Physicochemical Properties
| Molecular Formula | C152H257N43O44S2 |
| Molecular Weight | 3455.09 |
| Exact Mass | 3453.866 |
| CAS # | 136212-91-4 |
| Related CAS # | Dermaseptin TFA;646451-06-1 |
| PubChem CID | 16130489 |
| Appearance | White to off-white solid powder |
| LogP | -12.2 |
| Hydrogen Bond Donor Count | 49 |
| Hydrogen Bond Acceptor Count | 52 |
| Rotatable Bond Count | 118 |
| Heavy Atom Count | 241 |
| Complexity | 7840 |
| Defined Atom Stereocenter Count | 35 |
| SMILES | CC[C@@H]([C@@H](C(N[C@H](C(N[C@H](C(NCC(N[C@H](C(N[C@H](C(=O)O)CCC(=O)N)=O)[C@H](O)C)=O)=O)CCC(=O)N)=O)CO)=O)NC([C@H]([C@H](O)C)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H]([C@H](O)C)NC(CNC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H]([C@H](O)C)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](N)C)=O)CC(C)C)=O)CC1C2=C(C=CC=C2)NC=1)=O)CCCCN)=O)=O)CCSC)=O)CC(C)C)=O)CCCCN)=O)CCCCN)=O)CC(C)C)=O)=O)=O)CCSC)=O)C)=O)CC(C)C)=O)CC1N=CNC=1)=O)C)=O)=O)CCCCN)=O)C)=O)C)=O)CC(C)C)=O)=O)C)=O)C)=O)C)=O)CC(=O)O)=O)=O)C |
| InChi Key | YFHLIDBAPTWLGU-CTKMSOPVSA-N |
| InChi Code | InChI=1S/C152H257N43O44S2/c1-27-77(12)118(147(233)190-110(70-196)146(232)178-98(44-46-111(158)201)131(217)163-68-115(205)192-120(87(22)198)149(235)181-101(152(238)239)45-47-112(159)202)193-151(237)122(89(24)200)195-145(231)109(63-117(207)208)185-129(215)84(19)169-126(212)81(16)168-125(211)80(15)167-113(203)66-164-132(218)102(56-72(2)3)183-128(214)83(18)170-127(213)82(17)172-134(220)94(40-30-34-50-153)174-114(204)67-162-124(210)79(14)171-140(226)108(62-91-65-160-71-166-91)189-143(229)105(59-75(8)9)184-130(216)85(20)173-135(221)99(48-54-240-25)179-148(234)119(86(21)197)191-116(206)69-165-133(219)103(57-73(4)5)186-137(223)96(42-32-36-52-155)175-136(222)95(41-31-35-51-154)176-141(227)106(60-76(10)11)187-138(224)100(49-55-241-26)180-150(236)121(88(23)199)194-139(225)97(43-33-37-53-156)177-144(230)107(61-90-64-161-93-39-29-28-38-92(90)93)188-142(228)104(58-74(6)7)182-123(209)78(13)157/h28-29,38-39,64-65,71-89,94-110,118-122,161,196-200H,27,30-37,40-63,66-70,153-157H2,1-26H3,(H2,158,201)(H2,159,202)(H,160,166)(H,162,210)(H,163,217)(H,164,218)(H,165,219)(H,167,203)(H,168,211)(H,169,212)(H,170,213)(H,171,226)(H,172,220)(H,173,221)(H,174,204)(H,175,222)(H,176,227)(H,177,230)(H,178,232)(H,179,234)(H,180,236)(H,181,235)(H,182,209)(H,183,214)(H,184,216)(H,185,215)(H,186,223)(H,187,224)(H,188,228)(H,189,229)(H,190,233)(H,191,206)(H,192,205)(H,193,237)(H,194,225)(H,195,231)(H,207,208)(H,238,239)/t77-,78-,79-,80-,81-,82-,83-,84-,85-,86+,87+,88+,89+,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,118-,119-,120-,121-,122-/m0/s1 |
| Chemical Name | (2S)-5-amino-2-[[(2S,3R)-2-[[2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-4-methylsulfanylbutanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]propanoyl]amino]acetyl]amino]hexanoyl]amino]propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxybutanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-5-oxopentanoic acid |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | At micromolar concentrations, the water-soluble, heat-stable, non-hemolytic peptide dermaseptin exhibits strong antimicrobial activity against pathogenic fungi. Dermaseptin's 80% α-helical conformation is indicated by its circular dichroism spectra in hydrophobic media. Secondary structure predictions show that dermaseptin can be configured as an amphipathic α-helix that spans residues 1–27. This perturbation-regulated water structure of the membrane regulates flux. 1]. At micromolar concentrations, dermaseptin has a lytic effect on filamentous fungi, bacteria, yeast, and protozoa. Dermaseptin's superior antibacterial potency can be attributed to a molecular element: the NH2-terminal α-helical amphipathic fragment, which spans residues 1-18 of the molecule [1]. Dermaseptin (5-100 μg/ml; 48 hours) completely prevents the growth of the majority of tested microorganisms, including filamentous fungi, yeasts, bacteria, and parasites, at micromolar concentrations [2]. Dermaseptin treatment for one hour did not penetrate guinea pig lymphocytes up to the highest concentration assayed (200 μg/ml), and after 48 hours of incubation, it did not inhibit the proliferation of human KJ3 cells. ..Rabbit red blood cells were hemolyzed at 350 μg/ml, which resulted in a 50% hemolysis after an hour of treatment with a dose exceeding 200 μg/ml [2]. Aeromonas equi, Pseudomonas aeruginosa, Escherichia coli, Enterococcus faecalis, and L. are among the bacteria that Dermaseptin has antibacterial action against. Microsporum canis (IP1194) and mezicana (NF alpha strain) have MIC values of 50 μg/ml, 100 μg/ml, 25 μg/ml, 15 μg/ml, and 50 μg/ml, respectively [2]. |
| References |
[1]. Isolation, amino acid sequence, and synthesis of dermaseptin, a novel antimicrobial peptide of amphibian skin. Biochemistry. 1991 Sep 10;30(36):8824-30. [2]. The NH2-terminal alpha-helical domain 1-18 of dermaseptin is responsible for antimicrobial activity. J Biol Chem. 1994 Jan 21;269(3):1934-9. |
Solubility Data
| Solubility (In Vitro) | H2O : ~25 mg/mL (~7.24 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 50 mg/mL (14.47 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.2894 mL | 1.4471 mL | 2.8943 mL | |
| 5 mM | 0.0579 mL | 0.2894 mL | 0.5789 mL | |
| 10 mM | 0.0289 mL | 0.1447 mL | 0.2894 mL |