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MedKoo Cat#: 412608 | Name: Cetocycline (free base)

Description:

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

Cetocycline (free base) is structurally related to the tetracyclines with antimicrobial activity

Chemical Structure

Cetocycline (free base)
CAS#29144-42-1 (free base)

Theoretical Analysis

MedKoo Cat#: 412608

Name: Cetocycline (free base)

CAS#: 29144-42-1 (free base)

Chemical Formula: C22H21NO7

Exact Mass: 411.1318

Molecular Weight: 411.41

Elemental Analysis: C, 64.23; H, 5.15; N, 3.40; O, 27.22

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.
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Related CAS #
29144-42-1 (free base) 56433-46-6 (HCl)
Synonym
Cetocycline; Cetotetrine; Chelocardin
IUPAC/Chemical Name
(4R,4aS,12aS)-2-acetyl-4-amino-3,10,11,12a-tetrahydroxy-6,9-dimethyl-4a,12a-dihydrotetracene-1,12(4H,5H)-dione
InChi Key
IRCLZBUBOWPFCH-ONJZCGHCSA-N
InChi Code
InChI=1S/C22H21NO7/c1-7-4-5-10-8(2)11-6-12-16(23)19(27)13(9(3)24)20(28)22(12,30)21(29)15(11)18(26)14(10)17(7)25/h4-5,12,16,25-27,30H,6,23H2,1-3H3/t12-,16+,22+/m0/s1
SMILES Code
CC(C1=C([C@@H]([C@@H]2Cc(c3C)c(C([C@@]2(C1=O)O)=O)c(O)c4c3ccc(C)c4O)N)O)=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
>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 411.41 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: Mitscher LA, Swayze JK, Högberg T, Khanna I, Rao GS, Theriault RJ, Kohl W, Hanson C, Egan R. Biosynthesis of cetocycline. J Antibiot (Tokyo). 1983 Oct;36(10):1405-7. doi: 10.7164/antibiotics.36.1405. PMID: 6643286. 2: Proctor R, Craig W, Kunin C. Cetocycline, tetracycline analog: in vitro studies of antimicrobial activity, serum binding, lipid solubility, and uptake by bacteria. Antimicrob Agents Chemother. 1978 Apr;13(4):598-604. doi: 10.1128/aac.13.4.598. PMID: 666291; PMCID: PMC352294. 3: Theriault RJ, Guagliardi L, Hudson PB, Mitscher LA, Park YH, Swayze JK. Microbiological conversion of 4-epi-cetocycline to 2-decarboxamido-2-acetyl-4-dedimethyl-9-methyltetracycline. J Antibiot (Tokyo). 1982 Mar;35(3):364-6. doi: 10.7164/antibiotics.35.364. PMID: 7076581. 4: Grandclaudon C, Birudukota NVS, Elgaher WAM, Jumde RP, Yahiaoui S, Arisetti N, Hennessen F, Hüttel S, Stadler M, Herrmann J, Miethke M, Hartmann RW, Müller R, Hirsch AKH, Brönstrup M. Semisynthesis and biological evaluation of amidochelocardin derivatives as broad-spectrum antibiotics. Eur J Med Chem. 2020 Feb 15;188:112005. doi: 10.1016/j.ejmech.2019.112005. Epub 2019 Dec 20. PMID: 31911294. 5: Lukežič T, Fayad AA, Bader C, Harmrolfs K, Bartuli J, Groß S, Lešnik U, Hennessen F, Herrmann J, Pikl Š, Petković H, Müller R. Engineering Atypical Tetracycline Formation in Amycolatopsis sulphurea for the Production of Modified Chelocardin Antibiotics. ACS Chem Biol. 2019 Mar 15;14(3):468-477. doi: 10.1021/acschembio.8b01125. Epub 2019 Feb 12. PMID: 30747520. 6: Herrmann J, Lukežič T, Kling A, Baumann S, Hüttel S, Petković H, Müller R. Strategies for the Discovery and Development of New Antibiotics from Natural Products: Three Case Studies. Curr Top Microbiol Immunol. 2016;398:339-363. doi: 10.1007/82_2016_498. PMID: 27738913. 7: Stepanek JJ, Lukežič T, Teichert I, Petković H, Bandow JE. Dual mechanism of action of the atypical tetracycline chelocardin. Biochim Biophys Acta. 2016 Jun;1864(6):645-654. doi: 10.1016/j.bbapap.2016.03.004. Epub 2016 Mar 9. PMID: 26969785. 8: Chopra I. Tetracycline analogs whose primary target is not the bacterial ribosome. Antimicrob Agents Chemother. 1994 Apr;38(4):637-40. doi: 10.1128/aac.38.4.637. PMID: 8031024; PMCID: PMC284517. 9: Kornguth ML, Kunin CM. Minocycline-induced loss of potassium from erythrocytes: identification of a family with an augmented response. J Infect Dis. 1978 Oct;138(4):455-62. doi: 10.1093/infdis/138.4.455. PMID: 152337. 10: Hennessen F, Miethke M, Zaburannyi N, Loose M, Lukežič T, Bernecker S, Hüttel S, Jansen R, Schmiedel J, Fritzenwanker M, Imirzalioglu C, Vogel J, Westermann AJ, Hesterkamp T, Stadler M, Wagenlehner F, Petković H, Herrmann J, Müller R. Amidochelocardin Overcomes Resistance Mechanisms Exerted on Tetracyclines and Natural Chelocardin. Antibiotics (Basel). 2020 Sep 18;9(9):619. doi: 10.3390/antibiotics9090619. PMID: 32962088; PMCID: PMC7559539.