Dianemycin | CAS# 35865-33-9 | antibiotic

MedKoo Cat#: 413661 | Name: Dianemycin

Featured

Description:

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

Dianemycin is a polyether, polyalcohol, monocarboxylic acid (with 2 spiro links between rings) antibiotic from Streptomyces hygroscopicus which binds metal monovalent cations.

Chemical Structure

Dianemycin

CAS#35865-33-9 (free acid)

Theoretical Analysis

MedKoo Cat#: 413661

Name: Dianemycin

CAS#: 35865-33-9 (free acid)

Chemical Formula: C47H78O14

Exact Mass: 866.5392

Molecular Weight: 867.13

Elemental Analysis: C, 65.10; H, 9.07; O, 25.83

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

65101-87-3 (Sodium) 35865-33-9 (free acid)

Synonym

Dianemycin; Nanchangmycin (free acid); Nanchangmycin free acid;

IUPAC/Chemical Name

(2S,4R,8S,E)-8-((2S,2'R,4'S,5R,5'S,7R,7'R,8R,9S,9'S,10'R)-9-hydroxy-2'-((2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-9'-(((2S,5R,6S)-5-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,4',8,10'-tetramethyl-1,1',6,6'-tetraoxa[2,7'-bispiro[4.5]decan]-7-yl)-2,4,6-trimethyl-5-oxonon-6-enoic acid

InChi Key

FELYAZAWTURXNF-NNRRCCSUSA-N

InChi Code

InChI=1S/C47H78O14/c1-24(40(50)25(2)18-28(5)43(51)52)17-26(3)41-31(8)34(49)22-45(59-41)16-15-44(11,61-45)38-21-36(56-39-14-13-35(54-12)33(10)55-39)32(9)47(58-38)30(7)20-37(57-47)42-27(4)19-29(6)46(53,23-48)60-42/h17,25-39,41-42,48-49,53H,13-16,18-23H2,1-12H3,(H,51,52)/b24-17+/t25-,26+,27+,28+,29-,30+,31-,32-,33+,34+,35-,36+,37-,38-,39-,41-,42+,44+,45-,46+,47+/m1/s1

SMILES Code

C/C(C([C@@H](C[C@@H](C(O)=O)C)C)=O)=C\[C@@H]([C@]1(O[C@]2(C[C@@H]([C@H]1C)O)CC[C@](C)(O2)[C@@]3(O[C@]4([C@@H]([C@H](C3)O[C@]5(O[C@H]([C@@H](CC5)OC)C)[H])C)[C@H](C[C@@]([H])(O4)[C@@]6([C@H](C[C@H]([C@@](O)(O6)CO)C)C)[H])C)[H])[H])C

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 867.13 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

