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MedKoo Cat#: 555330 | Name: DDA-tetracycline

Description:

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

DDA-tetracycline, also known CMT-1 and 4-Des-dimethylaminotetracycline, is a Matrix Metalloproteinase Inhibitor.

Chemical Structure

DDA-tetracycline
DDA-tetracycline
CAS#2444-65-7

Theoretical Analysis

MedKoo Cat#: 555330

Name: DDA-tetracycline

CAS#: 2444-65-7

Chemical Formula: C20H19NO8

Exact Mass: 401.1111

Molecular Weight: 401.37

Elemental Analysis: C, 59.85; H, 4.77; N, 3.49; O, 31.89

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 #
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Synonym
DDA-tetracycline; 4-Des-dimethylaminotetracycline; 4-de-Dimethylaminotetracycline; CMT-1; CMT 1; CMT1;
IUPAC/Chemical Name
2-Naphthacenecarboxamide, 1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4aS-(4aalpha,5aalpha,6beta,12aalpha))-
InChi Key
SRPCXEFYFVDUFQ-KBKZQPOHSA-N
InChi Code
InChI=1S/C20H19NO8/c1-19(28)8-3-2-4-10(22)12(8)15(24)13-9(19)5-7-6-11(23)14(18(21)27)17(26)20(7,29)16(13)25/h2-4,7,9,22-23,25,28-29H,5-6H2,1H3,(H2,21,27)/t7-,9-,19+,20-/m0/s1
SMILES Code
O=C(C(C1=O)=C(O)C[C@]2([H])C[C@]3([H])[C@](C)(O)C4=C(C(C3=C(O)[C@@]21O)=O)C(O)=CC=C4)N
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 401.37 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: Klieber MA, Scholz O, Lochner S, Gmeiner P, Hillen W, Muller YA. Structural origins for selectivity and specificity in an engineered bacterial repressor-inducer pair. FEBS J. 2009 Oct;276(19):5610-21. doi: 10.1111/j.1742-4658.2009.07254.x. Epub 2009 Aug 27. PubMed PMID: 19712110. 2: D'Agostino P, Ferlazzo V, Milano S, La Rosa M, Di Bella G, Caruso R, Barbera C, Grimaudo S, Tolomeo M, Feo S, Cillari E. Chemically modified tetracyclines induce cytotoxic effects against J774 tumour cell line by activating the apoptotic pathway. Int Immunopharmacol. 2003 Jan;3(1):63-73. PubMed PMID: 12538035. 3: Grenier D, Plamondon P, Sorsa T, Lee HM, McNamara T, Ramamurthy NS, Golub LM, Teronen O, Mayrand D. Inhibition of proteolytic, serpinolytic, and progelatinase-b activation activities of periodontopathogens by doxycycline and the non-antimicrobial chemically modified tetracycline derivatives. J Periodontol. 2002 Jan;73(1):79-85. PubMed PMID: 11846203. 4: Nobbio L, Mancardi G, Grandis M, Levi G, Suter U, Nave KA, Windebank AJ, Abbruzzese M, Schenone A. PMP22 transgenic dorsal root ganglia cultures show myelin abnormalities similar to those of human CMT1A. Ann Neurol. 2001 Jul;50(1):47-55. PubMed PMID: 11456309. 5: Ryan ME, Usman A, Ramamurthy NS, Golub LM, Greenwald RA. Excessive matrix metalloproteinase activity in diabetes: inhibition by tetracycline analogues with zinc reactivity. Curr Med Chem. 2001 Feb;8(3):305-16. PubMed PMID: 11172685. 6: Lagueny A, Latour P, Vital A, Le Masson G, Rouanet M, Ferrer X, Vital C, Vandenberghe A. Mild recurrent neuropathy in CMT1B with a novel nonsense mutation in the extracellular domain of the MPZ gene. J Neurol Neurosurg Psychiatry. 2001 Feb;70(2):232-5. PubMed PMID: 11160475; PubMed Central PMCID: PMC1737217. 7: Ramamurthy NS, Schroeder KL, McNamara TF, Gwinnett AJ, Evans RT, Bosko C, Golub LM. Root-surface caries in rats and humans: inhibition by a non-antimicrobial property of tetracyclines. Adv Dent Res. 1998 Nov;12(2):43-50. PubMed PMID: 9972121. 