 8.10; O, 22.96

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Clerocidin; Antibiotic PR-1350; PR-1350
IUPAC/Chemical Name
1-Naphthalenecarboxaldehyde, 5,5'-((tetrahydro-3'a,7'a-dihydroxydispiro(oxirane-2,3'(2'H)-difuro(2,3-b:2',3'-e)(1,4)dioxin-7'(6'H),2''-oxirane)-2',6'-diyl)bis(methylene))bis(3,4,4a,5,6,7,8,8a-octahydro-5,6,8a-trimethyl-
InChi Key
LKJYEAJRWPUOGW-UHFFFAOYSA-N
InChi Code
InChI=1S/C40H56O10/c1-23-13-15-33(3)25(19-41)9-7-11-27(33)35(23,5)17-29-37(21-45-37)39(43)31(47-29)49-40(44)32(50-39)48-30(38(40)22-46-38)18-36(6)24(2)14-16-34(4)26(20-42)10-8-12-28(34)36/h9-10,19-20,23-24,27-32,43-44H,7-8,11-18,21-22H2,1-6H3
SMILES Code
OC12C(OC(CC3(C)C4CCC=C(C=O)C4(C)CCC3C)C25OC5)OC(C67OC6)(O)C(OC7CC8(C)C9CCC=C(C=O)C9(C)CCC8C)O1
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 696.88 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: Nadai M, Sattin G, Palù G, Palumbo M, Richter SN. Clerocidin-mediated DNA footprinting discriminates among different G-quadruplex conformations and detects tetraplex folding in a duplex environment. Biochim Biophys Acta. 2013 Oct;1830(10):4660-8. doi: 10.1016/j.bbagen.2013.05.039. Epub 2013 Jun 6. PubMed PMID: 23747297. 2: Gatto B, Richter S, Moro S, Capranico G, Palumbo M. The topoisomerase II poison clerocidin alkylates non-paired guanines of DNA: implications for irreversible stimulation of DNA cleavage. Nucleic Acids Res. 2001 Oct 15;29(20):4224-30. PubMed PMID: 11600711; PubMed Central PMCID: PMC60217. 3: Binaschi M, Zagotto G, Palumbo M, Zunino F, Farinosi R, Capranico G. Irreversible and reversible topoisomerase II DNA cleavage stimulated by clerocidin: sequence specificity and structural drug determinants. Cancer Res. 1997 May 1;57(9):1710-6. PubMed PMID: 9135013. 4: Richter SN, Menegazzo I, Nadai M, Moro S, Palumbo M. Reactivity of clerocidin towards adenine: implications for base-modulated DNA damage. Org Biomol Chem. 2009 Mar 7;7(5):976-85. doi: 10.1039/b819049f. Epub 2009 Jan 23. PubMed PMID: 19225681. 5: Kawada S, Yamashita Y, Fujii N, Nakano H. Induction of a heat-stable topoisomerase II-DNA cleavable complex by nonintercalative terpenoides, terpentecin and clerocidin. Cancer Res. 1991 Jun 1;51(11):2922-5. PubMed PMID: 1851667. 6: Richter SN, Fabris D, Moro S, Palumbo M. Dissecting reactivity of clerocidin toward common buffer systems by means of selected drug analogues. Chem Res Toxicol. 2005 Jan;18(1):35-40. PubMed PMID: 15651847. 7: Sehested M, Jensen PB. Mapping of DNA topoisomerase II poisons (etoposide, clerocidin) and catalytic inhibitors (aclarubicin, ICRF-187) to four distinct steps in the topoisomerase II catalytic cycle. Biochem Pharmacol. 1996 Apr 12;51(7):879-86. PubMed PMID: 8651936. 8: Nadai M, Palù G, Palumbo M, Richter SN. Differential targeting of unpaired bases within duplex DNA by the natural compound clerocidin: a valuable tool to dissect DNA secondary structure. PLoS One. 2012;7(12):e52994. doi: 10.1371/journal.pone.0052994. Epub 2012 Dec 28. PubMed PMID: 23285245; PubMed Central PMCID: PMC3532440. 