RP-1776
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| Category | Bioactive by-products |
| Catalog number | BBF-03381 |
| CAS | |
| Molecular Weight | 1483.61 |
| Molecular Formula | C75H94N12O20 |
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Description
RP-1776 is a cyclic peptide isolated from the culture broth of Streptomyces sp. KY11784. It selectively inhibits the binding of PDGF BB to the extracellular domain of the PDGF beta-receptor with an IC50 value of 11 ± 6 µmol/L.
Specification
| Synonyms | RP 1776; RP1776 |
Properties
| Appearance | White Powder |
| Melting Point | 228-230°C |
Reference Reading
1. Anulamycins A-F, Cinnamoyl-Containing Peptides from a Lake Sediment Derived Streptomyces
Han Wang, Huan Qi, Hui Zhang, Shao-Yong Zhang, Cheng-Hong Zhang, Li-Qin Zhang, Wen-Sheng Xiang, Ji-Dong Wang J Nat Prod. 2023 Feb 24;86(2):357-367. doi: 10.1021/acs.jnatprod.2c00967. Epub 2023 Feb 8.
Bioinformatics analysis of a whole genome sequence coupled with HPLC-DAD analysis revealed that Streptomyces sp. Hu103 has the capacity to produce skyllamycin analogues. A subsequent chemical investigation of this strain yielded four new cinnamoyl-containing cyclopeptides, anulamycins A-D (1-4), two new cinnamoyl-containing linear peptides, anulamycins E and F (5 and 6), and two known cyclopeptides, skyllamycins A (7) and B (8). Their structures including absolute configurations were elucidated by detailed analysis of NMR and HRESIMS/MS spectroscopic data and the advanced Marfey's method. Compounds 1-4 exhibited antibacterial activity comparable to those of skyllamycins A and B.
2. Natural products as inspiration for the development of bacterial antibiofilm agents
Roberta J Melander, Akash K Basak, Christian Melander Nat Prod Rep. 2020 Nov 1;37(11):1454-1477. doi: 10.1039/d0np00022a. Epub 2020 Jul 1.
Natural products have historically been a rich source of diverse chemical matter with numerous biological activities, and have played an important role in drug discovery in many areas including infectious disease. Synthetic and medicinal chemistry have been, and continue to be, important tools to realize the potential of natural products as therapeutics and as chemical probes. The formation of biofilms by bacteria in an infection setting is a significant factor in the recalcitrance of many bacterial infections, conferring increased tolerance to many antibiotics and to the host immune response, and as yet there are no approved therapeutics for combatting biofilm-based bacterial infections. Small molecules that interfere with the ability of bacteria to form and maintain biofilms can overcome antibiotic tolerance conferred by the biofilm phenotype, and have the potential to form combination therapies with conventional antibiotics. Many natural products with anti-biofilm activity have been identified from plants, microbes, and marine life, including: elligic acid glycosides, hamamelitannin, carolacton, skyllamycins, promysalin, phenazines, bromoageliferin, flustramine C, meridianin D, and brominated furanones. Total synthesis and medicinal chemistry programs have facilitated structure confirmation, identification of critical structural motifs, better understanding of mechanistic pathways, and the development of more potent, more accessible, or more pharmacologically favorable derivatives of anti-biofilm natural products.
3. Skyllamycins D and E, Non-Ribosomal Cyclic Depsipeptides from Lichen-Sourced Streptomyces anulatus
Joe Bracegirdle, Peng Hou, Vincent V Nowak, David F Ackerley, Robert A Keyzers, Jeremy G Owen J Nat Prod. 2021 Sep 24;84(9):2536-2543. doi: 10.1021/acs.jnatprod.1c00547. Epub 2021 Sep 7.
The skyllamycins are a class of heavily modified, non-ribosomal peptides, first isolated from Streptomyces sp. KY11784. A Streptomyces strain with potent antibiotic activity against Bacillus subtilis was isolated from a sample of the New Zealand lichen Pseudocyphellaria dissimilis. Whole genome sequencing and biosynthetic gene cluster genetic analysis coupled with GNPS LCMS/MS molecular networking revealed that this strain had the capacity to produce skyllamycins, including previously undescribed congeners, and that these were likely the source of the observed biological activity. Guided by the results of the molecular networking, we isolated the previously reported skyllamycins A-C (1-3), along with two new congeners, skyllamycins D (4) and E (5). The structures of these compounds were elucidated using comprehensive 1D and 2D NMR analyses, along with HRESIMS fragmentation experiments. Antibacterial assays revealed that skyllamycin D possessed improved activity against B. subtilis E168 compared to previously reported congeners.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