8: Craig RG, Yu Z, Xu L, Barr R, Ramamurthy N, Boland J, Schneir M, Golub LM. A chemically modified tetracycline inhibits streptozotocin-induced diabetic depression of skin collagen synthesis and steady-state type I procollagen mRNA. Biochim Biophys Acta. 1998 Apr 24;1402(3):250-60. PubMed PMID: 9606983. 9: Karimbux NY, Ramamurthy NS, Golub LM, Nishimura I. The expression of collagen I and XII mRNAs in Porphyromonas gingivalis-induced periodontitis in rats: the effect of doxycycline and chemically modified tetracycline. J Periodontol. 1998 Jan;69(1):34-40. PubMed PMID: 9527559. 10: Leung MK, Greenwald RA, Ramamurthy NS, Moak SA, Koszulinski R, Dieudonne D, Golub LM. Tenidap and flurbiprofen enhance uptake of matrix metalloproteinase inhibitor 4-dedimethylaminotetracycline in inflamed joints of adjuvant arthritic rats. J Rheumatol. 1995 Sep;22(9):1726-31. PubMed PMID: 8523353. 11: Golub LM, Evans RT, McNamara TF, Lee HM, Ramamurthy NS. A non-antimicrobial tetracycline inhibits gingival matrix metalloproteinases and bone loss in Porphyromonas gingivalis-induced periodontitis in rats. Ann N Y Acad Sci. 1994 Sep 6;732:96-111. PubMed PMID: 7978855. 12: Ramamurthy N, Greenwald R, Moak S, Scuibba J, Goren A, Turner G, Rifkin B, Golub L. CMT/Tenidap treatment inhibits temporomandibular joint destruction in adjuvant arthritic rats. Ann N Y Acad Sci. 1994 Sep 6;732:427-30. PubMed PMID: 7978829. 13: Uitto VJ, Firth JD, Nip L, Golub LM. Doxycycline and chemically modified tetracyclines inhibit gelatinase A (MMP-2) gene expression in human skin keratinocytes. Ann N Y Acad Sci. 1994 Sep 6;732:140-51. PubMed PMID: 7978787. 14: Chang KM, Ramamurthy NS, McNamara TF, Evans RT, Klausen B, Murray PA, Golub LM. Tetracyclines inhibit Porphyromonas gingivalis-induced alveolar bone loss in rats by a non-antimicrobial mechanism. J Periodontal Res. 1994 Jul;29(4):242-9. PubMed PMID: 7932017. 15: Golub LM, Wolff M, Roberts S, Lee HM, Leung M, Payonk GS. Treating periodontal diseases by blocking tissue-destructive enzymes. J Am Dent Assoc. 1994 Feb;125(2):163-9; discussion 169-71. Review. PubMed PMID: 8113524. 16: Ramamurthy N, Leung M, Moak S, Greenwald R, Golub L. CMT/NSAID combination increases bone CMT uptake and inhibits bone resorption. Ann N Y Acad Sci. 1993 Nov 30;696:420-1. PubMed PMID: 8109855. 17: Yu Z, Ramamurthy NS, Leung M, Chang KM, McNamara TF, Golub LM. Chemically-modified tetracycline normalizes collagen metabolism in diabetic rats: a dose-response study. J Periodontal Res. 1993 Nov;28(6 Pt 1):420-8. PubMed PMID: 8254459. 18: Zaidi M, Moonga BS, Huang CL, Towhidul Alam AS, Shankar VS, Pazianas M, Eastwood JB, Datta HK, Rifkin BR. The effect of tetracyclines on quantitative measures of osteoclast morphology. Biosci Rep. 1993 Jun;13(3):175-82. PubMed PMID: 8268425. 19: Bax CM, Shankar VS, Towhidul Alam AS, Bax BE, Moonga BS, Huang CL, Zaidi M, Rifkin BR. Tetracyclines modulate cytosolic Ca2+ responses in the osteoclast associated with "Ca2+ receptor" activation. Biosci Rep. 1993 Jun;13(3):169-74. PubMed PMID: 8268424. 20: Ingman T, Sorsa T, Suomalainen K, Halinen S, Lindy O, Lauhio A, Saari H, Konttinen YT, Golub LM. Tetracycline inhibition and the cellular source of collagenase in gingival crevicular fluid in different periodontal diseases. A review article. J Periodontol. 1993 Feb;64(2):82-8. Review. PubMed PMID: 8433257.