Synonym
GS-2989, NSC 78502, Meclocycline
IUPAC/Chemical Name
(4S,4aR,5S,5aR,12aS)-7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide
InChi Key
GGQJXCQBBONZFX-IWVLMIASSA-N
InChi Code
InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26,28-30,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1
SMILES Code
OC([C@@](C(C(C(N)=O)=C(O)[C@H]1N(C)C)=O)(O)[C@@]1([H])[C@H]2O)=C([C@@]2([H])C3=C)C(C4=C3C(Cl)=CC=C4O)=O
Purity
>95% (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
Biological target:
Meclocycline is a tetracycline antibiotic with broad antimicrobial activity.
In vivo activity:
In a screen of 2000 compounds, six were found to produce significant protection of C. elegans from delayed death. Four of the compounds were tested in an ex vivo mouse heart ischemia/reperfusion model and two, meclocycline and 3-amino-1,2,4-triazole, significantly reduced infarction size.
Reference: PLoS One. 2017 Apr 20;12(4):e0176061. https://pubmed.ncbi.nlm.nih.gov/28426808/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
476.87
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:
Sun CL, Zhang H, Liu M, Wang W, Crowder CM. A screen for protective drugs against delayed hypoxic injury. PLoS One. 2017 Apr 20;12(4):e0176061. doi: 10.1371/journal.pone.0176061. PMID: 28426808; PMCID: PMC5398677.
In vivo protocol:
Sun CL, Zhang H, Liu M, Wang W, Crowder CM. A screen for protective drugs against delayed hypoxic injury. PLoS One. 2017 Apr 20;12(4):e0176061. doi: 10.1371/journal.pone.0176061. PMID: 28426808; PMCID: PMC5398677.
1. Blackwood, R.K., Rennhard, H.H., Beereboom, J.J., et al. 6-Methylenetetracyclines. I. A new class of tetracycline antibiotics. J. Am. Chem. Soc. 83(12), 2773-2775 (1961).
2. Pulverer, G., and Jeljaszewicz, J. Susceptibility of Staphylococcus epidermidis to lysostaphin and major antimicrobial agents. Chemotherapy 19(2), 109-114 (1973).
3. Wang, W., Duan, W., Igarashi, S., et al. Compounds blocking mutant huntingtin toxicity identified using a Huntington’s disease neuronal cell model. Neurobiol. Dis. 20(2), 500-508 (2005).
