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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Intrauterine Drug Delivery Systems01:21

Intrauterine Drug Delivery Systems

Controlled-release systems for intravaginal and intrauterine drug delivery have been developed primarily for the administration of contraceptive steroid hormones. These delivery routes circumvent first-pass hepatic metabolism, thereby enhancing bioavailability and allowing for reduced systemic dosages compared to oral administration. Such approaches contribute to improved therapeutic efficacy and patient compliance, particularly in long-term contraceptive regimens.Intravaginal Drug Delivery...
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry, similar...
Birth Control Methods01:22

Birth Control Methods

Vasectomy is a surgical form of male sterilization that involves severing and sealing the vasa deferentia, preventing sperm from mixing with semen during ejaculation. Because a vasectomy does not impact the testes' ability to produce testosterone, hormone levels, libido, and sexual function generally remain unchanged. While vasectomy is highly effective in preventing pregnancy, with a success rate near 99.85%, rare cases of recanalization (spontaneous reconnection) can occur. Although vasectomy...
Combined Effects of Drugs: Synergism01:27

Combined Effects of Drugs: Synergism

Synergism is a useful mechanism where combining two or more drugs is more effective than each constituent used alone. Such combinations are also called supra-additive interactions. The drugs collectively enhance the final therapeutic effect by acting on different targets. Another advantage is that the low dose of each constituent drug is sufficient to achieve the desired effect. This helps reduce the duration of therapy and lower the adverse effects of these drugs.
Such synergistic combinations...

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Related Experiment Video

Updated: May 10, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
08:47

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Published on: March 6, 2019

Designed Chemical Intervention with Thiols for Prophylactic Contraception.

Monika Sharma1, Lokesh Kumar, Ashish Jain

  • 1Division of Endocrinology, CSIR-Central Drug Research Institute, Lucknow, India.

Plos One
|July 5, 2013
PubMed
Summary

Pyrrolidinium pyrrolidine-1-carbodithioate (PPC) is a novel thiol agent that rapidly immobilizes sperm and eliminates Trichomonas vaginalis. This compound shows promise for developing dual-protection vaginal contraceptives by targeting reactive thiols.

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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Last Updated: May 10, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
08:47

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Published on: March 6, 2019

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Area of Science:

  • Reproductive biology and pharmacology
  • Microbiology and infectious diseases

Background:

  • Sperm possess a high concentration of thiols susceptible to redox-active agents.
  • Existing contraceptives like nonoxynol-9 have non-specific mechanisms.
  • There is a need for novel, targeted contraceptive and microbicidal agents.

Purpose of the Study:

  • To investigate the mechanism of action of pyrrolidinium pyrrolidine-1-carbodithioate (PPC) against human sperm and Trichomonas vaginalis.
  • To evaluate PPC's potential as a prophylactic contraceptive and microbicide.
  • To assess the efficacy of a PPC-formulated vaginal film.

Main Methods:

  • Synthesis and evaluation of PPC and its derivatives against human sperm and Trichomonas vaginalis in vitro.
  • Assessment of sperm hexokinase activity using a coupled enzyme assay.
  • Formulation of PPC into a mucoadhesive vaginal film and evaluation of its contraceptive efficacy in rabbits.

Main Results:

  • PPC irreversibly immobilized 100% of human sperm within 30 seconds and eliminated Trichomonas vaginalis more effectively than nonoxynol-9 and metronidazole.
  • PPC significantly inhibited thiol-sensitive sperm hexokinase activity; activity was lost when the thiol group was blocked.
  • PPC-loaded vaginal films demonstrated significant contraceptive efficacy in rabbits, with rapid release in simulated vaginal fluid.

Conclusions:

  • PPC targets reactive thiols common to sperm and Trichomonas, offering a specific and potent mechanism for inactivation.
  • PPC demonstrates potential as a lead compound for developing dual-protective vaginal contraceptives.
  • The mucoadhesive vaginal film formulation of PPC is stable and effective for prophylactic contraception.