Synonym
Monazomycin; U 0142; U0142; U-0142
IUPAC/Chemical Name
(13E,17E,21E,29E)-48-(8-aminooctan-2-yl)-8,10,16,20,24,26,28,32,36,38,40,42,44,46-tetradecahydroxy-9,15,17,19,21,25,31,33,39,41,47-undecamethyl-23-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)oxacyclooctatetraconta-13,17,21,29-tetraen-2-one
InChi Key
BTUZNIQVZBANAX-FYSXOHQESA-N
InChi Code
InChI=1S/C72H133NO22/c1-39-22-19-20-25-55(79)46(8)54(78)24-17-15-18-26-62(84)95-71(42(4)23-16-13-14-21-31-73)50(12)59(83)37-53(77)36-58(82)48(10)66(88)47(9)56(80)34-51(75)29-27-40(2)63(85)41(3)28-30-52(76)35-57(81)49(11)67(89)60(33-45(7)65(87)44(6)32-43(5)64(39)86)93-72-70(92)69(91)68(90)61(38-74)94-72/h19,22,28,30,32-33,39-42,44,46-61,63-72,74-83,85-92H,13-18,20-21,23-27,29,31,34-38,73H2,1-12H3/b22-19+,30-28+,43-32+,45-33+
SMILES Code
O=C1OC(C(CCCCCCN)C)C(C)C(O)CC(O)CC(O)C(C)C(O)C(C)C(O)CC(O)CCC(C)C(O)C(C)/C=C/C(O)CC(O)C(C)C(O)C(OC2OC(CO)C(O)C(O)C2O)/C=C(C)/C(O)C(C)/C=C(C)/C(O)C(C)/C=C/CCC(O)C(C)C(O)CCCCC1
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
Biological target:
Monazomycin is a polyene-like antibiotic produced by Streptomyces.
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
45.5 |
33.34 |
| Ethanol |
58.0 |
42.50 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,364.84
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:
TBD
1: Heyer RJ, Muller RU, Finkelstein A. Inactivation of monazomycin-induced voltage-dependent conductance in thin lipid membranes. II. Inactivation produced by monazomycin transport through the membrane. J Gen Physiol. 1976 Jun;67(6):731-48. PubMed PMID: 932673; PubMed Central PMCID: PMC2214979.
2: Muller RU, Finkelstein A. Voltage-dependent conductance induced in thin lipid membranes by monazomycin. J Gen Physiol. 1972 Sep;60(3):263-84. PubMed PMID: 5055789; PubMed Central PMCID: PMC2226075.
3: Muller RU, Finkelstein A. The effect of surface charge on the voltage-dependent conductance induced in thin lipid membranes by monazomycin. J Gen Physiol. 1972 Sep;60(3):285-306. PubMed PMID: 5055790; PubMed Central PMCID: PMC2226073.
4: Kuo MS, Yurek DA, Laborde AL, Truesdell SE, Nielsen JW, Argoudelis AD, Baczynskyj L. Monazomycin B, a new macrolide antibiotic of the monazomycin family. J Antibiot (Tokyo). 1990 Apr;43(4):438-40. PubMed PMID: 2351615.
5: Mauro A, Nanavati RP, Heyer E. Time-variant conductance of bilayer membranes treated with monazomycin and alamethicin. Proc Natl Acad Sci U S A. 1972 Dec;69(12):3742-4. PubMed PMID: 4509338; PubMed Central PMCID: PMC389861.
6: Mitani M, Yamanishi T, Miyazaki Y, Otake N. Salinomycin effects on mitochondrial ion translocation and respiration. Antimicrob Agents Chemother. 1976 Apr;9(4):655-60. PubMed PMID: 131509; PubMed Central PMCID: PMC429593.
7: Heyer EJ, Muller RU, Finkelstein A. Inactivation of monazomycin-induced voltage-dependent conductance in thin lipid membranes. I. Inactivation produced by long chain quaternary ammonium ions. J Gen Physiol. 1976 Jun;67(6):703-29. PubMed PMID: 932672; PubMed Central PMCID: PMC2214977.
8: Becucci L, Guidelli R. Kinetics of channel formation in bilayer lipid membranes (BLMs) and tethered BLMs: monazomycin and melittin. Langmuir. 2007 May 8;23(10):5601-8. Epub 2007 Apr 10. PubMed PMID: 17419655.
9: Mitscher LA, Shay AJ, Bohonos N. LL-A491, a monazomycin-like antibiotic. Appl Microbiol. 1967 Sep;15(5):1002-5. PubMed PMID: 6077405; PubMed Central PMCID: PMC547130.
10: Andersen OS, Muller RU. Monazomycin-induced single channels. I. Characterization of the elementary conductance events. J Gen Physiol. 1982 Sep;80(3):403-26. PubMed PMID: 6292330; PubMed Central PMCID: PMC2228680.
11: Muller RU, Orin G, Peskin CS. The kinetics of monazomycin-induced voltage-dependent conductance. I. Proof of the validity of an empirical rate equation. J Gen Physiol. 1981 Aug;78(2):171-200. PubMed PMID: 7276907; PubMed Central PMCID: PMC2228606.
12: Bamberg E, Janko K. Single channel conductance at lipid bilayer membranes in presence of monazomycin. Biochim Biophys Acta. 1976 Mar 19;426(3):447-50. PubMed PMID: 57800.
13: Wanke E, Prestipino G. Monazomycin channel noise. Biochim Biophys Acta. 1976 Jul 1;436(3):721-6. PubMed PMID: 952916.
14: Kolb HA. Conductance noise of monazomycin-doped bilayer membranes. J Membr Biol. 1979 Apr 9;45(3-4):277-92. PubMed PMID: 458843.
15: Mitani M, Otake N. Studies on the ionophorous antibiotics. XV The monovalent cation selective ionophorous activities of carriomycin, lonomycin and etheromycin. J Antibiot (Tokyo). 1978 Aug;31(8):750-5. PubMed PMID: 690008.
16: Muller RU, Andersen OS. Monazomycin-induced single channels. II. Origin of the voltage dependence of the macroscopic conductance. J Gen Physiol. 1982 Sep;80(3):427-49. PubMed PMID: 6292331; PubMed Central PMCID: PMC2228681.
17: Muller RU, Peskin CS. The kinetics of monazomycin-induced voltage-dependent conductance. II. Theory and a demonstration of a form of memory. J Gen Physiol. 1981 Aug;78(2):201-29. PubMed PMID: 7276908; PubMed Central PMCID: PMC2228603.
18: NISHIMURA T, TANAKA N. BIOLOGICAL STUDIES ON BACIMETHRIN, A PYRIMIDINE ANTIBIOTIC, AND MONAZOMYCIN. J Antibiot (Tokyo). 1963 Sep;16:179-81. PubMed PMID: 14066391.
19: Moore LE, Neher E. Fluctuation and relaxation analysis of monazomycin-induced conductance in black lipid membranes. J Membr Biol. 1976 Jun 30;27(4):347-62. PubMed PMID: 966263.
20: Mueller P, Chien TF, Rudy B. Formation and properties of cell-size lipid bilayer vesicles. Biophys J. 1983 Dec;44(3):375-81. PubMed PMID: 6661493; PubMed Central PMCID: PMC1434845.
