WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H130514
CAS#: Laterocidine
Description: Laterocidine is a macrocyclic lipodepsipeptide antibiotic, exhibiting potent antimicrobial activity toward Gram-negative bacteria and has a low risk of antibiotic resistance development. These bacteria include Pseudonomas aeruginosa and colistin-resistant E. coli.
Hodoodo Cat#: H130514
Name: Laterocidine
CAS#: Laterocidine
Chemical Formula: C78H113N19O18
Exact Mass: 1,603.85
Molecular Weight: 1,604.880
Elemental Analysis: C, 58.38; H, 7.10; N, 16.58; O, 17.94
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Synonym: CHEMBL4878048
IUPAC/Chemical Name: N-[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-5-amino-1-[[(2S)-5-amino-1-[[2-[[(2R)-5-amino-1-[[(2S)-1-[[(9S,12S,15S,16R)-9-(2-amino-2-oxoethyl)-12-[(2S)-butan-2-yl]-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-15-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]-7-methyloctanamide
InChi Key: MIUUXMLKAKRFMK-PCBFYWCHSA-N
InChi Code: InChI=1S/C78H113N19O18/c1-6-44(4)67-77(113)95-60(36-62(82)100)70(106)86-39-64(102)85-41-66(104)115-45(5)68(78(114)96-67)97-75(111)59(35-48-38-84-53-21-13-11-19-51(48)53)93-71(107)55(23-15-31-80)88-65(103)40-87-69(105)54(22-14-30-79)90-72(108)56(24-16-32-81)91-74(110)58(34-47-37-83-52-20-12-10-18-50(47)52)94-73(109)57(33-46-26-28-49(99)29-27-46)92-76(112)61(42-98)89-63(101)25-9-7-8-17-43(2)3/h10-13,18-21,26-29,37-38,43-45,54-61,67-68,83-84,98-99H,6-9,14-17,22-25,30-36,39-42,79-81H2,1-5H3,(H2,82,100)(H,85,102)(H,86,106)(H,87,105)(H,88,103)(H,89,101)(H,90,108)(H,91,110)(H,92,112)(H,93,107)(H,94,109)(H,95,113)(H,96,114)(H,97,111)/t44-,45+,54-,55+,56+,57+,58+,59-,60-,61+,67-,68-/m0/s1
SMILES Code: CC(C)CCCCCC(N[C@H](CO)C(N[C@H](CC1=CC=C(O)C=C1)C(N[C@H](CC2=CNC3=C2C=CC=C3)C(N[C@H](CCCN)C(N[C@@H](CCCN)C(NCC(N[C@H](CCCN)C(N[C@@H](CC4=CNC5=C4C=CC=C5)C(N[C@@H]6C(N[C@@H]([C@H](CC)C)C(N[C@@H](CC(N)=O)C(NCC(NCC(O[C@@H]6C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O
Appearance: To be determined
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:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 1,604.88 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: | |
In vitro protocol: | |
In vivo protocol: |
1. Ballantine RD, Al Ayed K, Bann SJ, Hoekstra M, Martin NI, Cochrane SA. Linearization of the Brevicidine and Laterocidine Lipopeptides Yields Analogues That Retain Full Antibacterial Activity. J Med Chem. 2023 Apr 27;66(8):6002-6009. doi: 10.1021/acs.jmedchem.3c00308. Epub 2023 Apr 18. PMID: 37071814; PMCID: PMC10150354.
2. Ballantine RD, Al Ayed K, Bann SJ, Hoekstra M, Martin NI, Cochrane SA. Synthesis and structure-activity relationship studies of N-terminal analogues of the lipopeptide antibiotics brevicidine and laterocidine. RSC Med Chem. 2022 Oct 27;13(12):1640-1643. doi: 10.1039/d2md00281g. PMID: 36545437; PMCID: PMC9749936.
3. Hermant Y, Palpal-Latoc D, Kovalenko N, Cameron AJ, Brimble MA, Harris PWR. The Total Chemical Synthesis and Biological Evaluation of the Cationic Antimicrobial Peptides, Laterocidine and Brevicidine. J Nat Prod. 2021 Aug 27;84(8):2165-2174. doi: 10.1021/acs.jnatprod.1c00222. Epub 2021 Aug 2. PMID: 34338512.
4. Wang Z, Koirala B, Hernandez Y, Brady SF. Discovery of Paenibacillaceae Family Gram-Negative-Active Cationic Lipopeptide Antibiotics Using Evolution-Guided Chemical Synthesis. Org Lett. 2022 Jul 15;24(27):4943-4948. doi: 10.1021/acs.orglett.2c01879. Epub 2022 Jul 1. PMID: 35776528; PMCID: PMC10234496.
5. Al Ayed K, Ballantine RD, Hoekstra M, Bann SJ, Wesseling CMJ, Bakker AT, Zhong Z, Li YX, Brüchle NC, van der Stelt M, Cochrane SA, Martin NI. Synthetic studies with the brevicidine and laterocidine lipopeptide antibiotics including analogues with enhanced properties and in vivo efficacy. Chem Sci. 2022 Feb 23;13(12):3563-3570. doi: 10.1039/d2sc00143h. PMID: 35432860; PMCID: PMC8943889.
6. Li YX, Zhong Z, Zhang WP, Qian PY. Discovery of cationic nonribosomal peptides as Gram-negative antibiotics through global genome mining. Nat Commun. 2018 Aug 16;9(1):3273. doi: 10.1038/s41467-018-05781-6. PMID: 30115920; PMCID: PMC6095874.
7. Al Ayed K, Zamarbide Losada D, Machushynets NV, Terlouw B, Elsayed SS, Schill J, Trebosc V, Pieren M, Medema MH, van Wezel GP, Martin NI. Total Synthesis and Structure Assignment of the Relacidine Lipopeptide Antibiotics and Preparation of Analogues with Enhanced Stability. ACS Infect Dis. 2023 Apr 14;9(4):739-748. doi: 10.1021/acsinfecdis.3c00043. Epub 2023 Mar 31. PMID: 37000899; PMCID: PMC10111413.