Acylcarnitine analogues as topical, microbicidal spermicides.

Savle, Prashant S.; Doncel, Gustavo F.; Bryant, Stephen D.; Hubieki, M. Patricia; Robinette, R. Graham; Gandour, Richard D.

doi:10.1016/s0960-894x(99)00423-0

Cited by 19 publications

(15 citation statements)

References 25 publications

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“…On the basis of dose-and time-response data, the SL ethyl ester with a 20-carbon chain length displayed lower spermicidal activity than the SL hexyl ester with a 24-carbon chain length. This phenomenon has been reported for two other series of spermicidal lipids, albeit studying longer chains (22,33). Analysis of the ring-opened SL free acid (18 carbons) and the alkyl ester (19 to 24 carbons) structures shows that alkylation also increases cytotoxicity while decreasing antiviral activity.…”

Section: Discussionsupporting

confidence: 67%

“…Serial twofold dilutions of the test compounds in 0.9% NaCl were incubated with semen aliquots for 30 seconds. Motility was evaluated under the microscope during the first incubation and after dilution in buffer and further incubation for 1 h. Only those dilutions that immobilized 100% of the spermatozoa pass the test (22). Results were expressed as minimum effective concentrations (MECs) (also called ED100).…”

Section: Methodsmentioning

confidence: 99%

“…More than 40 million people are infected with HIV worldwide, and the death toll related to AIDS exceeded 3 million in 2004 (28) with women representing an increasing percentage of infected individuals (31). Many women want to control their fertility and reduce their risk of becoming infected with a STD (22). However, no currently available agent simultaneously protects against pregnancy and infection.…”

mentioning

confidence: 99%

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Sophorolipids, Microbial Glycolipids with Anti-Human Immunodeficiency Virus and Sperm-Immobilizing Activities

Shah¹,

Doncel

Seyoum

et al. 2005

Antimicrob Agents Chemother

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219

148

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The increased incidence of human immunodeficiency virus (HIV)/AIDS disease in women aged 15 to 49 years has identified the urgent need for a female-controlled, efficacious, and safe vaginal topical microbicide. To meet this challenge, sophorolipid (SL) produced by Candida bombicola and its structural analogs have been studied in this report for their spermicidal, anti-HIV, and cytotoxic activities. The sophorolipid diacetate ethyl ester derivative is the most potent spermicidal and virucidal agent of the series of SLs studied. Its virucidal activity against HIV and sperm-immobilizing activity against human semen are similar to those of nonoxynol-9. However, it also induced enough vaginal cell toxicity to raise concerns about its applicability for long-term microbicidal contraception. Its structure-activity relationship has been established for creating new analogs with less cytotoxicity and higher activity.

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Section: Discussionsupporting

confidence: 67%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Sophorolipids, Microbial Glycolipids with Anti-Human Immunodeficiency Virus and Sperm-Immobilizing Activities

Shah¹,

Doncel

Seyoum

et al. 2005

Antimicrob Agents Chemother

Self Cite

219

148

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“…With these ideas in mind, we discovered that a homologous series of compounds of type Z, where Z15 HPC, are active as anti-HIV spermicides and as anti-Candida agents, when compared to commercial products [52]. We later found that Z14 and Z15 have excellent antigonorrhea, antichlamydial, and anti-Haemophilus activities [53].…”

Section: Amphiphilic Zwitterions 31 Amphiphilic Zwitterions As Topmentioning

confidence: 99%

Rationalizing the Solution Properties of Zwitterions by Means of Computational Chemistry

Gandour¹

2005

C&B

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This short review describes our computational studies of carnitine, acetylcarnitines, and betaines over the past two decades. Interspersed among the three computational studies--a molecular mechanics study of the conformer population of carnitine and acetylcarnitine, an AM1 study of the energetics of hydrolysis of acetylcarnitine, and an HF 6-31G* study of the solvation energies and structures of a homologous series of betaines--are brief overviews of our research in designing and testing new therapeutic agents for non-insulin dependent diabetes and for protection against sexually transmitted diseases. The three studies also show how computational chemistry has evolved during this time to enable an evaluation of the structure and energetics of zwitterions in aqueous solution.

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“…Novel acylcarnitine analogues have proved to be potent inactivators of HIV as well as sperm [9], without showing significant vaginal irritation potential. These compounds are also effective against C. trachomatis, N. gonorrhoeae, Haemophilus ducreyi, and Candida albicans [10].…”

Section: Microbicidal Inactivatorsmentioning

confidence: 99%

An update on vaginal microbicides

Mauck

Doncel²

2001

Curr Infect Dis Rep

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In response to an increasing prevalence of sexually transmitted diseases, especially AIDS, efforts to prevent further infections have been heightened. One of those approaches has been the development of topical microbicidal agents or microbicides. These are compounds designed to protect the body's mucosal surfaces from infection by sexually transmitted disease-causing pathogens. Numerous candidates are currently in preclinical stages; however, only a handful have been tested for safety, and even fewer are ready for clinical efficacy trials. In this update, we describe some of the specific features of microbicide research and development, including preclinical screening algorithms, candidate's ideal properties, examples of compounds presently in the pipeline, and future prospects.

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Acylcarnitine analogues as topical, microbicidal spermicides.

Cited by 19 publications

References 25 publications

Sophorolipids, Microbial Glycolipids with Anti-Human Immunodeficiency Virus and Sperm-Immobilizing Activities

Sophorolipids, Microbial Glycolipids with Anti-Human Immunodeficiency Virus and Sperm-Immobilizing Activities

Rationalizing the Solution Properties of Zwitterions by Means of Computational Chemistry

An update on vaginal microbicides

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