1: Hamill RL, Hoehn MM, Pittenger GE, Chamberlin J, Gorman M. Dianemycin, an antibiotic of the group affecting ion transport. J Antibiot (Tokyo). 1969 Apr;22(4):161-4. doi: 10.7164/antibiotics.22.161. PMID: 4308163. 2: Czerwinski EW, Steinrauf LK. Structure of the antibiotic dianemycin. Biochem Biophys Res Commun. 1971 Dec 3;45(5):1284-7. doi: 10.1016/0006-291x(71)90157-4. PMID: 5135512. 3: Lee SJ, Kim HP, Park BK, Ahn SC, Lee HS, Ahn JS. Topical anti-inflammatory activity of dianemycin isolated fromStreptomyces sp. MT 2705-4. Arch Pharm Res. 1997 Aug;20(4):372-4. doi: 10.1007/BF02976203. PMID: 18975182. 4: Mizoue K, Seto H, Mizutani T, Yamagishi M, Kawashima A, Omura S, Ozeki M, Otake N. Studies on the ionophorous antibiotics. XXV. The assignments of the 13C-NMR spectra of dianemycin and lenoremycin. J Antibiot (Tokyo). 1980 Feb;33(2):144-56. doi: 10.7164/antibiotics.33.144. PMID: 7380725. 5: Steinrauf LK, Czerwinski EW, Pinkerton M. Comparison of the monovalent cation complexes of monensin, nigericin, and dianemycin. Biochem Biophys Res Commun. 1971 Dec 3;45(5):1279-83. doi: 10.1016/0006-291x(71)90156-2. PMID: 5135511. 6: Westley JW, Liu CM, Sello LH, Troupe N, Blount JF, Chiu AM, Todaro LJ, Miller PA, Liu M. Isolation and characterization of antibiotic X-14931A, the naturally occurring 19-deoxyaglycone of dianemycin. J Antibiot (Tokyo). 1984 Jul;37(7):813-5. doi: 10.7164/antibiotics.37.813. PMID: 6547948. 7: Dirlam JP, Presseau-Linabury L, Koss DA. The structure of CP-80,219, a new polyether antibiotic related to dianemycin. J Antibiot (Tokyo). 1990 Jun;43(6):727-30. doi: 10.7164/antibiotics.43.727. PMID: 2380117. 8: Cullen WP, Bordner J, Huang LH, Moshier PM, Oscarson JR, Presseau LA, Ware RS, Whipple EB, Kojima Y, Maeda H, et al. CP-60,993, a new dianemycin-like ionophore produced by Streptomyces hygroscopicus ATCC 39305: fermentation, isolation and characterization. J Ind Microbiol. 1990 Aug;5(6):365-74. doi: 10.1007/BF01578095. PMID: 1366760. 9: Kubota T, Hinoh G, Mayama M, Motokawa K, Yasuda Y. Antibiotic A-130, isolation and characterization. J Antibiot (Tokyo). 1975 Dec;28(12):931-4. doi: 10.7164/antibiotics.28.931. PMID: 1206005. 10: Mizutani T, Yamagishi M, Hara H, Kawashima A, Omura S, Ozeki M. Studies on the ionophorous antibiotics. XXIV. Leuseramycin, a new polyether antibiotic produced by Streptomyces hygroscopicus. J Antibiot (Tokyo). 1980 Feb;33(2):137-43. doi: 10.7164/antibiotics.33.137. PMID: 7380724. 11: Kawada M, Sumi S, Umezawa K, Inouye S, Sawa T, Seto H. Circumvention of multidrug resistance in human carcinoma KB cells by polyether antibiotics. J Antibiot (Tokyo). 1992 Apr;45(4):556-62. doi: 10.7164/antibiotics.45.556. PMID: 1592687. 12: Henderson PJ, McGivan JD, Chappell JB. The action of certain antibiotics on mitochondrial, erythrocyte and artificial phospholipid membranes. The role of induced proton permeability. Biochem J. 1969 Feb;111(4):521-35. doi: 10.1042/bj1110521. PMID: 5774477; PMCID: PMC1187573. 13: Sun Y, Zhou X, Liu J, Bao K, Zhang G, Tu G, Kieser T, Deng Z. 'Streptomyces nanchangensis', a producer of the insecticidal polyether antibiotic nanchangmycin and the antiparasitic macrolide meilingmycin, contains multiple polyketide gene clusters. Microbiology (Reading). 2002 Feb;148(Pt 2):361-371. doi: 10.1099/00221287-148-2-361. PMID: 11832500. 14: Cockrell RS. Ruthenium red-insensitive Ca2+ uptake and release by mitochondria. Arch Biochem Biophys. 1985 Nov 15;243(1):70-9. doi: 10.1016/0003-9861(85)90774-x. PMID: 2415064. 15: Robinson DG. The ionic sensitivity of secretion-associated organelles in root cap cells of maize. Eur J Cell Biol. 1981 Feb;23(2):267-72. PMID: 7202418. 16: Guo X, Liu T, Deng Z, Cane DE. Essential role of the donor acyl carrier protein in stereoselective chain translocation to a fully reducing module of the nanchangmycin polyketide synthase. Biochemistry. 2012 Jan 31;51(4):879-87. doi: 10.1021/bi201768v. Epub 2012 Jan 17. PMID: 22229794; PMCID: PMC3273620. 17: Cobley JG. Energy-conserving reactions in phosphorylating electron-transport particles from Nitrobacter winogradskyi. Activation of nitrite oxidation by the electrical component of the protonmotive force. Biochem J. 1976 Jun 15;156(3):481-91. doi: 10.1042/bj1560481c. PMID: 182152; PMCID: PMC1163779. 18: Quader H, Robinson DG. Structure, synthesis and orientation of microfibrils. VI. The role of ions in microfibril deposition in Oocystis solitaria. Eur J Cell Biol. 1979 Oct;20(1):51-6. PMID: 118010.