MedKoo Cat#: 558517 | Name: Kijanimicin
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Description:

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

Kijanimicin is an antitumor and antibiotic. Structurally the compound is a unique, large acid enol antibiotic and possesses an unusual in vitro spectrum of activity against some Gram-positive and anaerobic microorganisms. In vivo it has also shown interesting activity against malaria.

Chemical Structure

Kijanimicin
Kijanimicin
CAS#78798-08-0

Theoretical Analysis

MedKoo Cat#: 558517

Name: Kijanimicin

CAS#: 78798-08-0

Chemical Formula: C67H100N2O24

Exact Mass: 1316.6700

Molecular Weight: 1317.53

Elemental Analysis: C, 61.08; H, 7.65; N, 2.13; O, 29.14

Price and Availability

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500µg USD 650.00 2 Weeks
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Synonym
Kijanimicin; Kijanimicin sodium salt;
IUPAC/Chemical Name
Kijanimicin
InChi Key
AAHYWTFSLXCSNH-DLIYIRNRSA-N
InChi Code
InChI=1S/C67H100N2O24/c1-29-15-18-45(88-52-27-65(11,69(79)80)60(38(10)87-52)68-64(78)82-14)30(2)20-40-21-39(28-70)33(5)26-67(40)62(76)53(63(77)93-67)61(75)66(12)42(29)17-16-41-54(66)31(3)19-32(4)57(41)91-51-24-46(56(74)35(7)84-51)89-50-25-47(90-48-22-43(71)55(73)34(6)83-48)59(37(9)86-50)92-49-23-44(72)58(81-13)36(8)85-49/h15-17,20-21,31-38,40-52,54-60,70-74,76H,18-19,22-28H2,1-14H3,(H,68,78)/b29-15-,30-20+/t31-,32-,33+,34-,35-,36-,37-,38+,40+,41-,42-,43+,44+,45-,46+,47+,48-,49+,50-,51-,52-,54+,55-,56-,57-,58-,59-,60-,65-,66+,67?/m0/s1
SMILES Code
C[C@H]1C[C@H](C)[C@H](O[C@H]2C[C@@H](O[C@H]3C[C@@H](O[C@H]4C[C@@H](O)[C@@H](O)[C@H](C)O4)[C@@H](O[C@@H]5C[C@@H](O)[C@@H](OC)[C@H](C)O5)[C@H](C)O3)[C@@H](O)[C@H](C)O2)[C@@H]6[C@@H]1[C@@]7(C)[C@H](/C(C)=C\C[C@H](O[C@H]8C[C@](C)([N+]([O-])=O)[C@@H](NC(OC)=O)[C@@H](C)O8)/C(C)=C/[C@@H]9C=C(CO)[C@H](C)CC9%10C(O)=C(C(O%10)=O)C7=O)C=C6
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 1,317.53 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: Bradner WT, Claridge CA, Huftalen JB. Antitumor activity of kijanimicin. J Antibiot (Tokyo). 1983 Aug;36(8):1078-9. PubMed PMID: 6630059. 2: Waitz JA, Horan AC, Kalyanpur M, Lee BK, Loebenberg D, Marquez JA, Miller G, Patel MG. Kijanimicin (Sch 25663), a novel antibiotic produced by Actinomadura kijaniata SCC 1256. Fermentation, isolation, characterization and biological properties. J Antibiot (Tokyo). 1981 Sep;34(9):1101-6. PubMed PMID: 7328052. 3: Zhang H, White-Phillip JA, Melançon CE 3rd, Kwon HJ, Yu WL, Liu HW. Elucidation of the kijanimicin gene cluster: insights into the biosynthesis of spirotetronate antibiotics and nitrosugars. J Am Chem Soc. 2007 Nov 28;129(47):14670-83. Epub 2007 Nov 7. PubMed PMID: 17985890; PubMed Central PMCID: PMC2515274. 4: Cuthbertson L, Ahn SK, Nodwell JR. Deglycosylation as a mechanism of inducible antibiotic resistance revealed using a global relational tree for one-component regulators. Chem Biol. 2013 Feb 21;20(2):232-40. doi: 10.1016/j.chembiol.2012.11.011. PubMed PMID: 23438752. 