Physicochemical Properties
| Molecular Formula | C141H229N41O38S7 |
| Molecular Weight | 3331.05 |
| Exact Mass | 3329.532 |
| CAS # | 137061-46-2 |
| PubChem CID | 155489899 |
| Appearance | Off-white to light brown solid powder |
| Density | 1.40±0.1 g/cm3(Predicted) |
| Boiling Point | 2962.5±65.0 °C(Predicted) |
| LogP | -7.3 |
| Hydrogen Bond Donor Count | 41 |
| Hydrogen Bond Acceptor Count | 50 |
| Rotatable Bond Count | 67 |
| Heavy Atom Count | 227 |
| Complexity | 7810 |
| Defined Atom Stereocenter Count | 35 |
| SMILES | CC[C@H](C)[C@H]1C(=O)NC(=C)C(=O)N[C@H](C(=O)N[C@@H](CSC[C@H](C(=O)N1)NC(=O)/C(=C/C)/NC(=O)[C@H]([C@@H](C)CC)N)C(=O)N[C@@H]2[C@@H](SC[C@H](NC(=O)CNC(=O)[C@@H]3CCCN3C2=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]4[C@@H](SC[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC4=O)C)CC(C)C)CCSC)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]5[C@@H](SC[C@H]6C(=O)N[C@H](C(=O)N[C@@H](CS[C@H]([C@H](C(=O)N6)NC(=O)[C@@H](NC5=O)C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC7=CN=CN7)C(=O)N[C@@H](C(C)C)C(=O)NC(=C)C(=O)N[C@@H](CCCCN)C(=O)O)CC(=O)N)C)C)C)CC(C)C |
| InChi Key | PWFSAVZKCGCNRK-RDLXCTAXSA-N |
| InChi Code | InChI=1S/C141H229N41O38S7/c1-24-67(11)103(147)133(211)159-79(27-4)116(194)171-91-57-223-58-92(172-121(199)86(48-65(7)8)166-113(191)72(16)155-136(214)105(68(12)25-2)177-130(91)208)131(209)181-110-77(21)227-60-93(157-102(188)55-150-132(210)97-38-34-44-182(97)140(110)218)126(204)161-81(36-29-32-42-143)118(196)179-107-74(18)224-59-94(158-101(187)54-149-115(193)82(39-45-221-22)162-120(198)85(47-64(5)6)165-111(189)70(14)153-100(186)53-151-134(107)212)127(205)167-88(50-98(145)184)122(200)163-83(40-46-222-23)117(195)160-80(35-28-31-41-142)119(197)180-108-75(19)226-62-96-128(206)168-89(51-99(146)185)123(201)173-95(61-225-76(20)109(139(217)174-96)178-114(192)73(17)156-138(108)216)129(207)170-90(56-183)125(203)176-106(69(13)26-3)137(215)169-87(49-78-52-148-63-152-78)124(202)175-104(66(9)10)135(213)154-71(15)112(190)164-84(141(219)220)37-30-33-43-144/h27,52,63-70,73-77,80-97,103-110,183H,15-16,24-26,28-51,53-62,142-144,147H2,1-14,17-23H3,(H2,145,184)(H2,146,185)(H,148,152)(H,149,193)(H,150,210)(H,151,212)(H,153,186)(H,154,213)(H,155,214)(H,156,216)(H,157,188)(H,158,187)(H,159,211)(H,160,195)(H,161,204)(H,162,198)(H,163,200)(H,164,190)(H,165,189)(H,166,191)(H,167,205)(H,168,206)(H,169,215)(H,170,207)(H,171,194)(H,172,199)(H,173,201)(H,174,217)(H,175,202)(H,176,203)(H,177,208)(H,178,192)(H,179,196)(H,180,197)(H,181,209)(H,219,220)/b79-27-/t67-,68-,69-,70-,73-,74-,75-,76-,77-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91+,92-,93-,94-,95-,96-,97-,103-,104-,105-,106-,107+,108+,109+,110+/m0/s1 |
| Chemical Name | (2S)-6-amino-2-[2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(1S,4S,7S,8S,11R,14S,17R,20S)-7-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(3R,9S,12S,15S,21S,22S)-21-[[(2S)-6-amino-2-[[(3S,4S,7R,13S)-3-[[(3R,6S,12S,15S)-15-[[(Z)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]but-2-enoyl]amino]-12-[(2S)-butan-2-yl]-9-methylidene-6-(2-methylpropyl)-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetrazacyclohexadecane-3-carbonyl]amino]-4-methyl-2,9,12-trioxo-5-thia-1,8,11-triazabicyclo[11.3.0]hexadecane-7-carbonyl]amino]hexanoyl]amino]-15,22-dimethyl-12-(2-methylpropyl)-9-(2-methylsulfanylethyl)-5,8,11,14,17,20-hexaoxo-1-thia-4,7,10,13,16,19-hexazacyclodocosane-3-carbonyl]amino]-4-oxobutanoyl]amino]-4-methylsulfanylbutanoyl]amino]hexanoyl]amino]-14-(2-amino-2-oxoethyl)-4,8,20-trimethyl-3,6,12,15,21-pentaoxo-9,19-dithia-2,5,13,16,22-pentazabicyclo[9.9.2]docosane-17-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-methylbutanoyl]amino]prop-2-enoylamino]hexanoic 