MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 534926 | Name: MECAM

Description:

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

MECAM is a synthetic iron chelator related to enterobactin.

Chemical Structure

MECAM
MECAM
CAS#69146-59-4

Theoretical Analysis

MedKoo Cat#: 534926

Name: MECAM

CAS#: 69146-59-4

Chemical Formula: C30H27N3O9

Exact Mass: 573.1747

Molecular Weight: 573.56

Elemental Analysis: C, 62.82; H, 4.75; N, 7.33; O, 25.10

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
MECAM
IUPAC/Chemical Name
Benzamide, N,N',N''-(1,3,5-benzenetriyltris(methylene))tris(2,3-dihydroxy-
InChi Key
GCTFIRZGPIUOAK-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H27N3O9/c34-22-7-1-4-19(25(22)37)28(40)31-13-16-10-17(14-32-29(41)20-5-2-8-23(35)26(20)38)12-18(11-16)15-33-30(42)21-6-3-9-24(36)27(21)39/h1-12,34-39H,13-15H2,(H,31,40)(H,32,41)(H,33,42)
SMILES Code
O=C(NCC1=CC(CNC(C2=CC=CC(O)=C2O)=O)=CC(CNC(C3=CC=CC(O)=C3O)=O)=C1)C4=CC=CC(O)=C4O
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 573.56 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: Glautier S. Revisiting the learning curve (once again). Front Psychol. 2013 Dec 26;4:982. doi: 10.3389/fpsyg.2013.00982. PMID: 24421774; PMCID: PMC3872722. 2: Peuckert F, Ramos-Vega AL, Miethke M, Schwörer CJ, Albrecht AG, Oberthür M, Marahiel MA. The siderophore binding protein FeuA shows limited promiscuity toward exogenous triscatecholates. Chem Biol. 2011 Jul 29;18(7):907-19. doi: 10.1016/j.chembiol.2011.05.006. PMID: 21802011. 3: Wyckoff EE, Allred BE, Raymond KN, Payne SM. Catechol Siderophore Transport by Vibrio cholerae. J Bacteriol. 2015 Sep;197(17):2840-9. doi: 10.1128/JB.00417-15. Epub 2015 Jun 22. PMID: 26100039; PMCID: PMC4524036. 4: Müller A, Wilkinson AJ, Wilson KS, Duhme-Klair AK. An [{Fe(mecam)}2]6- bridge in the crystal structure of a ferric enterobactin binding protein. Angew Chem Int Ed Engl. 2006 Aug 4;45(31):5132-6. doi: 10.1002/anie.200601198. PMID: 16927323. 5: Ecker DJ, Matzanke BF, Raymond KN. Recognition and transport of ferric enterobactin in Escherichia coli. J Bacteriol. 1986 Aug;167(2):666-73. doi: 10.1128/jb.167.2.666-673.1986. PMID: 2942532; PMCID: PMC212941. 6: Matzanke BF, Ecker DJ, Yang TS, Huynh BH, Müller G, Raymond KN. Escherichia coli iron enterobactin uptake monitored by Mössbauer spectroscopy. J Bacteriol. 1986 Aug;167(2):674-80. doi: 10.1128/jb.167.2.674-680.1986. PMID: 2942533; PMCID: PMC212942. 7: Heidinger S, Braun V, Pecoraro VL, Raymond KN. Iron supply to Escherichia coli by synthetic analogs of enterochelin. J Bacteriol. 1983 Jan;153(1):109-15. PMID: 6217190; PMCID: PMC217347. 8: Anderson MT, Armstrong SK. The Bordetella bfe system: growth and transcriptional response to siderophores, catechols, and neuroendocrine catecholamines. J Bacteriol. 2006 Aug;188(16):5731-40. doi: 10.1128/JB.00495-06. PMID: 16885441; PMCID: PMC1540089. 9: Smith M, Francq B, McConnachie A, Wetherall K, Pelosi A, Morrison J. Clinical judgement, case complexity and symptom scores as predictors of outcome in depression: an exploratory analysis. BMC Psychiatry. 2020 Mar 16;20(1):125. doi: 10.1186/s12888-020-02532-0. PMID: 32183799; PMCID: PMC7076946. 10: Brickman TJ, McIntosh MA. Overexpression and purification of ferric enterobactin esterase from Escherichia coli. Demonstration of enzymatic hydrolysis of enterobactin and its iron complex. J Biol Chem. 1992 Jun 15;267(17):12350-5. PMID: 1534808. 11: Hay BP, Dixon DA, Vargas R, Garza J, Raymond KN. Structural criteria for the rational design of selective ligands. 3. Quantitative structure-stability relationship for iron(III) complexation by tris-catecholamide siderophores. Inorg Chem. 2001 Jul 30;40(16):3922-35. doi: 10.1021/ic001380s. PMID: 11466050. 12: Peckmann K, von Willert DJ, Martin CE, Herppich WB. Mitochondrial respiration in ME-CAM, PEPCK-CAM, and C₃ succulents: comparative operation of the cytochrome, alternative, and rotenone-resistant pathways. J Exp Bot. 2012 May;63(8):2909-19. doi: 10.1093/jxb/err458. Epub 2012 Feb 13. PMID: 22330897. 13: Peuckert F, Miethke M, Albrecht AG, Essen LO, Marahiel MA. Structural basis and stereochemistry of triscatecholate siderophore binding by FeuA. Angew Chem Int Ed Engl. 2009;48(42):7924-7. doi: 10.1002/anie.200902495. PMID: 19746494. 14: Durbin PW, Jeung N, Jones ES, Weitl FL, Raymond KN. Specific sequestering agents for the actinides: 10. Enhancement of 238Pu elimination from mice by poly(catechoylamide) ligands. Radiat Res. 1984 Jul;99(1):85-105. PMID: 6547538. 15: Zhou XH, van der Helm D, Adjimani J. Purification of outer membrane iron transport receptors from Escherichia coli by fast protein liquid chromatography: FepA and FecA. Biometals. 1993 Spring;6(1):25-35. doi: 10.1007/BF00154229. PMID: 8471822. 16: Kondo A, Nose A, Yuasa H, Ueno O. Species variation in the intracellular localization of pyruvate, Pi dikinase in leaves of crassulacean-acid-metabolism plants: an immunogold electron-microscope study. Planta. 2000 Mar;210(4):611-21. doi: 10.1007/s004250050051. PMID: 10787055.