5: Pramanik BN, Mallams AK, Bartner PL, Rossman RR, Morton JB, McGlotten JH. Special techniques of fast atom bombardment mass spectrometry for the study of oligosaccharide containing macrotetronolide antibiotic, kijanimicin. J Antibiot (Tokyo). 1984 Jul;37(7):818-21. PubMed PMID: 6469873. 6: Dow GT, Thoden JB, Holden HM. Structural studies on KijD1, a sugar C-3'-methyltransferase. Protein Sci. 2016 Dec;25(12):2282-2289. doi: 10.1002/pro.3034. Epub 2016 Sep 16. PubMed PMID: 27595766; PubMed Central PMCID: PMC5119555. 7: Wei RB, Xi T, Li J, Wang P, Li FC, Lin YC, Qin S. Lobophorin C and D, new kijanimicin derivatives from a marine sponge-associated actinomycetal strain AZS17. Mar Drugs. 2011 Mar 17;9(3):359-68. doi: 10.3390/md9030359. PubMed PMID: 21556165; PubMed Central PMCID: PMC3083656. 8: Lacoske MH, Theodorakis EA. Spirotetronate polyketides as leads in drug discovery. J Nat Prod. 2015 Mar 27;78(3):562-75. doi: 10.1021/np500757w. Epub 2014 Dec 1. Review. PubMed PMID: 25434976; PubMed Central PMCID: PMC4380204. 9: Thoden JB, Branch MC, Zimmer AL, Bruender NA, Holden HM. Active site architecture of a sugar N-oxygenase. Biochemistry. 2013 May 14;52(19):3191-3. doi: 10.1021/bi400407x. Epub 2013 Apr 30. PubMed PMID: 23621882. 10: Bruender NA, Thoden JB, Kaur M, Avey MK, Holden HM. Molecular architecture of a C-3'-methyltransferase involved in the biosynthesis of D-tetronitrose. Biochemistry. 2010 Jul 20;49(28):5891-8. doi: 10.1021/bi100782b. PubMed PMID: 20527922. 11: Bruender NA, Thoden JB, Holden HM. X-ray structure of kijd3, a key enzyme involved in the biosynthesis of D-kijanose. Biochemistry. 2010 May 4;49(17):3517-24. doi: 10.1021/bi100318v. PubMed PMID: 20334431. 12: Köpper S, Thiem J. One-pot-synthesis of alpha-linked deoxy sugar trisaccharides. Carbohydr Res. 1994 Jul 16;260(2):219-32. PubMed PMID: 8069874. 13: Jiang ZD, Jensen PR, Fenical W. Lobophorins A and B, new antiinflammatory macrolides produced by a tropical marine bacterium. Bioorg Med Chem Lett. 1999 Jul 19;9(14):2003-6. PubMed PMID: 10450970. 14: Kubiak RL, Holden HM. Combined structural and functional investigation of a C-3''-ketoreductase involved in the biosynthesis of dTDP-L-digitoxose. Biochemistry. 2011 Jul 5;50(26):5905-17. doi: 10.1021/bi200514b. Epub 2011 Jun 8. PubMed PMID: 21598943. 15: Ohtsuka T, Nakayama N, Itezono Y, Shimma N, Kuwahara T, Yokose K, Seto H. Tetronothiodin, a novel cholecystokinin type-B receptor antagonist produced by Streptomyces sp. NR0489. III. Structural elucidation. J Antibiot (Tokyo). 1993 Jan;46(1):18-24. PubMed PMID: 8436552. 16: Chen L, Heng J, Qin S, Bian K. A comprehensive understanding of the biocontrol potential of Bacillus velezensis LM2303 against Fusarium head blight. PLoS One. 2018 Jun 1;13(6):e0198560. doi: 10.1371/journal.pone.0198560. eCollection 2018. PubMed PMID: 29856856; PubMed Central PMCID: PMC5983450.