Quinaldopeptin
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| Category | Antibiotics |
| Catalog number | BBF-04192 |
| CAS | 130743-07-6 |
| Molecular Weight | 1243.37 |
| Molecular Formula | C62H78N14O14 |
| Purity | >95% by HPLC |
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Description
It is a symmetrical, cyclic decapeptide from an amycolatopsis sp. This is a bis-intercalator of DNA. It exhibits strong in vitro antimicrobial and cytotoxic activity. It significantly prolongs the survival time of mice inoculated with a murine tumour, and also shows weak nematocidal activity. It is related to the luzopeptins and sandramycin.
Specification
| Synonyms | Antibiotic BMY 28662; Antibiotic BU 3845T; BMY 28662; BU 3845T |
| Storage | Store at -20°C |
| IUPAC Name | 3-hydroxy-N-[(3R,4S,7S,20S,27R,28S,31S,44R)-27-[(3-hydroxyquinoline-2-carbonyl)amino]-4,15,28,39-tetramethyl-2,6,13,16,19,26,30,37,40,43-decaoxo-1,5,12,15,18,25,29,36,39,42-decazapentacyclo[42.4.0.07,12.020,25.031,36]octatetracontan-3-yl]quinoline-2-carboxamide |
| Canonical SMILES | CC1C(C(=O)N2CCCCC2C(=O)NCC(=O)N(CC(=O)N3CCCCC3C(=O)NC(C(C(=O)N4CCCCC4C(=O)NCC(=O)N(CC(=O)N5CCCCC5C(=O)N1)C)NC(=O)C6=NC7=CC=CC=C7C=C6O)C)C)NC(=O)C8=NC9=CC=CC=C9C=C8O |
| InChI | InChI=1S/C62H78N14O14/c1-35-51(69-59(87)53-45(77)29-37-17-5-7-19-39(37)67-53)61(89)75-27-15-11-21-41(75)55(83)63-31-47(79)72(4)34-50(82)74-26-14-10-24-44(74)58(86)66-36(2)52(70-60(88)54-46(78)30-38-18-6-8-20-40(38)68-54)62(90)76-28-16-12-22-42(76)56(84)64-32-48(80)71(3)33-49(81)73-25-13-9-23-43(73)57(85)65-35/h5-8,17-20,29-30,35-36,41-44,51-52,77-78H,9-16,21-28,31-34H2,1-4H3,(H,63,83)(H,64,84)(H,65,85)(H,66,86)(H,69,87)(H,70,88)/t35-,36-,41-,42+,43-,44-,51+,52+/m0/s1 |
| InChI Key | KIPSHYPQCJYONU-WZMSAHAESA-N |
| Source | Amycolatopsis sp. |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Parasites |
| Melting Point | 300°C |
| Density | 1.45 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Chloroform, Acetone |
Reference Reading
1. Structure of actinotetraose hexatiglate, a unique glucotetraose from an actinomycete bacterium
E Lacey, R W Rickards, J M Rothschild J Antibiot (Tokyo) . 1998 Dec;51(12):1093-8. doi: 10.7164/antibiotics.51.1093.
An Actinomycete strain A499 belonging to the genera Amycolatopsis or Amycolata isolated from a Western Australian soil sample produced the cyclic decapeptide antibiotic quinaldopeptin (1), together with the actinotetraose hexatiglate (2), the hexa-ester of a novel non-reducing glucotetraose.
2. Synthesis and biological evaluation of quinaldopeptin
Takuya Sunadome, Satoshi Ichikawa, Koji Nakagawa, Motoo Shiro, Takuya Okamura, Katsushi Katayama, Hiroshi Takeda, Akira Matsuda J Org Chem . 2014 Mar 21;79(6):2580-90. doi: 10.1021/jo500039d.
The second-generation total synthesis of quinaldopeptin (1) was established via a Staudinger/aza-Wittig/diastereoselective Ugi three-component reaction sequence and a racemization-free [5 + 5] coupling and macrolactamization. A single-crystal X-ray structure of the chromophore analogue 26 confirmed the structural and stereochemical assignments of the macrocycle. Synthetic 1 successfully unwound supercoiled DNA to form a relaxed DNA in a dose-dependent manner, the binding affinity of 1 to four dsODNs was within a similar range (K(b) = 1.45-2.53 × 10(7) M(-1)), and the sequence selectivity was subtle. It was suggested that 1 possesses biological behaviors similar to those of sandramycin (2) in terms of cytotoxic activity against human cancer cell lines (IC50 = 3.2-12 nM) and HIF-1 inhibitory activity.
3. Quinaldopeptin, a novel antibiotic of the quinomycin family
K Sugawara, N Ohkusa, M Konishi, T Oki, S Toda, M Ohbayashi, Y Nishiyama, H Yamamoto J Antibiot (Tokyo) . 1990 Jul;43(7):796-808. doi: 10.7164/antibiotics.43.796.
Quinaldopeptin, a new type of quinomycin antibiotic, was isolated from the culture of Streptoverticillium album strain Q132-6. The antibiotic exhibited strong in vitro antimicrobial and cytotoxic activity and significantly prolonged the survival time of mice inoculated with a murine tumor. Quinaldopeptin is a symmetric cyclic peptide linked only by peptide bonds and differs from known antibiotics of the quinomycin family by the lack of ester linkage.
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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 ╳
