Sandramycin

Sandramycin ia a cyclic depsipeptide antibiotic isolated from cultured broth of a Nocardioides sp. Sandramycin is also a DNA intercalator that potently binds DNA and is an ADC cytotoxin. Sandramycin is active against Gram-positive bacteria and has potent antitumor activity.

Product information

CAS Number: 100940-65-6

Molecular Weight: 1221.32

Formula: C60H76N12O16

Chemical Name: 3-hydroxy-N-[(3R, 7S, 16S, 23R, 27S, 36S)-23-(3-hydroxyquinoline-2-amido)-8, 11, 28, 31-tetramethyl-2, 6, 9, 12, 15, 22, 26, 29, 32, 35-decaoxo-7, 27-bis(propan-2-yl)-5, 25-dioxa-1, 8, 11, 14, 21, 28, 31, 34-octaazatricyclo[34.4.0.0, ]tetracontan-3-yl]quinoline-2-carboxamide

Smiles: CN1CC(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)C2=NC3=CC=CC=C3C=C2O)C(=O)N2CCCC[C@H]2C(=O)NCC(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)C2=NC3=CC=CC=C3C=C2O)C(=O)N2CCCC[C@H]2C(=O)NCC1=O

InChiKey: WXIVYIYCEBUEHL-RTQGILJWSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Sandramycin has antimicrobial activity wtih MIC values of 0.024 μg/mL, 0.012 μg/mL, 0.012 μg/mL, 0.098 μg/mL, 0.024 μg/mL, 12.5 μg/mL and 12.5 μg/mL for Bacillus subtilis (Rec+) A22508-2, B. subtilis (Rec-) A22509-2-2, Staphylocccus aureus 209P-A9497, S. aureus (echinomycin-resistant) A9628, Streptococcus faecalis A96 1 1, Escherichia coli A151 19 and E. coli (actinomycin-sensitive) A21780 (AS-19), respectively. Sandramycin inhibits cancer cells growth of L1210, B16, HCT118, RPMI8226, A431, RKO, SU-DHL6 and SU-DHL10 cells 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.

In Vivo:

Sandramycin (0.0125-1.6 mg/kg; intraperitoneal injection; daily; for 5 days; CDF1 female mice) treatment shows moderately active in vivo against leukemia P388 in mice.

References:

1. J A Matson, et al. 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. Katsushi Katayama, et al. Total Synthesis of Sandramycin and Its Analogues via a Multicomponent Assemblage. Org Lett. 2014 Jan 17;16(2):428-31.

Products are for research use only. Not for human use.