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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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 | Gingival fibroblasts are more likely to detach and differentiate when exposed to Nisin Z (10 μg/mL, 24 h) [2]. For 24 hours, nisin Z (25–75 μg/mL) prevents C from adhering. gingival cells to albicans[2]. Nisin Z (500 and 1000 μg/mL, 24 hours) prevents C from forming germ tubes. albicans [3]. Nisin Z (10-100 μg/mL, 12 h) inhibits LPS-induced activation of ERK1/2 and p38 MAPK signaling pathways in MCF10A cells [4]. Nisin Z (100 μg/mL, 12 h) lowers LPS-induced production of pro-inflammatory cytokines (i.e., IL-6, TNF-α, IL-1β) in MCF10A cells [4]. |
| ln Vivo | In an LPS-induced mouse mastitis model, nisin Z (1, 5 and 10 mg/kg, ip) inhibits pathological damage [4]. |
| Cell Assay |
Cell Viability Assay[3] Cell Types: C. albicans Tested Concentrations: 100, 500, 1000 μg/mL Incubation Duration: 24, 48, and 72 h Experimental Results: decreased C. albicans growth. Western Blot Analysis[4] Cell Types: LPS-induced MCF10A cells Tested Concentrations: 10-100 μg/mL Incubation Duration: 12 h Experimental Results: Inhibited the phosphorylation of p38 and and ERK1/ 2. |
| Animal Protocol |
Animal/Disease Models: Mastitis mouse model[4] Doses: 1, 5, and 10 mg/kg Route of Administration: ip, one hour before treatment of LPS. Experimental Results: diminished inflammatory cell infiltration. demonstrated a reduction in inflammatory cytokine levels. |
| References |
[1]. Incorporation and antimicrobial activity of nisin Z within carrageenan/chitosan multilayers. Sci Rep. 2021 Jan 18;11(1):1690. [2]. In vitro efficacy of nisin Z against Candida albicans adhesion and transition following contact with normal human gingival cells. J Appl Microbiol. 2009 Oct;107(4):1298-307. [3]. Nisin Z inhibits the growth of Candida albicans and its transition from blastospore to hyphal form. J Appl Microbiol. 2008 Nov;105(5):1630-9. [4]. Nisin Z attenuates lipopolysaccharide-induced mastitis by inhibiting the ERK1/2 and p38 mitogen-activated protein kinase signaling pathways. J Dairy Sci. 2022 Apr;105(4):3530-3543. |
Solubility Data
| Solubility (In Vitro) |
H2O : ~10 mg/mL (~3.00 mM) DMSO : ~2 mg/mL (~0.60 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.2 mg/mL (0.06 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 2.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: ≥ 0.2 mg/mL (0.06 mM) (saturation unknown) in 10% DMSO + 90% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 3: ≥ 0.14 mg/mL (0.04 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 1.4 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.3002 mL | 1.5010 mL | 3.0021 mL | |
| 5 mM | 0.0600 mL | 0.3002 mL | 0.6004 mL | |
| 10 mM | 0.0300 mL | 0.1501 mL | 0.3002 mL |