PeptideDB

Sandramycin 100940-65-6

Sandramycin 100940-65-6

CAS No.: 100940-65-6

Sandramycin is a cyclic decapeptide antibiotic extracted from the culture medium of Nocardioides sp. Sandramycin also bi
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Sandramycin is a cyclic decapeptide antibiotic extracted from the culture medium of Nocardioides sp. Sandramycin also binds DNA efficiently and is an ADC toxin molecule. Sandramycin has activity against Gram-positive (Gram+) bacteria and has potent anti-tumor activity.

Physicochemical Properties


Molecular Formula C60H76N12O16
Molecular Weight 1221.32
Exact Mass 1220.55
CAS # 100940-65-6
PubChem CID 485905
Appearance Typically exists as solid at room temperature
Density 1.42g/cm3
Boiling Point 1518.4ºC at 760 mmHg
Flash Point 872.1ºC
Vapour Pressure 0mmHg at 25°C
Index of Refraction 1.659
LogP 1.135
Hydrogen Bond Donor Count 6
Hydrogen Bond Acceptor Count 18
Rotatable Bond Count 6
Heavy Atom Count 88
Complexity 2400
Defined Atom Stereocenter Count 6
SMILES

O=C1CNC(=O)[C@@H]2CCCCN2C(=O)[C@H](NC(C2=NC3=CC=CC=C3C=C2O)=O)COC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)CNC(=O)[C@@H]2CCCCN2C(=O)[C@H](NC(C2=NC3=CC=CC=C3C=C2O)=O)COC(=O)[C@H](C(C)C)N(C)C(=O)CN1C

InChi Key WXIVYIYCEBUEHL-RTQGILJWSA-N
InChi Code

InChI=1S/C60H76N12O16/c1-33(2)51-59(85)87-31-39(65-55(81)49-43(73)25-35-17-9-11-19-37(35)63-49)57(83)71-23-15-13-21-41(71)53(79)62-28-46(76)68(6)30-48(78)70(8)52(34(3)4)60(86)88-32-40(66-56(82)50-44(74)26-36-18-10-12-20-38(36)64-50)58(84)72-24-16-14-22-42(72)54(80)61-27-45(75)67(5)29-47(77)69(51)7/h9-12,17-20,25-26,33-34,39-42,51-52,73-74H,13-16,21-24,27-32H2,1-8H3,(H,61,80)(H,62,79)(H,65,81)(H,66,82)/t39-,40-,41+,42+,51+,52+/m1/s1
Chemical Name

3-hydroxy-N-[(3R,7S,16S,23R,27S,36S)-23-[(3-hydroxyquinoline-2-carbonyl)amino]-8,11,28,31-tetramethyl-2,6,9,12,15,22,26,29,32,35-decaoxo-7,27-di(propan-2-yl)-5,25-dioxa-1,8,11,14,21,28,31,34-octazatricyclo[34.4.0.016,21]tetracontan-3-yl]quinoline-2-carboxamide
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

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


Targets Traditional Cytotoxic Agents
ln Vitro Sandramycin exhibits antimicrobial activity against Bacillus subtilis (Rec+) A22508-2, B, with minimum inhibitory concentrations (MIC) of 0.024 μg/mL, 0.012 μg/mL, 0.012 μg/mL, 0.098 μg/mL, 0.024 μg/mL, and 12.5 μg/mL. Staphyloccus aureus 209P-A9497, subtilis (Rec-) A22509-2-2, S. Streptococcus faecalis A96 1 1, Escherichia coli A151 19, E. aureus (echinomycin-resistant) A9628, and E. coli A21780 (AS-19), which is actinomycin-sensitive[1]. L1210, B16, HCT118, RPMI8226, A431, RKO, SU-DHL6, and SU-DHL10 cells' proliferation is inhibited by sanamycin, with IC50 values of 0.02 nM, 0.07 nM, 0.8 nM, 3.8 nM, 3.1 nM, 1.3 nM, 5.9 nM, and 3.3 nM, respectively[2].
ln Vivo In vivo, sanamycin therapy (0.0125-1.6 mg/kg; intraperitoneal injection; daily; for 5 days; CDF1 female mice) is somewhat effective against leukemia P388 in mice[1].
Animal Protocol Animal/Disease Models: CDF1 female mice injected with leukemia P388 cells[1]
Doses: 0.0125 mg/kg, 0.025 mg/kg, 0.05 mg/kg, 0.1 mg/kg, 0.2 mg/kg, 0.4 mg/kg, 0.8 mg/kg, 1.6 mg/kg
Route of Administration: intraperitoneal (ip)injection; daily; for 5 days
Experimental Results: Was moderately active in vivo against leukemia P388 in mice.
References

[1]. Sandramycin, a Novel Antitumor Antibiotic Produced by a Nocardioides Sp. Production, Isolation, Characterization and Biological Properties. J Antibiot (Tokyo). 1989 Dec;42(12):1763-7.

[2]. Total Synthesis of Sandramycin and Its Analogues via a Multicomponent Assemblage. Org Lett. 2014 Jan 17;16(2):428-31.

[3]. DNA Binding Properties of Key Sandramycin Analogues: Systematic Examination of the Intercalation Chromophore. Bioorg Med Chem. 1999 Feb;7(2):315-21.

Additional Infomation Sandramycin has been reported in Nocardioides with data available.

Solubility Data


Solubility (In Vitro) May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo) Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)

Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 0.8188 mL 4.0939 mL 8.1879 mL
5 mM 0.1638 mL 0.8188 mL 1.6376 mL
10 mM 0.0819 mL 0.4094 mL 0.8188 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.