9: Pan XS, Dias M, Palumbo M, Fisher LM. Clerocidin selectively modifies the gyrase-DNA gate to induce irreversible and reversible DNA damage. Nucleic Acids Res. 2008 Oct;36(17):5516-29. doi: 10.1093/nar/gkn539. Epub 2008 Aug 22. PubMed PMID: 18723572; PubMed Central PMCID: PMC2553588. 10: Richter S, Gatto B, Fabris D, Takao K, Kobayashi S, Palumbo M. Clerocidin alkylates DNA through its epoxide function: evidence for a fine tuned mechanism of action. Nucleic Acids Res. 2003 Sep 1;31(17):5149-56. PubMed PMID: 12930966; PubMed Central PMCID: PMC212796. 11: Richter SN, Menegazzo I, Fabris D, Palumbo M. Concerted bis-alkylating reactivity of clerocidin towards unpaired cytosine residues in DNA. Nucleic Acids Res. 2004 Oct 19;32(18):5658-67. Print 2004. PubMed PMID: 15494453; PubMed Central PMCID: PMC524306. 12: Richter SN, Leo E, Giaretta G, Gatto B, Fisher LM, Palumbo M. Clerocidin interacts with the cleavage complex of Streptococcus pneumoniae topoisomerase IV to induce selective irreversible DNA damage. Nucleic Acids Res. 2006 Apr 13;34(7):1982-91. Print 2006. PubMed PMID: 16614448; PubMed Central PMCID: PMC1435983. 13: Richter S, Fabris D, Binaschi M, Gatto B, Capranico G, Palumbo M. Effects of common buffer systems on drug activity: the case of clerocidin. Chem Res Toxicol. 2004 Apr;17(4):492-501. PubMed PMID: 15089091. 14: McCullough JE, Muller MT, Howells AJ, Maxwell A, O'Sullivan J, Summerill RS, Parker WL, Wells JS, Bonner DP, Fernandes PB. Clerocidin, a terpenoid antibiotic, inhibits bacterial DNA gyrase. J Antibiot (Tokyo). 1993 Mar;46(3):526-30. PubMed PMID: 8386713. 15: Jamora C, Theodoraki MA, Malhotra V, Theodorakis EA. Investigation of the biological mode of action of clerocidin using whole cell assays. Bioorg Med Chem. 2001 Jun;9(6):1365-70. PubMed PMID: 11408157. 16: Borgnetto ME, Tinelli S, Carminati L, Capranico G. Genomic sites of topoisomerase II activity determined by comparing DNA breakage enhanced by three distinct poisons. J Mol Biol. 1999 Jan 15;285(2):545-54. PubMed PMID: 9878428. 17: Xiang AX, Watson DA, Ling T, Theodorakis EA. Total Synthesis of Clerocidin via a Novel, Enantioselective Homoallenylboration Methodology. J Org Chem. 1998 Oct 2;63(20):6774-6775. PubMed PMID: 11672290. 18: Andersen NR, Lorck HO, Rasmussen PR. Fermentation, isolation and characterization of antibiotic PR-1350. J Antibiot (Tokyo). 1983 Jul;36(7):753-60. PubMed PMID: 6684107. 19: Nakano H. [Antitumor agents targeting mammalian topoisomerases]. Gan To Kagaku Ryoho. 1991 Aug;18(10):1550-5. Review. Japanese. PubMed PMID: 1651681. 20: Kawada SZ, Yamashita Y, Uosaki Y, Gomi K, Iwasaki T, Takiguchi T, Nakano H. UCT4B, a new antitumor antibiotic with topoisomerase II mediated DNA cleavage activity, from Streptomyces sp. J Antibiot (Tokyo). 1992 Jul;45(7):1182-4. PubMed PMID: 1325436.